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Sample records for cyanogenic glucoside dhurrin

  1. Biosynthesis of the Cyanogenic Glucoside Dhurrin in Seedlings of Sorghum bicolor (L.) Moench and Partial Purification of the Enzyme System Involved 1

    PubMed Central

    Halkier, Barbara Ann; Møller, Birger Lindberg

    1989-01-01

    The cyanogenic glucoside dhurrin is rapidly synthesized in etiolated seedlings of Sorghum bicolor (L.) Moench. The dhurrin content of the seedlings increases sigmoidally with the germination time. Shoots of 10 centimeters height contain 850 nanomoles of dhurrin per shoot corresponding to 6% of the dry weight. The biosynthetic activity sharply rises upon germination and reaches a maximum level of 10 nanomoles dhurrin/(hour × shoot) after 48 hours when the shoots are 3 centimeters high. This maximum level is followed by a sharp decline in activity when germination time exceeds 65 hours. Dhurrin and the dhurrin-synthesizing enzyme system are primarily located in the upper part of the etiolated shoot where both are evenly distributed between the coleoptile, the primary leaves and the upper 0.5 centimeter of the first internode including the shoot apex. Dhurrin constitutes 30% of the dry weight of the upper 1.2 centimeter of 10 centimeter high shoots. The seed and root contain neither dhurrin nor the dhurrin-synthesizing enzyme system. The codistribution of dhurrin and the enzyme system throughout the seedling indicates that production and storage sites are located within the same cell. Purification of the dhurrin-synthesizing enzyme by gel filtration or by sucrose gradient centrifugations results in a tenfold increase in specific activity. Further purification is accompained by a decline in specific activity due to loss of essential components as demonstrated by reconstitution experiments. Images Figure 7 Figure 8 PMID:16666964

  2. Isolation and reconstitution of cytochrome P450ox and in vitro reconstitution of the entire biosynthetic pathway of the cyanogenic glucoside dhurrin from sorghum.

    PubMed Central

    Kahn, R A; Bak, S; Svendsen, I; Halkier, B A; Møller, B L

    1997-01-01

    A cytochrome P450, designated P450ox, that catalyzes the conversion of (Z)-p-hydroxyphenylacetaldoxime (oxime) to p-hydroxymandelonitrile in the biosynthesis of the cyanogenic glucoside beta-D-glucopyranosyloxy-(S)-p-hydroxymandelonitrile (dhurrin), has been isolated from microsomes prepared from etiolated seedlings of sorghum (Sorghum bicolor L. Moench). P450ox was solubilized using nonionic detergents, and isolated by ion-exchange chromatography, Triton X-114 phase partitioning, and dye-column chromatography. P450ox has an apparent molecular mass of 55 kD, its N-terminal amino acid sequence is -ATTATPQLLGGSVP, and it contains the internal sequence MDRLVADLDRAAA. Reconstitution of P450ox with NADPH-P450 oxidoreductase in micelles of L-alpha-dilauroyl phosphatidylcholine identified P450ox as a multifunctional P450 catalyzing dehydration of (Z)-oxime to p-hydroxyphenylaceto-nitrile (nitrile) and C-hydroxylation of p-hydroxyphenylacetonitrile to nitrile. P450ox is extremely labile compared with the P450s previously isolated from sorghum. When P450ox is reconstituted in the presence of a soluble uridine diphosphate glucose glucosyltransferase, oxime is converted to dhurrin. In vitro reconstitution of the entire dhurrin biosynthetic pathway from tyrosine was accomplished by the insertion of CYP79 (tyrosine N-hydroxylase), P450ox, and NADPH-P450 oxidoreductase in lipid micelles in the presence of uridine diphosphate glucose glucosyltransferase. The catalysis of the conversion of Tyr into nitrile by two multifunctional P450s explains why all intermediates in this pathway except (Z)-oxime are channeled. PMID:9414567

  3. The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase that catalyzes the last step in synthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor. Isolation, cloning, heterologous expression, and substrate specificity.

    PubMed

    Jones, P R; Moller, B L; Hoj, P B

    1999-12-10

    The final step in the biosynthesis of the cyanogenic glucoside dhurrin in Sorghum bicolor is the transformation of the labile cyanohydrin into a stable storage form by O-glucosylation of (S)-p-hydroxymandelonitrile at the cyanohydrin function. The UDP-glucose:p-hydroxymandelonitrile-O-glucosyltransferase was isolated from etiolated seedlings of S. bicolor employing Reactive Yellow 3 chromatography with UDP-glucose elution as the critical step. Amino acid sequencing allowed the cloning of a full-length cDNA encoding the glucosyltransferase. Among the few characterized glucosyltransferases, the deduced translation product showed highest overall identity to Zea mays flavonoid-glucosyltransferase (Bz-Mc-2 allele). The substrate specificity of the enzyme was established using isolated recombinant protein. Compared with endogenous p-hydroxymandelonitrile, mandelonitrile, benzyl alcohol, and benzoic acid were utilized at maximum rates of 78, 13, and 4%, respectively. Surprisingly, the monoterpenoid geraniol was glucosylated at a maximum rate of 11% compared with p-hydroxymandelonitrile. The picture that is emerging regarding plant glucosyltransferase substrate specificity is one of limited but extended plasticity toward metabolites of related structure. This in turn ensures that a relatively high, but finite, number of glucosyltransferases can give rise to the large number of glucosides found in plants.

  4. Rate of hydrolysis and degradation of the cyanogenic glycoside - dhurrin - in soil.

    PubMed

    Johansen, Henrik; Rasmussen, Lars Holm; Olsen, Carl Erik; Bruun Hansen, Hans Christian

    2007-02-01

    Cyanogenic glycosides are common plant toxins. Toxic hydrogen cyanide originating from cyanogenic glycosides may affect soil processes and water quality. In this study, hydrolysis, degradation and sorption of dhurrin (4-hydroxymandelonitrile-beta-d-glucoside) produced by sorghum has been studied in order to assess its fate in soil. The log K(ow) of dhurrin was -1.18+/-0.08 (22 degrees C). Hydrolysis was a first-order reaction with respect to dhurrin and hydroxyl ion concentrations. Half lives ranged from 1.2h (pH 8.6; 25 degrees C) to 530d (pH 4; 25 degrees C). The activation energy of hydrolysis was 112+9kJ. At pH 5.8 and room temperature, addition of humic acids (50gl(-1)) increased the rate of hydrolysis tenfold, while addition of kaolinite or goethite (100-250gl(-1)) both decreased the rate considerably. No significant sorption to soil components could be observed. The degradation rates of dhurrin in top and subsoils of Oxisols, Ultisols, Alfisols and Mollisols were studied at 22 degrees C (25mgl(-1), soil:liquid 1:1 (w:V), pH 3.8-8.1). Half-lives were 0.25-2h for topsoils, and 5-288h in subsoils. Hydrolysis in solution explained up to 45% of the degradation in subsoils whereas the contribution in topsoils was less than 14%, indicating the importance of enzymatic degradation processes. The highest risk of dhurrin leaching will take place when the soil is a low activity acid shallow soil with low content of clay minerals, iron oxides and humic acids. PMID:17126881

  5. General and Stereocontrolled Approach to the Chemical Synthesis of Naturally Occurring Cyanogenic Glucosides.

    PubMed

    Møller, Birger L; Olsen, Carl E; Motawia, Mohammed S

    2016-04-22

    An effective method for the chemical synthesis of cyanogenic glucosides has been developed as demonstrated by the synthesis of dhurrin, taxiphyllin, prunasin, sambunigrin, heterodendrin, and epiheterodendrin. O-Trimethylsilylated cyanohydrins were prepared and subjected directly to glucosylation using a fully acetylated glucopyranosyl fluoride donor with boron trifluoride-diethyl etherate as promoter to afford a chromatographically separable epimeric mixture of the corresponding acetylated cyanogenic glucosides. The isolated epimers were deprotected using a triflic acid/MeOH/ion-exchange resin system without any epimerization of the cyanohydrin function. The method is stereocontrolled and provides an efficient approach to chemical synthesis of other naturally occurring cyanogenic glucosides including those with a more complex aglycone structure.

  6. Discovery of a dhurrin QTL in sorghum bicolor: colocalization of dhurrin biosynthesis and a novel stay-green QTL

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Dhurrin [(S)-p-hydroxymandelonitrile-ß-D-glucopyranoside] is a cyanogenic glucoside produced by (Sorghum bicolor L. Moench) and is generally considered a natural defense compound capable of producing the toxin hydrogen cyanide (HCN) to deter animal herbivory. Recently, high levels of leaf dhurrin h...

  7. Effects of PEG-induced osmotic stress on growth and dhurrin levels of forage sorghum.

    PubMed

    O'Donnell, Natalie H; Møller, Birger Lindberg; Neale, Alan D; Hamill, John D; Blomstedt, Cecilia K; Gleadow, Roslyn M

    2013-12-01

    Sorghum (Sorghum bicolor L. Moench) is a valuable forage crop in regions with low soil moisture. Sorghum may accumulate high concentrations of the cyanogenic glucoside dhurrin when drought stressed resulting in possible cyanide (HCN) intoxication of grazing animals. In addition, high concentrations of nitrate, also potentially toxic to ruminants, may accumulate during or shortly after periods of drought. Little is known about the degree and duration of drought-stress required to induce dhurrin accumulation, or how changes in dhurrin concentration are influenced by plant size or nitrate metabolism. Given that finely regulating soil moisture under controlled conditions is notoriously difficult, we exposed sorghum plants to varying degrees of osmotic stress by growing them for different lengths of time in hydroponic solutions containing polyethylene glycol (PEG). Plants grown in medium containing 20% PEG (-0.5 MPa) for an extended period had significantly higher concentrations of dhurrin in their shoots but lower dhurrin concentrations in their roots. The total amount of dhurrin in the shoots of plants from the various treatments was not significantly different on a per mass basis, although a greater proportion of shoot N was allocated to dhurrin. Following transfer from medium containing 20% PEG to medium lacking PEG, shoot dhurrin concentrations decreased but nitrate concentrations increased to levels potentially toxic to grazing ruminants. This response is likely due to the resumption of plant growth and root activity, increasing the rate of nitrate uptake. Data presented in this article support a role for cyanogenic glucosides in mitigating oxidative stress. PMID:24080394

  8. The cyanogenic glucoside composition of Zygaena filipendulae (Lepidoptera: Zygaenidae) as effected by feeding on wild-type and transgenic lotus populations with variable cyanogenic glucoside profiles.

    PubMed

    Zagrobelny, Mika; Bak, Søren; Ekstrøm, Claus Thorn; Olsen, Carl Erik; Møller, Birger Lindberg

    2007-01-01

    Zygaena larvae sequester the cyanogenic glucosides linamarin and lotaustralin from their food plants (Fabaceae) as well as carry out de novo biosynthesis of these compounds. In this study, Zygaena filipendulae were reared on wild-type Lotus corniculatus and wild-type and transgenic L. japonicus plants with differing content and ratios of the cyanogenic glucosides linamarin and lotaustralin and of the cyanoalkenyl glucosides rhodiocyanoside A and D. LC-MS analyses, free choice feeding experiments and developmental studies were used to examine the effect of varying content and ratios of these secondary metabolites on the feeding preferences, growth and development of Z. filipendulae. Larvae reared on cyanogenic L. corniculatus developed faster compared to larvae reared on L. japonicus although free choice feeding trials demonstrated that the latter plant source was the preferred food plant. Larvae reared on acyanogenic L. corniculatus showed decelerated development. Analysis of different life stages and tissues demonstrate that Z. filipendulae strive to maintain certain threshold content and ratios of cyanogenic glucosides regardless of the composition of the food plants. Despite this, the ratios of cyanogenic glucosides in Z. filipendulae remain partly affected by the ratio of the food plant due to the high proportion of sequestering that takes place. PMID:17175442

  9. Sequestration, tissue distribution and developmental transmission of cyanogenic glucosides in a specialist insect herbivore.

    PubMed

    Zagrobelny, Mika; Olsen, Carl Erik; Pentzold, Stefan; Fürstenberg-Hägg, Joel; Jørgensen, Kirsten; Bak, Søren; Møller, Birger Lindberg; Motawia, Mohammed Saddik

    2014-01-01

    Considering the staggering diversity of bioactive natural products present in plants, insects are only able to sequester a small number of phytochemicals from their food plants. The mechanisms of how only some phytochemicals are sequestered and how the sequestration process takes place remains largely unknown. In this study the model system of Zygaena filipendulae (Lepidoptera) and their food plant Lotus corniculatus is used to advance the knowledge of insect sequestration. Z. filipendulae larvae are dependent on sequestration of the cyanogenic glucosides linamarin and lotaustralin from their food plant, and have a much lower fitness if reared on plants without these compounds. This study investigates the fate of the cyanogenic glucosides during ingestion, sequestration in the larvae, and in the course of insect ontogeny. To this purpose, double-labeled linamarin and lotaustralin were chemically synthesized carrying two stable isotopes, a (2)H labeled aglucone and a (13)C labeled glucose moiety. In addition, a small amount of (14)C was incorporated into the glucose residue. The isotope-labeled compounds were applied onto cyanogenic L. corniculatus leaves that were subsequently presented to the Z. filipendulae larvae. Following ingestion by the larvae, the destiny of the isotope labeled cyanogenic glucosides was monitored in different tissues of larvae and adults at selected time points, using radio-TLC and LC-MS analyses. It was shown that sequestered compounds are taken up intact, contrary to earlier hypotheses where it was suggested that the compounds would have to be hydrolyzed before transport across the gut. The uptake from the larval gut was highly stereo selective as the β-glucosides were retained while the α-glucosides were excreted and recovered in the frass. Sequestered compounds were rapidly distributed into all analyzed tissues of the larval body, partly retained throughout metamorphosis and transferred into the adult insect where they were

  10. Cyanogenic glucosides in the biological warfare between plants and insects: the Burnet moth-Birdsfoot trefoil model system.

    PubMed

    Zagrobelny, Mika; Møller, Birger Lindberg

    2011-09-01

    Cyanogenic glucosides are important components of plant defense against generalist herbivores due to their bitter taste and the release of toxic hydrogen cyanide upon tissue disruption. Some specialized herbivores, especially insects, preferentially feed on cyanogenic plants. Such herbivores have acquired the ability to metabolize cyanogenic glucosides or to sequester them for use in their own predator defense. Burnet moths (Zygaena) sequester the cyanogenic glucosides linamarin and lotaustralin from their food plants (Fabaceae) and, in parallel, are able to carry out de novo synthesis of the very same compounds. The ratio and content of cyanogenic glucosides is tightly regulated in the different stages of the Zygaena filipendulae lifecycle and the compounds play several important roles in addition to defense. The transfer of a nuptial gift of cyanogenic glucosides during mating of Zygaena has been demonstrated as well as the possible involvement of hydrogen cyanide in male assessment and nitrogen metabolism. As the capacity to de novo synthesize cyanogenic glucosides was developed independently in plants and insects, the great similarities of the pathways between the two kingdoms indicate that cyanogenic glucosides are produced according to a universal route providing recruitment of the enzymes required. Pyrosequencing of Z. filipendulae larvae de novo synthesizing cyanogenic glucosides served to provide a set of good candidate genes, and demonstrated that the genes encoding the pathway in plants and Z. filipendulae are not closely related phylogenetically. Identification of insect genes involved in the biosynthesis and turn-over of cyanogenic glucosides will provide new insights into biological warfare as a determinant of co-evolution between plants and insects.

  11. Cyanogen

    Integrated Risk Information System (IRIS)

    Jump to main content . Integrated Risk Information System Recent Additions | Contact Us Search : All EPA IRIS • You are here : EPA Home • Research • Environmental Assessment • IRIS • IRIS Summaries Redirect Page As of September 28 , 2010 , the assessment summary for cyanogen is included in the hydro

  12. Quantitative trait loci controlling cyanogenic glucoside and dry matter content in cassava (Manihot esculenta Crantz) roots.

    PubMed

    Balyejusa Kizito, Elizabeth; Rönnberg-Wästljung, Ann-Christin; Egwang, Thomas; Gullberg, Urban; Fregene, Martin; Westerbergh, Anna

    2007-09-01

    Cassava (Manihot esculenta Crantz) is a starchy root crop grown in the tropics mainly by small-scale farmers even though agro-industrial processing is rapidly increasing. For this processing market improved varieties with high dry matter root content (DMC) is required. Potentially toxic cyanogenic glucosides are synthesized in the leaves and translocated to the roots. Selection for varieties with low cyanogenic glucoside potential (CNP) and high DMC is among the principal objectives in cassava breeding programs. However, these traits are highly influenced by the environmental conditions and the genetic control of these traits is not well understood. An S(1) population derived from a cross between two bred cassava varieties (MCOL 1684 and Rayong 1) that differ in CNP and DMC was used to study the heritability and genetic basis of these traits. A broad-sense heritability of 0.43 and 0.42 was found for CNP and DMC, respectively. The moderate heritabilities for DMC and CNP indicate that the phenotypic variation of these traits is explained by a genetic component. We found two quantitative trait loci (QTL) on two different linkage groups controlling CNP and six QTL on four different linkage groups controlling DMC. One QTL for CNP and one QTL for DMC mapped near each other, suggesting pleiotrophy and/or linkage of QTL. The two QTL for CNP showed additive effects while the six QTL for DMC showed additive effect, dominance or overdominance. This study is a first step towards developing molecular marker tools for efficient breeding of CNP and DMC in cassava.

  13. Dirigent Protein-Mediated Lignan and Cyanogenic Glucoside Formation in Flax Seed: Integrated Omics and MALDI Mass Spectrometry Imaging.

    PubMed

    Dalisay, Doralyn S; Kim, Kye Won; Lee, Choonseok; Yang, Hong; Rübel, Oliver; Bowen, Benjamin P; Davin, Laurence B; Lewis, Norman G

    2015-06-26

    An integrated omics approach using genomics, transcriptomics, metabolomics (MALDI mass spectrometry imaging, MSI), and bioinformatics was employed to study spatiotemporal formation and deposition of health-protecting polymeric lignans and plant defense cyanogenic glucosides. Intact flax (Linum usitatissimum) capsules and seed tissues at different development stages were analyzed. Transcriptome analyses indicated distinct expression patterns of dirigent protein (DP) gene family members encoding (-)- and (+)-pinoresinol-forming DPs and their associated downstream metabolic processes, respectively, with the former expressed at early seed coat development stages. Genes encoding (+)-pinoresinol-forming DPs were, in contrast, expressed at later development stages. Recombinant DP expression and DP assays also unequivocally established their distinct stereoselective biochemical functions. Using MALDI MSI and ion mobility separation analyses, the pinoresinol downstream derivatives, secoisolariciresinol diglucoside (SDG) and SDG hydroxymethylglutaryl ester, were localized and detectable only in early seed coat development stages. SDG derivatives were then converted into higher molecular weight phenolics during seed coat maturation. By contrast, the plant defense cyanogenic glucosides, the monoglucosides linamarin/lotaustralin, were detected throughout the flax capsule, whereas diglucosides linustatin/neolinustatin only accumulated in endosperm and embryo tissues. A putative biosynthetic pathway to the cyanogens is proposed on the basis of transcriptome coexpression data. Localization of all metabolites was at ca. 20 μm resolution, with the web based tool OpenMSI enabling not only resolution enhancement but also an interactive system for real-time searching for any ion in the tissue under analysis.

  14. Genomic clustering of cyanogenic glucoside biosynthetic genes aids their identification in Lotus japonicus and suggests the repeated evolution of this chemical defence pathway.

    PubMed

    Takos, Adam M; Knudsen, Camilla; Lai, Daniela; Kannangara, Rubini; Mikkelsen, Lisbeth; Motawia, Mohammed S; Olsen, Carl E; Sato, Shusei; Tabata, Satoshi; Jørgensen, Kirsten; Møller, Birger L; Rook, Fred

    2011-10-01

    Cyanogenic glucosides are amino acid-derived defence compounds found in a large number of vascular plants. Their hydrolysis by specific β-glucosidases following tissue damage results in the release of hydrogen cyanide. The cyanogenesis deficient1 (cyd1) mutant of Lotus japonicus carries a partial deletion of the CYP79D3 gene, which encodes a cytochrome P450 enzyme that is responsible for the first step in cyanogenic glucoside biosynthesis. The genomic region surrounding CYP79D3 contains genes encoding the CYP736A2 protein and the UDP-glycosyltransferase UGT85K3. In combination with CYP79D3, these genes encode the enzymes that constitute the entire pathway for cyanogenic glucoside biosynthesis. The biosynthetic genes for cyanogenic glucoside biosynthesis are also co-localized in cassava (Manihot esculenta) and sorghum (Sorghum bicolor), but the three gene clusters show no other similarities. Although the individual enzymes encoded by the biosynthetic genes in these three plant species are related, they are not necessarily orthologous. The independent evolution of cyanogenic glucoside biosynthesis in several higher plant lineages by the repeated recruitment of members from similar gene families, such as the CYP79s, is a likely scenario.

  15. Characterization and expression profile of two UDP-glucosyltransferases, UGT85K4 and UGT85K5, catalyzing the last step in cyanogenic glucoside biosynthesis in cassava.

    PubMed

    Kannangara, Rubini; Motawia, Mohammed S; Hansen, Natascha K K; Paquette, Suzanne M; Olsen, Carl E; Møller, Birger L; Jørgensen, Kirsten

    2011-10-01

    Manihot esculenta (cassava) contains two cyanogenic glucosides, linamarin and lotaustralin, biosynthesized from l-valine and l-isoleucine, respectively. In this study, cDNAs encoding two uridine diphosphate glycosyltransferase (UGT) paralogs, assigned the names UGT85K4 and UGT85K5, have been isolated from cassava. The paralogs display 96% amino acid identity, and belong to a family containing cyanogenic glucoside-specific UGTs from Sorghum bicolor and Prunus dulcis. Recombinant UGT85K4 and UGT85K5 produced in Escherichia coli were able to glucosylate acetone cyanohydrin and 2-hydroxy-2-methylbutyronitrile, forming linamarin and lotaustralin. UGT85K4 and UGT85K5 show broad in vitro substrate specificity, as documented by their ability to glucosylate other hydroxynitriles, some flavonoids and simple alcohols. Immunolocalization studies indicated that UGT85K4 and UGT85K5 co-occur with CYP79D1/D2 and CYP71E7 paralogs, which catalyze earlier steps in cyanogenic glucoside synthesis in cassava. These enzymes are all found in mesophyll and xylem parenchyma cells in the first unfolded cassava leaf. In situ PCR showed that UGT85K4 and UGT85K5 are co-expressed with CYP79D1 and both CYP71E7 paralogs in the cortex, xylem and phloem parenchyma, and in specific cells in the endodermis of the petiole of the first unfolded leaf. Based on the data obtained, UGT85K4 and UGT85K5 are concluded to be the UGTs catalyzing in planta synthesis of cyanogenic glucosides. The localization of the biosynthetic enzymes suggests that cyanogenic glucosides may play a role in both defense reactions and in fine-tuning nitrogen assimilation in cassava.

  16. Transfer of the cytochrome P450-dependent dhurrin pathway from Sorghum bicolor into Nicotiana tabacum chloroplasts for light-driven synthesis

    PubMed Central

    Gnanasekaran, Thiyagarajan; Karcher, Daniel; Nielsen, Agnieszka Zygadlo; Martens, Helle Juel; Ruf, Stephanie; Kroop, Xenia; Olsen, Carl Erik; Motawie, Mohammed Saddik; Pribil, Mathias; Møller, Birger Lindberg; Bock, Ralph; Jensen, Poul Erik

    2016-01-01

    Plant chloroplasts are light-driven cell factories that have great potential to act as a chassis for metabolic engineering applications. Using plant chloroplasts, we demonstrate how photosynthetic reducing power can drive a metabolic pathway to synthesise a bio-active natural product. For this purpose, we stably engineered the dhurrin pathway from Sorghum bicolor into the chloroplasts of Nicotiana tabacum (tobacco). Dhurrin is a cyanogenic glucoside and its synthesis from the amino acid tyrosine is catalysed by two membrane-bound cytochrome P450 enzymes (CYP79A1 and CYP71E1) and a soluble glucosyltransferase (UGT85B1), and is dependent on electron transfer from a P450 oxidoreductase. The entire pathway was introduced into the chloroplast by integrating CYP79A1, CYP71E1, and UGT85B1 into a neutral site of the N. tabacum chloroplast genome. The two P450s and the UGT85B1 were functional when expressed in the chloroplasts and converted endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1–0.2% of leaf dry weight compared to 6% in sorghum. The results obtained pave the way for plant P450s involved in the synthesis of economically important compounds to be engineered into the thylakoid membrane of chloroplasts, and demonstrate that their full catalytic cycle can be driven directly by photosynthesis-derived electrons. PMID:26969746

  17. Transfer of the cytochrome P450-dependent dhurrin pathway from Sorghum bicolor into Nicotiana tabacum chloroplasts for light-driven synthesis.

    PubMed

    Gnanasekaran, Thiyagarajan; Karcher, Daniel; Nielsen, Agnieszka Zygadlo; Martens, Helle Juel; Ruf, Stephanie; Kroop, Xenia; Olsen, Carl Erik; Motawie, Mohammed Saddik; Pribil, Mathias; Møller, Birger Lindberg; Bock, Ralph; Jensen, Poul Erik

    2016-04-01

    Plant chloroplasts are light-driven cell factories that have great potential to act as a chassis for metabolic engineering applications. Using plant chloroplasts, we demonstrate how photosynthetic reducing power can drive a metabolic pathway to synthesise a bio-active natural product. For this purpose, we stably engineered the dhurrin pathway from Sorghum bicolor into the chloroplasts of Nicotiana tabacum (tobacco). Dhurrin is a cyanogenic glucoside and its synthesis from the amino acid tyrosine is catalysed by two membrane-bound cytochrome P450 enzymes (CYP79A1 and CYP71E1) and a soluble glucosyltransferase (UGT85B1), and is dependent on electron transfer from a P450 oxidoreductase. The entire pathway was introduced into the chloroplast by integrating CYP79A1, CYP71E1, and UGT85B1 into a neutral site of the N. tabacum chloroplast genome. The two P450s and the UGT85B1 were functional when expressed in the chloroplasts and converted endogenous tyrosine into dhurrin using electrons derived directly from the photosynthetic electron transport chain, without the need for the presence of an NADPH-dependent P450 oxidoreductase. The dhurrin produced in the engineered plants amounted to 0.1-0.2% of leaf dry weight compared to 6% in sorghum. The results obtained pave the way for plant P450s involved in the synthesis of economically important compounds to be engineered into the thylakoid membrane of chloroplasts, and demonstrate that their full catalytic cycle can be driven directly by photosynthesis-derived electrons. PMID:26969746

  18. Biosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme.

    PubMed

    Jørgensen, Kirsten; Morant, Anne Vinther; Morant, Marc; Jensen, Niels Bjerg; Olsen, Carl Erik; Kannangara, Rubini; Motawia, Mohammed Saddik; Møller, Birger Lindberg; Bak, Søren

    2011-01-01

    Cassava (Manihot esculenta) is a eudicotyledonous plant that produces the valine- and isoleucine-derived cyanogenic glucosides linamarin and lotaustralin with the corresponding oximes and cyanohydrins as key intermediates. CYP79 enzymes catalyzing amino acid-to-oxime conversion in cyanogenic glucoside biosynthesis are known from several plants including cassava. The enzyme system converting oxime into cyanohydrin has previously only been identified in the monocotyledonous plant great millet (Sorghum bicolor). Using this great millet CYP71E1 sequence as a query in a Basic Local Alignment Search Tool-p search, a putative functional homolog that exhibited an approximately 50% amino acid sequence identity was found in cassava. The corresponding full-length cDNA clone was obtained from a plasmid library prepared from cassava shoot tips and was assigned CYP71E7. Heterologous expression of CYP71E7 in yeast afforded microsomes converting 2-methylpropanal oxime (valine-derived oxime) and 2-methylbutanal oxime (isoleucine-derived oxime) to the corresponding cyanohydrins, which dissociate into acetone and 2-butanone, respectively, and hydrogen cyanide. The volatile ketones were detected as 2.4-dinitrophenylhydrazone derivatives by liquid chromatography-mass spectrometry. A K(S) of approximately 0.9 μm was determined for 2-methylbutanal oxime based on substrate-binding spectra. CYP71E7 exhibits low specificity for the side chain of the substrate and catalyzes the conversion of aliphatic and aromatic oximes with turnovers of approximately 21, 17, 8, and 1 min(-1) for the oximes derived from valine, isoleucine, tyrosine, and phenylalanine, respectively. A second paralog of CYP71E7 was identified by database searches and showed approximately 90% amino acid sequence identity. In tube in situ polymerase chain reaction showed that in nearly unfolded leaves, the CYP71E7 paralogs are preferentially expressed in specific cells in the endodermis and in most cells in the first cortex

  19. Biosynthesis of the Cyanogenic Glucosides Linamarin and Lotaustralin in Cassava: Isolation, Biochemical Characterization, and Expression Pattern of CYP71E7, the Oxime-Metabolizing Cytochrome P450 Enzyme1[OA

    PubMed Central

    Jørgensen, Kirsten; Morant, Anne Vinther; Morant, Marc; Jensen, Niels Bjerg; Olsen, Carl Erik; Kannangara, Rubini; Motawia, Mohammed Saddik; Møller, Birger Lindberg; Bak, Søren

    2011-01-01

    Cassava (Manihot esculenta) is a eudicotyledonous plant that produces the valine- and isoleucine-derived cyanogenic glucosides linamarin and lotaustralin with the corresponding oximes and cyanohydrins as key intermediates. CYP79 enzymes catalyzing amino acid-to-oxime conversion in cyanogenic glucoside biosynthesis are known from several plants including cassava. The enzyme system converting oxime into cyanohydrin has previously only been identified in the monocotyledonous plant great millet (Sorghum bicolor). Using this great millet CYP71E1 sequence as a query in a Basic Local Alignment Search Tool-p search, a putative functional homolog that exhibited an approximately 50% amino acid sequence identity was found in cassava. The corresponding full-length cDNA clone was obtained from a plasmid library prepared from cassava shoot tips and was assigned CYP71E7. Heterologous expression of CYP71E7 in yeast afforded microsomes converting 2-methylpropanal oxime (valine-derived oxime) and 2-methylbutanal oxime (isoleucine-derived oxime) to the corresponding cyanohydrins, which dissociate into acetone and 2-butanone, respectively, and hydrogen cyanide. The volatile ketones were detected as 2.4-dinitrophenylhydrazone derivatives by liquid chromatography-mass spectrometry. A KS of approximately 0.9 μm was determined for 2-methylbutanal oxime based on substrate-binding spectra. CYP71E7 exhibits low specificity for the side chain of the substrate and catalyzes the conversion of aliphatic and aromatic oximes with turnovers of approximately 21, 17, 8, and 1 min−1 for the oximes derived from valine, isoleucine, tyrosine, and phenylalanine, respectively. A second paralog of CYP71E7 was identified by database searches and showed approximately 90% amino acid sequence identity. In tube in situ polymerase chain reaction showed that in nearly unfolded leaves, the CYP71E7 paralogs are preferentially expressed in specific cells in the endodermis and in most cells in the first cortex cell

  20. Natural variation in synthesis and catabolism genes influences dhurrin content in sorghum (Sorghum bicolor L. Moench)

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Cyanogenic glucosides are natural compounds found in over 1,000 species of angiosperms that produce HCN and are deemed undesirable for agricultural use. However, these compounds are important components of primary defensive mechanisms of many plant species. One of the best-studied cyanogenic glucos...

  1. Cyanogen bromide

    Integrated Risk Information System (IRIS)

    Cyanogen bromide ; CASRN 506 - 68 - 3 Human health assessment information on a chemical substance is included in the IRIS database only after a comprehensive review of toxicity data , as outlined in the IRIS assessment development process . Sections I ( Health Hazard Assessments for Noncarcinogenic

  2. Functional characterization, homology modeling and docking studies of β-glucosidase responsible for bioactivation of cyanogenic hydroxynitrile glucosides from Leucaena leucocephala (subabul).

    PubMed

    Shaik, Noor M; Misra, Anurag; Singh, Somesh; Fatangare, Amol B; Ramakumar, Suryanarayanarao; Rawal, Shuban K; Khan, Bashir M

    2013-02-01

    Glycosyl hydrolase family 1 β-glucosidases are important enzymes that serve many diverse functions in plants including defense, whereby hydrolyzing the defensive compounds such as hydroxynitrile glucosides. A hydroxynitrile glucoside cleaving β-glucosidase gene (Llbglu1) was isolated from Leucaena leucocephala, cloned into pET-28a (+) and expressed in E. coli BL21 (DE3) cells. The recombinant enzyme was purified by Ni-NTA affinity chromatography. The optimal temperature and pH for this β-glucosidase were found to be 45 °C and 4.8, respectively. The purified Llbglu1 enzyme hydrolyzed the synthetic glycosides, pNPGlucoside (pNPGlc) and pNPGalactoside (pNPGal). Also, the enzyme hydrolyzed amygdalin, a hydroxynitrile glycoside and a few of the tested flavonoid and isoflavonoid glucosides. The kinetic parameters K (m) and V (max) were found to be 38.59 μM and 0.8237 μM/mg/min for pNPGlc, whereas for pNPGal the values were observed as 1845 μM and 0.1037 μM/mg/min. In the present study, a three dimensional (3D) model of the Llbglu1 was built by MODELLER software to find out the substrate binding sites and the quality of the model was examined using the program PROCHEK. Docking studies indicated that conserved active site residues are Glu 199, Glu 413, His 153, Asn 198, Val 270, Asn 340, and Trp 462. Docking of rhodiocyanoside A with the modeled Llbglu1 resulted in a binding with free energy change (ΔG) of -5.52 kcal/mol on which basis rhodiocyanoside A could be considered as a potential substrate. PMID:23079707

  3. Turnover of dhurrin in green sorghum seedlings. [Sorghum bicolor

    SciTech Connect

    Adewusi, S.R.A. )

    1990-11-01

    The turnover of dhurrin in green seedlings of Sorghum bicolor (Linn) Moench var Redland x Greenleaf, Sudan 70 has been investigated using glyphosate and pulse-labeling studies with {sup 14}C-tyrosine and ({sup 14}C)shikimic acid. The rate of dhurrin breakdown was 4.8 nanomoles per hour in the shoot and 1.4 nanomoles per hour in the root. The rate of dhurrin accumulation in the shoot of 4- to 5-day-old seedlings was high but decreased with age until at the peak period of dhurrin accumulation, the rates of dhurrin synthesis and breakdown were equal. Using a first order equation (an approximation) the rate of dhurrin synthesis (which equals accumulation plus breakdown rates) was 17.4 nanomoles per hour in the shoot and 4.1 nanomoles per hour in the root. In both tissues, the breakdown rate was between 27 and 34% of their synthetic capacity within the experimental period. Dhurrin synthesis in green sorghum seedlings occurred in both the light and dark photoperiods but was faster in the dark period. The result is discussed in relation to the possible metabolic roles of the turnover.

  4. Convergent evolution in biosynthesis of cyanogenic defence compounds in plants and insects.

    PubMed

    Jensen, Niels Bjerg; Zagrobelny, Mika; Hjernø, Karin; Olsen, Carl Erik; Houghton-Larsen, Jens; Borch, Jonas; Møller, Birger Lindberg; Bak, Søren

    2011-01-01

    For more than 420 million years, plants, insects and their predators have co-evolved based on a chemical arms race including deployment of refined chemical defence systems by each player. Cyanogenic glucosides are produced by numerous plants and by some specialized insects and serve an important role as defence compounds in these intimate interactions. Burnet moth larvae are able to sequester cyanogenic glucosides from their food plant as well as to carry out de novo biosynthesis. Here we show that three genes (CYP405A2, CYP332A3 and UGT33A1) encode the entire biosynthetic pathway of cyanogenic glucosides in the Burnet moth Zygaena filipendulae. In both plants and insects, convergent evolution has led to two multifunctional P450 enzymes each catalysing unusual reactions and a glucosyl-transferase acting in sequence to catalyse cyanogenic glucoside formation. Thus, plants and insects have independently found a way to package a cyanide time bomb to fend off herbivores and predators. PMID:21505429

  5. In silico ligand binding studies of cyanogenic β-glucosidase, dhurrinase-2 from Sorghum bicolor.

    PubMed

    Mahajan, Chavi; Patel, Krunal; Khan, Bashir M; Rawal, Shuban S

    2015-07-01

    Dhurrinase, a cyanogenic β-glucosidase from Sorghum bicolor is the key enzyme responsible for the hydrolysis of dhurrin to produce toxic hydrogen cyanide, as a part of plant defence mechanism. Dhurrinase 1 (SbDhr1) and dhurrinase 2 (SbDhr2), two isozymes have been isolated and characterized from S. bicolor. However, there is no information in the literature about the three dimensional (3D) structure of SbDhr2 and molecular interactions involved between the protein and ligand. In this study, the three dimensional structure of SbDhr2 was built based on homology modeling by using the X-ray crystallographic structure of its close homologue SbDhr1 as the template. The generated 3D model was energy minimized and the quality was validated by Ramachndran plot, various bioinformatic tools and their relevant parameters. Stability, folding-unfolding and flexibility of the modeled SbDhr2 was evaluated on the basis of RMSD, radius of gyration (Rg) and RMSF values respectively, obtained through molecular dynamic (MD) simulation. Further, molecular docking was performed with its natural substrate dhurrin, one substrate analogue, three un-natural substrates, and one inhibitor. Analysis of molecular interactions in the SbDhr2-ligand complexes revealed the key amino acid residues responsible to stabilize the ligands within the binding pocket through non-bonded interactions and some of them were found to be conserved (Glu239, Tyr381, Trp426, Glu454, Trp511). Reasonably broader substrate specificity of SbDhr2 was explained through the wider entrance passage observed in comparison to SbDhr1.

  6. Lotus japonicus flowers are defended by a cyanogenic β-glucosidase with highly restricted expression to essential reproductive organs.

    PubMed

    Lai, Daniela; Pičmanová, Martina; Abou Hachem, Maher; Motawia, Mohammed Saddik; Olsen, Carl Erik; Møller, Birger Lindberg; Rook, Fred; Takos, Adam M

    2015-09-01

    Flowers and leaves of Lotus japonicus contain α-, β-, and γ-hydroxynitrile glucoside (HNG) defense compounds, which are bioactivated by β-glucosidase enzymes (BGDs). The α-HNGs are referred to as cyanogenic glucosides because their hydrolysis upon tissue disruption leads to release of toxic hydrogen cyanide gas, which can deter herbivore feeding. BGD2 and BGD4 are HNG metabolizing BGD enzymes expressed in leaves. Only BGD2 is able to hydrolyse the α-HNGs. Loss of function mutants of BGD2 are acyanogenic in leaves but fully retain cyanogenesis in flowers pointing to the existence of an alternative cyanogenic BGD in flowers. This enzyme, named BGD3, is identified and characterized in this study. Whereas all floral tissues contain α-HNGs, only those tissues in which BGD3 is expressed, the keel and the enclosed reproductive organs, are cyanogenic. Biochemical analysis, active site architecture molecular modelling, and the observation that L. japonicus accessions lacking cyanogenic flowers contain a non-functional BGD3 gene, all support the key role of BGD3 in floral cyanogenesis. The nectar of L. japonicus flowers was also found to contain HNGs and additionally their diglycosides. The observed specialisation in HNG based defence in L. japonicus flowers is discussed in the context of balancing the attraction of pollinators with the protection of reproductive structures against herbivores.

  7. Dhurrin content relates to sorghum (Sorghum bicolor (L) Moench) seedling growth in marginal soils.

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Dhurrin content in leaves of mature sorghum plant is a quantitative measure of the level of pre-and postflowering drought tolerance (Burke et al., 2013). Postflowering drought tolerance in sorghum is linked to the staygreen (delayed senescence) trait (Howarth, 2000; Rosenow et al., 1977) which has b...

  8. Dhurrin content relates to sorghum [sorghum bicolor (L.) Moench] seedling growth in marginal soils

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Dhurrin content in leaves of mature sorghum plant is a quantitative measure of the level of pre-and postflowering drought tolerance (Burke et al., 2013). Postflowering drought tolerance in sorghum is linked to the staygreen (delayed senescence) trait (Howarth, 2000; Rosenow et al., 1977) which has ...

  9. Analysis of cyanogens with resorcinol and picrate.

    PubMed

    Drochioiu, Gabi; Arsene, Cecilia; Murariu, Manuela; Oniscu, Corneliu

    2008-11-01

    The total cyanogenic potential of various substrates (flax seed, stones of peach, plum, nectarine and apricot as well as apple seeds, and various model compounds) was investigated by using the acid hydrolysis method, picrate method, and a novel method based on the reaction of cyanide liberated from plants with resorcinol and picrate. The hydrocyanic acid liberated from cyanogens was trapped by using a 1% sodium bicarbonate. Then, 1 ml of extract was mixed with 1 ml of working reagent containing 160 microg of resorcinol, 320 microg of picric acid, and 30 mg of sodium carbonate, and heated on a boiling water bath for 10 min. The absorbance was measured at 488 nm in 1cm glass cuvettes at room temperature. The color system obeys Beer's law in the range of 0-5 microg ml(-1) total HCN. Using model compounds and real samples including replicate analyses on prunasin, the resorcinol method proved to be more accurate, reproducible, and especially more sensitive than the known spectrophotometric methods such as the acid hydrolysis method and the picrate method. PMID:18824068

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

    PubMed

    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-(14)C]-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.

  11. 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

  12. The adsorption and oxidation of cyanogen on copper surfaces

    NASA Astrophysics Data System (ADS)

    Carley, A. F.; Chinn, M.; Parkinson, C. R.

    2003-07-01

    The adsorption of cyanogen on clean and oxygen pre-treated graphite supported copper films, and a polycrystalline copper surface, and the co-adsorption of cyanogen and oxygen on graphite supported copper films, and a polycrystalline copper surface has been studied using X-ray photoelectron spectroscopy. Cyanogen dissociates on the copper surfaces at 300 K, yielding an adsorbed cyano group, CN (a). On the oxygen pre-treated copper surface cyanogen reacts quantitatively with the adsorbed oxygen at 300 K to form a surface cyanate species, NCO. On annealing to 600 K this species decomposes, leaving only N adatoms and residual adsorbed CN on the surface. The co-adsorption of cyanogen and oxygen from a cyanogen-oxygen mixture enhances the formation of NCO to the extent that all available surface oxygen is consumed to form NCO on annealing at 450 K. In the absence of available atomic surface oxygen NCO does not decompose at temperatures up to 600 K. NCO and NCO 2 are shown to be the intermediates in the oxidation of cyanogen on copper films and a polycrystalline copper foil.

  13. Toxicity of cyanogen to insects of stored grain.

    PubMed

    Hooper, Jacqueline L; Desmarchelier, James M; Ren, Yonglin; Allen, Sylvia E

    2003-03-01

    Range-finding studies on the toxicity of cyanogen to all stages of five species of stored product Coleoptera are reported. The species were Rhyzopertha dominica (F), Sitophilus granarius (L), Sitophilus Oryzae (L), Tribolium castaneum (Herbst), Tribolium confusum Jacquelin du Val and Ephestia cautella (Walker). Exposures for 24 h to cyanogen at 1.3 mg litre(-1) controlled all external stages. Control of internal stages of Sitophilus species was achieved by a 5-day exposure to initial concentrations between 13.7 and 27.4 mg litre(-1), whereas R. dominica was controlled at 13.7 mg litre(-1). Cyanogen showed similar toxicity to all tested external stages and, in this respect, was more similar to methyl bromide than to phosphine. Its toxicity to insects increased with both relative humidity and concentration of carbon dioxide. Cyanogen was toxic to insects whether applied as a gas or in an aqueous solution.

  14. Formation of cyanogen iodide by lactoperoxidase.

    PubMed

    Schlorke, Denise; Flemmig, Jörg; Birkemeyer, Claudia; Arnhold, Jürgen

    2016-01-01

    The haem protein lactoperoxidase (LPO) is an important component of the anti-microbial immune defence in external secretions and is also applied as preservative in food, oral care and cosmetic products. Upon oxidation of SCN(-) and I(-) by the LPO-hydrogen peroxide system, oxidised species are formed with bacteriostatic and/or bactericidal activity. Here we describe the formation of the inter(pseudo)halogen cyanogen iodide (ICN) by LPO. This product is formed when both, thiocyanate and iodide, are present together in the reaction mixture. Using (13)C nuclear magnetic resonance spectroscopy and gas chromatography-mass spectrometry we could identify this inter(pseudo)halogen after applying iodide in slight excess over thiocyanate. The formation of ICN is based on the reaction of oxidised iodine species with thiocyanate. Further, we could demonstrate that ICN is also formed by the related haem enzyme myeloperoxidase and, in lower amounts, in the enzyme-free system. As I(-) is not competitive for SCN(-) under physiologically relevant conditions, the formation of ICN is not expected in secretions but may be relevant for LPO-containing products. PMID:26580225

  15. Formation of cyanogen iodide by lactoperoxidase.

    PubMed

    Schlorke, Denise; Flemmig, Jörg; Birkemeyer, Claudia; Arnhold, Jürgen

    2016-01-01

    The haem protein lactoperoxidase (LPO) is an important component of the anti-microbial immune defence in external secretions and is also applied as preservative in food, oral care and cosmetic products. Upon oxidation of SCN(-) and I(-) by the LPO-hydrogen peroxide system, oxidised species are formed with bacteriostatic and/or bactericidal activity. Here we describe the formation of the inter(pseudo)halogen cyanogen iodide (ICN) by LPO. This product is formed when both, thiocyanate and iodide, are present together in the reaction mixture. Using (13)C nuclear magnetic resonance spectroscopy and gas chromatography-mass spectrometry we could identify this inter(pseudo)halogen after applying iodide in slight excess over thiocyanate. The formation of ICN is based on the reaction of oxidised iodine species with thiocyanate. Further, we could demonstrate that ICN is also formed by the related haem enzyme myeloperoxidase and, in lower amounts, in the enzyme-free system. As I(-) is not competitive for SCN(-) under physiologically relevant conditions, the formation of ICN is not expected in secretions but may be relevant for LPO-containing products.

  16. Cyanogen induced phosphorylation of D-fructose. [prebiotic modeling

    NASA Technical Reports Server (NTRS)

    Degani, CH.; Kawatsuji, M.; Halmann, M.

    1975-01-01

    It has been demonstrated that a phosphorylated sugar, identified as alpha-D-fructopyranose, can be formed as the result of cyanogen-induced phosphorylation of D-fructose at pH 8.8. The product was isolated from barium and cyclohexylammonium salts and identified on the basis of its chromatographic and electrophoretic properties, its lability to hydrolysis by alkaline phosphatase, the rate of its acid-catalyzed hydrolysis, and the results of periodate oxidation and optical rotatory measurements. These results support the suggestion that the cyanogen-induced phosphorylation of free sugars could be a possible process for formation of sugar phosphates under prebiotic conditions (Halman et al., 1969).

  17. Engineering cyanogen synthesis and turnover in cassava (Manihot esculenta).

    PubMed

    Siritunga, Dimuth; Sayre, Richard

    2004-11-01

    Cassava is the major root crop for a quarter billion subsistence farmers in sub-Saharan Africa. It is valued for its ability to grow in adverse environments and the food security it provides. Cassava contains potentially toxic levels of cyanogenic glycosides (linamarin) which protect the plant from herbivory and theft. The cyanogens, including linamarin and its deglycosylated product, acetone cyanohydrin, can be efficiently removed from the root by various processing procedures. Short-cuts in processing, which may occur during famines, can result in only partial removal of cyanogens. Residual cyanogens in cassava foods may cause neurological disorders or paralysis, particularly in nutritionally compromised individuals. To address this problem and to further understand the function of cyanogenic glycosides in cassava, we have generated transgenic cassava in which cyanogenic glycoside synthesis has been selectively inhibited in leaves and roots by antisense expression of CYP79D1/D2 gene fragments. The CYP79D1/D2 genes encode two highly similar cytochrome P450s that catalyze the first-dedicated step in cyanogenic glycoside synthesis. Transgenic plants in which the expression of these genes was selectively inhibited in leaves had substantially reduced (60- 94% reduction) linamarin leaf levels. Surprisingly, these plants also had a greater than a 99% reduction in root linamarin content. In contrast, transgenic plants in which the CYP79D1/D2 transcripts were reduced to non-detectable levels in roots had normal root linamarin levels. These results demonstrate that linamarin synthesized in leaves is transported to the roots and accounts for nearly all of the root linamarin content. Importantly, transgenic plants having reduced leaf and root linamarin content were unable to grow in the absence of reduced nitrogen (NH3) . Cassava roots have previously been demonstrated to have an active cyanide assimilation pathway leading to the synthesis of amino acids. We propose that

  18. Sorghum recombinant inbred lines segregating for stay-green QTL's and leaf dhurrin content show differential reaction to stalk rot diseases

    Technology Transfer Automated Retrieval System (TEKTRAN)

    The association between post-flowering drought tolerance and the stay-green phenotype in sorghum is well established. More recent studies link the stay-green phenotype with levels of dhurrin and soluble sugars in the leaves. Post-flowering drought response has always been associated with stalk rot r...

  19. Forward Genetics by Genome Sequencing Reveals That Rapid Cyanide Release Deters Insect Herbivory of Sorghum bicolor

    PubMed Central

    Krothapalli, Kartikeya; Buescher, Elizabeth M.; Li, Xu; Brown, Elliot; Chapple, Clint; Dilkes, Brian P.; Tuinstra, Mitchell R.

    2013-01-01

    Whole genome sequencing has allowed rapid progress in the application of forward genetics in model species. In this study, we demonstrated an application of next-generation sequencing for forward genetics in a complex crop genome. We sequenced an ethyl methanesulfonate-induced mutant of Sorghum bicolor defective in hydrogen cyanide release and identified the causal mutation. A workflow identified the causal polymorphism relative to the reference BTx623 genome by integrating data from single nucleotide polymorphism identification, prior information about candidate gene(s) implicated in cyanogenesis, mutation spectra, and polymorphisms likely to affect phenotypic changes. A point mutation resulting in a premature stop codon in the coding sequence of dhurrinase2, which encodes a protein involved in the dhurrin catabolic pathway, was responsible for the acyanogenic phenotype. Cyanogenic glucosides are not cyanogenic compounds but their cyanohydrins derivatives do release cyanide. The mutant accumulated the glucoside, dhurrin, but failed to efficiently release cyanide upon tissue disruption. Thus, we tested the effects of cyanide release on insect herbivory in a genetic background in which accumulation of cyanogenic glucoside is unchanged. Insect preference choice experiments and herbivory measurements demonstrate a deterrent effect of cyanide release capacity, even in the presence of wild-type levels of cyanogenic glucoside accumulation. Our gene cloning method substantiates the value of (1) a sequenced genome, (2) a strongly penetrant and easily measurable phenotype, and (3) a workflow to pinpoint a causal mutation in crop genomes and accelerate in the discovery of gene function in the postgenomic era. PMID:23893483

  20. Determination of cyanogenic compounds in edible plants by ion chromatography.

    PubMed

    Cho, Hye-Jeon; Do, Byung-Kyung; Shim, Soon-Mi; Kwon, Hoonjeong; Lee, Dong-Ha; Nah, Ahn-Hee; Choi, Youn-Ju; Lee, Sook-Yeon

    2013-06-01

    Cyanogenic glycosides are HCN-producing phytotoxins; HCN is a powerful and a rapidly acting poison. It is not difficult to find plants containing these compounds in the food supply and/or in medicinal herb collections. The objective of this study was to investigate the distribution of total cyanide in nine genera (Dolichos, Ginkgo, Hordeum, Linum, Phaseolus, Prunus, Phyllostachys, Phytolacca, and Portulaca) of edible plants and the effect of the processing on cyanide concentration. Total cyanide content was measured by ion chromatography following acid hydrolysis and distillation. Kernels of Prunus genus are used medicinally, but they possess the highest level of total cyanide of up to 2259.81 CN(-)/g dry weight. Trace amounts of cyanogenic compounds were detected in foodstuffs such as mungbeans and bamboo shoots. Currently, except for the WHO guideline for cassava, there is no global standard for the allowed amount of cyanogenic compounds in foodstuffs. However, our data emphasize the need for the guidelines if plants containing cyanogenic glycosidesare to be developed as dietary supplements.

  1. Determination of Cyanogenic Compounds in Edible Plants by Ion Chromatography

    PubMed Central

    Cho, Hye-Jeon; Do, Byung-Kyung; Shim, Soon-Mi; Lee, Dong-Ha; Nah, Ahn-Hee; Choi, Youn-Ju; Lee, Sook-Yeon

    2013-01-01

    Cyanogenic glycosides are HCN-producing phytotoxins; HCN is a powerful and a rapidly acting poison. It is not difficult to find plants containing these compounds in the food supply and/or in medicinal herb collections. The objective of this study was to investigate the distribution of total cyanide in nine genera (Dolichos, Ginkgo, Hordeum, Linum, Phaseolus, Prunus, Phyllostachys, Phytolacca, and Portulaca) of edible plants and the effect of the processing on cyanide concentration. Total cyanide content was measured by ion chromatography following acid hydrolysis and distillation. Kernels of Prunus genus are used medicinally, but they possess the highest level of total cyanide of up to 2259.81 CN−/g dry weight. Trace amounts of cyanogenic compounds were detected in foodstuffs such as mungbeans and bamboo shoots. Currently, except for the WHO guideline for cassava, there is no global standard for the allowed amount of cyanogenic compounds in foodstuffs. However, our data emphasize the need for the guidelines if plants containing cyanogenic glycosidesare to be developed as dietary supplements. PMID:24278641

  2. Acute toxicity of cyanogen chloride to Daphnia magna

    SciTech Connect

    Kononen, D.W.

    1988-09-01

    The destruction of cyanide in waste waters by chlorination has been shown to result in the formation of the extremely toxic compound, cyanogen chloride. Industrial cyanide-containing waste waters may be treated by a batch chlorination process under highly alkaline conditions prior to being discharged into a receiving water systems. Alternatively, if the concentration of cyanide is relatively low, and such waste waters may be diverted to municipal waste treatment facilities where they may be subjected to a process of chlorination which may not be sufficient for the complete oxidative destruction of the available cyanide. Although a large body of literature exists concerning the toxicity of HCN and metallic cyanide compounds to aquatic organisms, there is a comparative scarcity of information concerning cyanogen chloride toxicity. This study was designed to determine the acute toxicity of CNCl to Daphnia magna neonates under static bioassay conditions.

  3. Overexpression of hydroxynitrile lyase in cassava roots elevates protein and free amino acids while reducing residual cyanogen levels.

    PubMed

    Narayanan, Narayanan N; Ihemere, Uzoma; Ellery, Claire; Sayre, Richard T

    2011-01-01

    Cassava is the major source of calories for more than 250 million Sub-Saharan Africans, however, it has the lowest protein-to-energy ratio of any major staple food crop in the world. A cassava-based diet provides less than 30% of the minimum daily requirement for protein. Moreover, both leaves and roots contain potentially toxic levels of cyanogenic glucosides. The major cyanogen in cassava is linamarin which is stored in the vacuole. Upon tissue disruption linamarin is deglycosylated by the apolplastic enzyme, linamarase, producing acetone cyanohydrin. Acetone cyanohydrin can spontaneously decompose at pHs >5.0 or temperatures >35°C, or is enzymatically broken down by hydroxynitrile lyase (HNL) to produce acetone and free cyanide which is then volatilized. Unlike leaves, cassava roots have little HNL activity. The lack of HNL activity in roots is associated with the accumulation of potentially toxic levels of acetone cyanohydrin in poorly processed roots. We hypothesized that the over-expression of HNL in cassava roots under the control of a root-specific, patatin promoter would not only accelerate cyanogenesis during food processing, resulting in a safer food product, but lead to increased root protein levels since HNL is sequestered in the cell wall. Transgenic lines expressing a patatin-driven HNL gene construct exhibited a 2-20 fold increase in relative HNL mRNA levels in roots when compared with wild type resulting in a threefold increase in total root protein in 7 month old plants. After food processing, HNL overexpressing lines had substantially reduced acetone cyanohydrin and cyanide levels in roots relative to wild-type roots. Furthermore, steady state linamarin levels in intact tissues were reduced by 80% in transgenic cassava roots. These results suggest that enhanced linamarin metabolism contributed to the elevated root protein levels.

  4. Coevolution of Cyanogenic Bamboos and Bamboo Lemurs on Madagascar.

    PubMed

    Ballhorn, Daniel J; Rakotoarivelo, Fanny Patrika; Kautz, Stefanie

    2016-01-01

    Feeding strategies of specialist herbivores often originate from the coevolutionary arms race of plant defenses and counter-adaptations of herbivores. The interaction between bamboo lemurs and cyanogenic bamboos on Madagascar represents a unique system to study diffuse coevolutionary processes between mammalian herbivores and plant defenses. Bamboo lemurs have different degrees of dietary specialization while bamboos show different levels of chemical defense. In this study, we found variation in cyanogenic potential (HCNp) and nutritive characteristics among five sympatric bamboo species in the Ranomafana area, southeastern Madagascar. The HCNp ranged from 209±72 μmol cyanide*g-1 dwt in Cathariostachys madagascariensis to no cyanide in Bambusa madagascariensis. Among three sympatric bamboo lemur species, the greater bamboo lemur (Prolemur simus) has the narrowest food range as it almost exclusively feeds on the highly cyanogenic C. madagascariensis. Our data suggest that high HCNp is the derived state in bamboos. The ancestral state of lemurs is most likely "generalist" while the ancestral state of bamboo lemurs was determined as equivocal. Nevertheless, as recent bamboo lemurs comprise several "facultative specialists" and only one "obligate specialist" adaptive radiation due to increased flexibility is likely. We propose that escaping a strict food plant specialization enabled facultative specialist bamboo lemurs to inhabit diverse geographical areas. PMID:27532127

  5. Coevolution of Cyanogenic Bamboos and Bamboo Lemurs on Madagascar

    PubMed Central

    Ballhorn, Daniel J.; Rakotoarivelo, Fanny Patrika; Kautz, Stefanie

    2016-01-01

    Feeding strategies of specialist herbivores often originate from the coevolutionary arms race of plant defenses and counter-adaptations of herbivores. The interaction between bamboo lemurs and cyanogenic bamboos on Madagascar represents a unique system to study diffuse coevolutionary processes between mammalian herbivores and plant defenses. Bamboo lemurs have different degrees of dietary specialization while bamboos show different levels of chemical defense. In this study, we found variation in cyanogenic potential (HCNp) and nutritive characteristics among five sympatric bamboo species in the Ranomafana area, southeastern Madagascar. The HCNp ranged from 209±72 μmol cyanide*g-1 dwt in Cathariostachys madagascariensis to no cyanide in Bambusa madagascariensis. Among three sympatric bamboo lemur species, the greater bamboo lemur (Prolemur simus) has the narrowest food range as it almost exclusively feeds on the highly cyanogenic C. madagascariensis. Our data suggest that high HCNp is the derived state in bamboos. The ancestral state of lemurs is most likely "generalist" while the ancestral state of bamboo lemurs was determined as equivocal. Nevertheless, as recent bamboo lemurs comprise several "facultative specialists" and only one "obligate specialist" adaptive radiation due to increased flexibility is likely. We propose that escaping a strict food plant specialization enabled facultative specialist bamboo lemurs to inhabit diverse geographical areas. PMID:27532127

  6. Geospatial association of endemicity of ataxic polyneuropathy and highly cyanogenic cassava cultivars

    PubMed Central

    2013-01-01

    Background Exposure to cyanide from cassava foods is present in communities where ataxic polyneuropathy is endemic. Ataxic polyneuropathy is endemic in coastal parts of southwest and southeast Nigeria, and coastal Newala, south India, but it has been reported in epidemic or endemic forms from Africa, Asia, or Caribbean. This study was done to determine if cyanogenicity of cassava cultivars is higher in lowland than highland areas, and if areas of endemicity of ataxic polyneuropathy colocalize with areas of highest cyanogenicity of cassava. Methods Roots of cassava cultivars were collected from 150 farmers in 32 of 37 administrative areas in Nigeria. Global positioning system was used to determine the location of the roots. Roots were assayed for concentrations of cyanogens. Thin Plate Spline regression was used to produce the contour map of cyanogenicity of the study area. Contour maps of altitude of the endemic areas were produced. Relationship of cyanogenicity of cassava cultivars and altitude, and of locations of areas of high cyanogenicity and areas of endemicity were determined. Results Geometrical mean (95% CI) cyanogen concentration was 182 (142–233) mg HCN eq/kg dry wt for cassava cultivars in areas ≤ 25 m above sea level, but 54 (43–66) mg HCN eq/kg dry wt for areas > 375 m. Non-spatial linear regression of altitude on logarithm transformed concentrations of cyanogens showed highly significant association, (p < 0.0001). Contour map of concentrations of cyanogens in cassava cultivars in Nigeria showed four areas with average concentrations of cassava cyanogens > 250 mg HCN eq/kg dry wt, and one area of moderately high cyanogen concentration > 150 mg HCN eq/kg dry wt. The endemic areas colocalized with areas of highest cassava cyanogenicity in lowland areas close to the Atlantic Ocean. Conclusion This study shows strong geospatial association of areas of endemicity of ataxic polyneuropathy and areas of highest cyanogenicity of

  7. Enzymatic Synthesis of Novel Phloretin Glucosides

    PubMed Central

    Pandey, Ramesh Prasad; Li, Tai Feng; Kim, Eun-Hee; Yamaguchi, Tokutaro; Park, Yong Il; Kim, Joong Su

    2013-01-01

    A UDP-glycosyltransferase from Bacillus licheniformis was exploited for the glycosylation of phloretin. The in vitro glycosylation reaction confirmed the production of five phloretin glucosides, including three novel glucosides. Consequently, we demonstrated the application of the same glycosyltransferase for the efficient whole-cell biocatalysis of phloretin in engineered Escherichia coli. PMID:23542617

  8. Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur.

    PubMed

    Senica, Mateja; Stampar, Franci; Veberic, Robert; Mikulic-Petkovsek, Maja

    2016-07-15

    Popular liqueurs made from apricot/cherry pits were evaluated in terms of their phenolic composition and occurrence of cyanogenic glycosides (CGG). Analyses consisted of detailed phenolic and cyanogenic profiles of cherry and apricot seeds as well as beverages prepared from crushed kernels. Phenolic groups and cyanogenic glycosides were analyzed with the aid of high-performance liquid chromatography (HPLC) and mass spectrophotometry (MS). Lower levels of cyanogenic glycosides and phenolics have been quantified in liqueurs compared to fruit kernels. During fruit pits steeping in the alcohol, the phenolics/cyanogenic glycosides ratio increased and at the end of beverage manufacturing process higher levels of total analyzed phenolics were detected compared to cyanogenic glycosides (apricot liqueur: 38.79 μg CGG per ml and 50.57 μg phenolics per ml; cherry liqueur 16.08 μg CGG per ml and 27.73 μg phenolics per ml). Although higher levels of phenolics are characteristic for liqueurs made from apricot and cherry pits these beverages nevertheless contain considerable amounts of cyanogenic glycosides.

  9. Transition of phenolics and cyanogenic glycosides from apricot and cherry fruit kernels into liqueur.

    PubMed

    Senica, Mateja; Stampar, Franci; Veberic, Robert; Mikulic-Petkovsek, Maja

    2016-07-15

    Popular liqueurs made from apricot/cherry pits were evaluated in terms of their phenolic composition and occurrence of cyanogenic glycosides (CGG). Analyses consisted of detailed phenolic and cyanogenic profiles of cherry and apricot seeds as well as beverages prepared from crushed kernels. Phenolic groups and cyanogenic glycosides were analyzed with the aid of high-performance liquid chromatography (HPLC) and mass spectrophotometry (MS). Lower levels of cyanogenic glycosides and phenolics have been quantified in liqueurs compared to fruit kernels. During fruit pits steeping in the alcohol, the phenolics/cyanogenic glycosides ratio increased and at the end of beverage manufacturing process higher levels of total analyzed phenolics were detected compared to cyanogenic glycosides (apricot liqueur: 38.79 μg CGG per ml and 50.57 μg phenolics per ml; cherry liqueur 16.08 μg CGG per ml and 27.73 μg phenolics per ml). Although higher levels of phenolics are characteristic for liqueurs made from apricot and cherry pits these beverages nevertheless contain considerable amounts of cyanogenic glycosides. PMID:26948641

  10. Chemisorption of cyanogen chloride by spinel ferrite magnetic nanoparticles.

    PubMed

    Glover, T Grant; DeCoste, Jared B; Sabo, Daniel; Zhang, Z John

    2013-05-01

    Spinel ferrite magnetic nanoparticles, MnFe2O4, NiFe2O4, and CoFe2O4, were synthesized and used as gas-phase adsorbents for the removal of cyanogen chloride from dry air. Fixed-bed adsorption breakthrough experiments show adsorption wave behavior at the leading edge of the breakthrough curve that is not typical of physically adsorbed species. Fourier transform infrared spectroscopy (FTIR) results indicate that CK is reacting with the spinel ferrite surface and forming a carbamate species. The reaction is shown to be a function of the hydroxyl groups and adsorbed water on the surface of the particles as well as the metallic composition of the particles. The surface reaction decreases the remnant and saturation magnetism of the MnFe2O4 and CoFe2O4 particles by approximately 25%.

  11. Synthesis and Characterization of Hapten-Protein Conjugates for Antibody Production against Cyanogenic Glycosides.

    PubMed

    Bolarinwa, Islamiyat Folashade

    2015-07-01

    Consumption of cyanogenic plants can cause serious health problems for humans. The ability to detect and quantify cyanogenic glycosides, capable of generating cyanide, could contribute to prevention of cyanide poisoning from the consumption of improperly processed cyanogenic plants. Hapten-protein conjugates were synthesized with amygdalin and linamarin by using a novel approach. Polyclonal antibodies were generated by immunizing four New Zealand White rabbits with synthesized amygdalin-bovine serum albumin and linamarin-bovine serum albumin immunogen. This is the first time an antibody was produced against linamarin. Antibody titer curves were obtained from all the four rabbits by using a noncompetitive enzyme-linked immunosorbent assay. High antibody titer was obtained at dilutions greater than 1:50,000 from both immunogens. This new method is an important step forward in preventing ingestion of toxic cyanogenic glycosides. PMID:26197297

  12. Positive effects of cyanogenic glycosides in food plants on larval development of the common blue butterfly.

    PubMed

    Goverde, Marcel; Bazin, Alain; Kéry, Marc; Shykoff, Jacqui A; Erhardt, Andreas

    2008-09-01

    Cyanogenesis is a widespread chemical defence mechanism in plants against herbivory. However, some specialised herbivores overcome this protection by different behavioural or metabolic mechanisms. In the present study, we investigated the effect of presence or absence of cyanogenic glycosides in birdsfoot trefoil (Lotus corniculatus, Fabaceae) on oviposition behaviour, larval preference, larval development, adult weight and nectar preference of the common blue butterfly (Polyommatus icarus, Lycaenidae). For oviposition behaviour there was a female-specific reaction to cyanogenic glycoside content; i.e. some females preferred to oviposit on cyanogenic over acyanogenic plants, while other females behaved in the opposite way. Freshly hatched larvae did not discriminate between the two plant morphs. Since the two plant morphs differed not only in their content of cyanogenic glycoside, but also in N and water content, we expected these differences to affect larval growth. Contrary to our expectations, larvae feeding on cyanogenic plants showed a faster development and stronger weight gain than larvae feeding on acyanogenic plants. Furthermore, female genotype affected development time, larval and pupal weight of the common blue butterfly. However, most effects detected in the larval phase disappeared for adult weight, indicating compensatory feeding of larvae. Adult butterflies reared on the two cyanogenic glycoside plant morphs did not differ in their nectar preference. But a gender-specific effect was found, where females preferred amino acid-rich nectar while males did not discriminate between the two nectar mimics. The presented results indicate that larvae of the common blue butterfly can metabolise the surplus of N in cyanogenic plants for growth. Additionally, the female-specific behaviour to oviposit preferably on cyanogenic or acyanogenic plant morphs and the female-genotype-specific responses in life history traits indicate the genetic flexibility of this

  13. Identification of essential active-site residues in the cyanogenic beta-glucosidase (linamarase) from cassava (Manihot esculenta Crantz) by site-directed mutagenesis.

    PubMed Central

    Keresztessy, Z; Brown, K; Dunn, M A; Hughes, M A

    2001-01-01

    The coding sequence of the mature cyanogenic beta-glucosidase (beta-glucoside glucohydrolase, EC 3.2.1.21; linamarase) was cloned into the vector pYX243 modified to contain the SUC2 yeast secretion signal sequence and expressed in Saccharomyces cerevisiae. The recombinant enzyme is active, glycosylated and showed similar stability to the plant protein. Michaelis constants for hydrolysis of the natural substrate, linamarin (K(m)=1.06 mM) and the synthetic p-nitrophenyl beta-D-glucopyranoside (PNP-Glc; K(m)=0.36 mM), as well as apparent pK(a) values of the free enzyme and the enzyme-substrate complexes (pK(E)(1)=4.4-4.8, pK(E)(2)=6.7-7.2, pK(ES)(1)=3.9-4.4, pK(ES)(2)=8.3) were very similar to those of the plant enzyme. Site-directed mutagenesis was carried out to study the function of active-site residues based on a homology model generated for the enzyme using the MODELLER program. Changing Glu-413 to Gly destroyed enzyme activity, consistent with it being the catalytic nucleophile. The Gln-339Glu mutation also abolished activity, confirming a function in positioning the catalytic diad. The Ala-201Val mutation shifted the pK(a) of the acid/base catalyst Glu-198 from 7.22 to 7.44, reflecting a change in its hydrophobic environment. A Phe-269Asn change increased K(m) for linamarin hydrolysis 16-fold (16.1 mM) and that for PNP-Glc only 2.5-fold (0.84 mM), demonstrating that Phe-269 contributes to the cyanogenic specificity of the cassava beta-glucosidase. PMID:11139381

  14. Development of QSARs for predicting the joint effects between cyanogenic toxicants and aldehydes.

    PubMed

    Lin, Zhifen; Yin, Kedong; Shi, Ping; Wang, Liansheng; Yu, Hongxia

    2003-10-01

    Quantitative structure-activity relationship (QSAR) approaches are proposed in this study to predict the joint effects of mixture toxicity. The initial investigation studies the joint effects between cyanogenic toxicants and aldehydes to Photobacterium phosphoreum. Joint effects are found to result from the formation of a carbanion intermediate produced through the chemical interactions between cyanogenic toxicants and aldehydes. Further research indicates that the formation of carbanion intermediate is highly correlated with not only the charge of the carbon atom in the -CHO of aldehydes but also the charge of the carbon atom (C) in the carbochain of cyanogenic toxicants. The charge of the carbon atom in the -CHO of aldehydes is quantified by using the Hammett constant (sigma(p)), and then, sigma(p)-based QSAR models are proposed to describe the relationships between the joint effects and the chemical structures of the aldehydes. By using the charge of carbon atom (C) in the carbochain of cyanogenic toxicants, another QSAR model is proposed to describe the relationship between the joint effects and the chemical structures of cyanogenic toxicants.

  15. Mild method for removal of cyanogens from cassava leaves with retention of vitamins and protein.

    PubMed

    Bradbury, J Howard; Denton, Ian C

    2014-09-01

    A mild method was developed to remove cyanogens from cassava leaves that involved three consecutive steps (1) pounding, (2) standing for 2h in the sun or 5h in the shade in the tropics and (3) washing three times in water. Four cassava cultivars were used and the mean residual total cyanide content after steps 1, 2 and 3 was 28%, 12% and 1%, respectively. The pounded cassava leaves retained their bright green colour and texture. The traditional method for removing cyanogens from pounded cassava leaves is by boiling in water which removed all cyanogens in 10 min. However this method caused the pounded leaves to become dull green in colour and would cause considerable losses of vitamins, protein and methionine, which are already in short supply in the diet of poor village people in tropical Africa.

  16. Cytogenetic activity of the coumarin glucoside seseloside

    SciTech Connect

    Arshava, E.A.

    1986-05-01

    The cytogenetic effect of the coumarin glucoside seseloside on plant objects was studied. It was established that low concentrations of the preparation (from 1 x 10/sup -5/ to 1 x 10/sup -3/ ..mu..g/ml) inhibit both spontaneous and radiation-induced mutagenesis. The effect of high concentrations (10 and 100 ..mu..g/ml) causes a mutagenic effect.

  17. Oligomeric secoiridoid glucosides from Jasminum abyssinicum.

    PubMed

    Gallo, Francesca Romana; Palazzino, Giovanna; Federici, Elena; Iurilli, Raffaella; Monache, Franco Delle; Chifundera, Kusamba; Galeffi, Corrado

    2006-03-01

    From the root bark of Jasminum abyssinicum (Oleaceae) collected in Congo was isolated tree oligomeric secoiridoid glucosides named craigosides A-C. The three compounds are esters of a cyclopentanoid monoterpene with an iridane skeleton, esterified with three, two and two, respectively, units of oleoside 11-methyl ester. The structures were elucidated by spectroscopic methods and chemical correlations. PMID:16376958

  18. Iridoid Glucosides and Diterpenoids from Caryopteris glutinosa.

    PubMed

    Luo, Guoyong; Ye, Qi; Du, Baowen; Wang, Fei; Zhang, Guo-Lin; Luo, Yinggang

    2016-04-22

    Five new iridoid glucoside derivatives (1-5), three new diterpenoids (7, 12, and 15), and 11 known compounds were isolated from the aqueous EtOH extract of Caryopteris glutinosa. Cell-based estrogen biosynthesis assays indicated that caryopteriside C (3) and caryopterisoid B (12) promote the biosynthesis of estrogen E2, with EC50 values of 11.1 and 8.0 μM, respectively, in human ovarian granulosa-like KGN cells via upregulating the expression of aromatase.

  19. Metabolically Active Glucosides in Oleaceae Seeds

    PubMed Central

    Sondheimer, E.; Blank, G. E.; Galson, Eva C.; Sheets, F. M.

    1970-01-01

    The seeds of six woody species of Oleaceae representing three genera, contain high concentrations of water-soluble glucosides, with major absorption maxima below 240 nanometers. In Fraxinus americana seeds three of these compounds, designated GL-3, GL-5, and GL-6, account for almost 10% of the dry weight. They are found in the endosperm and embryo but not in the pericarp. While the level of GL-5 is not particularly influenced by the physiological state of the embryo, that of GL-3 and GL-6 decreases as a result of germination and growth during a 10-day period. As the concentrations of GL-3 and GL-6 decrease, new ultraviolet-absorbing compounds are formed. The changes in the concentration of the ultraviolet-absorbing glucosides during cold temperature after-ripening, prior to germination, are small. When germination of dormant embryos is induced with gibberellic acid, the concentrations of GL-3 and GL-6 decrease in a manner similar to that observed with nondormant embryos. In the presence of abscisic acid no losses of GL-3 and GL-6 were observed. It is suggested that GL-3 and GL-6 fulfill some definite functions in the germination and growth of F. americana embryos, and that gibberellic acid and abscisic acid can exert a regulatory effect on the metabolism of these glucosides. Images PMID:16657368

  20. Mycotoxins and cyanogenic glycosides in staple foods of three indigenous people of the Colombian Amazon.

    PubMed

    Diaz, Gonzalo J; Krska, Rudolf; Sulyok, Michael

    2015-01-01

    A study was conducted to determine the incidence and levels of mycotoxins in the main staple foods of three indigenous people of the Colombian Amazon. A total of 20 corn, 24 rice and 59 cassava samples were analysed by a multi-analyte liquid chromatography-tandem mass spectrometry method covering the major classes of mycotoxins. In addition, cassava samples were also analysed for cyanogenic glycosides. The indigenous Amazon communities tested are exposed to potentially carcinogenic mycotoxins (particularly aflatoxins), as well as other mycotoxins, mainly through the intake of locally grown corn. Citrinin content in this corn was unusually high and has not been reported elsewhere. Two cassava samples contained high levels of cyanogenic glycosides. It is strongly recommended not to grow corn in the Amazon but instead purchase it from vendors capable of guaranteeing mycotoxin levels below the maximum allowable concentration in Colombia.

  1. Cassava cyanogens and free amino acids in raw and cooked leaves.

    PubMed

    Ngudi, D Diasolua; Kuo, Y-H; Lambein, F

    2003-08-01

    Cassava leaves (Manihot esculenta Crantz) constitute the main daily source of protein as supplement to the major staple food, the processed cassava roots in remote rural areas of Africa. Konzo, an upper motoneurone disease with permanent spastic paralysis of both legs, has been reported among populations consuming this unbalanced diet. In commercial pounded cassava leaves residual cyanogens and the presence of inherent potentially toxic non-protein amino acids were analysed to check their safety. The initial total cyanogens before cooking ranged from 35.9+/-0.4 to 107.5+/-0.8 mg HCN (hydrogen cyanide) equivalent kg(-1) dry weight. After cooking, the residual cyanogens were significantly reduced (P<0.05) ranging from 0.30+/-0.04 to 1.9+/-0.2 mg HCN equivalent kg(-1) dry weight, and were below the recommended FAO/WHO safe limit set at 10 mg HCN equivalent kg(-1) dry weight. The total free amino acids and trigonelline (N-methyl-nicotinic acid) detected varied from 10.8 g kg(-1) dry weight to 38.2 g kg(-1) dry weight in the raw and from 7.4 g kg(-1) dry weight to 25.6 g kg(-1) dry weight in the cooked cassava leaves. The non-protein amino acids gamma-amino butyric acid (GABA) and alpha-amino butyric acid (alpha-ABA) were detected. No known potentially toxic non-protein amino acid was found. In konzo-affected areas, cassava leaves with inadequate preparation and cooking can be a non-negligible source of dietary exposure to cyanogens apart from the cassava roots that are suggested to be involved in the aetiology of konzo.

  2. Probing non-polar interstellar molecules through their protonated form: Detection of protonated cyanogen (NCCNH+)

    NASA Astrophysics Data System (ADS)

    Agúndez, M.; Cernicharo, J.; de Vicente, P.; Marcelino, N.; Roueff, E.; Fuente, A.; Gerin, M.; Guélin, M.; Albo, C.; Barcia, A.; Barbas, L.; Bolaño, R.; Colomer, F.; Diez, M. C.; Gallego, J. D.; Gómez-González, J.; López-Fernández, I.; López-Fernández, J. A.; López-Pérez, J. A.; Malo, I.; Serna, J. M.; Tercero, F.

    2015-07-01

    Cyanogen (NCCN) is the simplest member of the series of dicyanopolyynes. It has been hypothesized that this family of molecules can be important constituents of interstellar and circumstellar media, although the lack of a permanent electric dipole moment prevents its detection through radioastronomical techniques. Here we present the first solid evidence of the presence of cyanogen in interstellar clouds by detection of its protonated form toward the cold dark clouds TMC-1 and L483. Protonated cyanogen (NCCNH+) has been identified through the J = 5-4 and J = 10-9 rotational transitions using the 40 m radiotelescope of Yebes and the IRAM 30 m telescope. We derive beam-averaged column densities for NCCNH+ of (8.6 ± 4.4) × 1010 cm-2 in TMC-1 and (3.9 ± 1.8) × 1010 cm-2 in L483, which translate into fairly low fractional abundances relative to H2, in the range (1-10) × 10-12. The chemistry of protonated molecules in dark clouds is discussed, and it is found that, in general terms, the abundance ratio between the protonated and non-protonated forms of a molecule increases with increasing proton affinity. Our chemical model predicts an abundance ratio NCCNH+/NCCN of ~10-4, which implies that the abundance of cyanogen in dark clouds could be as high as (1-10) × 10-8 relative to H2, i.e., comparable to that of other abundant nitriles such as HCN, HNC, and HC3N. Based on observations carried out with the IRAM 30 m Telescope and the Yebes 40 m Telescope. IRAM is supported by INSU/CNRS (France), MPG (Germany) and IGN (Spain). The 40 m radiotelescope at Yebes Observatory is operated by the Spanish National Geographic Institute (IGN, Ministerio de Fomento).

  3. Probing non polar interstellar molecules through their protonated form: Detection of protonated cyanogen (NCCNH+)★

    PubMed Central

    Agúndez, M.; Cernicharo, J.; de Vicente, P.; Marcelino, N.; Roueff, E.; Fuente, A.; Gerin, M.; Guélin, M.; Albo, C.; Barcia, A.; Barbas, L.; Bolaño, R.; Colomer, F.; Diez, M. C.; Gallego, J. D.; Gómez-González, J.; López-Fernández, I.; López-Fernández, J. A.; López-Pérez, J. A.; Malo, I.; Serna, J. M.; Tercero, F.

    2015-01-01

    Cyanogen (NCCN) is the simplest member of the series of dicyanopolyynes. It has been hypothesized that this family of molecules can be important constituents of interstellar and circumstellar media, although the lack of a permanent electric dipole moment prevents its detection through radioastronomical techniques. Here we present the first solid evidence of the presence of cyanogen in interstellar clouds through the detection of its protonated form toward the cold dark clouds TMC-1 and L483. Protonated cyanogen (NCCNH+) has been identified through the J = 5 – 4 and J = 10 – 9 rotational transitions using the 40m radiotelescope of Yebes and the IRAM 30m telescope. We derive beam averaged column densities for NCCNH+ of (8.6 ± 4.4) × 1010 cm−2 in TMC-1 and (3.9 ± 1.8) × 1010 cm−2 in L483, which translate to fairly low fractional abundances relative to H2, in the range (1-10) × 10−12. The chemistry of protonated molecules in dark clouds is discussed, and it is found that, in general terms, the abundance ratio between the protonated and non protonated forms of a molecule increases with increasing proton affinity. Our chemical model predicts an abundance ratio NCCNH+/NCCN of ~ 10−4, which implies that the abundance of cyanogen in dark clouds could be as high as (1-10) × 10−8 relative to H2, i.e., comparable to that of other abundant nitriles such as HCN, HNC, and HC3N. PMID:26543239

  4. Cyanogenic glycosides in plant-based foods available in New Zealand.

    PubMed

    Cressey, Peter; Saunders, Darren; Goodman, Janet

    2013-01-01

    Cyanogenic glycosides occur in a wide range of plant species. The potential toxicity of cyanogenic glycosides arises from enzymatic degradation to produce hydrogen cyanide, which may result in acute cyanide poisoning and has also been implicated in the aetiology of several chronic diseases. One hundred retail foods were sampled and analysed for the presence of total hydrocyanic acid using an acid hydrolysis-isonicotinic/barbituric acid colourimetric method. Food samples included cassava, bamboo shoots, almonds and almond products, pome fruit products, flaxseed/linseed, stone fruit products, lima beans, and various seeds and miscellaneous products, including taro leaves, passion fruit, spinach and canned stuffed vine leaves. The concentrations of total hydrocyanic acid (the hydrocyanic acid equivalents of all cyanogenic compounds) found were consistent with or lower than concentrations reported in the scientific literature. Linseed/flaxseed contained the highest concentrations of total hydrocyanic acid of any of the analysed foods (91-178 mg kg(-1)). Linseed-containing breads were found to contain total hydrocyanic acid at concentrations expected from their linseed content, indicating little impact of processing on the total hydrocyanic acid content. Simulation modelling was used to assess the risk due to the total hydrocyanic acid in fruit juice and linseed-containing bread.  PMID:23984870

  5. Cyanogenic potential of cassava peels and their detoxification for utilization as livestock feed.

    PubMed

    Tweyongyere, Robert; Katongole, Ignatious

    2002-12-01

    This study determined the cyanogenic potential of the cassava peels and assess the effectiveness of sun drying, heap fermentation and wet fermentation (soaking) in reducing the cyanide potential of the peels. Fresh cassava peels from major fresh food markets in Kampala and cassava grown in various parts of Uganda from Namolonge Agricultural and Animal Research Institute were used. The fresh peels from the market were subjected to the different detoxification methods foe 5 d; the cyanide potential was determined by enzymatic assay. The mean potential of the cassava peels from the food markets Kampala was 856 mg cyanide equivalen/kg of dry matter. The potential of the peels of the 14 cultivars fell between 253 and 1081 mg cyanide eQuivalent/kg of dry matter. High cyanogenic potential cultivars dominate on the market and pose danger of poisoning to livestock fed on fresh cassava peels. Treatment of the peels by sun-drying, heap fermentation on soaking reduced the cyanide potential to below 100 mg cyanide equivalent/kg of dry matter at 48, 72 and 96 h respectively. Sun-dying caused an early sharp fall in the cyanide potential, but heap fermentation or soaking gave the lowest residual cyanide after 120 h. Cassava peels could be safely used as livestock feed if they are treated to reduce the cyanogenic potential.

  6. Cyanogenic glycosides in plant-based foods available in New Zealand.

    PubMed

    Cressey, Peter; Saunders, Darren; Goodman, Janet

    2013-01-01

    Cyanogenic glycosides occur in a wide range of plant species. The potential toxicity of cyanogenic glycosides arises from enzymatic degradation to produce hydrogen cyanide, which may result in acute cyanide poisoning and has also been implicated in the aetiology of several chronic diseases. One hundred retail foods were sampled and analysed for the presence of total hydrocyanic acid using an acid hydrolysis-isonicotinic/barbituric acid colourimetric method. Food samples included cassava, bamboo shoots, almonds and almond products, pome fruit products, flaxseed/linseed, stone fruit products, lima beans, and various seeds and miscellaneous products, including taro leaves, passion fruit, spinach and canned stuffed vine leaves. The concentrations of total hydrocyanic acid (the hydrocyanic acid equivalents of all cyanogenic compounds) found were consistent with or lower than concentrations reported in the scientific literature. Linseed/flaxseed contained the highest concentrations of total hydrocyanic acid of any of the analysed foods (91-178 mg kg(-1)). Linseed-containing breads were found to contain total hydrocyanic acid at concentrations expected from their linseed content, indicating little impact of processing on the total hydrocyanic acid content. Simulation modelling was used to assess the risk due to the total hydrocyanic acid in fruit juice and linseed-containing bread. 

  7. Acute toxicity of some synthetic cyanogens in rats and their response to oral treatment with alpha-ketoglutarate.

    PubMed

    Bhattacharya, R; Satpute, R M; Hariharakrishnan, J; Tripathi, H; Saxena, P B

    2009-09-01

    Oral toxicity of several cyanogens and their reversal by alpha-ketoglutarate (A-KG; oral) were studied in rats. LD(50) of acetonitrile (ATCN), acrylonitrile (ACN), malononitrile (MCN), propionitrile (PCN), sodium nitroprusside (SNP), and succinonitrile (SCN) was 4891, 143.3, 69.8, 122.9, 69.8 and 488.7 mg/kg, respectively while the protection index of A-KG (ratio of LD(50) of cyanogens in the presence or absence of A-KG) was>2.0 against MCN (7.6), PCN (2.7) and SNP (3.6) only. We further studied the efficacy of A-KG against acute toxicity of these three cyanogens (0.75 LD(50)) on various hematological and biochemical variables in blood and soft tissues 24h post-exposure. We observed increase in white blood cells (SNP), plasma alanine (PCN, SNP) and aspartate (PCN) aminotransferase, lactate dehydrogenase (MCN, PCN, SNP), Na(+) (MCN, PCN) and cyanide (PCN), and decrease in K(+) (MCN, SNP) accompanied by an increase in brain, kidney and liver malondialdehyde (PCN), decrease in brain glutathione peroxidase, glutathione reductase (PCN, SNP), reduced glutathione (MCN, PCN, SNP) and cytochrome oxidase (PCN), liver rhodanese (PCN, SNP), and kidney cytochrome oxidase (PCN). The study indicates that (i) PCN was most toxic among all the cyanogens and (ii) beside cyanide, A-KG could be considered as an effective antidote for cyanogens.

  8. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 172.816... § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is the methyl glucoside-coconut oil...

  9. The spectrum and spatial distribution of cyanogen in comet Hale-Bopp (C/1995 O1) at large heliocentric distance.

    PubMed

    Wagner, R M; Schleicher, D G

    1997-03-28

    Optical spectra of comet Hale-Bopp (C/1995 O1) at a heliocentric distance of 6.45 astronomical units showed emission from cyanogen gas. The spatial distribution of cyanogen was considerably more diffuse and extended compared to the spatial profile of the dust or grains which were sharply peaked near the center. This behavior is consistent with comets at smaller heliocentric distances suggesting the same or a similar formation mechanism. A cyanogen gas production rate of (1.2 +/- 0.3) x10(26) molecules per second was derived. A model band profile derived from fluorescence equilibrium calculations for the comet's heliocentric velocity and distance agrees with the observed band profile.

  10. The Reactions of Methanimine and Cyanogen with Carbon Monoxide in Prebiotic Molecular Evolution on Earth

    NASA Astrophysics Data System (ADS)

    Aylward, Nigel; Bofinger, Neville

    2001-12-01

    A primeval atmosphere is proposed containing simple molecules such as formaldehyde, ammonia, carbon monoxide, cyanogen and hydrogen cyanide, which have been detected in space. Chemical reactions are described for the formation of aziridine-2-one and di-azirine-3-one derivatives as potential precursors for the original synthesesis of amino-acids, proteins, pyrimidines, purines, nicotinamide and flavin. The reactions have been shown to be kinetically feasible from the overall enthalpy changes in the ZKE approximation at the MP2/6-31G^* level.

  11. Chemical-chemical interaction between cyanogenic toxicants and aldehydes: a mechanism-based QSAR approach to assess toxicological joint effects.

    PubMed

    Lin, Z; Wei, D; Wang, X; Yin, K; Zhao, D

    2004-04-01

    A QSAR approach was proposed to assess toxicological joint effects based on the mechanism of chemical-chemical interactions between cyanogenic toxicants and aldehydes. It has been observed that the chemical-chemical interaction between cyanogenic toxicants and aldehydes resulted in the formation of carbanion intermediates, and therefore this interaction led to different toxicological joint effects between cyanogenic toxicants and aldehydes. Analysis of this chemical-chemical interaction showed that the formation of carbanion intermediate highly depended on the charge of the carbon atom in the -CHO of aldehydes and this of the carbon atom (C*) in the carbochain of cyanogenic toxicant. By using the Hammett Constant (sigma(p)) to measure the charge of carbon atom in the -CHO of aldehydes, a mechanism-based QSAR approach (M = 0.316 - 4.386sigma(p) with r2 = 0.933, SE = 0.082, F = 55.389, p = 0.002, M = sum of toxic units) was proposed to assess the toxicological joint effects between alpha-hydroxy-isobutyronitrile and individual aliphatic aldehydes. Another one (M = 0.978 - 0.720sigma(p) with r2 = 0.852, SE = 0.152, F = 40.148, p = 0.0001) was also proposed to assess the toxicological joint effects between alpha-hydroxy-isobutyronitrile and individual aromatic aldehydes. Lastly, by using the charge of carbon atom (C*) in the carbochain of cyanogenic toxicant, a mechanism-based QSAR model (M = -0.161 - 7.721C* with r2 = 0.847, SE = 0.227, F = 27.657, p = 0.003) was derived to assess toxicological joint effects between p-nitrobenzaldehyde and cyanogenic toxicants.

  12. Strategies for elimination of cyanogens from cassava for reducing toxicity and improving food safety.

    PubMed

    Nambisan, Bala

    2011-03-01

    Toxicity of cassava arises due to the presence of the cyanoglucosides linamarin and lotaustralin which are hydrolysed by endogenous enzyme linamarase to acetonecyanohydrin (ACN) and cyanide (CN) which are toxic. Major research efforts to eliminate/reduce cyanoglucosides have focused on (i) development of acyanogenic cassava varieties by breeding; (ii) controlling its metabolism; and (iii) processing to remove cyanogens. The cyanoglucoside (CNG) content in cassava is genetically controlled and cultivars may be classified as low (<50 μg/g), medium (50-100 μg/g) and high CN (>100 μg CN eq./g) varieties. Molecular techniques for reducing tuber CNG have focused on development of transgenic plants with reduced expression of cyt P 450 in leaves, or increased expression of hydroxynitrilelyase in tuber. For immediate solution, CNG content can be reduced using several processing methods. Traditional methods used for processing include boiling, drying, parboiling and drying, baking, steaming, frying and preparation of flour. These processes result in CN losses ranging from 25% to 98%. The cyanogen level in the final product is influenced both by the tuber CNG and the method of processing. In order to achieve safe levels of 10 μg/g in cassava products, new methods of processing, especially for cassava containing more than 250 μg CN eq./g, remains a challenging problem.

  13. Comparison of the Use of Gas Chromotography, Spectrophotometry, and Near Infrared Spectropscopy to Quantify Prussic Acid Potential in Forages

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Sorghum [Sorghum bicolor (L.) Moench] has been shown to contain the cyanogenic glycoside dhurrin, which is responsible for the disorder known as prussic acid poisoning in livestock. The current standard method for estimating HCN uses spectrophotometery to measure the aglycone of the dhurrin, p-hydro...

  14. Nicotinamide metabolism in ferns: formation of nicotinic acid glucoside.

    PubMed

    Ashihara, Hiroshi; Yin, Yuling; Watanabe, Shin

    2011-03-01

    The metabolic fate of [carbonyl-(14)C]nicotinamide was investigated in 9 fern species, Psilotum nudum, Angiopteris evecta, Lygodium japonicum, Acrostichum aureum, Asplenium antiquum, Diplazium subsinuatum, Thelypteris acuminate, Blechnum orientale and Crytomium fortune. All fern species produce a large quantity of nicotinic acid glucoside from [(14)C]nicotinamide, but trigonelline formation is very low. Increases in the release of (14)CO(2) with incubation time was accompanied by decreases in [carboxyl-(14)C]nicotinic acid glucoside. There was slight stimulation of nicotinic acid glucoside formation by 250 mM NaCl in mature leaves of the mangrove fern, Acrostichum aureum, but it is unlikely that this compound acts as a compatible solute. Nicotinamide and nicotinic acid salvage for pyridine nucleotide synthesis was detected in all fern species, although this activity was always less than nicotinic acid glucoside synthesis. Predominant formation of nicotinic acid glucoside is characteristic of nicotinic acid metabolism in ferns. This reaction appears to act as a detoxication mechanism, removing excess nicotinic acid.

  15. Selective detection of toxic cyanogen gas in the presence of O2, and H2O molecules using a AlN nanocluster

    NASA Astrophysics Data System (ADS)

    Solimannejad, Mohammad; Kamalinahad, Saeedeh; Shakerzadeh, Ehsan

    2016-08-01

    The interaction of cyanogen molecule with Al12N12 nanocage has been studied using density functional theory (DFT) at CAM-B3LYP/6-31+G(d) level. Geometric, electronic structure and natural bond orbitals (NBO) analysis display that adsorption of cyanogen onto exterior surface of Al12N12 is physisorption with adsorption energy (Eads) equal to -55.36 kJ/mol. UV-vis study shows a high intensity peak in 388.9 nm due to interaction of gas with nanocage. It is expected that Al12N12 will be used in designing novel materials for potential applications to detect toxic cyanogen molecule.

  16. Production of a cyanogenic secretion by a thyridid caterpillar (Calindoea trifascialis, Thyrididae, Lepidoptera)

    NASA Astrophysics Data System (ADS)

    Darling, Christopher; Schroeder, Frank; Meinwald, Jerrold; Eisner, Maria; Eisner, Thomas

    2001-06-01

    The thyridid caterpillar, Calindoea trifascialis, when disturbed, emits a defensive secretion from two sac-like glands that open dorsolaterally on the first abdominal segment. The larva has two arm-like protuberances that project outward from the body just in front of the gland openings. These "arms", which are wetted by secretion when the larva activates its glands, appear to function specifically for administration of the fluid. A primary component of the secretion is mandelonitrile, a cyanogenic compound, but the fluid also contains other potential deterrents, including benzaldehyde, benzoic acid, (E,E)-α-farnesene, and 3-methylbutyl-3-methylbutanoate. Tests done in the field in Vietnam, where the species is native, showed the secretion to be protective against ants.

  17. Characterization of the major cyanogen bromide fragment of alpha-A crystallin

    NASA Technical Reports Server (NTRS)

    Ifeanyi, F.; Takemoto, L.; Spooner, B. S. (Principal Investigator)

    1991-01-01

    Alpha crystallin from the bovine lens has been digested with cyanogen bromide, and the major fragment (CB-1) has been purified using reverse phase HPLC. Characterization of this fragment by Edman degradation and antisera to synthetic peptides indicates that it originates from alpha-A crystallin, but lacks the N-terminal methionine and the last 35 amino acids from the C-terminus of the molecule. The purified CB-1 fragment binds as well as native alpha crystallin to lens membrane, but is unable to self-assemble into the correct size of high molecular weight oligomeric complexes characteristic of the intact alpha-A chain. Together, these results demonstrate that the alpha-A chain is comprised of at least two functional domains, one of which is involved in binding of alpha-A crystallin to lens membrane, and another which is necessary for correct self-assembly of the molecule into high molecular weight oligomers.

  18. Konzo: From Poverty, Cassava, and Cyanogen Intake to Toxico-Nutritional Neurological Disease

    PubMed Central

    Nzwalo, Hipólito; Cliff, Julie

    2011-01-01

    Konzo is a distinct neurological entity with selective upper motor neuron damage, characterized by an abrupt onset of an irreversible, non-progressive, and symmetrical spastic para/tetraparesis. Despite its severity, konzo remains a neglected disease. The disease is associated with high dietary cyanogen consumption from insufficiently processed roots of bitter cassava combined with a protein-deficient diet. Epidemics occur when these conditions coincide at times of severe food shortage. Up to 1993, outbreaks in poor rural areas in Africa contributed to more than 3,700 cases of konzo. The number of affected people is underestimated. From unofficial reports, the number of cases was estimated to be at least 100,000 in 2000, in contrast to the 6,788 cases reported up to 2009 from published papers. PMID:21738800

  19. A method for near real time continuous air monitoring of phosgene, hydrogen cyanide, and cyanogen chloride

    SciTech Connect

    Lattin, F.G.; Paul, D.G.

    1996-12-31

    A sorbent-based gas chromatographic method provides continuous quantitative measurement of phosgene, hydrogen cyanide, and cyanogen chloride in ambient air. These compounds are subject to workplace exposure limits as well as regulation under terms of the Chemical Arms Treaty and Title III of the 1990 Clean Air Act amendments. The method was developed for on-site use in a mobile laboratory during remediation operations. Incorporated into the method are automated multi-level calibrations at time weighted average (TW) concentrations, or lower. Gaseous standards are prepared in fused silica lined air sampling canisters, then transferred to the analytical system through dynamic spiking. Precision and accuracy studies performed to validate the method are described. Also described are system deactivation and passivation techniques critical to optimum method performance.

  20. Anti-allergic inflammatory effects of cyanogenic and phenolic glycosides from the seed of Prunus persica.

    PubMed

    Kim, Geum Jin; Choi, Hyun Gyu; Kim, Ji Hyang; Kim, Sang Hyun; Kim, Jeong Ah; Lee, Seung Ho

    2013-12-01

    A methanol extract of the seed of Prunus persica (Rosaceae) was found to inhibit histamine release in human mast cells. Activity-guided fractionation of the methanol extract yielded three cyanogenic glycosides (1-3) and other phenolic compounds (4-8). To evaluate their anti-allergic and anti-inflammatory activities, the isolates (1-8) were tested for their inhibitory effects on histamine release and on the gene expressions of tumor necrosis factor (TNF)-alpha and interleukin (IL)-6 in human mast cells. Of these, phenolic glycosides 7 and 8 suppressed histamine release and inhibited the pro-inflammatory cytokines TNF-alpha and IL-6. These results suggest that isolates from P. persica are among the anti-allergic inflammatory principles in this medicinal plant.

  1. The Case of the Missing Cyanogen-rich AGB Stars in Galactic Globular Clusters

    NASA Astrophysics Data System (ADS)

    Campbell, S. W.; Yong, D.; Wylie-de Boer, E. C.; Stancliffe, R. J.; Lattanzio, J. C.; Angelou, G. C.; Grundahl, F.; Sneden, C.

    2012-08-01

    The handful of available observations of AGB stars in Galactic Globular Clusters suggest that the GC AGB populations are dominated by cyanogen-weak stars (eg. Norris et al. 1981; Sneden et al. 2000). This contrasts strongly with the distributions on the RGB (and other) populations, which generally show a 50:50 bimodality in CN band strength. If this is a real difference then it presents a serious problem for low metallicity stellar evolution theory - since such a surface abundance change going from the RGB to AGB is not predicted by stellar models. However this is only a tentative conclusion, since it is based on very small AGB sample sizes. To test whether this problem really exists we have carried out an observational campaign targeting AGB stars in GCs. Our preliminary results indicate there is indeed a lack of CN-strong AGB stars.

  2. Absorption and excretion of conjugated flavonols, including quercetin-4'-O-beta-glucoside and isorhamnetin-4'-O-beta-glucoside by human volunteers after the consumption of onions.

    PubMed

    Aziz, A A; Edwards, C A; Lean, M E; Crozier, A

    1998-09-01

    Flavonols are polyphenols found ubiquitously in plants and plant-products. Flavonols, particularly quercetin, are potent antioxidants in vitro and their intake has been associated inversely with the incidence of coronary heart disease. The aim of this study was to investigate the accumulation in plasma and excretion in urine of flavonol glucosides following ingestion of lightly fried onions. Five healthy volunteers followed a low-flavonoid diet for 3 days. On day 4, after an overnight fast, subjects were given 300 g of lightly fried yellow onions which contain conjugates of quercetin and isorhamnetin, including quercetin-3,4 '-diO-beta-glucoside, isorhamnetin-4'-O-beta-glucoside and quercetin-4'-O-beta-glucoside. Blood collection was carried out at 0 min, 0.5, 1.0, 1.5, 2, 3, 4, 5 and 24h after the supplement. In addition, subjects collected all their urine for 24h following the onion supplement. Isorhamnetin-4'-O-beta-glucoside and quercetin-4 '-O-beta-glucoside accumulated in plasma with maximum levels, defined as proportion of intake, of 10.7+/-2.6% and 0.13+/-0.03% respectively. The time of the quercetin-4'glucoside peak plasma concentration was 1.3+/-0.2 h after the ingestion of onions while a value of 1.8+/-0.7 h was obtained for isorhamnetin-4'-glucoside. Excretion in urine, as a proportion of intake, was 17.4+/-8.3% for isorhamnetin-4'-O-beta-glucoside and 0.2+/-0.1% for quercetin-4'-O-beta-glucoside. Possible reasons for the accumulation and excretion of isorhamnetin-4'-glucoside in proportionally much higher amounts than quercetin-4'-glucoside are discussed. It is concluded that flavonols are absorbed into the bloodstream as glucosides and minor structural differences affect markedly both the level of accumulation and the extent to which the conjugates are excreted. PMID:9802557

  3. Intestinal Bacterium Eubacterium cellulosolvens Deglycosylates Flavonoid C- and O-Glucosides

    PubMed Central

    Blaut, Michael

    2012-01-01

    Eubacterium cellulosolvens cleaved the flavone C-glucosides homoorientin and isovitexin to their aglycones luteolin and apigenin, respectively. The corresponding isomers, orientin and vitexin, or other polyphenolic C-glucosides were not deglycosylated. E. cellulosolvens also cleaved several O-coupled glucosides of flavones and isoflavones to their corresponding aglycones. PMID:22961906

  4. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 6 2010-04-01 2010-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  5. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 172.816 Section... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  6. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2010 CFR

    2010-04-01

    ... 21 Food and Drugs 3 2010-04-01 2009-04-01 true Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  7. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  8. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  9. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... 21 Food and Drugs 3 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester. 178.3600 Section 178.3600 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester...

  10. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... 21 Food and Drugs 3 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  11. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... 21 Food and Drugs 3 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  12. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2014 CFR

    2014-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2014-04-01 2014-04-01 false Methyl glucoside-coconut oil ester....

  13. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2013 CFR

    2013-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2013-04-01 2013-04-01 false Methyl glucoside-coconut oil ester....

  14. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2012 CFR

    2012-04-01

    ... (CONTINUED) ANIMAL DRUGS, FEEDS, AND RELATED PRODUCTS FOOD ADDITIVES PERMITTED IN FEED AND DRINKING WATER OF ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil... 21 Food and Drugs 6 2012-04-01 2012-04-01 false Methyl glucoside-coconut oil ester....

  15. 21 CFR 178.3600 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 178.3600... SANITIZERS Certain Adjuvants and Production Aids § 178.3600 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester identified in § 172.816(a) of this chapter may be safely used as a...

  16. 21 CFR 172.816 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 3 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 172.816... HUMAN CONSUMPTION Multipurpose Additives § 172.816 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut oil ester may be safely used in food in accordance with the following conditions: (a) It is...

  17. 21 CFR 573.660 - Methyl glucoside-coconut oil ester.

    Code of Federal Regulations, 2011 CFR

    2011-04-01

    ... 21 Food and Drugs 6 2011-04-01 2011-04-01 false Methyl glucoside-coconut oil ester. 573.660 Section 573.660 Food and Drugs FOOD AND DRUG ADMINISTRATION, DEPARTMENT OF HEALTH AND HUMAN SERVICES... ANIMALS Food Additive Listing § 573.660 Methyl glucoside-coconut oil ester. Methyl glucoside-coconut...

  18. Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica.

    PubMed

    Chen, Dawei; Sun, Lili; Chen, Ridao; Xie, Kebo; Yang, Lin; Dai, Jungui

    2016-04-18

    A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5'-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides. PMID:26918309

  19. Enzymatic Synthesis of Acylphloroglucinol 3-C-Glucosides from 2-O-Glucosides using a C-Glycosyltransferase from Mangifera indica.

    PubMed

    Chen, Dawei; Sun, Lili; Chen, Ridao; Xie, Kebo; Yang, Lin; Dai, Jungui

    2016-04-18

    A green and cost-effective process for the convenient synthesis of acylphloroglucinol 3-C-glucosides from 2-O-glucosides was exploited using a novel C-glycosyltransferase (MiCGTb) from Mangifera indica. Compared with previously characterized CGTs, MiCGTb exhibited unique de-O-glucosylation promiscuity and high regioselectivity toward structurally diverse 2-O-glucosides of acylphloroglucinol and achieved high yields of C-glucosides even with a catalytic amount of uridine 5'-diphosphate (UDP). These findings demonstrate for the first time the significant potential of a single-enzyme approach to the synthesis of bioactive C-glucosides from both natural and unnatural acylphloroglucinol 2-O-glucosides.

  20. Differential effects on the cyanogenic glycoside content of fermenting cassava root pulp by beta-glucosidase and microbial activities.

    PubMed

    Maduagwu, E N

    1983-03-01

    The degradation of cyanogenic glycosides was studied in spontaneously fermenting cassava root pulp and in fresh pulp samples pretreated to prevent either endogenous beta-glycosidase activity, fermentation, or both. The rate of disappearance of the glycosides, as measured by hydrocyanic acid (HCN) production in situ, in membrane-sterilised media or in samples containing 1% sodium iodoacetate, was comparable with the untreated control in which 85% of the substrate was broken down within 72 h. Pretreatment of the fresh pulp with the beta-glucosidase inhibitor 1,5-gluconolactone (1%) markedly reduced the rate of disappearance of the cyanogens while inclusion of glucose in this test medium at the 3% level appeared to induce some hydrolysis. Loss of bound (glycosidic) cyanide in sterilised medium containing the glucosidase inhibitor was negligible. The results suggest that the contribution of the fermentation process in cyanide detoxification of pulped cassava roots is minimal. PMID:6404010

  1. Recent Developments of C-Aryl Glucoside SGLT2 Inhibitors.

    PubMed

    Zhang, Yang; Liu, Zhao-Peng

    2016-01-01

    Sodium-glucose cotransporter 2 (SGLT2) is almost exclusively expressed in the proximal renal tubules. It is responsible for about 90% of the glucose reabsorption from tubular fluid. Selective inhibition of SGLT2 is expected to favor in the normalization of plasma glucose levels in T2DM patients through the prevention of renal glucose reabsorption and the promotion of glucose excretion from urine. Selective SGLT2 inhibitors have the merits to minimize the gastrointestinal side effects associated with SGLT1 inhibition, and selective SGLT2 inhibition may have a low risk of hypoglycemia. Since the C-aryl glucosides are metabolically more stable than the O-glucosides, numerous efforts have been made in the development of potent and selective C-aryl glucoside SGLT2 inhibitors, and a number of them are now used as anti-diabetes drugs in clinic or at various stages of clinical developments. Based on their structural features, in this review, these SGLT2 inhibitors are classified as three types: the phenyl/arylmethylphenyl C-glucosides, with an emphasis on the modifications on the proximal and/or the distal phenyl ring, and the spacer; the heteroarylmethylphenyl Cglucosides, with a replacement of the distal phenyl ring by a heterocycle like pyridazine, pyrimidine, thiophene and benzothiophene, thiazole, 1,3,4-thiadiazole, and triazolopyridinone; and the glucose-modified Caryl glucosides, including the glucose C-1 derived O-spiroketals, C-4 gem-difluoro analogues, C-5 and C-6 modified derivatives, dioxa-bicyclo[3.2.1]octane bridged ketals, the thioglucosides, and carbasugars. The structure-activity relationships (SARs) of each type along with their inhibitory potency against human SGLT2 and selectivity over human SGLT1 are discussed. PMID:26861002

  2. Recent Developments of C-Aryl Glucoside SGLT2 Inhibitors.

    PubMed

    Zhang, Yang; Liu, Zhao-Peng

    2016-01-01

    Sodium-glucose cotransporter 2 (SGLT2) is almost exclusively expressed in the proximal renal tubules. It is responsible for about 90% of the glucose reabsorption from tubular fluid. Selective inhibition of SGLT2 is expected to favor in the normalization of plasma glucose levels in T2DM patients through the prevention of renal glucose reabsorption and the promotion of glucose excretion from urine. Selective SGLT2 inhibitors have the merits to minimize the gastrointestinal side effects associated with SGLT1 inhibition, and selective SGLT2 inhibition may have a low risk of hypoglycemia. Since the C-aryl glucosides are metabolically more stable than the O-glucosides, numerous efforts have been made in the development of potent and selective C-aryl glucoside SGLT2 inhibitors, and a number of them are now used as anti-diabetes drugs in clinic or at various stages of clinical developments. Based on their structural features, in this review, these SGLT2 inhibitors are classified as three types: the phenyl/arylmethylphenyl C-glucosides, with an emphasis on the modifications on the proximal and/or the distal phenyl ring, and the spacer; the heteroarylmethylphenyl Cglucosides, with a replacement of the distal phenyl ring by a heterocycle like pyridazine, pyrimidine, thiophene and benzothiophene, thiazole, 1,3,4-thiadiazole, and triazolopyridinone; and the glucose-modified Caryl glucosides, including the glucose C-1 derived O-spiroketals, C-4 gem-difluoro analogues, C-5 and C-6 modified derivatives, dioxa-bicyclo[3.2.1]octane bridged ketals, the thioglucosides, and carbasugars. The structure-activity relationships (SARs) of each type along with their inhibitory potency against human SGLT2 and selectivity over human SGLT1 are discussed.

  3. Analysis of limonoid glucosides from citrus by electrospray ionization liquid chromatography-mass spectrometry.

    PubMed

    Schoch, T K; Manners, G D; Hasegawa, S

    2001-03-01

    An electrospray ionization liquid chromatography-mass spectrometry (ESI-LC-MS) method for the detection and quantitation of limonoid glucosides has been developed. Negative ions [M - H(+)](-) characteristic of six limonoid glucosides can be detected and quantified from selected ion monitoring chromatograms using carminic acid as an internal standard. The described method has been applied to the analysis of limonoid glucoside content in various liquid and solid Citrus spp. samples as well as complex mixtures of partially purified limonoid glucosides. Rapid and sensitive qualitative screening of samples for limonoid glucosides can also be accomplished with slight modifications of the method. PMID:11312819

  4. One New Conjugate of a Secoiridoid Glucoside with a Sesquiterpene Glucoside from the Flower Buds of Lonicera japonica.

    PubMed

    Yang, Biao; Meng, Zhaoqing; Ma, Yimin; Wang, Zhenzhong; Ding, Gang; Huang, Wenzhe; Sun, Lin; Hu, Yumei; Liu, Wenjun; Zhang, Chunxiao; Cao, Zeyu; Li, Jiachun; Zhong, Yan; Xiao, Wei

    2015-09-01

    Secosesquside (1), a new secoiridoid glucoside-sesquiterpene conjugate, together with three known secoiridoid derivatives, were isolated from flower buds of Lonicerajaponica. The isolated compounds were elucidated by extensive spectroscopic analyses, especially 2D NMR experiments. The anti-inflammatory activities of the new compound were also evaluated by enzyme-linked immunosorbent assay. PMID:26594743

  5. Urinary excretion of bile acid glucosides and glucuronides in extrahepatic cholestasis.

    PubMed

    Wietholtz, H; Marschall, H U; Reuschenbach, R; Matern, H; Matern, S

    1991-04-01

    Recently the formation of bile acid glucosides has been described as a novel conjugation mechanism in vitro and in vivo. In 10 patients with extrahepatic cholestasis caused by carcinoma of the head of the pancreas we investigated excretion rates and profiles of urinary bile acid glucosides. Urinary bile acid glucosides and, for comparison, bile acid glucuronides were extracted and characterized according to established methods. In controls total urinary bile acid glucoside excretion was 0.22 +/- 0.03 mumol/24 hr (mean +/- S.E.M.)-in the range of bile acid glucuronide excretion (0.41 +/- 0.06 mumol/24 hr; mean +/- S.E.M.). A gas chromatography-mass spectrometry-characterized trihydroxy bile acid glucoside of still-unknown hydroxyl positions accounted for 65% of total urinary bile acid glucosides. In extrahepatic cholestasis total urinary bile acid glucoside excretion was 0.52 +/- 0.13 mumol/24 hr (mean +/- SEM), yet significantly lower than bile acid glucuronide excretion (1.53 +/- 0.13 mumol/24 hr; mean +/- SEM; p less than 0.001). In cholestasis the primary bile acid derivatives cholic and chenodeoxycholic acid glucosides amounted to 90%, whereas the trihydroxy bile acid glucoside had decreased to 5% of total bile acid glucoside excretion, indicating its alteration during enterohepatic circulation. The data establish the composition and quantity of urinary bile acid glucosides in healthy controls and cholestasis and constitute a quantitative comparison with another glycosidic conjugation reaction, bile acid glucuronidation.

  6. Binding and relaxometric properties of heme complexes with cyanogen bromide fragments of human serum albumin.

    PubMed Central

    Monzani, Enrico; Curto, Maria; Galliano, Monica; Minchiotti, Lorenzo; Aime, Silvio; Baroni, Simona; Fasano, Mauro; Amoresano, Angela; Salzano, Anna Maria; Pucci, Piero; Casella, Luigi

    2002-01-01

    The spectroscopic and reactivity properties of hemin complexes formed with cyanogen bromide fragments B (residues 1-123), C (124-298), A (299-585), and D (1-298) of human serum albumin (HSA) have been investigated. The complex hemin-D exhibits binding, spectral, circular dichroism, and reactivity characteristics very similar to those of hemin-HSA, indicating that fragment D contains the entire HSA domain involved in heme binding. The characteristics of the other hemin complexes are different, and a detailed investigation of the properties of hemin-C has been carried out because this fragment contains the HSA binding region of several important drugs. Hemin-C contains a low-spin Fe(III) center, with two imidazole ligands, but the complex undergoes a reversible structural transition at basic pH leading to a high-spin, five-coordinated Fe(III) species. This change determines a marked increase in the relaxation rate of water protons. Limited proteolysis experiments and mass spectral analysis carried out on fragment C and hemin-C show that the region encompassing residues Glu-208 to Trp-214 is protected from activity of proteases in the complex and, therefore, is involved in the interaction with hemin. A structural model of fragment C enables us to propose that His-242 and His-288 are the axial ligands for the Fe(III) center. PMID:12324442

  7. An efficient fermentation method for the degradation of cyanogenic glycosides in flaxseed.

    PubMed

    Wu, C-F; Xu, X-M; Huang, S-H; Deng, M-C; Feng, A-J; Peng, J; Yuan, J-P; Wang, J-H

    2012-01-01

    Recently, flaxseed has become increasingly popular in the health food market because it contains a considerable amount of specific beneficial nutrients such as lignans and omega-3 fatty acids. However, the presence of cyanogenic glycosides (CGs) in flaxseed severely limits the exploitation of its health benefits and nutritive value. We, therefore, developed an effective fermentation method, optimised by response surface methodology (RSM), for degrading CGs with an enzymatic preparation that includes 12.5% β-glucosidase and 8.9% cyanide hydratase. These optimised conditions resulted in a maximum CG degradation level of 99.3%, reducing the concentration of cyanide in the flaxseed power from 1.156 to 0.015 mg g(-1) after 48 h of fermentation. The avoidance of steam heat to evaporate hydrocyanic acid (HCN) results in lower energy consumption and no environmental pollution. In addition, the detoxified flaxseed retained the beneficial nutrients, lignans and fatty acids at the same level as untreated flaxseed, and this method could provide a new means of removing CGs from other edible plants, such as cassava, almond and sorghum by simultaneously expressing cyanide hydratase and β-glucosidase. PMID:22530603

  8. CYANOGEN IN NGC 1851 RED GIANT BRANCH AND ASYMPTOTIC GIANT BRANCH STARS: QUADRIMODAL DISTRIBUTIONS

    SciTech Connect

    Campbell, S. W.; Stancliffe, R. J.; Lattanzio, J. C.; Angelou, G. C.; D'Orazi, V.; Yong, D.; Wylie-de Boer, E. C.; Martell, S. L.; Grundahl, F.; Sneden, C. E-mail: david.yong@anu.edu.au

    2012-12-10

    The Galactic globular cluster NGC 1851 has raised much interest since Hubble Space Telescope photometry revealed that it hosts a double subgiant branch. Here we report on our homogeneous study into the cyanogen (CN) band strengths in the red giant branch (RGB) population (17 stars) and asymptotic giant branch (AGB) population (21 stars) using AAOmega/2dF spectra with R {approx} 3000. We discover that NGC 1851 hosts a quadrimodal distribution of CN band strengths in its RGB and AGB populations. This result supports the merger formation scenario proposed for this cluster, such that the CN quadrimodality could be explained by the superposition of two 'normal' bimodal populations. A small sample overlap with an abundance catalog allowed us to tentatively explore the relationship between our CN populations and a range of elemental abundances. We found a striking correlation between CN and [O/Na]. We also found that the four CN peaks may be paired-the two CN-weaker populations being associated with low Ba and the two CN-stronger populations with high Ba. If true, then s-process abundances would be a good diagnostic for disentangling the two original clusters in the merger scenario. More observations are needed to confirm the quadrimodality and also the relationship between the subpopulations. We also report CN results for NGC 288 as a comparison. Our relatively large samples of AGB stars show that both clusters have a bias toward CN-weak AGB populations.

  9. An efficient fermentation method for the degradation of cyanogenic glycosides in flaxseed.

    PubMed

    Wu, C-F; Xu, X-M; Huang, S-H; Deng, M-C; Feng, A-J; Peng, J; Yuan, J-P; Wang, J-H

    2012-01-01

    Recently, flaxseed has become increasingly popular in the health food market because it contains a considerable amount of specific beneficial nutrients such as lignans and omega-3 fatty acids. However, the presence of cyanogenic glycosides (CGs) in flaxseed severely limits the exploitation of its health benefits and nutritive value. We, therefore, developed an effective fermentation method, optimised by response surface methodology (RSM), for degrading CGs with an enzymatic preparation that includes 12.5% β-glucosidase and 8.9% cyanide hydratase. These optimised conditions resulted in a maximum CG degradation level of 99.3%, reducing the concentration of cyanide in the flaxseed power from 1.156 to 0.015 mg g(-1) after 48 h of fermentation. The avoidance of steam heat to evaporate hydrocyanic acid (HCN) results in lower energy consumption and no environmental pollution. In addition, the detoxified flaxseed retained the beneficial nutrients, lignans and fatty acids at the same level as untreated flaxseed, and this method could provide a new means of removing CGs from other edible plants, such as cassava, almond and sorghum by simultaneously expressing cyanide hydratase and β-glucosidase.

  10. Antibiotic-modifying activity of riachin, a non-cyanogenic cyanoglycoside extracted from Bauhinia pentandra

    PubMed Central

    de Farias, Pablo Antonio Maia; Figueredo, Fernando Gomes; Lucas, Aline Maria Brito; de Moura, Rafael Barbosa; Coutinho, Henrique Douglas Melo; da Silva, Tania Maria Sarmento; Martin, Ana Luiza de Aguiar Rocha; Fonteles, Marta Maria de França

    2015-01-01

    Background The search for new active compounds from the Brazilian flora has intensified in recent years, especially for new drugs with antibiotic potential. Accordingly, the aim of this study was to determine whether riachin has antibiotic activity in itself or is able to modulate the activity of conventional antibiotics. Methods A non-cyanogenic cyanoglycoside known as riachin was isolated from Bauhinia pentandra, and was tested alone and in combination with three antibiotics (clindamycin, amikacin, and gentamicin) against multiresistant bacterial strains (Escherichia coli, Pseudomonas aeruginosa, and Staphylococcus aureus). Results Riachin did not show significant antibiotic activity when tested alone against any strain (P>0.05). However, when combined with conventional antibiotics, it showed drug-modifying activity against strains of S. aureus exposed to clindamycin (P<0.001) as well as against P. aeruginosa exposed to amikacin (P<0.001). Although riachin did not show direct antibiotic activity, it had synergistic activity when combined with amikacin or clindamycin. The mechanism of action of this synergism is under investigation. Conclusion The results of this work demonstrate that some substances of natural origin can enhance the effectiveness of certain antibiotics, which means a substantial reduction in the drug dose required and possibly in consequent adverse events for patients. PMID:26109849

  11. Subtilisin and cyanogen bromide cleavage products of fibronectin that retain gelatin-binding activity.

    PubMed Central

    Gold, L I; Garcia-Pardo, A; Frangione, B; Franklin, E C; Pearlstein, E

    1979-01-01

    The gelatin-binding region of fibronectin has been obtained by subtilisin digestion and cyanogen bromide cleavage of the molecule. Enzymatic digestion yielded two fragments of molecular weights 50,000 (S50K) and 30,000 (S30K) which were isolated by elution from gelatin-Sepharose affinity columns. Because the S50K fragment also mediated the adhesion of fibroblasts to collagen, it contains both the collagen and cell binding sites on the fibronectin molecule. Both fragments had valine as the NH2-terminal residue, were enriched in half-cystine and methionine residues compared to the whole molecule, and were identical by immunodiffusion. The S50K fragment begins with the sequence Val-Tyr-Gln-Pro-Gln-Pro-His-Pro-Gln-Pro-(Pro)-(Gly)-Tyr-Gly-His-( )-Val, a region with an extended conformation which is susceptible to proteolysis and connects this domain to the remainder of the fibronectin molecule. The S50K fragment appears to be located in the COOH-terminal one-third of the fibronectin molecule but does not contain the interchain disulfide bridge(s); the S30K fragment is probably derived from the NH2-terminal region of S50K. Images PMID:116223

  12. Two new γ-pyrone glucosides from Paeonia albiflora.

    PubMed

    Chen, Shao-Dan; Wang, Dong-Mei; Lu, Chuan-Jian; Zhao, Rui-Zhi

    2016-01-01

    Two new γ-pyrone glucosides, along with three known compounds, were isolated from the roots of Paeonia albiflora, and their structures were elucidated by spectral experiments, chemical analysis, and comparison with literature data. The structures of the new compounds were established as 2-(hydroxymethyl)-4-oxo-4H-pyran-3-yl-6-O-α-L-rhamnopyranosyl-β-D-glucopyranoside (1), and 2-(hydroxymethyl)-4-oxo-4H-pyran-3-yl-6-O-galloyl-β-D-glucopyranoside (2). The inhibitory activity on the release of TNF-α of compounds 1-5 was evaluated in vitro. This is the first report of the presence of γ-pyrone glucoside in P. albiflora.

  13. Prenylated xanthone glucosides from Ural's lichen Umbilicaria proboscidea.

    PubMed

    Rezanka, Tomás; Jáchymová, Jitka; Dembitsky, Valery M

    2003-02-01

    Two new compounds isolated from an extract of a Central Asian lichen [Umbilicaria proboscidea (L.) Schrader=Syn.: Gyrophora proboscidea (L.) Ach.] are glucosides with mono- and di-prenylated xanthones as the aglycones and a saccharide moiety from two glucoses linked at C-7. The structures were elucidated on the basis of extensive spectroscopic analysis (1D and 2D NMR, MS, IR and UV) and by hydrolysis.

  14. The glucosidic pathways and glucose production by frog muscle.

    PubMed

    Fournier, P A; Petrof, E O; Guderley, H

    1992-04-25

    Resting muscle is generally perceived as a glucose-utilizing organ; however, we show that resting well-oxygenated frog muscle recovering from strenuous exercise can release significant amounts of glucose. The metabolic pathway responsible for this process does not involve glucose-6-phosphatase because this enzyme is undetectable in frog muscle. The participation of amylo-1,6-glucosidase in the production of glucose is also ruled out since neither marked net phosphorolytic breakdown of glycogen nor considerable cycling between glycogen and glucose 6-phosphate occur. The glucosidic pathways of glycogen breakdown are the likely source of glucose as they are the only metabolic avenues with sufficient capacity to account for the rate at which glucose is released from post-exercised muscle. This rate of glucose production is high enough to be of physiological importance. Our results clearly indicate that to measure lactate glycogenesis in muscle, the simultaneous hydrolysis of muscle glycogen by the glucosidic pathways must be taken into account to prevent marked underestimation of the rate of glycogen synthesis. The glucosidic pathways seem the predominant avenues of glycogen breakdown in post-exercised resting frog muscle and are active enough to account for the rate of glycogen breakdown in resting muscle, suggesting that these rather than the phosphorolytic pathways are the chief routes of glycogen breakdown in resting muscle. PMID:1569076

  15. Acute toxicity of some synthetic cyanogens in rats: time-dependent cyanide generation and cytochrome oxidase inhibition in soft tissues after sub-lethal oral intoxication.

    PubMed

    Rao, Pooja; Singh, Poonam; Yadav, Shiv Kumar; Gujar, Niranjan L; Bhattacharya, Rahul

    2013-09-01

    Cyanogens include complex nitrile-containing compounds that can generate free cyanide of toxicological significance. Acute toxicity, time-dependent cyanide generation and cytochrome oxidase (CYTOX) inhibition in soft tissues, and urinary thiocyanate levels were measured after acute cyanogen intoxication in rats. Order of cyanogens in terms of LD₅₀ was: malononitrile (MCN)>propionitrile (PCN)≈sodium nitroprusside (SNP)>acrylonitrile (ACN)>succinonitrile (SCN)>acetonitrile (ATCN) for oral, and SNP>MCN>ACN>PCN>SCN>ATCN for intraperitoneal and subcutaneous routes. MCN was most toxic by oral (LD₅₀=66.4 mg/kg) and SNP by intraperitoneal (LD₅₀=16.7 mg/kg) and subcutaneous (LD₅₀=11.9 mg/kg) routes. Minimum survival time (25 min) was recorded after 4.0 LD₅₀ ATCN. Order of cyanogens (0.75 LD₅₀; oral) on the basis of maximum blood cyanide and time of peak cyanide generation were: ATCN>SNP>SCN>PCN>MCN>ACN, and MCN (30 min)cyanogens, suitable therapeutic windows can be designed for their management.

  16. Dianthosaponins A-F, triterpene saponins, flavonoid glycoside, aromatic amide glucoside and γ-pyrone glucoside from Dianthus japonicus.

    PubMed

    Nakano, Takahiro; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2011-01-01

    From aerial parts of Dianthus japonicus, six new and seven known oleanane-type triterpene saponins were isolated. The structures of the new saponins, named dianthosaponins A-F, were elucidated by means of high resolution mass spectrometry, and extensive inspection of one- and two-dimensional NMR spectroscopic data. A new C-glycosyl flavone, a glycosidic derivative of anthranilic acid amide and a maltol glucoside were also isolated.

  17. Absolute Line Intensities in the 2ν 02 Band of Cyanogen Chloride at 12.8 μm

    NASA Astrophysics Data System (ADS)

    Lepère, Muriel; Blanquet, Ghislain; Walrand, Jacques

    2000-05-01

    Absolute line intensities were measured at high resolution with a tunable diode laser. This work concerns the 2ν02 band of cyanogen chloride ClCN in the region 780 cm-1. Thirty-two absorption lines were recorded for the isotopomer 35ClCN and 26 lines for 37ClCN. From the analysis of these lines, we determined the bandstrengths: S0v = 19.14 cm-2 atm-1 for 35ClCN and S0v = 17.84 cm-2 atm-1 for 37ClCN.

  18. Guaiane-type sesquiterpenoid glucosides from Gardenia jasminoides Ellis.

    PubMed

    Yu, Yang; Gao, Hao; Dai, Yi; Xiao, Gao-Keng; Zhu, Hua-Jie; Yao, Xin-Sheng

    2011-05-01

    Two new guaiane-type sesquiterpenoid glucosides (1 and 2) were isolated from the fruit of Gardenia jasminoides Ellis. Their structures were elucidated to be (1R,7R,10S)-11-O-β-D-glucopyranosyl-4-guaien-3-one (1) and (1R,7R,10S)-7-hydroxy-11-O-β-D-glucopyranosyl-4-guaien-3-one (2) by one- and two-dimensional NMR techniques ((1)H NMR, (13)C NMR, HSQC, HMBC and NOESY), MS, CD spectrometry and chemical methods. PMID:21491483

  19. Synergic actions of polyphenols and cyanogens of peanut seed coat (Arachis hypogaea) on cytological, biochemical and functional changes in thyroid.

    PubMed

    Chandra, Amar K; Mondal, Chiranjit; Sinha, Sabyasachi; Chakraborty, Arijit; Pearce, Elizabeth N

    2015-03-01

    In animals, long-term feeding with peanut (Arachis hypogaea) seed coats causes hypertrophy and hyperplasia of the thyroid gland. However, to date there have been no detailed studies. Here, we explored the thyroidal effects of dietary peanut seed coats (PSC) in rats. The PSC has high levels of pro-goitrogenic substances including phenolic and other cyanogenic constituents. The PSC was mixed with a standard diet and fed to rats for 30 and 60 days, respectively. Animals fed with the PSC-supplemented diet showed a significant increase in urinary excretion of thiocyanate and iodine, thyroid enlargement, and hypertrophy and/or hyperplasia of thyroid follicles. In addition, there was inhibition of thyroid peroxidase (TPO) activity, 5'-deiodinase-I (DIO1) activity, and (Na+-K+)-ATPase activity in the experimental groups of rats as compared to controls. Furthermore, the PSC fed animals exhibited decreased serum circulating total T4 and T3 levels, severe in the group treated for longer duration. These data indicate that PSC could be a novel disruptor of thyroid function, due to synergistic actions of phenolic as well as cyanogenic constituents. PMID:25872244

  20. Synergic actions of polyphenols and cyanogens of peanut seed coat (Arachis hypogaea) on cytological, biochemical and functional changes in thyroid.

    PubMed

    Chandra, Amar K; Mondal, Chiranjit; Sinha, Sabyasachi; Chakraborty, Arijit; Pearce, Elizabeth N

    2015-03-01

    In animals, long-term feeding with peanut (Arachis hypogaea) seed coats causes hypertrophy and hyperplasia of the thyroid gland. However, to date there have been no detailed studies. Here, we explored the thyroidal effects of dietary peanut seed coats (PSC) in rats. The PSC has high levels of pro-goitrogenic substances including phenolic and other cyanogenic constituents. The PSC was mixed with a standard diet and fed to rats for 30 and 60 days, respectively. Animals fed with the PSC-supplemented diet showed a significant increase in urinary excretion of thiocyanate and iodine, thyroid enlargement, and hypertrophy and/or hyperplasia of thyroid follicles. In addition, there was inhibition of thyroid peroxidase (TPO) activity, 5'-deiodinase-I (DIO1) activity, and (Na+-K+)-ATPase activity in the experimental groups of rats as compared to controls. Furthermore, the PSC fed animals exhibited decreased serum circulating total T4 and T3 levels, severe in the group treated for longer duration. These data indicate that PSC could be a novel disruptor of thyroid function, due to synergistic actions of phenolic as well as cyanogenic constituents.

  1. Anomericity of T-2 toxin-glucoside: masked mycotoxin in cereal crops.

    PubMed

    McCormick, Susan P; Kato, Takayuki; Maragos, Chris M; Busman, Mark; Lattanzio, Veronica M T; Galaverna, Gianni; Dall-Asta, Chiara; Crich, David; Price, Neil P J; Kurtzman, Cletus P

    2015-01-21

    T-2 toxin is a trichothecene mycotoxin produced when Fusarium fungi infect grains, especially oats and wheat. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal in livestock. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called masked mycotoxins, which are a potential food safety concern because they are not detectable by standard approaches and may be converted back to the parent toxin during digestion or food processing. The work reported here addresses four aspects of T-2 toxin-glucosides: phytotoxicity, stability after ingestion, antibody detection, and the anomericity of the naturally occurring T-2 toxin-glucoside found in cereal plants. T-2 toxin-β-glucoside was chemically synthesized and compared to T-2 toxin-α-glucoside prepared with Blastobotrys muscicola cultures and the T-2 toxin-glucoside found in naturally contaminated oats and wheat. The anomeric forms were separated chromatographically and differ in both NMR and mass spectrometry. Both anomers were significantly degraded to T-2 toxin and HT-2 toxin under conditions that mimic human digestion, but with different kinetics and metabolic end products. The naturally occurring T-2 toxin-glucoside from plants was found to be identical to T-2 toxin-α-glucoside prepared with B. muscicola. An antibody test for the detection of T-2 toxin was not effective for the detection of T-2 toxin-α-glucoside. This anomer was produced in sufficient quantity to assess its animal toxicity.

  2. Glucosides from MBOA and BOA detoxification by Zea mays and Portulaca oleracea.

    PubMed

    Hofmann, Diana; Knop, Mona; Hao, Huang; Hennig, Lothar; Sicker, Dieter; Schulz, Margot

    2006-01-01

    Incubation of Zea mays cv. Nicco seedlings with 6-methoxybenzoxazolin-2(3H)-one (MBOA) led to a minor detoxification product hitherto only found in Poaceae. This new compound was identified as 1-(2-hydroxy-4-methoxyphenylamino)-1-deoxy-beta-glucoside 1,2-carbamate (1) (methoxy glucoside carbamate) and represents an analogue to the previously described 1-(2-hydroxyphenylamino)-1-deoxy-beta-glucoside 1,2-carbamate (glucoside carbamate) from benzoxazolin-2(3H)-one (BOA). In Portulaca oleracea var. sativa cv. Gelber treatment with BOA resulted in further unknown detoxification products, which were not synthesized in detectable amounts after BOA absorption in all other species tested. Compound 1 easily undergoes decay into BOA-5-O-glucoside (2). Z. mays seedlings, known to produce BOA-6-O-Glc on incubation with BOA, are able to transform BOA-5-OH into BOA-5-O-glucoside (2). Besides the known compounds, maize contained a formerly unseen product that accumulated during late stages of the detoxification process. It was isolated and identified as 1-(2-hydroxyphenylamino)-6-O-malonyl-1-deoxy-beta-glucoside 1,2-carbamate (3) (malonyl glucoside carbamate).

  3. Water-soluble constituents of caraway: carvone derivatives and their glucosides.

    PubMed

    Matsumura, Tetsuko; Ishikawa, Toru; Kitajima, Junichi

    2002-01-01

    Nine monoterpenoids related to carvone and seven glucosides were isolated from the water-soluble portion of the methanolic extract of the caraway (fruit of Carum carvi L.), and their structures were clarified by spectral investigation. Among them, eight monoterpenoids and six glucosides were new.

  4. Citrus limonin glucoside supplementation decreased biomarkers of liver disease in overweight human subjects

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Orange juice and mixtures of citrus limonoid glucosides isolated from orange juice or its byproducts demonstrated health benefits in human and animal studies. However, the risks and benefits of purified limonin glucoside (LG) in humans are unknown. Aim of this study was to determine the safety and m...

  5. Anomericity of T-2 Toxin-glucoside: Masked Mycotoxin in Cereal Crops

    PubMed Central

    2015-01-01

    T-2 toxin is a trichothecene mycotoxin produced when Fusarium fungi infect grains, especially oats and wheat. Ingestion of T-2 toxin contaminated grain can cause diarrhea, hemorrhaging, and feed refusal in livestock. Cereal crops infected with mycotoxin-producing fungi form toxin glycosides, sometimes called masked mycotoxins, which are a potential food safety concern because they are not detectable by standard approaches and may be converted back to the parent toxin during digestion or food processing. The work reported here addresses four aspects of T-2 toxin-glucosides: phytotoxicity, stability after ingestion, antibody detection, and the anomericity of the naturally occurring T-2 toxin-glucoside found in cereal plants. T-2 toxin-β-glucoside was chemically synthesized and compared to T-2 toxin-α-glucoside prepared with Blastobotrys muscicola cultures and the T-2 toxin-glucoside found in naturally contaminated oats and wheat. The anomeric forms were separated chromatographically and differ in both NMR and mass spectrometry. Both anomers were significantly degraded to T-2 toxin and HT-2 toxin under conditions that mimic human digestion, but with different kinetics and metabolic end products. The naturally occurring T-2 toxin-glucoside from plants was found to be identical to T-2 toxin-α-glucoside prepared with B. muscicola. An antibody test for the detection of T-2 toxin was not effective for the detection of T-2 toxin-α-glucoside. This anomer was produced in sufficient quantity to assess its animal toxicity. PMID:25520274

  6. Enzymatic Synthesis of Apigenin Glucosides by Glucosyltransferase (YjiC) from Bacillus licheniformis DSM 13

    PubMed Central

    Gurung, Rit Bahadur; Kim, Eun-Hee; Oh, Tae-Jin; Sohng, Jae Kyung

    2013-01-01

    Apigenin, a member of the flavone subclass of flavonoids, has long been considered to have various biological activities. Its glucosides, in particular, have been reported to have higher water solubility, increased chemical stability, and enhanced biological activities. Here, the synthesis of apigenin glucosides by the in vitro glucosylation reaction was successfully performed using a UDP-glucosyltransferase YjiC, from Bacillus licheniformis DSM 13. The glucosylation has been confirmed at the phenolic groups of C-4′ and C-7 positions ensuing apigenin 4′-O-glucoside, apigenin 7-O-glucoside and apigenin 4′,7-O-diglucoside as the products leaving the C-5 position unglucosylated. The position of glucosylation and the chemical structures of glucosides were elucidated by liquid chromatography/mass spectroscopy and nuclear magnetic resonance spectroscopy. The parameters such as pH, UDP glucose concentration and time of incubation were also analyzed during this study. PMID:24170092

  7. Biochemical, oxidative and histological changes caused by sub-acute oral exposure of some synthetic cyanogens in rats: ameliorative effect of α-ketoglutarate.

    PubMed

    Bhattacharya, Rahul; Rao, Pooja; Singh, Poonam; Yadav, Shiv Kumar; Upadhyay, Preeti; Malla, Sandhya; Gujar, Niranjan Laxman; Lomash, Vinay; Pant, Satish Chandra

    2014-05-01

    Time-dependent cyanide generation and acute toxicity of six different cyanogens were reported earlier, out of which malononitrile (MCN), propionitrile (PCN), and sodium nitroprusside (SNP) were found to be very toxic. We report here 14 d sub-acute toxicity of MCN, PCN, and SNP (oral; 1/10 LD50 daily) in female rats, and its amelioration by α-ketoglutarate (α-KG; oral; 5.26 mmol/kg; +5 min), a potential cyanide antidote. Significant decrease in white blood cells (PCN, SNP), platelets count (PCN), and blood glucose levels (MCN, PCN, SNP) was accompanied by elevated levels of alanine aminotransferase, lactate dehydrogenase (MCN, PCN, SNP), and aspartate aminotransferase (PCN, SNP). Oxidative damage was evidenced by diminished total antioxidant status in plasma and enhanced malondialdehyde levels in liver and kidney. This was accompanied by diminished levels of reduced glutathione, glutathione peroxidase, glutathione reductase, superoxide dismutase, and catalase in the brain, liver and kidney. We also observed increased levels of blood cyanide and thiocyanate, together with inhibition of cytochrome c oxidase and thiosulfate-sulfur transferase activities in total brain and liver homogenate, respectively. Cyanogens also produced several histological changes in all the organs studied. Post-treatment with α-KG significantly abrogated the toxicity of cyanogens, indicating its utility as an antidote for long-term cyanogen exposure.

  8. Amaranthin in feather cockscombs is synthesized via glucuronylation at the cyclo-DOPA glucoside step in the betacyanin biosynthetic pathway.

    PubMed

    Sasaki, Nobuhiro; Abe, Yutaka; Wada, Katsuhiro; Koda, Takatoshi; Goda, Yukihiro; Adachi, Taiji; Ozeki, Yoshihiro

    2005-12-01

    Uridine 5'-diphosphate (UDP)-glucuronic acid: cyclo-DOPA 5-glucoside glucuronosyltransferase activity was detected in a crude extract prepared from the purple flowers of feather cockscombs. This suggests that the glucuronic acid moiety of amaranthin and its derivatives may be introduced at the cyclo-DOPA glucoside step, but not at the betanidin glucoside step.

  9. A molecular and biochemical analysis of the structure of the cyanogenic beta-glucosidase (linamarase) from cassava (Manihot esculenta Cranz).

    PubMed

    Hughes, M A; Brown, K; Pancoro, A; Murray, B S; Oxtoby, E; Hughes, J

    1992-06-01

    The cyanogenic beta-glucosidase (linamarase) of cassava is responsible for the first step in the sequential break-down of two related cyanoglucosides. Hydrolysis of these cyanoglucosides occurs following tissue damage and leads to the production of hydrocyanic acid. This mechanism is widely regarded as a defense mechanism against predation. A linamarase cDNA clone (pCAS5) was isolated from a cotyledon cDNA library using a white clover beta-glucosidase heterologous probe. The nucleotide and derived amino acid sequence is reported and five putative N-asparagine glycosylation sites are identified. Concanavalin A affinity chromatography and endoglycosidase H digestion demonstrate that linamarase from cassava is glycosylated, having high-mannose-type N-asparagine-linked oligosaccharides. Consistent with this structure and the extracellular location of the active enzyme is the identification of an N-terminal signal peptide on the deduced amino acid sequence of pCAS5. PMID:1586156

  10. Three new lignan glucosides from the roots of Scutellaria baicalensis

    PubMed Central

    Long, Hailin; Zhang, Haijing; Deng, Anjun; Ma, Lin; Wu, Lianqiu; Li, Zhihong; Zhang, Zhihui; Wang, Wenjie; Jiang, Jiandong; Qin, Hailin

    2016-01-01

    Three new lignan glucosides, baicalensinosides A–C (1–3), were isolated from the roots of Scutellaria baicalensis. The structural elucidation was achieved by in-depth spectroscopic examinations and qualitative chemical test. Structurally, these compounds belong to the 3,4-dibenzyltetrahydrofuran-type lignan glycoside with a mono-hydroxyl substitution at the 7′-position of benzylidene group on the numbering system of lignans being one of their shared critical features. The anti-osteoporotic activity of the isolated compounds was assessed in an in vitro osteoprotegerin (OPG) transcriptional activity assay using dual luciferase reporter detection. At 10 μmol/L, compounds 1–3 increased the relative activating ratio of OPG transcription to 1.83, 0.84 and 0.98 times that of the control group, respectively. PMID:27175334

  11. Officinalioside, a new lignan glucoside from Borago officinalis L.

    PubMed

    Samy, Mamdouh Nabil; Hamed, Ashraf Nageeb El-Sayed; Sugimoto, Sachiko; Otsuka, Hideaki; Kamel, Mohamed Salah; Matsunami, Katsuyoshi

    2016-01-01

    A new lignan glucoside, officinalioside (1), was isolated from n-BuOH fraction of the aerial parts of Borago officinalis L., together with four known compounds: actinidioionoside (2), roseoside (3), crotalionoside C (4) and kaempferol 3-O-β-D-galactopyranoside (5). The structure of the new compound was established by means of spectroscopic and chemical analyses. Compounds 1 and 2 showed a moderate DPPH radical scavenging activity (IC50: 52.6 ± 1.70 and 41.3 ± 0.25 μM, respectively) comparable with that of the standard trolox (16.6 ± 2.2 μM) without any significant cytotoxicity towards human cell line A549 (IC50 > 100 μM). PMID:26382913

  12. Four new neolignan glucosides from the fruits of Arctium lappa.

    PubMed

    Huang, Xiao-Ying; Feng, Zi-Ming; Yang, Ya-Nan; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2015-05-01

    Four new neolignan glucosides named (7S, 8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan-9'-O-β-d-apiofuranosyl-(1 → 6)-O-β-d-glucopyranoside (1), (8R)-4,9,9'-trihydroxy-3,3'-dimethoxy-7-oxo-8-O-4'-neolignan-4-O-β-d-glucopyranoside (2), (7R, 8S)-dihydrodehydrodiconiferyl alcohol-7'-oxo-4-O-β-d-glucopyranoside (3), and (7'S, 8'R, 8S)-4,4',9'-trihydroxy-3,3'-dimethoxy-7',9-epoxylignan-7-oxo-4-O-β-d-glucopyranoside (4) were isolated from the fruits of Arctium lappa L. Their structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with known analogues in the literature.

  13. Four new neolignan glucosides from the fruits of Arctium lappa.

    PubMed

    Huang, Xiao-Ying; Feng, Zi-Ming; Yang, Ya-Nan; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2015-05-01

    Four new neolignan glucosides named (7S, 8R)-4,7,9,9'-tetrahydroxy-3,3'-dimethoxy-8-O-4'-neolignan-9'-O-β-d-apiofuranosyl-(1 → 6)-O-β-d-glucopyranoside (1), (8R)-4,9,9'-trihydroxy-3,3'-dimethoxy-7-oxo-8-O-4'-neolignan-4-O-β-d-glucopyranoside (2), (7R, 8S)-dihydrodehydrodiconiferyl alcohol-7'-oxo-4-O-β-d-glucopyranoside (3), and (7'S, 8'R, 8S)-4,4',9'-trihydroxy-3,3'-dimethoxy-7',9-epoxylignan-7-oxo-4-O-β-d-glucopyranoside (4) were isolated from the fruits of Arctium lappa L. Their structures and absolute configurations were elucidated on the basis of comprehensive spectroscopic analyses (UV, IR, HR-ESI-MS, 1D and 2D NMR, CD), as well as by comparison with known analogues in the literature. PMID:25978776

  14. Officinalioside, a new lignan glucoside from Borago officinalis L.

    PubMed

    Samy, Mamdouh Nabil; Hamed, Ashraf Nageeb El-Sayed; Sugimoto, Sachiko; Otsuka, Hideaki; Kamel, Mohamed Salah; Matsunami, Katsuyoshi

    2016-01-01

    A new lignan glucoside, officinalioside (1), was isolated from n-BuOH fraction of the aerial parts of Borago officinalis L., together with four known compounds: actinidioionoside (2), roseoside (3), crotalionoside C (4) and kaempferol 3-O-β-D-galactopyranoside (5). The structure of the new compound was established by means of spectroscopic and chemical analyses. Compounds 1 and 2 showed a moderate DPPH radical scavenging activity (IC50: 52.6 ± 1.70 and 41.3 ± 0.25 μM, respectively) comparable with that of the standard trolox (16.6 ± 2.2 μM) without any significant cytotoxicity towards human cell line A549 (IC50 > 100 μM).

  15. Olive leaf components apigenin 7-glucoside and luteolin 7-glucoside direct human hematopoietic stem cell differentiation towards erythroid lineage.

    PubMed

    Samet, Imen; Villareal, Myra O; Motojima, Hideko; Han, Junkyu; Sayadi, Sami; Isoda, Hiroko

    2015-06-01

    The generation of blood cellular components from hematopoietic stem cells is important for the therapy of a broad spectrum of hematological disorders. In recent years, several lines of evidence suggested that certain nutrients, vitamins and flavonoids may have important roles in controlling the stem cell fate decision by maintaining their self-renewal or stimulating the lineage-specific differentiation. In this study, main olive leaf phytochemicals oleuropein (Olp), apigenin 7-glucoside (Api7G) and luteolin 7-glucoside (Lut7G) were investigated for their potential effects on hematopoietic stem cell differentiation using both phenotypic and molecular analysis. Oleuropein and the combination of the three compounds enhanced the differentiation of CD34+ cells into myelomonocytic cells and lymphocytes progenitors and inhibited the commitment to megakaryocytic and erythroid lineages. Treatment with Lut7G stimulated both the erythroid and the myeloid differentiation, while treatment with Api7G specifically induced the differentiation of CD34+ cells towards the erythroid lineage and inhibited the myeloid differentiation. Erythroid differentiation induced by Api7G and Lut7G treatments was confirmed by the increase in hemoglobin genes expressions (α-hemoglobin, β-hemoglobin and γ-hemoglobin) and erythroid transcription factor GATA1 expression. As revealed by microarray analysis, the mechanisms underlying the erythroid differentiation-inducing effect of Api7G on hematopoietic stem cells involves the activation of JAK/STAT signaling pathway. These findings prove the differentiation-inducing effects of olive leaf compounds on hematopoietic stem cells and highlight their potential use in the ex vivo generation of blood cells.

  16. Olive leaf components apigenin 7-glucoside and luteolin 7-glucoside direct human hematopoietic stem cell differentiation towards erythroid lineage.

    PubMed

    Samet, Imen; Villareal, Myra O; Motojima, Hideko; Han, Junkyu; Sayadi, Sami; Isoda, Hiroko

    2015-06-01

    The generation of blood cellular components from hematopoietic stem cells is important for the therapy of a broad spectrum of hematological disorders. In recent years, several lines of evidence suggested that certain nutrients, vitamins and flavonoids may have important roles in controlling the stem cell fate decision by maintaining their self-renewal or stimulating the lineage-specific differentiation. In this study, main olive leaf phytochemicals oleuropein (Olp), apigenin 7-glucoside (Api7G) and luteolin 7-glucoside (Lut7G) were investigated for their potential effects on hematopoietic stem cell differentiation using both phenotypic and molecular analysis. Oleuropein and the combination of the three compounds enhanced the differentiation of CD34+ cells into myelomonocytic cells and lymphocytes progenitors and inhibited the commitment to megakaryocytic and erythroid lineages. Treatment with Lut7G stimulated both the erythroid and the myeloid differentiation, while treatment with Api7G specifically induced the differentiation of CD34+ cells towards the erythroid lineage and inhibited the myeloid differentiation. Erythroid differentiation induced by Api7G and Lut7G treatments was confirmed by the increase in hemoglobin genes expressions (α-hemoglobin, β-hemoglobin and γ-hemoglobin) and erythroid transcription factor GATA1 expression. As revealed by microarray analysis, the mechanisms underlying the erythroid differentiation-inducing effect of Api7G on hematopoietic stem cells involves the activation of JAK/STAT signaling pathway. These findings prove the differentiation-inducing effects of olive leaf compounds on hematopoietic stem cells and highlight their potential use in the ex vivo generation of blood cells. PMID:26299581

  17. Regioselective glucosidation of trans-resveratrol in Escherichia coli expressing glucosyltransferase from Phytolacca americana.

    PubMed

    Ozaki, Shin-ichi; Imai, Hiroya; Iwakiri, Tomoya; Sato, Takehiro; Shimoda, Kei; Nakayama, Toru; Hamada, Hiroki

    2012-03-01

    A glucosyltransferase (GT) of Phytolacca americana (PaGT3) was expressed in Escherichia coli and purified for the synthesis of two O-β-glucoside products of trans-resveratrol. The reaction was moderately regioselective with a ratio of 4'-O-β-glucoside: 3-O-β-glucoside at 10:3. We used not only the purified enzyme but also the E. coli cells containing the PaGT3 gene for the synthesis of glycoconjugates. E. coli cell cultures also have other advantages, such as a shorter incubation time compared with cultured plant cells, no need for the addition of exogenous glucosyl donor compounds such as UDP-glucose, and almost complete conversion of the aglycone to the glucoside products. Furthermore, a homology model of PaGT3 and mutagenesis studies suggested that His-20 would be a catalytically important residue.

  18. Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.

    PubMed

    Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

    2002-06-01

    The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis. PMID:12031432

  19. Isolation of gibberellin A8-glucoside from shoot apices of Althaea rosea.

    PubMed

    Harada, H; Yokota, T

    1970-03-01

    Gibberellin A8-glucoside has been isolated from shoot apices of Althaea rosea. It showed a weak growth-promoting activity on rice seedlings and oat mesocotyl sections but did not induce germination of lettuce seeds in darkness.

  20. Small intestinal hydrolysis of plant glucosides: higher glucohydrolase activities in rodents than passerine birds.

    PubMed

    Lessner, Krista M; Dearing, M Denise; Izhaki, Ido; Samuni-Blank, Michal; Arad, Zeev; Karasov, William H

    2015-09-01

    Glycosides are a major group of plant secondary compounds characterized by one or more sugars conjugated to a lipophilic, possibly toxic aglycone, which is released upon hydrolysis. We compared small intestinal homogenate hydrolysis activity of three rodent and two avian species against four substrates: amygdalin and sinigrin, two plant-derived glucosides, the sugar lactose, whose hydrolysis models some activity against flavonoid and isoflavonoid glucosides, and the disaccharide sugar maltose (from starch), used as a comparator. Three new findings extend our understanding of physiological processing of plant glucosides: (1) the capacity of passerine birds to hydrolyze plant glucosides seems relatively low, compared with rodents; (2) in this first test of vertebrates' enzymic capacity to hydrolyze glucosinolates, sinigrin hydrolytic capacity seems low; (3) in laboratory mice, hydrolytic activity against lactose resides on the enterocytes' apical membrane facing the intestinal lumen, but activity against amygdalin seems to reside inside enterocytes.

  1. Thesinine-4'-O-beta-D-glucoside the first glycosylated plant pyrrolizidine alkaloid from Borago officinalis.

    PubMed

    Herrmann, Martina; Joppe, Holger; Schmaus, Gerhard

    2002-06-01

    The glycosylated pyrrolizidine alkaloid, thesinine-4'-O-beta-D-glucoside, has been isolated from the aqueous methanol extract of dried, defatted seeds of Borago officinalis (Boraginaceae). The structure was established by means of spectroscopic and chemical analysis.

  2. Quantification of nitropropanoyl glucosides in karaka nuts before and after treatment.

    PubMed

    MacAskill, J J; Manley-Harris, M; Field, Richard J

    2015-05-15

    A high performance liquid chromatography (HPLC) method was developed to assay nitropropanoyl glucosides in the nuts of karaka (Corynocarpus laevigatus) a traditional food of New Zealand Māori. Levels of glucosides, measured as 3-nitropropanoic acid, ranged from 50.25 to 138.62 g kg(-1) (5.0-13.9% w/w) and were highest in nuts from unripe drupes; these levels are higher than any previously reported. Other parts of the drupe also contained nitropropanoyl glucosides but at lower levels than the nut. Treatment procedures to remove the glucosides from the nuts varied in their efficacy with soxhlet extraction removing 98.7% and prolonged boiling and cold water extraction both removing 96%. These findings confirm the traditional methods for preparation of these nuts for consumption.

  3. Soy isoflavone aglycones are absorbed faster and in higher amounts than their glucosides in humans.

    PubMed

    Izumi, T; Piskula, M K; Osawa, S; Obata, A; Tobe, K; Saito, M; Kataoka, S; Kubota, Y; Kikuchi, M

    2000-07-01

    Isoflavones are contained in soybean or soy foods in two chemical forms, i.e., aglycones and glucosides. We investigated the difference in the absorption of soy isoflavone aglycones and glucosides in humans. After a single, low dose intake (0.11 mmol), the highest isoflavone concentrations in plasma were reached 2 and 4 h after ingestion of aglycones and glucosides, respectively; subjects were four men (41 y old) and four women (45 y old). The highest plasma concentration after aglycone intake was more than two times greater than that after glucoside ingestion. In a similar manner, we then compared the plasma isoflavone concentration profiles after intake of a single, high dose of isoflavones (1.7 mmol) in eight subjects (four men, 40 y old; four women, 47 y old) and found the highest plasma concentration after aglycone intake was more than five times higher than that after glucoside intake. In both high and low dose intake tests, the plasma concentration of genistein was significantly higher than that of daidzein despite the similar levels of intake. After long-term (4 wk) intakes (0.30 mmol/d), we also measured the plasma concentration of isoflavones (eight men, 45 y old). After 2 and 4 wk, these concentrations remained >100% higher after ingestion of aglycones than of glucosides. The isoflavone aglycones were absorbed faster and in greater amounts than their glucosides in humans. Isoflavone aglycone-rich products may be more effective than glucoside-rich products in preventing chronic disease such as coronary heart disease.

  4. Growth inhibitory activity of cucurbitacin glucosides isolated from Citrullus colocynthis on human breast cancer cells.

    PubMed

    Tannin-Spitz, Tehila; Grossman, Shlomo; Dovrat, Sara; Gottlieb, Hugo E; Bergman, Margalit

    2007-01-01

    Our aim was to study the effects of cucurbitacin glucosides extracted from Citrullus colocynthis leaves on human breast cancer cell growth. Leaves were extracted, resulting in the identification of cucurbitacin B/E glucosides. The cucurbitacin glucoside combination (1:1) inhibited growth of ER(+) MCF-7 and ER(-) MDA-MB-231 human breast cancer cell lines. Cell-cycle analysis showed that treatment with isolated cucurbitacin glucoside combination resulted in accumulation of cells at the G(2)/M phase of the cell cycle. Treated cells showed rapid reduction in the level of the key protein complex necessary to the regulation of G(2) exit and initiation of mitosis, namely the p34(CDC2)/cyclin B1 complex. cucurbitacin glucoside treatment also caused changes in the overall cell morphology from an elongated form to a round-shaped cell, which indicates that cucurbitacin treatment caused impairment of actin filament organization. This profound morphological change might also influence intracellular signaling by molecules such as PKB, resulting in inhibition in the transmission of survival signals. Reduction in PKB phosphorylation and inhibition of survivin, an anti-apoptosis family member, was observed. The treatment caused elevation in p-STAT3 and in p21(WAF), proven to be a STAT3 positive target in absence of survival signals. Cucurbitacin glucoside treatment also induced apoptosis, as measured by Annexin V/propidium iodide staining and by changes in mitochondrial membrane potential (DeltaPsi) using a fluorescent dye, JC-1. We suggest that cucurbitacin glucosides exhibit pleiotropic effects on cells, causing both cell cycle arrest and apoptosis. These results suggest that cucurbitacin glucosides might have therapeutic value against breast cancer cells.

  5. New α-glucosides of caffeoyl quinic acid from the leaves of Moringa oleifera Lam.

    PubMed

    Kashiwada, Yoshiki; Ahmed, Fakhruddin Ali; Kurimoto, Shin-ichiro; Kim, Sang-Yong; Shibata, Hirofumi; Fujioka, Toshihiro; Takaishi, Yoshihisa

    2012-01-01

    Two new caffeoyl quinic acid α-glucosides, together with three known caffeoyl quinic acids and five known flavonoid glucosides, were isolated from the leaves of Moringa oleifera Lam. The structures of the new compounds were elucidated as 4-O-(4'-O-α-D-glucopyranosyl)-caffeoyl quinic acid (1) and 4-O-(3'-O-α-D-glucopyranosyl)-caffeoyl quinic acid (2) by spectroscopic analyses.

  6. The cyanogenic syndrome in rubber tree Hevea brasiliensis: tissue-damage-dependent activation of linamarase and hydroxynitrile lyase accelerates hydrogen cyanide release

    PubMed Central

    Kadow, Daniel; Voß, Karsten; Selmar, Dirk; Lieberei, Reinhard

    2012-01-01

    Background and Aims The release of hydrogen cyanide (HCN) from injured plant tissue affects multiple ecological interactions. Plant-derived HCN can act as a defence against herbivores and also plays an important role in plant–pathogen interactions. Crucial for activity as a feeding deterrent is the amount of HCN generated per unit time, referred to as cyanogenic capacity (HCNc). Strong intraspecific variation in HCNc has been observed among cyanogenic plants. This variation, in addition to genotypic variability (e.g. in Trifolium repens), can result from modifications in the expression level of the enzymes involved in either cyanogenic precursor formation or HCN release (as seen in Sorghum bicolor and Phaseolus lunatus). Thus, a modification or modulation of HCNc in reaction to the environment can only be achieved from one to the next generation when under genetic control and within days or hours when transcriptional regulations are involved. In the present study, it is shown that in rubber tree (Hevea brasiliensis) HCNc is modulated by post-translational activity regulation of the key enzymes for cyanide release. Methods Linamarase (LIN) and hydroxynitrile lyase (HNL) activity was determined by colorimetric assays utilizing dissociation of the substrates p-nitrophenyl-β-d-glucopyranoside and acetone cyanohydrin, respectively. Key Results In rubber tree leaves, LIN and HNL show up to ten-fold increased activity in response to tissue damage. This enzyme activation occurs within seconds and results in accelerated HCN formation. It is restricted to the damaged leaf area and depends on the severity of tissue damage. Conclusions LIN and HNL activation (in contrast to genetic and transcriptional regulations) allows an immediate, local and damage type-dependent modulation of the cyanogenic response. Accordingly, this post-translational activation plays a decisive role in the defence of H. brasiliensis against herbivores as well as pathogens and may allow more flexible

  7. Low Toxicity of Deoxynivalenol-3-Glucoside in Microbial Cells

    PubMed Central

    Suzuki, Tadahiro; Iwahashi, Yumiko

    2015-01-01

    Host plants excrete a glucosylation enzyme onto the plant surface that changes mycotoxins derived from fungal secondary metabolites to glucosylated products. Deoxynivalenol-3-glucoside (DON3G) is synthesized by grain uridine diphosphate-glucosyltransferase, and is found worldwide, although information on its toxicity is lacking. Here, we conducted growth tests and DNA microarray analysis to elucidate the characteristics of DON3G. The Saccharomyces cerevisiae PDR5 mutant strain exposed to DON3G demonstrated similar growth to the dimethyl sulfoxide control, and DNA microarray analysis revealed limited differences. Only 10 genes were extracted, and the expression profile of stress response genes was similar to that of DON, in contrast to metabolism genes like SER3, which encodes 3-phosphoglycerate dehydrogenase. Growth tests with Chlamydomonas reinhardtii also showed a similar growth rate to the control sample. These results suggest that DON3G has extremely low toxicity to these cells, and the glucosylation of mycotoxins is a useful protective mechanism not only for host plants, but also for other species. PMID:25609182

  8. The β-Glucosidases Responsible for Bioactivation of Hydroxynitrile Glucosides in Lotus japonicus1[W

    PubMed Central

    Morant, Anne Vinther; Bjarnholt, Nanna; Kragh, Mads Emil; Kjærgaard, Christian Hauge; Jørgensen, Kirsten; Paquette, Suzanne Michelle; Piotrowski, Markus; Imberty, Anne; Olsen, Carl Erik; Møller, Birger Lindberg; Bak, Søren

    2008-01-01

    Lotus japonicus accumulates the hydroxynitrile glucosides lotaustralin, linamarin, and rhodiocyanosides A and D. Upon tissue disruption, the hydroxynitrile glucosides are bioactivated by hydrolysis by specific β-glucosidases. A mixture of two hydroxynitrile glucoside-cleaving β-glucosidases was isolated from L. japonicus leaves and identified by protein sequencing as LjBGD2 and LjBGD4. The isolated hydroxynitrile glucoside-cleaving β-glucosidases preferentially hydrolyzed rhodiocyanoside A and lotaustralin, whereas linamarin was only slowly hydrolyzed, in agreement with measurements of their rate of degradation upon tissue disruption in L. japonicus leaves. Comparative homology modeling predicted that LjBGD2 and LjBGD4 had nearly identical overall topologies and substrate-binding pockets. Heterologous expression of LjBGD2 and LjBGD4 in Arabidopsis (Arabidopsis thaliana) enabled analysis of their individual substrate specificity profiles and confirmed that both LjBGD2 and LjBGD4 preferentially hydrolyze the hydroxynitrile glucosides present in L. japonicus. Phylogenetic analyses revealed a third L. japonicus putative hydroxynitrile glucoside-cleaving β-glucosidase, LjBGD7. Reverse transcription-polymerase chain reaction analysis showed that LjBGD2 and LjBGD4 are expressed in aerial parts of young L. japonicus plants, while LjBGD7 is expressed exclusively in roots. The differential expression pattern of LjBGD2, LjBGD4, and LjBGD7 corresponds to the previously observed expression profile for CYP79D3 and CYP79D4, encoding the two cytochromes P450 that catalyze the first committed step in the biosyntheis of hydroxynitrile glucosides in L. japonicus, with CYP79D3 expression in aerial tissues and CYP79D4 expression in roots. PMID:18467457

  9. Grappling the High Altitude for Safe Edible Bamboo Shoots with Rich Nutritional Attributes and Escaping Cyanogenic Toxicity

    PubMed Central

    Waikhom, Sayanika Devi; Louis, Bengyella; Sharma, Chandradev K.; Kumari, Pushpa; Somkuwar, Bharat G.; Singh, Mohendro W.; Talukdar, Narayan C.

    2013-01-01

    Consumption of bamboo species with high level of total cyanogenic content (TCC) in Asia by many ethnic groups is significantly associated with food poisoning and occasionally Konzo (a neurological disorder). Adequate characterization of edible bamboo species with low level of TCC and high nutritious attributes is required for consumer's safety as well as for the conservation of the gene pool. Here, we employed morphological descriptors, atomic absorption spectrophotometer, RAPD, and trnL-F intergenic spacer to characterize 15 indigenous edible bamboo species of north-east India. The study indicates that morphologically and genetically evolved edible bamboo species having large and robust bamboo-shoot texture and growing at low altitude contain high level of TCC, low antioxidant properties, and low levels of beneficial macronutrients and micronutrients. Importantly, Dendrocalamus species are shown to be rich in TCC irrespective of the growing altitude while Bambusa species are found to have moderate level of TCC. The findings clearly demonstrated that Chimonobambusa callosa growing at high altitude represents safe edible bamboo species with nutritious attributes. PMID:24350255

  10. Daily bursts of biogenic cyanogen bromide (BrCN) control biofilm formation around a marine benthic diatom

    PubMed Central

    Vanelslander, Bart; Paul, Carsten; Grueneberg, Jan; Prince, Emily K.; Gillard, Jeroen; Sabbe, Koen; Pohnert, Georg; Vyverman, Wim

    2012-01-01

    The spatial organization of biofilms is strongly regulated by chemical cues released by settling organisms. However, the exact nature of these interactions and the repertoire of chemical cues and signals that micro-organisms produce and exude in response to the presence of competitors remain largely unexplored. Biofilms dominated by microalgae often show remarkable, yet unexplained fine-scale patchy variation in species composition. Because this occurs even in absence of abiotic heterogeneity, antagonistic interactions might play a key role. Here we show that a marine benthic diatom produces chemical cues that cause chloroplast bleaching, a reduced photosynthetic efficiency, growth inhibition and massive cell death in naturally co-occurring competing microalgae. Using headspace solid phase microextraction (HS-SPME)-GC-MS, we demonstrate that this diatom exudes a diverse mixture of volatile iodinated and brominated metabolites including the natural product cyanogen bromide (BrCN), which exhibits pronounced allelopathic activity. Toxin production is light-dependent with a short BrCN burst after sunrise. BrCN acts as a short-term signal, leading to daily “cleaning” events around the algae. We show that allelopathic effects are H2O2 dependent and link BrCN production to haloperoxidase activity. This strategy is a highly effective means of biofilm control and may provide an explanation for the poorly understood role of volatile halocarbons from marine algae, which contribute significantly to the atmospheric halocarbon budget. PMID:22308324

  11. Implementation of New TPD Analysis Techniques in the Evaluation of Second Order Desorption Kinetics of Cyanogen from Cu(001)

    SciTech Connect

    Hinch, B.J.; Senanayake, S.; Ciftlikli, E.Z.; Lee, E.Y.M.; Lallo, J.; Rangan, S.

    2010-12-21

    The interactions of cyanide species with a copper (001) surface were studied with temperature programmed desorption (TPD) and X-ray photoelectron spectroscopy (XPS). Adsorbed cyanide species (CN{sub (a)}) undergo recombinative desorption evolving molecular cyanogen (C{sub 2}N{sub 2}). As the adsorbed CN species charge upon adsorption, mutually repulsive dipolar interactions lead to a marked desorption energy reduction with increasing CN{sub (a)} coverages. Two new TPD analysis approaches were developed, which used only accurately discernible observables and which do not assume constant desorption energies, E{sub d}, and pre-exponential values, v. These two approaches demonstrated a linear variation of E{sub d} with instantaneous coverage. The first approach involved an analysis of the variations of desorption peak asymmetry with initial CN coverages. The second quantitative approach utilized only temperatures and intensities of TPD peaks, together with deduced surface coverages at the peak maxima, also as a function of initial surface coverages. Parameters derived from the latter approach were utilized as initial inputs for a comprehensive curve fit analysis technique. Excellent fits for all experimental desorption curves were produced in simulations. The curve fit analysis confirms that the activation energy of desorption of 170-180 kJ/mol at low coverage decreases by up to 14-15 kJ/mol at CN saturation.

  12. Implementation of New TPD Analysis Techniques in the Evaluation of Second Order Desorption Kinetics of Cyanogen from Cu(001)

    SciTech Connect

    E Ciftlikli; E Lee; J Lallo; S Rangan; S Senanayake; B Hinch

    2011-12-31

    The interactions of cyanide species with a copper (001) surface were studied with temperature programmed desorption (TPD) and X-ray photoelectron spectroscopy (XPS). Adsorbed cyanide species (CN{sub (a)}) undergo recombinative desorption evolving molecular cyanogen (C{sub 2}N{sub 2}). As the adsorbed CN species charge upon adsorption, mutually repulsive dipolar interactions lead to a marked desorption energy reduction with increasing CN{sub (a)} coverages. Two new TPD analysis approaches were developed, which used only accurately discernible observables and which do not assume constant desorption energies, E{sub d}, and pre-exponential values, v. These two approaches demonstrated a linear variation of E{sub d} with instantaneous coverage. The first approach involved an analysis of the variations of desorption peak asymmetry with initial CN coverages. The second quantitative approach utilized only temperatures and intensities of TPD peaks, together with deduced surface coverages at the peak maxima, also as a function of initial surface coverages. Parameters derived from the latter approach were utilized as initial inputs for a comprehensive curve fit analysis technique. Excellent fits for all experimental desorption curves were produced in simulations. The curve fit analysis confirms that the activation energy of desorption of 170-180 kJ/mol at low coverage decreases by up to 14-15 kJ/mol at CN saturation.

  13. Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers.

    PubMed

    Boyer, Jeanelle; Brown, Dan; Liu, Rui Hai

    2004-11-17

    Evidence suggests that regular consumption of fruits and vegetables may reduce the risk of chronic diseases, and phytochemicals from fruits and vegetables may be responsible for this health benefit. However, there is limited knowledge on the bioavailability of specific phytochemicals from whole fruits and vegetables. This study used Caco-2 cells to examine uptake of quercetin aglycon and quercetin 3-glucoside as purified compounds and from whole onion and apple peel extracts. Pure quercetin aglycon was absorbed by the Caco-2 cells in higher concentrations than quercetin 3-glucoside (p < 0.05). Caco-2 cells treated with quercetin 3-glucoside accumulated both quercetin 3-glucoside and quercetin. Caco-2 cells absorbed more onion quercetin aglycon than onion quercetin 3-glucoside (p < 0.05), and the percentage of onion quercetin absorbed was greater than that of pure quercetin, most likely due to enzymatic hydrolysis of quercetin 3-glucoside and other quercetin glucosides found in the onion by the Caco-2 cells. Caco-2 cells absorbed low levels of quercetin 3-glucoside from apple peel extracts, but quercetin aglycon absorption was not detected. Caco-2 cell homogenates demonstrated both lactase and glucosidase activities when incubated with lactose and quercetin 3-glucoside, respectively. This use of the Caco2 cell model appears to be a simple and useful system for studying bioavailability of whole food phytochemicals and may be used to assess differences in bioavailability between foods. PMID:15537334

  14. Uptake of quercetin and quercetin 3-glucoside from whole onion and apple peel extracts by Caco-2 cell monolayers.

    PubMed

    Boyer, Jeanelle; Brown, Dan; Liu, Rui Hai

    2004-11-17

    Evidence suggests that regular consumption of fruits and vegetables may reduce the risk of chronic diseases, and phytochemicals from fruits and vegetables may be responsible for this health benefit. However, there is limited knowledge on the bioavailability of specific phytochemicals from whole fruits and vegetables. This study used Caco-2 cells to examine uptake of quercetin aglycon and quercetin 3-glucoside as purified compounds and from whole onion and apple peel extracts. Pure quercetin aglycon was absorbed by the Caco-2 cells in higher concentrations than quercetin 3-glucoside (p < 0.05). Caco-2 cells treated with quercetin 3-glucoside accumulated both quercetin 3-glucoside and quercetin. Caco-2 cells absorbed more onion quercetin aglycon than onion quercetin 3-glucoside (p < 0.05), and the percentage of onion quercetin absorbed was greater than that of pure quercetin, most likely due to enzymatic hydrolysis of quercetin 3-glucoside and other quercetin glucosides found in the onion by the Caco-2 cells. Caco-2 cells absorbed low levels of quercetin 3-glucoside from apple peel extracts, but quercetin aglycon absorption was not detected. Caco-2 cell homogenates demonstrated both lactase and glucosidase activities when incubated with lactose and quercetin 3-glucoside, respectively. This use of the Caco2 cell model appears to be a simple and useful system for studying bioavailability of whole food phytochemicals and may be used to assess differences in bioavailability between foods.

  15. The synthesis and antitumor activity of twelve galloyl glucosides.

    PubMed

    Li, Chang-Wei; Dong, Hua-Jin; Cui, Cheng-Bin

    2015-01-27

    Twelve galloyl glucosides 1-12, showing diverse substitution patterns with two or three galloyl groups, were synthesized using commercially available, low-cost D-glucose and gallic acid as starting materials. Among them, three compounds, methyl 3,6-di-O-galloyl-α-D-glucopyranoside (9), ethyl 2,3-di-O-galloyl-α-D-glucopyranoside (11) and ethyl 2,3-di-O-galloyl-β-D-glucopyranoside (12), are new compounds and other six, 1,6-di-O-galloyl-β-D-glucopyranose (1), 1,4,6-tri-O-galloyl-β-D-glucopyranose (2), 1,2-di-O-galloyl-β-D-glucopyranose (3), 1,3-di-O-galloyl-β-D-glucopyranose (4), 1,2,3-tri-O-galloyl-α-D-glucopyranose (6) and methyl 3,4,6-tri-O-galloyl-α-D-glucopyranoside (10), were synthesized for the first time in the present study. In in vitro MTT assay, 1-12 inhibited human cancer K562, HL-60 and HeLa cells with inhibition rates ranging from 64.2% to 92.9% at 100 μg/mL, and their IC50 values were determined to be varied in 17.2-124.7 μM on the tested three human cancer cell lines. In addition, compounds 1-12 inhibited murine sarcoma S180 cells with inhibition rates ranging from 38.7% to 52.8% at 100 μg/mL in the in vitro MTT assay, and in vivo antitumor activity of 1 and 2 was also detected in murine sarcoma S180 tumor-bearing Kunming mice using taxol as positive control.

  16. Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in rats.

    PubMed

    Nagl, Veronika; Schwartz, Heidi; Krska, Rudolf; Moll, Wulf-Dieter; Knasmüller, Siegfried; Ritzmann, Mathias; Adam, Gerhard; Berthiller, Franz

    2012-09-18

    Deoxynivalenol-3-β-D-glucoside (D3G), a plant metabolite of the Fusarium mycotoxin deoxynivalenol (DON), might be hydrolyzed in the digestive tract of mammals, thus contributing to the total dietary DON exposure of individuals. Yet, D3G has not been considered in regulatory limits set for DON for foodstuffs due to the lack of in vivo data. The aim of our study was to evaluate whether D3G is reactivated in vivo by investigation of its metabolism in rats. Six Sprague-Dawley rats received water, DON (2.0 mg/kg body weight (b.w.)) and the equimolar amount of D3G (3.1 mg/kg b.w.) by gavage on day 1, 8 and 15, respectively. Urine and feces were collected for 48 h and analyzed for D3G, DON, deoxynivalenol-glucuronide (DON-GlcA) and de-epoxy deoxynivalenol (DOM-1) by a validated LC-tandem mass spectrometry (MS/MS) based biomarker method. After administration of D3G, only 3.7±0.7% of the given dose were found in urine in the form of analyzed analytes, compared to 14.9±5.0% after administration of DON, and only 0.3±0.1% were detected in the form of urinary D3G. The majority of administered D3G was recovered as DON and DOM-1 in feces. These results suggest that D3G is little bioavailable, hydrolyzed to DON during digestion, and partially converted to DOM-1 and DON-GlcA prior to excretion. Our data indicate that D3G is of considerably lower toxicological relevance than DON, at least in rats.

  17. Enzyme bread improvers affect the stability of deoxynivalenol and deoxynivalenol-3-glucoside during breadmaking.

    PubMed

    Vidal, Arnau; Ambrosio, Asier; Sanchis, Vicente; Ramos, Antonio J; Marín, Sonia

    2016-10-01

    The stability of deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON-3-glucoside) during the breadmaking process was studied. Some enzymes used in the bakery industry were examined to evaluate their effects on DON and DON-3-glucoside. The level of DON in breads without added enzymes was reduced (17-21%). Similarly, the addition of cellulase, protease, lipase and glucose-oxidase did not modify this decreasing trend. The effect of xylanase and α-amylase on DON content depended on the fermentation temperature. These enzymes reduced the DON content by 10-14% at 45°C. In contrast, at 30°C, these enzymes increased the DON content by 13-23%. DON-3-glucoside levels decreased at the end of fermentation, with a final reduction of 19-48% when no enzymes were used. However, the presence of xylanase, α-amylase, cellulase and lipase resulted in bread with greater quantities of DON-3-glucoside when fermentation occurred at 30°C. The results showed that wheat bran and flour may contain hidden DON that may be enzymatically released during the breadmaking process when the fermentation temperature is close to 30°C. PMID:27132852

  18. [Research on the separation of limonoid glucosides by reversed-phase preparative high performance liquid chromatography].

    PubMed

    Tian, Q G; Dai, J; Ding, X L

    2000-03-01

    Obacunone-17-beta-D-glucopyranoside (OG) was isolated from the seeds of Citrus Sinensis Osbeck by using solvent extraction, classical polymer adsorption column separation and weak base anion ion-exchange separation, OG was finally purified by C18 reversed-phase preparative high performance liquid chromatography and was identified by thin-layer chromatography. The purity of OG was analyzed by analytical reversed-phase HPLC. At last the structure of OG was determined by 1H and 13C nuclear magnetic resonance spectrometry (NMR). In this work, the conditions of the reversed-phase preparative HPLC technique to purify limonoid glucosides was optimized. The reversed-phase preparative HPLC on a C18 column with a mobile phase of acidic acetonitrile-water (about 0.2% TFA, V/V) at pH 3 enabled the baseline separation of limonoid glucosides in the extract. The results show that OG is the predominant limonoid glucoside in the seeds of Citrus Sinensis Osbeck and nomilin glucoside is the second one. The results also show that the classical polymer adsorption column separation and weak base anion ion-exchange separation are effective for purifying limonoid glucosides.

  19. Enzyme bread improvers affect the stability of deoxynivalenol and deoxynivalenol-3-glucoside during breadmaking.

    PubMed

    Vidal, Arnau; Ambrosio, Asier; Sanchis, Vicente; Ramos, Antonio J; Marín, Sonia

    2016-10-01

    The stability of deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON-3-glucoside) during the breadmaking process was studied. Some enzymes used in the bakery industry were examined to evaluate their effects on DON and DON-3-glucoside. The level of DON in breads without added enzymes was reduced (17-21%). Similarly, the addition of cellulase, protease, lipase and glucose-oxidase did not modify this decreasing trend. The effect of xylanase and α-amylase on DON content depended on the fermentation temperature. These enzymes reduced the DON content by 10-14% at 45°C. In contrast, at 30°C, these enzymes increased the DON content by 13-23%. DON-3-glucoside levels decreased at the end of fermentation, with a final reduction of 19-48% when no enzymes were used. However, the presence of xylanase, α-amylase, cellulase and lipase resulted in bread with greater quantities of DON-3-glucoside when fermentation occurred at 30°C. The results showed that wheat bran and flour may contain hidden DON that may be enzymatically released during the breadmaking process when the fermentation temperature is close to 30°C.

  20. Purification and structure determination of glucosides of capsaicin and dihydrocapsaicin from various Capsicum fruits.

    PubMed

    Higashiguchi, Fumiharu; Nakamura, Hiroyasu; Hayashi, Hideo; Kometani, Takashi

    2006-08-01

    Two new glucosides, capsaicin-beta-D-glucopyranoside (1) and dihydrocapsaicin-beta-D-glucopyranoside (2), were discovered in the fruit of the Capsicum annuum cultivar 'High Heat'. They were sequentially purified by acetone extraction, n-hexane extraction, and acetonitrile extraction, followed by medium-pressure liquid chromatography and high-performance liquid chromatography performed on an octadecylsilane column. Their chemical structures were elucidated by proton nuclear magnetic resonance, carbon nuclear magnetic resonance, and hydrolysis with alpha- and beta-glucosidases. The glucosides were also detected in various pungent cultivars of C. annuum, Capsicum frutescens, and Capsicum chinense by liquid chromatography-mass spectrometry. However, they were not detected in nonpungent cultivars of C. annuum. Furthermore, a positive correlation was observed between the quantity of the capsaicinoids, capsaicin, and dihydrocapsaicin and their glucosides.

  1. Metabolism of the masked mycotoxin deoxynivalenol-3-glucoside in pigs.

    PubMed

    Nagl, Veronika; Woechtl, Bettina; Schwartz-Zimmermann, Heidi Elisabeth; Hennig-Pauka, Isabel; Moll, Wulf-Dieter; Adam, Gerhard; Berthiller, Franz

    2014-08-17

    Plants can metabolize the Fusarium mycotoxin deoxynivalenol (DON) by forming the masked mycotoxin deoxynivalenol-3-β-D-glucoside (D3G). D3G might be cleaved during digestion, thus increasing the total DON burden of an individual. Due to a lack of in vivo data, D3G has not been included in the various regulatory limits established for DON so far. The aim of our study was to contribute to the risk assessment of D3G by determination of its metabolism in pigs. Four piglets received water, D3G (116 μg/kg b.w.) and the equimolar amount of DON (75 μg/kg b.w.) by gavage on day 1, 5 and 9 of the experiment, respectively. Additionally, 15.5 μg D3G/kg b.w. were administered intravenously on day 13. Urine and feces were collected for 24 h and analyzed for DON, D3G, deoxynivalenol-3-glucuronide (DON-3-GlcA), deoxynivalenol-15-GlcA (DON-15-GlcA) and deepoxy-deoxynivalenol (DOM-1) by UHPLC-MS/MS. After oral application of DON and D3G, in total 84.8±9.7% and 40.3±8.5% of the given dose were detected in urine, respectively. The majority of orally administered D3G was excreted in form of DON, DON-15-GlcA, DOM-1 and DON-3-GlcA, while urinary D3G accounted for only 2.6±1.4%. In feces, just trace amounts of metabolites were found. Intravenously administered D3G was almost exclusively excreted in unmetabolized form via urine. Data indicate that D3G is nearly completely hydrolyzed in the intestinal tract of pigs, while the toxin seems to be rather stable after systemic absorption. Compared to DON, the oral bioavailability of D3G and its metabolites seems to be reduced by a factor of up to 2, approximately.

  2. C-Terminal Protein Characterization by Mass Spectrometry: Isolation of C-Terminal Fragments from Cyanogen Bromide-Cleaved Protein

    PubMed Central

    Nika, Heinz; Hawke, David H.; Angeletti, Ruth Hogue

    2014-01-01

    A sample preparation method for protein C-terminal peptide isolation from cyanogen bromide (CNBr) digests has been developed. In this strategy, the analyte was reduced and carboxyamidomethylated, followed by CNBr cleavage in a one-pot reaction scheme. The digest was then adsorbed on ZipTipC18 pipette tips for conjugation of the homoserine lactone-terminated peptides with 2,2′-dithiobis (ethylamine) dihydrochloride, followed by reductive release of 2-aminoethanethiol from the derivatives. The thiol-functionalized internal and N-terminal peptides were scavenged on activated thiol sepharose, leaving the C-terminal peptide in the flow-through fraction. The use of reversed-phase supports as a venue for peptide derivatization enabled facile optimization of the individual reaction steps for throughput and completeness of reaction. Reagents were replaced directly on the support, allowing the reactions to proceed at minimal sample loss. By this sequence of solid-phase reactions, the C-terminal peptide could be recognized uniquely in mass spectra of unfractionated digests by its unaltered mass signature. The use of the sample preparation method was demonstrated with low-level amounts of a whole, intact model protein. The C-terminal fragments were retrieved selectively and efficiently from the affinity support. The use of covalent chromatography for C-terminal peptide purification enabled recovery of the depleted material for further chemical and/or enzymatic manipulation. The sample preparation method provides for robustness and simplicity of operation and is anticipated to be expanded to gel-separated proteins and in a scaled-up format to high-throughput protein profiling in complex biological mixtures. PMID:24688319

  3. Further characterization and regulation of malonyl-coenzyme A: flavonoid glucoside malonyltransferases from parsley cell suspension cultures

    SciTech Connect

    Matern, U.; Feser, C.; Hammer, D.

    1983-10-01

    Two malonyltransferases, malonyl-CoA:flavone/flavonol 7-O-glucoside malonyltransferase and malonyl-CoA:flavonol 3-O-glucoside malonyltransferase, were purified to apparent homogeneity from uv-irradiated parsley cell cultures. Both purified enzymes appear to be specific for flavonoid glycosides. Additional malonyltransferases, active toward several phenol glucosides other than flavonoids, were present in partially purified 7-O-glucoside malonyltransferase preparations. Antibodies raised against the purified 3-O-glucoside malonyltransferase did not inhibit the activity of the 7-O-glucoside malonyltransferase over a wide antibody concentration range. Determination of the rate of synthesis in vivo of the 3-O-glucoside malonyltransferase after ultraviolet light-pulse induction of parsley cells revealed two maxima at 6 and 30 h, respectively. These results indicate that the induced changes in 3-O-glucoside malonyltransferase activity were the consequence of either a repeated change in the rate of synthesis of one enzyme species or changes in the synthesis rates of more than one enzyme species.

  4. Metabolic utilization of pyridoxine-beta-glucoside in rats: influence of vitamin B-6 status and route of administration

    SciTech Connect

    Trumbo, P.R.; Gregory, J.F. 3d.

    1988-11-01

    (3H)5'-O-(beta-D-glucopyranosyl) pyridoxine (PN-glucoside) and (14C)pyridoxine (PN) were administered orally or intraperitoneally to vitamin B-6-adequate or -deficient rats. Analysis of intestinal contents and feces indicated effective intestinal absorption of PN-glucoside relative to PN. There was greater retention of 14C than 3H in the liver and carcass regardless of the route of administration of the radiolabeled vitamins. There was no major difference in the relative distribution of 3H and 14C among the vitamin B-6 metabolites in the liver between the treatment groups, and no (3H)PN-glucoside was detected in any of the livers. For all groups, the majority of the 3H administered was detected in the urine within 24 h. Less excretion of both 3H and 14C in the urine was observed for the deficient rats. There was no major difference in the relative proportion of urinary (3H)PN-glucoside or (3H)4-PA between rats fed or injected with the radiolabeled vitamins. These results indicate that vitamin B-6 status influences the clearance of metabolites derived from PN and PN-glucoside, as well as the clearance of intact PN-glucoside. Vitamin B-6 status, however, has little or no effect on the utilization of PN-glucoside. This study also suggests that the intestine is the primary site of the limited conversion of PN-glucoside to biologically active PN in the rat.

  5. Genotoxic activity in vivo of the naturally occurring glucoside, cycasin, in the Drosophila wing spot test.

    PubMed

    Kawai, K; Furukawa, H; Hirono, I

    1995-03-01

    Cycasin, methylazoxymethanol-beta-glucoside, is a naturally occurring carcinogenic compound. The genotoxicity of cycasin was assayed in the Drosophila wing spot test. Cycasin induced small single and large single spots on feeding at 10 mumol/g medium. The presence of these spots indicates that cycasin is genotoxic in Drosophila melanogaster. Microorganisms which showed beta-glucosidase activity for cleaving cycasin to toxic aglycon were isolated from gut flora of the Drosophila larvae. Consequently, the Drosophila wing spot test would be useful for mutagenicity screening of other naturally occurring glucosides.

  6. N-Glucosides as human sodium-dependent glucose cotransporter 2 (hSGLT2) inhibitors.

    PubMed

    Yamamoto, Yasuo; Kawanishi, Eiji; Koga, Yuichi; Sakamaki, Shigeki; Sakamoto, Toshiaki; Ueta, Kiichiro; Matsushita, Yasuaki; Kuriyama, Chiaki; Tsuda-Tsukimoto, Minoru; Nomura, Sumihiro

    2013-10-15

    Inhibition of renal sodium-dependent glucose cotransporter 2 (SGLT2) increases urinary glucose excretion (UGE), and thus reduces blood glucose levels in hyperglycemia. A series of N-glucosides was synthesized for biological evaluation as human SGLT2 (hSGLT2) inhibitors. Among these compounds, N-glucoside 9d possessing an indole core structure showed good in vitro activity (IC50=7.1 nM against hSGLT2). Furthermore, 9d exhibited favorable in vivo potency with regard to UGE in rats based on good pharmacokinetic profiles. PMID:23999047

  7. [Study on antioxidant activity of two major secoiridoid glucosides in the fruits of Ligustrum lucidum Ait].

    PubMed

    Li, Yang; Zuo, Yan; Sun, Wen-Ji

    2007-05-01

    The antioxidant effects of two major secoiridoid glucosides (nuezhenoside and G13, separated in our laboratory) from Fructus Ligustri Lucidi had already been assayed though DPPH radicals, respectively. The results revealed that these ingredients showed significant antioxidant activities. A positive correlation existed between total content and antioxidant activity. G13 had shown higher antioxidant activity than nuezhenoside. It implied that the structure of secoiridoid glucoside was postitive to antioxidant activity. Otherwise, the results could promote the deep research of Furctus Ligustri Lucidi on antioxidant mechanism. PMID:17727057

  8. Identification of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside, a postulated intermediate in the biosynthesis of ternatin C5 in the blue petals of Clitoria ternatea (butterfly pea).

    PubMed

    Kazuma, Kohei; Kogawa, Koichiro; Noda, Naonobu; Kato, Naoki; Suzuki, Masahiko

    2004-11-01

    Ternatins are blue anthocyanins found in the petals of Clitoria ternata (butterfly pea). Among them, ternatin C5 (delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3',5'-di-O-beta-glucoside; 2) has the structure common to all the ternatins, which is characterized by its glucosylation pattern: a 3,3',5'-triglucosylated anthocyanidin. In the course of studying biosynthetic pathways of ternatins, the key enzymatic activities to produce ternatin C5 were discovered in a crude enzyme preparation from the petals of a blue petal line of C. ternatea. When this preparation was tested for activity against several delphinidin glycosides, delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside (6), a postulated intermediate, was found in the reaction mixture, together with three known anthocyanins, which were spectroscopically structurally identified. As a result of structural identification, the following enzymatic activities were identified: UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside-3'-O-beta-glucoside 5'-O-glucosyltransferase (5'GT), UDP-glucose :delphinidin 3-O-(6''-O-malonyl)-beta-glucoside 3'-O-glucosyltransferase (3'GT), UDP-glucose :delphinidin 3-O-glucosyltransferase, and malonyl-CoA :delphinidin 3-O-beta-glucoside 6''-malonyltransferase. In a mauve petal line, which did not accumulate ternatins but delphinidin 3-O-(6''-O-malonyl)-beta-glucoside in its petal, there were neither 5'GT nor 3'GT activities. Thus, the early biosynthetic pathway of ternatins may be characterized by the stepwise transfer of two glucose residues to 3'- and 5'-position of delphinidin 3-O-(6''-O-malonyl)-beta-glucoside (1; Scheme) from UDP-glucose. PMID:17191814

  9. Demonstration of long-chain n-alkyl caffeates and delta7-steryl glucosides in the bark of Acacia species by gas chromatography-mass spectrometry.

    PubMed

    Freire, Carmen S R; Silvestre, Armando J D; Neto, Carlos Pascoal

    2007-01-01

    The GC-MS identification of several abundant long-chain aliphatic n-alkyl caffeates, together with other phydroxycinnamic acid esters, in the dichloromethane extracts of the bark of Acacia dealbata and A. melanoxylon, is reported. In addition, the unambiguous differentiation between two delta7-steryl glucosides (namely, spinasteryl glucoside and dihydrospinasteryl glucosides) and the homologous delta5-steryl glucosides was achieved based on the EI-MS fragmentation features of their trimethylsilyl derivatives. PMID:17439016

  10. Purification and functional characterization of the first stilbene glucoside-specific β-glucosidase isolated from Lactobacillus kimchi.

    PubMed

    Ko, Jin-A; Park, J Y; Kwon, H J; Ryu, Y B; Jeong, H J; Park, S J; Kim, C Y; Oh, H M; Park, C S; Lim, Y H; Kim, D; Rho, M C; Lee, W S; Kim, Y M

    2014-12-01

    This study aimed to develop viable enzymes for bioconversion of resveratrol-glucoside into resveratrol. Out of 13 bacterial strains tested, Lactobacillus kimchi JB301 could completely convert polydatin into resveratrol. The purified enzyme had an optimum temperature of 30-40°C and optimum pH of pH 5.0 against polydatin. This enzyme showed high substrate specificities towards different substrates in the following order: isorhaponticin>polydatin>mulberroside A>oxyresveratrol-3-O-glucoside. Additionally, it rarely hydrolyzed astringin and desoxyrhaponticin. Based on these catalytic specificities, we suggest this enzyme be named stilbene glucoside-specific β-glucosidase. Furthermore, polydatin extracts from Polygonum cuspidatum were successfully converted to resveratrol with a high yield (of over 99%). Stilbene glucoside-specific β-glucosidase is the first enzyme isolated from lactic acid bacteria capable of bio-converting various stilbene glucosides into stilbene. PMID:25442950

  11. Purification and functional characterization of the first stilbene glucoside-specific β-glucosidase isolated from Lactobacillus kimchi.

    PubMed

    Ko, Jin-A; Park, J Y; Kwon, H J; Ryu, Y B; Jeong, H J; Park, S J; Kim, C Y; Oh, H M; Park, C S; Lim, Y H; Kim, D; Rho, M C; Lee, W S; Kim, Y M

    2014-12-01

    This study aimed to develop viable enzymes for bioconversion of resveratrol-glucoside into resveratrol. Out of 13 bacterial strains tested, Lactobacillus kimchi JB301 could completely convert polydatin into resveratrol. The purified enzyme had an optimum temperature of 30-40°C and optimum pH of pH 5.0 against polydatin. This enzyme showed high substrate specificities towards different substrates in the following order: isorhaponticin>polydatin>mulberroside A>oxyresveratrol-3-O-glucoside. Additionally, it rarely hydrolyzed astringin and desoxyrhaponticin. Based on these catalytic specificities, we suggest this enzyme be named stilbene glucoside-specific β-glucosidase. Furthermore, polydatin extracts from Polygonum cuspidatum were successfully converted to resveratrol with a high yield (of over 99%). Stilbene glucoside-specific β-glucosidase is the first enzyme isolated from lactic acid bacteria capable of bio-converting various stilbene glucosides into stilbene.

  12. Bioavailability of cyanide after consumption of a single meal of foods containing high levels of cyanogenic glycosides: a crossover study in humans.

    PubMed

    Abraham, Klaus; Buhrke, Thorsten; Lampen, Alfonso

    2016-03-01

    The acute toxicity of cyanide is determined by its peak levels reached in the body. Compared to the ingestion of free cyanide, lower peak levels may be expected after consumption of foods containing cyanogenic glycosides with the same equivalent dose of cyanide. This is due to possible delayed and/or incomplete release of cyanide from the cyanogenic glycosides depending on many factors. Data on bioavailability of cyanide after consumption of foods containing high levels of cyanogenic glycosides as presented herein were necessary to allow a meaningful risk assessment for these foods. A crossover study was carried out in 12 healthy adults who consumed persipan paste (equivalent total cyanide: 68 mg/kg), linseed (220 mg/kg), bitter apricot kernels (about 3250 mg/kg), and fresh cassava roots (76-150 mg/kg), with each "meal" containing equivalents of 6.8 mg cyanide. Cyanide levels were determined in whole blood using a GC-MS method with K(13)C(15)N as internal standard. Mean levels of cyanide at the different time points were highest after consumption of cassava (15.4 µM, after 37.5 min) and bitter apricot kernels (14.3 µM, after 20 min), followed by linseed (5.7 µM, after 40 min) and 100 g persipan (1.3 µM, after 105 min). The double dose of 13.6 mg cyanide eaten with 200 g persipan paste resulted in a mean peak level of 2.9 µM (after 150 min). An acute reference dose of 0.075 mg/kg body weight was derived being valid for a single application/meal of cyanides or hydrocyanic acid as well as of unprocessed foods with cyanogenic glycosides also containing the accompanying intact β-glucosidase. For some of these foods, this approach may be overly conservative due to delayed release of cyanide, as demonstrated for linseed. In case of missing or inactivated β-glucosidase, the hazard potential is much lower. PMID:25708890

  13. Bioavailability of cyanide after consumption of a single meal of foods containing high levels of cyanogenic glycosides: a crossover study in humans.

    PubMed

    Abraham, Klaus; Buhrke, Thorsten; Lampen, Alfonso

    2016-03-01

    The acute toxicity of cyanide is determined by its peak levels reached in the body. Compared to the ingestion of free cyanide, lower peak levels may be expected after consumption of foods containing cyanogenic glycosides with the same equivalent dose of cyanide. This is due to possible delayed and/or incomplete release of cyanide from the cyanogenic glycosides depending on many factors. Data on bioavailability of cyanide after consumption of foods containing high levels of cyanogenic glycosides as presented herein were necessary to allow a meaningful risk assessment for these foods. A crossover study was carried out in 12 healthy adults who consumed persipan paste (equivalent total cyanide: 68 mg/kg), linseed (220 mg/kg), bitter apricot kernels (about 3250 mg/kg), and fresh cassava roots (76-150 mg/kg), with each "meal" containing equivalents of 6.8 mg cyanide. Cyanide levels were determined in whole blood using a GC-MS method with K(13)C(15)N as internal standard. Mean levels of cyanide at the different time points were highest after consumption of cassava (15.4 µM, after 37.5 min) and bitter apricot kernels (14.3 µM, after 20 min), followed by linseed (5.7 µM, after 40 min) and 100 g persipan (1.3 µM, after 105 min). The double dose of 13.6 mg cyanide eaten with 200 g persipan paste resulted in a mean peak level of 2.9 µM (after 150 min). An acute reference dose of 0.075 mg/kg body weight was derived being valid for a single application/meal of cyanides or hydrocyanic acid as well as of unprocessed foods with cyanogenic glycosides also containing the accompanying intact β-glucosidase. For some of these foods, this approach may be overly conservative due to delayed release of cyanide, as demonstrated for linseed. In case of missing or inactivated β-glucosidase, the hazard potential is much lower.

  14. Structural determination of a nivalenol glucoside and development of an analytical method for the simultaneous determination of nivalenol and deoxynivalenol, and their glucosides, in wheat.

    PubMed

    Yoshinari, Tomoya; Sakuda, Shohei; Furihata, Kazuo; Furusawa, Hiroko; Ohnishi, Takahiro; Sugita-Konishi, Yoshiko; Ishizaki, Naoto; Terajima, Jun

    2014-02-01

    Trichothecene mycotoxins such as nivalenol and deoxynivalenol frequently contaminate foodstuffs. Recently, several trichothecene glucosides have been found in trichothecene-contaminated foods, and information about their chemistry, toxicity, and occurrence is required. In this study, a glucoside of nivalenol was isolated from nivalenol-contaminated wheat and was identified as nivalenol-3-O-β-D-glucopyranoside. Analytical methods using a multifunctional column or an immunoaffinity column have been developed for the simultaneous determination of nivalenol, nivalenol-3-O-β-D-glucopyranoside, deoxynivalenol, and deoxynivalenol-3-O-β-D-glucopyranoside in wheat. The methods were validated in a single laboratory, and recovery from wheat samples spiked at four levels ranged between 86.4 and 103.5% for the immunoaffinity column cleanup. These mycotoxins in contaminated wheat samples were quantitated by the validated method. Nivalenol-3-O-β-D-glucopyranoside was detected in the nivalenol-contaminated wheat, and the percentage of nivalenol-3-O-β-D-glucopyranoside to nivalenol ranged from 12 to 27%. This result indicates that the analytical method developed in this study is useful for obtaining data concerning the state and level of food contamination by nivalenol, deoxynivalenol, and their glucosides.

  15. Simultaneous extraction of bioactive limonoid aglycones and glucoside from Citrus aurantium L. using hydrotropy.

    PubMed

    Dandekar, Deepak V; Jayaprakasha, Guddadarangavvanahally K; Patil, Bhimanagouda S

    2008-01-01

    Citrus limonoids were demonstrated to possess potential biological activities in reducing the risk of certain diseases. Limonoids are present in citrus fruits in the form of aglycones and glucosides. At present, limonoid aglycones and limonoid glucosides are extracted in multiple steps using different solvents. In order to understand their potential bioactivity, it may be beneficial to isolate and purify these compounds using environment friendly methods. A new method of extraction and purification of limonoids was established using a hydrotrope polystyrene adsorbent resin. Extraction of aglycones and glucosides was achieved in a single step, using an aqueous solution of sodium cumene sulphonate (Na-CuS). Sour orange (Citrus aurantium L.) seed powder was extracted with 2 M Na-CuS solution at 45 degrees C for 6 h. The filtered extract was diluted with water and loaded on an SP 700 adsorbent column. The column was washed with distilled water to remove the hydrotrope and then eluted using water and methanol in different compositions to obtain three compounds. The structures of the isolated compounds were confirmed by NMR spectroscopy as deacetyl nomilinic acid glucoside (DNAG), deacetyl nomilin (DAN) and limonin (LIM).

  16. Effect of different exposed lights on quercetin and quercetin glucoside content in onion (Allium cepa L.).

    PubMed

    Ko, Eun Young; Nile, Shivraj Hariram; Sharma, Kavita; Li, Guan Hao; Park, Se Won

    2015-07-01

    Quercetin and quercetin glucosides are the major flavonols present in onion (Allium cepa L.) and are predominantly present as quercetin, quercetin-3,4'-diglucoside and quercetin-4'-glucoside. Effect of different light wavelengths on onion after harvest and storage, with fluorescent, blue, red and ultra violet light influenced the quercetin and quercetin glucosides profile. In a peeled onion, all the light treatments elevated quercetin content in bulb. Among them, particularly fluorescent light effect was more eminent which stimulates the maximum synthesis of quercetin in onion. In case of whole onion bulb, skin and pulp showed different responses to light treatment, respectively. The pulp had the highest quercetin glucosides under blue light, whereas the lowest under fluorescent light. Onion skin showed nearly opposite pattern as compared to the pulp. In particular, light treatment proved to be a better way to increase the level of quercetin content in onions which might be utilized for industrial production of bioactive compounds from onion and onion waste products.

  17. Serotonin 5-O-β-Glucoside and Its N-Methylated Forms in Citrus Genus Plants.

    PubMed

    Servillo, Luigi; Giovane, Alfonso; Casale, Rosario; D'Onofrio, Nunzia; Ferrari, Giovanna; Cautela, Domenico; Balestrieri, Maria Luisa; Castaldo, Domenico

    2015-04-29

    Citrus genus is characterized by a specific presence of indole metabolites deriving from the N-methylation of tryptamine and its hydroxylated form, 5-hydroxytryptamine (serotonin), which are likely involved in plant defense mechanisms. In this study, we identified for the first time the occurrence in Citrus plants of serotonin 5-O-β-glucoside and all its N-methylated derivatives, that is, N-methylserotonin 5-O-β-glucoside, N,N-dimethylserotonin (bufotenine) 5-O-β-glucoside, and N,N,N-trimethylserotonin (bufotenidine) 5-O-β-glucoside. The identification of the glucosylated compounds was based on mass spectrometric studies, hydrolysis by glucosidase, and in some cases, comparison to authentic compounds. Beside leaves, the distribution of the glucosylated forms and their aglycones in some Citrus species was evaluated in flavedo, albedo, juice, and seeds. The simultaneous presence of serotonin and its N-methylated derivatives, together with the corresponding glucosylated forms, is consistent with the occurrence of a metabolic pathway, specific for Citrus, aimed at potentiating the defensive response to biotic stress through the optimization of the production and use of the most toxic of such metabolites. PMID:25893818

  18. Water-soluble constituents of caraway: aromatic compound, aromatic compound glucoside and glucides.

    PubMed

    Matsumura, Tetsuko; Ishikawa, Toru; Kitajima, Junichi

    2002-10-01

    From the water-soluble portion of the methanolic extract of caraway (fruit of Carum carvi L.), an aromatic compound, an aromatic compound glucoside and a glucide were isolated together with 16 known compounds. Their structures were clarified as 2-methoxy-2-(4'-hydroxyphenyl)ethanol, junipediol A 2-O-beta-D-glucopyranoside and L-fucitol, respectively.

  19. A new coumarin glucoside, coumarins and alkaloids from Ruta corsica roots.

    PubMed

    Bertrand, Cédric; Fabre, Nicolas; Moulis, Claude

    2004-03-01

    A new coumarin glucoside, 3'(S)-hydroxy-2',2'-dimethyl-dihydropyranocoumarin-8-beta-d-glucopyranosyl, one coumarin, five furanocoumarins, three bicoumarins, three quinoline alkaloids and one sinapoyl sucrose derivative have been isolated from the roots of Ruta corsica.

  20. [Preparation of soybean isoflavone glucosides by reversed-phase high performance liquid chromatography].

    PubMed

    Yang, Xuedong; Deng, Zhicheng; Wang, Jing; Ding, Mingyu

    2006-07-01

    A method was established for the isolation of soybean isoflavone glucosides from the total isoflavone extracts of soybean using preparative reversed-phase high performance liquid chromatography (RP-HPLC). The total isoflavone extracts were separated into four parts by solvent extraction, those are the ethyl acetate extract, butanol extract, precipitate (D4), and the remaining aqueous phase. The part D4 containing soybean isoflavone glucosides was acquired and subjected to preparative HPLC for the isolation of target components. A preparative Nova-Pak HR C18 column (100 mm x 25 mm i. d. , 6 microm) was used in the preparation process. By isocratic elution with methanol-0.1% aqueous acetic acid (23:77, v/v) as the mobile phase at a flow rate of 20 mL/min, followed by concentration and desalination, three soybean isoflavone glucosides were obtained and subsequently identified by mass spectrometry as daidzin, glycitin, and genistin. HPLC analysis showed that the purities of the three soybean isoflavone glucosides were all higher than 99%.

  1. Serotonin 5-O-β-Glucoside and Its N-Methylated Forms in Citrus Genus Plants.

    PubMed

    Servillo, Luigi; Giovane, Alfonso; Casale, Rosario; D'Onofrio, Nunzia; Ferrari, Giovanna; Cautela, Domenico; Balestrieri, Maria Luisa; Castaldo, Domenico

    2015-04-29

    Citrus genus is characterized by a specific presence of indole metabolites deriving from the N-methylation of tryptamine and its hydroxylated form, 5-hydroxytryptamine (serotonin), which are likely involved in plant defense mechanisms. In this study, we identified for the first time the occurrence in Citrus plants of serotonin 5-O-β-glucoside and all its N-methylated derivatives, that is, N-methylserotonin 5-O-β-glucoside, N,N-dimethylserotonin (bufotenine) 5-O-β-glucoside, and N,N,N-trimethylserotonin (bufotenidine) 5-O-β-glucoside. The identification of the glucosylated compounds was based on mass spectrometric studies, hydrolysis by glucosidase, and in some cases, comparison to authentic compounds. Beside leaves, the distribution of the glucosylated forms and their aglycones in some Citrus species was evaluated in flavedo, albedo, juice, and seeds. The simultaneous presence of serotonin and its N-methylated derivatives, together with the corresponding glucosylated forms, is consistent with the occurrence of a metabolic pathway, specific for Citrus, aimed at potentiating the defensive response to biotic stress through the optimization of the production and use of the most toxic of such metabolites.

  2. Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides.

    PubMed

    Wiczkowski, Wieslaw; Romaszko, Jerzy; Bucinski, Adam; Szawara-Nowak, Dorota; Honke, Joanna; Zielinski, Henryk; Piskula, Mariusz K

    2008-05-01

    The lipophilic character of quercetin suggests that it can cross enterocyte membranes via simple diffusion. Therefore, it should be more bioavailable than its glucosides, which require preliminary hydrolysis or active transport for absorption. However, the published human studies show that quercetin is less bioavailable than its glucosides. Assuming that low bioavailability of quercetin aglycone provided to humans as a pure substance is the result of its low solubility in the digestive tract, we studied its bioavailability from dietary sources in which quercetin was dispersed in the food matrix. In a randomized crossover study, 9 volunteers took a single dose of either shallot flesh (99.2% quercetin glucosides and 0.8% quercetin aglycone) or dry shallot skin (83.3% quercetin aglycone and 16.7% quercetin glucosides), providing 1.4 mg quercetin per kg of body weight. Blood samples were collected before and after consumption of shallot preparations. Plasma quercetin was measured on HPLC with electrochemical detection after plasma enzymatic treatment. The maximum plasma quercetin concentration of 1.02 +/- 0.13 micromol/L was reached at 2.33 +/- 0.50 h after shallot flesh consumption compared with 3.95 +/- 0.62 micromol/L at 2.78 +/- 0.15 h after dry skin consumption. The area under the concentration-time curve after dry skin consumption was 47.23 +/- 7.53 micromol x h(-1) x L(-1) and was significantly higher than that after shallot flesh intake (22.23 +/- 2.32 micromol x h(-1) x L(-1)). When provided along with dietary sources, quercetin aglycone is more bioavailable than its glucosides in humans. Results point to the food matrix as a key factor.

  3. Quercetin from shallots (Allium cepa L. var. aggregatum) is more bioavailable than its glucosides.

    PubMed

    Wiczkowski, Wieslaw; Romaszko, Jerzy; Bucinski, Adam; Szawara-Nowak, Dorota; Honke, Joanna; Zielinski, Henryk; Piskula, Mariusz K

    2008-05-01

    The lipophilic character of quercetin suggests that it can cross enterocyte membranes via simple diffusion. Therefore, it should be more bioavailable than its glucosides, which require preliminary hydrolysis or active transport for absorption. However, the published human studies show that quercetin is less bioavailable than its glucosides. Assuming that low bioavailability of quercetin aglycone provided to humans as a pure substance is the result of its low solubility in the digestive tract, we studied its bioavailability from dietary sources in which quercetin was dispersed in the food matrix. In a randomized crossover study, 9 volunteers took a single dose of either shallot flesh (99.2% quercetin glucosides and 0.8% quercetin aglycone) or dry shallot skin (83.3% quercetin aglycone and 16.7% quercetin glucosides), providing 1.4 mg quercetin per kg of body weight. Blood samples were collected before and after consumption of shallot preparations. Plasma quercetin was measured on HPLC with electrochemical detection after plasma enzymatic treatment. The maximum plasma quercetin concentration of 1.02 +/- 0.13 micromol/L was reached at 2.33 +/- 0.50 h after shallot flesh consumption compared with 3.95 +/- 0.62 micromol/L at 2.78 +/- 0.15 h after dry skin consumption. The area under the concentration-time curve after dry skin consumption was 47.23 +/- 7.53 micromol x h(-1) x L(-1) and was significantly higher than that after shallot flesh intake (22.23 +/- 2.32 micromol x h(-1) x L(-1)). When provided along with dietary sources, quercetin aglycone is more bioavailable than its glucosides in humans. Results point to the food matrix as a key factor. PMID:18424596

  4. Iridoid glucosides and p-coumaroyl iridoids from Viburnum luzonicum and their cytotoxicity.

    PubMed

    Fukuyama, Yoshiyasu; Minoshima, Yuka; Kishimoto, Yoshiko; Chen, Ih-Sheng; Takahashi, Hironobu; Esumi, Tomoyuki

    2004-11-01

    Four new iridoids glucosides (1-4) and seven new iridoid aglycons (5-11) bearing (E)- or (Z)-p-coumaroyl groups were isolated from a methanol extract of the dried leaves of Viburnum luzonicum collected in Kaoshiung, Taiwan. The structures of the new compounds, named luzonoside A (1), luzonoside B (2), luzonoside C (3), luzonoside D (4), luzonoid A (5), luzonoid B (6), luzonoid C (7), luzonoid D (8), luzonoid E (9), luzonoid F (10), and luzonoid G (11), were elucidated by analysis of spectroscopic data and comparison with values for previously known analogues. Among the iridoids isolated in the present study, glucosides 1 and 2, and their aglycons 5-9, exhibited moderate inhibitory activity against HeLa S3 cancer cells, whereas 3 and 4 showed no cytotoxicity even at 100 microM.

  5. Exclusive accumulation of Z-isomers of monolignols and their glucosides in bark of Fagus grandifolia

    NASA Technical Reports Server (NTRS)

    Lewis, N. G.; Inciong, E. J.; Ohashi, H.; Towers, G. H.; Yamamoto, E.

    1988-01-01

    In addition to Z-coniferyl and Z-sinapyl alcohols, bark extracts of Fagus grandifolia also contain significant amounts of the glucosides, Z-coniferin, Z-isoconiferin (previously called faguside) and Z-syringin. The corresponding E-isomers of these glucosides do not accumulate to a detectable level. The accumulation of the Z-isomers suggests that either they are not lignin precursors or that they are reservoirs of monolignols for subsequent lignin biosynthesis; it is not possible to distinguish between these alternatives. The co-occurrence of Z-coniferin and Z-isoconiferin demonstrate that glucosylation of monolignols can occur at either the phenolic or the allylic hydroxyl groups.

  6. Effects of caffeoyl conjugates of isoprenyl-hydroquinone glucoside and quinic acid on leukocyte function.

    PubMed

    Góngora, Luis; Giner, Rosa María; Máñez, Salvador; Recio, María del Carmen; Schinella, Guillermo; Ríos, José Luis

    2002-11-01

    The activity of three prenylhydroquinone glucosides (1-3) and four caffeoylquinic esters (4-7), obtained from Phagnalon rupestre, on elastase release, myeloperoxidase activity and superoxide and leukotriene B(4) production from polymorphonuclear leukocytes was determined. 4,5-Dicaffeoylquinic acid strongly inhibited elastase release with an IC(50) value of 4.8 microM. Methylated caffeoylquinic derivatives were the most potent inhibitors of myeloperoxidase (IC(50) near 60 microM), whereas both methylated and free carboxyl isomers inhibited superoxide production with similar potency (IC(50) between 27 and 42 microM). The monocaffeoyl conjugate of prenylhydroquinone glucoside (3), the most potent inhibitor of leukotriene B(4) production (IC(50) = 33 microM), possesses a mixed hydroquinone-caffeoyl character that could be considered as a potential anti-inflammatory entity.

  7. Effective catalytic conversion of cellulose into high yields of methyl glucosides over sulfonated carbon based catalyst.

    PubMed

    Dora, Sambha; Bhaskar, Thallada; Singh, Rawel; Naik, Desavath Viswanatha; Adhikari, Dilip Kumar

    2012-09-01

    An amorphous carbon based catalyst was prepared by sulfonation of the bio-char obtained from fast pyrolysis (N(2) atm; ≈ 550°C) of biomass. The sulfonated carbon catalyst contained high acidity of 6.28 mmol/g as determined by temperature programmed desorption of ammonia of sulfonated carbon catalyst and exhibited high catalytic performance for the hydrolysis of cellulose. Amorphous carbon based catalyst containing -SO(3)H groups was successfully tested and the complete conversion of cellulose in methanol at moderate temperatures with high yields ca. ≥ 90% of α, β-methyl glucosides in short reaction times was achieved. The methyl glucosides formed in methanol are more stable for further conversion than the products formed in water. The carbon catalyst was demonstrated to be stable for five cycles with slight loss in catalytic activity. The utilization of bio-char as a sulfonated carbon catalyst provides a green and efficient process for cellulose conversion. PMID:22776237

  8. Hepatoprotective activity of twelve novel 7'-hydroxy lignan glucosides from Arctii Fructus.

    PubMed

    Yang, Ya-Nan; Huang, Xiao-Ying; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2014-09-17

    Twelve novel 7'-hydroxy lignan glucosides (1-12), including two benzofuran-type neolignans, two 8-O-4' neolignans, two dibenzylbutyrolactone lignans, and six tetrahydrofuranoid lignans, together with six known lignan glucosides (13-18), were isolated from the fruit of Arctium lappa L. (Asteraceae), commonly known as Arctii Fructus. Their structures were elucidated using spectroscopy (1D and 2D NMR, MS, IR, ORD, and UV) and on the basis of chemical evidence. The absolute configurations of compounds 1-12 were confirmed using rotating frame nuclear overhauser effect spectroscopy (ROESY), the circular dichroic (CD) exciton chirality method, and Rh2(OCOCF3)4-induced CD spectrum analysis. All of the isolated compounds were tested for hepatoprotective effects against D-galactosamine-induced cytotoxicity in HL-7702 hepatic cells. Compounds 1, 2, 7-12, and 17 showed significantly stronger hepatoprotective activity than the positive control bicyclol at a concentration of 1 × 10(-5) M.

  9. Hepatoprotective activity of twelve novel 7'-hydroxy lignan glucosides from Arctii Fructus.

    PubMed

    Yang, Ya-Nan; Huang, Xiao-Ying; Feng, Zi-Ming; Jiang, Jian-Shuang; Zhang, Pei-Cheng

    2014-09-17

    Twelve novel 7'-hydroxy lignan glucosides (1-12), including two benzofuran-type neolignans, two 8-O-4' neolignans, two dibenzylbutyrolactone lignans, and six tetrahydrofuranoid lignans, together with six known lignan glucosides (13-18), were isolated from the fruit of Arctium lappa L. (Asteraceae), commonly known as Arctii Fructus. Their structures were elucidated using spectroscopy (1D and 2D NMR, MS, IR, ORD, and UV) and on the basis of chemical evidence. The absolute configurations of compounds 1-12 were confirmed using rotating frame nuclear overhauser effect spectroscopy (ROESY), the circular dichroic (CD) exciton chirality method, and Rh2(OCOCF3)4-induced CD spectrum analysis. All of the isolated compounds were tested for hepatoprotective effects against D-galactosamine-induced cytotoxicity in HL-7702 hepatic cells. Compounds 1, 2, 7-12, and 17 showed significantly stronger hepatoprotective activity than the positive control bicyclol at a concentration of 1 × 10(-5) M. PMID:25180661

  10. Biosynthesis of isoxazolin-5-one and 3-nitropropanoic acid containing glucosides in juvenile Chrysomelina.

    PubMed

    Becker, Tobias; Ploss, Kerstin; Boland, Wilhelm

    2016-07-14

    Stable-isotope-labeled precursors were used to establish the biosynthetic pathway leading from β-alanine towards isoxazolin-5-one glucoside 1 and its 3-nitropropanoate (3-NPA) ester 2 in Chrysomelina larvae. Both structural elements originate from sequestered plant-derived β-alanine or from propanoyl-CoA that is derived from the degradation of some essential amino acids, e.g. valine. β-Alanine is converted into 3-NPA and isoxazolinone 5 by consecutive oxidations of the amino group of β-Ala. Substituting the diphospho group of α-UDP-glucose with 5 generates the isoxazolin-5-one glucoside 1, which serves in the circulating hemolymph of the larva as a platform for esterification with 3-nitropropanoyl-CoA. The pathway was validated with larvae of Phaedon cochleariae, Chrysomela populi as well as Gastrophysa viridula. PMID:27272952

  11. Purunusides A-C, alpha-glucosidase inhibitory homoisoflavone glucosides from Prunus domestica.

    PubMed

    Kosar, Shaheen; Fatima, Itrat; Mahmood, Azhar; Ahmed, Rehana; Malik, Abdul; Talib, Sumaira; Chouhdary, Muhammad Iqbal

    2009-12-01

    Purunusides A-C (1-3), new homoisoflavone glucosides together with the known compounds beta-sitosterol (4) and 6,7-methylenedioxy-8-methoxycoumarin (5) have been isolated from n-butanol and ethyl acetate soluble fractions of Prunus domestica. Their structures were assigned on the basis of spectral studies. The compounds 1-3 showed potent inhibitory activity against the enzyme alpha-glucosidase.

  12. New isopimarane diterpene and new cineole type glucoside from Nepeta prattii.

    PubMed

    Hou, Zhen-Fu; Tu, Yong-Qiang; Li, Yu

    2002-04-01

    Together with sixteen known compounds, a new isopimarane diterpene (prattol) and a new cineole type glucoside were isolated from Nepeta prattii. Their structures were elucidated on the basis of spectral methods as isopimar-15-en-3 beta,8 beta,20-triol, and (1R, 2R, 4S)-1,8-epoxy-p-methan-2-O-beta-D-glucopyranosyl(1-->6)-beta- D-glucopyranoside.

  13. Three important amino acids control the regioselectivity of flavonoid glucosidation in glycosyltransferase-1 from Bacillus cereus.

    PubMed

    Chiu, Hsi-Ho; Hsieh, Yin-Cheng; Chen, Ya-Huei; Wang, Hsin-Ying; Lu, Chia-Yu; Chen, Chun-Jung; Li, Yaw-Kuen

    2016-10-01

    Glycosyltransferase-1 from Bacillus cereus (BcGT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type BcGT1. Preliminary assays demonstrated that the F240A mutant significantly improves the regioselectivity of enzymatic glucosidation toward quercetin. To unveil and further to control the catalytic function of BcGT1, mutation of F240 to other amino acids, such as C, E, G, R, Y, W, and K, was performed. Among these mutants, F240A, F240G, F240R, and F240K greatly altered the regioselectivity. The quercetin-3-O-glucoside, instead of quercetin-7-O-glucoside as for the wild-type enzyme, was obtained as the major product. Among these mutants, F240R showed nearly 100 % product specificity but only retained 25 % catalytic efficiency of wild-type enzyme. From an inspection of the protein structure, we found two other amino acids, F132 and F138, together with F240, are likely to form a hydrophobic binding region, which is sufficiently spacious to accommodate substrates with varied aromatic moieties. Through the replacement of a phenylalanine by a tyrosine residue in the substrate-binding region, the mutants may be able to fix the orientation of flavonoids, presumably through the formation of a hydrogen bond between substrates and mutants. Multiple mutants-F240R_F132Y, F240R_F138Y, and F240R_F132Y_F138Y-were thus constructed for further investigation. The multiple points of mutants not only maintained the high product specificity but also significantly improved the catalytic efficiency, relative to F240R. The same product specificity was obtained when kaempferol and myricetin were used as a substrate. PMID:27198725

  14. Three important amino acids control the regioselectivity of flavonoid glucosidation in glycosyltransferase-1 from Bacillus cereus.

    PubMed

    Chiu, Hsi-Ho; Hsieh, Yin-Cheng; Chen, Ya-Huei; Wang, Hsin-Ying; Lu, Chia-Yu; Chen, Chun-Jung; Li, Yaw-Kuen

    2016-10-01

    Glycosyltransferase-1 from Bacillus cereus (BcGT1) catalyzes a reaction that transfers a glucosyl moiety to flavonoids, such as quercetin, kaempferol, and myricetin. The enzymatic glucosidation shows a broad substrate specificity when the reaction is catalyzed by wild-type BcGT1. Preliminary assays demonstrated that the F240A mutant significantly improves the regioselectivity of enzymatic glucosidation toward quercetin. To unveil and further to control the catalytic function of BcGT1, mutation of F240 to other amino acids, such as C, E, G, R, Y, W, and K, was performed. Among these mutants, F240A, F240G, F240R, and F240K greatly altered the regioselectivity. The quercetin-3-O-glucoside, instead of quercetin-7-O-glucoside as for the wild-type enzyme, was obtained as the major product. Among these mutants, F240R showed nearly 100 % product specificity but only retained 25 % catalytic efficiency of wild-type enzyme. From an inspection of the protein structure, we found two other amino acids, F132 and F138, together with F240, are likely to form a hydrophobic binding region, which is sufficiently spacious to accommodate substrates with varied aromatic moieties. Through the replacement of a phenylalanine by a tyrosine residue in the substrate-binding region, the mutants may be able to fix the orientation of flavonoids, presumably through the formation of a hydrogen bond between substrates and mutants. Multiple mutants-F240R_F132Y, F240R_F138Y, and F240R_F132Y_F138Y-were thus constructed for further investigation. The multiple points of mutants not only maintained the high product specificity but also significantly improved the catalytic efficiency, relative to F240R. The same product specificity was obtained when kaempferol and myricetin were used as a substrate.

  15. Regulation of gene expression: cryptic β-glucoside (bgl) operon of Escherichia coli as a paradigm.

    PubMed

    Harwani, Dharmesh

    2014-01-01

    Bacteria have evolved various mechanisms to extract utilizable substrates from available resources and consequently acquire fitness advantage over competitors. One of the strategies is the exploitation of cryptic cellular functions encoded by genetic systems that are silent under laboratory conditions, such as the bgl (β-glucoside) operon of E. coli. The bgl operon of Escherichia coli, involved in the uptake and utilization of aromatic β-glucosides salicin and arbutin, is maintained in a silent state in the wild type organism by the presence of structural elements in the regulatory region. This operon can be activated by mutations that disrupt these negative elements. The fact that the silent bgl operon is retained without accumulating deleterious mutations seems paradoxical from an evolutionary view point. Although this operon appears to be silent, specific physiological conditions might be able to regulate its expression and/or the operon might be carrying out function(s) apart from the utilization of aromatic β-glucosides. This is consistent with the observations that the activated operon confers a Growth Advantage in Stationary Phase (GASP) phenotype to Bgl(+) cells and exerts its regulation on at least twelve downstream target genes.

  16. Analysis of iridoid glucosides from Paederia scandens using HPLC-ESI-MS/MS.

    PubMed

    Wu, Zhi-Jun; Wang, Jian-Hua; Fang, Dong-Mei; Zhang, Guo-Lin

    2013-04-01

    Iridoid glycosides are an important class of natural products and have many biological activities. Iridoid glucosides in an extract of the plant species Paederia scandens were investigated using reversed-phase high performance liquid chromatography and electrospray quadrupole time-of-flight-type tandem mass spectrometry. The elemental composition of most of the compounds was determined by accurate mass and relative isotopic abundance (RIA) measurements. In positive ion mode, the fragmentation of [M+NH4](+) precursor ions was carried out using low energy collision-induced electrospray ionization tandem spectrometry. The neutral losses of NH3, H2O, Glc, and the side chain of the iridoid moiety were the main fragmentation patterns observed. For simple iridoid glycosides, the main differences were related to the side chains. Fragmentation of the [M-H](-)precursor ions was achieved for the compounds possibly having phenolic acid group. The connection order of the iridoid, sugar, and phenolic acid moieties, and the linkage of the 6-OH group of the sugar to the phenolic acid were unambiguously confirmed using a combination of MS/MS spectra in both positive and negative ion modes, and our previous work. For some trace dimeric iridoid glucosides, the connection order between the asperuloside and paederoside moieties was determined by the characteristic product ions; this was supported by D-labeling experiments. A total of 24 iridoid glucosides, including 14 new species, were identified or tentatively characterized based on exact mass, RIA values, tandem mass spectra, and D-labeling experiments. PMID:23466447

  17. Regulation of gene expression: cryptic β-glucoside (bgl) operon of Escherichia coli as a paradigm.

    PubMed

    Harwani, Dharmesh

    2014-01-01

    Bacteria have evolved various mechanisms to extract utilizable substrates from available resources and consequently acquire fitness advantage over competitors. One of the strategies is the exploitation of cryptic cellular functions encoded by genetic systems that are silent under laboratory conditions, such as the bgl (β-glucoside) operon of E. coli. The bgl operon of Escherichia coli, involved in the uptake and utilization of aromatic β-glucosides salicin and arbutin, is maintained in a silent state in the wild type organism by the presence of structural elements in the regulatory region. This operon can be activated by mutations that disrupt these negative elements. The fact that the silent bgl operon is retained without accumulating deleterious mutations seems paradoxical from an evolutionary view point. Although this operon appears to be silent, specific physiological conditions might be able to regulate its expression and/or the operon might be carrying out function(s) apart from the utilization of aromatic β-glucosides. This is consistent with the observations that the activated operon confers a Growth Advantage in Stationary Phase (GASP) phenotype to Bgl(+) cells and exerts its regulation on at least twelve downstream target genes. PMID:25763016

  18. Platinum and rhenium extraction from a spent refinery catalyst using Bacillus megaterium as a cyanogenic bacterium: statistical modeling and process optimization.

    PubMed

    Motaghed, M; Mousavi, S M; Rastegar, S O; Shojaosadati, S A

    2014-11-01

    The present study evaluated the potential of Bacillus megaterium as a cyanogenic bacterium to produce cyanide for solubilization of platinum and rhenium from a spent refinery catalyst. Response surface methodology was applied to study the effects and interaction between two main effective parameters including initial glycine concentration and pulp density. Maximum Pt and Re recovery was obtained 15.7% and 98%, respectively, under optimum conditions of 12.8 g/l initial glycine concentration and 4% (w/v) pulp density after 7 days. Increasing the free cyanide concentration to 3.6 mg/l, varying the pH from 6.7 to 9, and increasing the dissolved oxygen from 2 to 5mg/l demonstrated the growth characteristics of B. megaterium during bioleaching process. The modified shrinking core model was used to determine the rate limiting step of the process. It was found that diffusion through the product layer is the rate controlling step.

  19. Molecular and biochemical characterization of a cyanogenic β-glucosidase in the inner bark tissues of rubber tree (Hevea brasiliensis Muell. Arg.).

    PubMed

    Tian, Wei-Min; Zhang, Hua; Yang, Shu-Guang; Shi, Min-Jing; Wang, Xu-Chu; Dai, Long-Jun; Chen, Yue-Yi

    2013-05-15

    Tapping causes the loss of large amounts of latex from laticifers and subsequently enhances latex regeneration, a high carbon- and nitrogen-cost activity in rubber tree. It is suggested that a 67 kDa protein associated with protein-storing cells in the inner bark tissues of rubber tree plays an important role in meeting the nitrogen demand for latex regeneration. Here, the 67 kDa protein was further characterized by a combination of cell biological, molecular biological and biochemical techniques. Immunogold labeling showed that the 67 kDa protein was specifically localized in the central vacuole of protein-storing cells. A full-length cDNA, referred to as HbVSP1, was cloned. The HbVSP1 contained a 1584 bp open reading frame encoding a protein of 527 amino acids. The putative protein HbVSP1 shared high identity with the P66 protein from rubber tree and proteins of the linamarase, and bg1A from cassava (Manihot esculenta). HbVSP1 contained the active site sequences of β-glucosidase, TFNEP and I/VTENG. In vitro analysis showed that the 67 kDa protein exhibited the activity of both β-glucosidase and linamarase and was thus characterized as a cyanogenic β-glucosidase. Proteins immuno-related to the 67 kDa protein were present in leaves and lutoids of laticifers. Tapping down-regulated the expression of HbVSP1, but up-regulated the expression of genes encoding the key enzymes for rubber biosynthesis, while the effect of resting from tapping was the reverse. Taken together, the results suggest that the 67 kDa protein is a vacuole-localized cyanogenic β-glucosidase encoded by HbVSP1 and may have a role in nitrogen storage in inner bark tissues of trunk during the leafless periods when rubber tree is rested from tapping.

  20. Quantitative Analysis of Phenylpropanoid Glycerol Glucosides in Different Organs of Easter Lily (Lilium longiflorum Thunb.).

    PubMed

    Munafo, John P; Gianfagna, Thomas J

    2015-05-20

    The Easter lily (Lilium longiflorum Thunb.) is esteemed worldwide as an attractive ornamental plant, and the flower buds and bulbs are used for both culinary and medicinal purposes in many parts of the world. L. longiflorum contains significant amounts of phenylpropanoid glycerol glucosides, a group of compounds that may contribute to plant pathogen defense, ultraviolet/high-intensity visible light (UV/high light) protection, and the purported medicinal uses of lilies. To define the natural distribution of these compounds within the plant, a liquid chromatography-mass spectrometry (LC-MS) method performed in selected ion monitoring (SIM) mode was employed for the quantitative analysis of five phenylpropanoid glycerol glucosides, namely, (2S)-1-O-caffeoyl-2-O-β-D-glucopyranosylglycerol, 1; (2R)-1-O-β-D-glucopyranosyl-2-O-p-coumaroylglycerol, 2; (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosylglycerol, 3; (2S)-1-O-caffeoyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, 4; and (2S)-1-O-p-coumaroyl-2-O-β-D-glucopyranosyl-3-O-acetylglycerol, 5, in the different organs of L. longiflorum. The p-coumaroyl-based 3 and its acetylated derivative 5 were determined to be the most abundant of the phenylpropanoid glycerol glucosides found in Easter lily bulbs, at 776.3 ± 8.4 and 650.7 ± 32.6 μg/g dry weight, respectively. The acetylated p-coumaroyl- and caffeoyl-based derivatives, 5 and 4, accumulated to the highest concentration in the closed flower buds, at 4925.2 ± 512.8 and 3216.8 ± 406.4 μg/g dry weight, respectively. Compound 4, followed by 5 and 1, proved to be the most abundant in the mature flowers, occurring at 6006.2 ± 625.8, 2160.3 ± 556.5, and 1535.8 ± 174.1 μg/g dry weight, respectively. Total concentrations of the phenylpropanoid glycerol glucosides were 10-100-fold higher in the above-ground plant organs as compared to the bulbs and fleshy roots. Two of the five compounds, 1 and 2, were identified in L. longiflorum for the first time. The quantitative

  1. Chemical Synthesis of Deoxynivalenol-3-β-d-[(13)C₆]-glucoside and Application in Stable Isotope Dilution Assays.

    PubMed

    Habler, Katharina; Frank, Oliver; Rychlik, Michael

    2016-01-01

    Modified mycotoxins have been gaining importance in recent years and present a certain challenge in LC-MS/MS analysis. Due to the previous lack of a labeled isotopologue of the modified mycotoxin deoxynivalenol-3-glucoside, in our study we synthesized the first (13)C-labeled internal standard. Therefore, we used the Königs-Knorr method to synthesize deoxynivalenol-3-β-d-[(13)C₆]-glucoside originated from unlabeled deoxynivalenol and [(13)C₆]-labeled glucose. Using the synthesized isotopically-labeled standard deoxynivalenol-3-β-d-[(13)C₆]-glucoside and the purchased labeled standard [(13)C15]-deoxynivalenol, a stable isotope dilution LC-MS/MS method was firstly developed for deoxynivalenol-3-glucoside and deoxynivalenol in beer. The preparation and purification of beer samples was based on a solid phase extraction. The validation data of the newly developed method gave satisfying results. Intra- and interday precision studies revealed relative standard deviations below 0.5% and 7%, respectively. The recoveries ranged for both analytes between 97% and 112%. The stable isotope dilution assay was applied to various beer samples from four different countries. In summary, deoxynivalenol-3-glucoside and deoxynivalenol mostly appeared together in varying molar ratios but were quantified in rather low contents in the investigated beers. PMID:27355938

  2. Chemical Synthesis of Deoxynivalenol-3-β-d-[(13)C₆]-glucoside and Application in Stable Isotope Dilution Assays.

    PubMed

    Habler, Katharina; Frank, Oliver; Rychlik, Michael

    2016-06-27

    Modified mycotoxins have been gaining importance in recent years and present a certain challenge in LC-MS/MS analysis. Due to the previous lack of a labeled isotopologue of the modified mycotoxin deoxynivalenol-3-glucoside, in our study we synthesized the first (13)C-labeled internal standard. Therefore, we used the Königs-Knorr method to synthesize deoxynivalenol-3-β-d-[(13)C₆]-glucoside originated from unlabeled deoxynivalenol and [(13)C₆]-labeled glucose. Using the synthesized isotopically-labeled standard deoxynivalenol-3-β-d-[(13)C₆]-glucoside and the purchased labeled standard [(13)C15]-deoxynivalenol, a stable isotope dilution LC-MS/MS method was firstly developed for deoxynivalenol-3-glucoside and deoxynivalenol in beer. The preparation and purification of beer samples was based on a solid phase extraction. The validation data of the newly developed method gave satisfying results. Intra- and interday precision studies revealed relative standard deviations below 0.5% and 7%, respectively. The recoveries ranged for both analytes between 97% and 112%. The stable isotope dilution assay was applied to various beer samples from four different countries. In summary, deoxynivalenol-3-glucoside and deoxynivalenol mostly appeared together in varying molar ratios but were quantified in rather low contents in the investigated beers.

  3. A New Non-glucosidic Iridoid from the Roots of Strychnos nux-blanda.

    PubMed

    Sichaem, Jirapast; Khumkratok, Suttira; Siripong, Pongpun; Tip-pyang, Santi

    2016-06-01

    Strychnuxin (1), a new non-glucosidic iridoid, together with four known compounds, IX (2), loganetin (3), loganin (4) and sweroside (5), were isolated from the roots of Strychnos nux-blanda. The structures of all isolated compounds (1-5) were elucidated through their physical properties and by the use of spectroscopic methods, as well as comparisons with the previous literature. To the best of our knowledge, this is the first isolation of compounds 1-5 from this plant. All isolated compounds were evaluated for their in vitro cytotoxicity against five human cancer cell lines.

  4. Total glucosides of peony attenuates experimental autoimmune encephalomyelitis in C57BL/6 mice.

    PubMed

    Huang, Qiling; Ma, Xiaomeng; Zhu, Dong Liang; Chen, Li; Jiang, Ying; Zhou, Linli; Cen, Lei; Pi, Rongbiao; Chen, Xiaohong

    2015-07-15

    Total glucosides of peony (TGP), an active compound extracted from the roots of Paeonia lactiflora Pall, has wide pharmacological effects on nervous system. Here we examined the effects of TGP on experimental autoimmune encephalomyelitis (EAE), an established model of multiple sclerosis (MS). The results showed that TGP can reduce the severity and progression of EAE in C57 BL/6 mice. In addition, TGP also down-regulated the Th1/Th17 inflammatory response and prevented the reduced expression of brain-derived neurotrophic factor and 2',3'-cyclic nucleotide 3'-phosphodiesterase of EAE. These findings suggest that TGP could be a potential therapeutic agent for MS.

  5. Functional and antiischemic effects of luteolin-7-glucoside in isolated rabbit hearts.

    PubMed

    Rump, A F; Schüssler, M; Acar, D; Cordes, A; Theisohn, M; Rösen, R; Klaus, W; Fricke, U

    1994-10-01

    1. The functional effects of the flavonoid luteolin-7-glucoside (LUT) were investigated in Langendorff-rabbit hearts perfused at constant pressure. Repetitive myocardial ischemia was induced by coronary artery ligature and quantified from NADH-fluorescence photography. 2. LUT significantly enhanced left ventricular pressure and the global and relative coronary flow (= global coronary flow/pressure-rate product). 3. LUT significantly diminished epicardial NADH-fluorescence area and intensity. 4. LUT is an inodilator possessing cardioprotective properties. These might be related to an improvement of myocardial perfusion and/or to free radical scavenging properties.

  6. Functional and antiischemic effects of luteolin-7-glucoside in isolated rabbit hearts.

    PubMed

    Rump, A F; Schüssler, M; Acar, D; Cordes, A; Theisohn, M; Rösen, R; Klaus, W; Fricke, U

    1994-10-01

    1. The functional effects of the flavonoid luteolin-7-glucoside (LUT) were investigated in Langendorff-rabbit hearts perfused at constant pressure. Repetitive myocardial ischemia was induced by coronary artery ligature and quantified from NADH-fluorescence photography. 2. LUT significantly enhanced left ventricular pressure and the global and relative coronary flow (= global coronary flow/pressure-rate product). 3. LUT significantly diminished epicardial NADH-fluorescence area and intensity. 4. LUT is an inodilator possessing cardioprotective properties. These might be related to an improvement of myocardial perfusion and/or to free radical scavenging properties. PMID:7875536

  7. Total glucosides of peony attenuates experimental autoimmune encephalomyelitis in C57BL/6 mice.

    PubMed

    Huang, Qiling; Ma, Xiaomeng; Zhu, Dong Liang; Chen, Li; Jiang, Ying; Zhou, Linli; Cen, Lei; Pi, Rongbiao; Chen, Xiaohong

    2015-07-15

    Total glucosides of peony (TGP), an active compound extracted from the roots of Paeonia lactiflora Pall, has wide pharmacological effects on nervous system. Here we examined the effects of TGP on experimental autoimmune encephalomyelitis (EAE), an established model of multiple sclerosis (MS). The results showed that TGP can reduce the severity and progression of EAE in C57 BL/6 mice. In addition, TGP also down-regulated the Th1/Th17 inflammatory response and prevented the reduced expression of brain-derived neurotrophic factor and 2',3'-cyclic nucleotide 3'-phosphodiesterase of EAE. These findings suggest that TGP could be a potential therapeutic agent for MS. PMID:26025060

  8. On the masked mycotoxin zearalenone-14-glucoside. Does the mask truly hide?

    PubMed

    Dellafiora, Luca; Perotti, Alessio; Galaverna, Gianni; Buschini, Annamaria; Dall'Asta, Chiara

    2016-03-01

    In the matter of foodborne mycotoxins, beside a number of regulated compounds, regulations are totally missing for phase-II plant metabolites--the toxicological knowledge of which is still in its infancy. Currently, zearalenone-14-glucoside is in the pipeline and its toxicological role is under a glowing scientific debate. In our work it clearly showed high toxicological concerns as it is prone to conversion to well-known toxic compounds (i.e. zearalenone and both zearalenol isomers) when exposed to breast cancer cells culture. The need of future risk assessment studies has been pointed out accordingly. PMID:26792714

  9. A new flavonol glucoside from the aerial parts of Sida glutinosa.

    PubMed

    Das, Niranjan; Achari, Basudev; Harigaya, Yoshihiro; Dinda, Biswanath

    2011-10-01

    Phytochemical investigation on the dried aerial parts of Sida glutinosa has led to the isolation of a new flavonol glucoside, glutinoside (1), along with seven known compounds, 24(28)-dehydromakisterone A (2), 1,2,3,9-tetrahydropyrrolo[2,1-b]-quinazolin-3-amine (3), docosanoic acid, 1-triacontanol, campesterol, stigmasterol, and β-sitosterol. The structures of these compounds were elucidated by means of extensive spectroscopic techniques as well as GC/MS analysis (for sterols) and comparison with the literature data. All these seven known compounds are reported from this plant for the first time.

  10. Fusion of Ferredoxin and Cytochrome P450 Enables Direct Light-Driven Biosynthesis

    PubMed Central

    2016-01-01

    Cytochrome P450s (P450s) are key enzymes in the synthesis of bioactive natural products in plants. Efforts to harness these enzymes for in vitro and whole-cell production of natural products have been hampered by difficulties in expressing them heterologously in their active form, and their requirement for NADPH as a source of reducing power. We recently demonstrated targeting and insertion of plant P450s into the photosynthetic membrane and photosynthesis-driven, NADPH-independent P450 catalytic activity mediated by the electron carrier protein ferredoxin. Here, we report the fusion of ferredoxin with P450 CYP79A1 from the model plant Sorghum bicolor, which catalyzes the initial step in the pathway leading to biosynthesis of the cyanogenic glucoside dhurrin. Fusion with ferredoxin allows CYP79A1 to obtain electrons for catalysis by interacting directly with photosystem I. Furthermore, electrons captured by the fused ferredoxin moiety are directed more effectively toward P450 catalytic activity, making the fusion better able to compete with endogenous electron sinks coupled to metabolic pathways. The P450-ferredoxin fusion enzyme obtains reducing power solely from its fused ferredoxin and outperforms unfused CYP79A1 in vivo. This demonstrates greatly enhanced electron transfer from photosystem I to CYP79A1 as a consequence of the fusion. The fusion strategy reported here therefore forms the basis for enhanced partitioning of photosynthetic reducing power toward P450-dependent biosynthesis of important natural products. PMID:27119279

  11. The unusual canangafruticosides A-E: five monoterpene glucosides, two monoterpenes and a monoterpene glucoside diester of the aryldihydronaphthalene lignan dicarboxylic acid from leaves of Cananga odorata var. fruticosa.

    PubMed

    Nagashima, Jiro; Matsunami, Katsuyoshi; Otsuka, Hideaki; Lhieochaiphant, Duangporn; Lhieochaiphant, Sorasak

    2010-09-01

    From the leaves of Cananga odorata var. fruticosa, five unusual monoterpene glucosides, named canangafruticosides A-E (1-5), along with two unusual non-glucosidic monoterpenes (6, 7) were isolated. An aryldihydronaphthalene-type lignan dicarboxylate (8) was also isolated, with two moles of canangafruticoside A (1) on its ester moiety. This lignan also showed strong blue fluorescence emission under basic conditions. The structures of these compounds were elucidated by means of spectroscopic methods, with their absolute configurations determined by application of the modified Mosher's method to a compound chemically derived from canangafruticoside E. PMID:20619865

  12. Megastigmane glucosides and an unusual monoterpene from the leaves of Cananga odorata var. odorata, and absolute structures of megastigmane glucosides isolated from C. odorata var. odorata and Breynia officinalis.

    PubMed

    Matsunami, Katsuyoshi; Nagashima, Jiro; Sugimoto, Sachiko; Otsuka, Hideaki; Takeda, Yoshio; Lhieochaiphant, Duangporn; Lhieochaiphant, Sorasak

    2010-10-01

    From a 1-BuOH-soluble fraction of a MeOH extract of Cananga odorata var. odorata, collected at the Botanical Garden of Chiang Mai University, a new megastigmane glucoside, named canangaionoside, and an irregular monoterpene were isolated. A known compound, breyniaionoside A, which has been obtained from the leaves of Breynia officinalis, was also isolated, and its absolute structure was substantiated for the first time in this study. On this occasion, the absolute stereochemistries of structurally related megastigmane glucosides, breyniaionosides B and C, isolated from B. officinalis were examined. PMID:20571926

  13. Specific accumulation and revised structures of acridone alkaloid glucosides in the tips of transformed roots of Ruta graveolens.

    PubMed

    Kuzovkina, Inna; Al'terman, Irina; Schneider, Bernd

    2004-04-01

    The root tips of Ruta graveolens (common rue) show strong autofluorescence of acridone alkaloids, which are characteristic secondary metabolites of this plant. To study the specific distribution and accumulation of acridone alkaloids in various root segments of Ruta graveolens, root material was harvested from genetically transformed root cultures and extracts were investigated by chromatographic techniques and HPLC-(1)H NMR spectroscopy. The cells of the elongation and differentiation zones contained acridone glucosides and large amounts of acridone alkaloids, mainly rutacridone. Gravacridondiol glucoside was identified as the dominant secondary compound of the root tips and its structure revised by means of spectroscopic methods. In addition, minor acridones, including the structurally revised gravacridontriol glucoside and unknown natural products, were found in the root tip.

  14. Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes

    PubMed Central

    2013-01-01

    Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the human SGLT2 (hSGLT2) inhibitory potential of novel substituted 3-benzylindole-N-glucosides 6. Optimization of 6 resulted in the discovery of 3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside 6a-4 (TA-1887), a highly potent and selective hSGLT2 inhibitor, with pronounced antihyperglycemic effects in high-fat diet-fed KK (HF-KK) mice. Our results suggest the potential of indole-N-glucosides as novel antihyperglycemic agents through inhibition of renal SGLT2. PMID:24900773

  15. Cyanogenesis in plants and arthropods.

    PubMed

    Zagrobelny, Mika; Bak, Søren; Møller, Birger Lindberg

    2008-05-01

    Cyanogenic glucosides are phytoanticipins known to be present in more than 2500 plant species. They are regarded as having an important role in plant defense against herbivores due to bitter taste and release of toxic hydrogen cyanide upon tissue disruption, but recent investigations demonstrate additional roles as storage compounds of reduced nitrogen and sugar that may be mobilized when demanded for use in primary metabolism. Some specialized herbivores, especially insects, preferentially feed on cyanogenic plants. Such herbivores have acquired the ability to metabolize cyanogenic glucosides or to sequester them for use in their own defense against predators. A few species of arthropods (within diplopods, chilopods and insects) are able to de novo biosynthesize cyanogenic glucosides and some are able to sequester cyanogenic glucosides from their food plant as well. This applies to larvae of Zygaena (Zygaenidae). The ratio and content of cyanogenic glucosides is tightly regulated in Zygaena filipendulae, and these compounds play several important roles in addition to defense in the life cycle of Zygaena. The transfer of a nuptial gift of cyanogenic glucosides during mating of Zygaena has been demonstrated as well as the involvement of hydrogen cyanide in male attraction and nitrogen metabolism. As more plant and arthropod species are examined, it is likely that cyanogenic glucosides are found to be more widespread than formerly thought and that cyanogenic glucosides are intricately involved in many key processes in the life cycle of plants and arthropods.

  16. In vitro digestion and lactase treatment influence uptake of quercetin and quercetin glucoside by the Caco-2 cell monolayer

    PubMed Central

    Boyer, Jeanelle; Brown, Dan; Liu, Rui Hai

    2005-01-01

    Background Quercetin and quercetin glycosides are widely consumed flavonoids found in many fruits and vegetables. These compounds have a wide range of potential health benefits, and understanding the bioavailability of flavonoids from foods is becoming increasingly important. Methods This study combined an in vitro digestion, a lactase treatment and the Caco-2 cell model to examine quercetin and quercetin glucoside uptake from shallot and apple homogenates. Results The in vitro digestion alone significantly decreased quercetin aglycone recovery from the shallot digestate (p < 0.05), but had no significant effect on quercetin-3-glucoside recovery (p > 0.05). Digestion increased the Caco-2 cell uptake of shallot quercetin-4'-glucoside by 2-fold when compared to the non-digested shallot. Despite the loss of quercetin from the digested shallot, the bioavailability of quercetin aglycone to the Caco-2 cells was the same in both the digested and non-digested shallot. Treatment with lactase increased quercetin recovery from the shallot digestate nearly 10-fold and decreased quercetin-4'-glucoside recovery by more than 100-fold (p < 0.05), but had no effect on quercetin recovery from apple digestates. Lactase treatment also increased shallot quercetin bioavailability to the Caco-2 cells approximately 14-fold, and decreased shallot quercetin-4'-glucoside bioavailability 23-fold (p < 0.05). These Caco-2 cells had lactase activity similar to that expressed by a lactose intolerant human. Conclusions The increase in quercetin uptake following treatment with lactase suggests that dietary supplementation with lactase may increase quercetin bioavailability in lactose intolerant humans. Combining the digestion, the lactase treatment and the Caco-2 cell culture model may provide a reliable in vitro model for examining flavonoid glucoside bioavailability from foods. PMID:15644141

  17. Protective Effect of Cyanidin-3-O-Glucoside against Ultraviolet B Radiation-Induced Cell Damage in Human HaCaT Keratinocytes

    PubMed Central

    Hu, Yunfeng; Ma, Yuetang; Wu, Shi; Chen, Tianfeng; He, Yong; Sun, Jianxia; Jiao, Rui; Jiang, Xinwei; Huang, Yadong; Deng, Liehua; Bai, Weibin

    2016-01-01

    Ultraviolet radiation is the major environmental harmful factor that has emotional impact on human skin. The aim of the present study was to determine the mechanism of protection of cyanidin-3-O-glucoside against ultraviolet B (UVB)-induced damage to human HaCaT keratinocytes. Our results show that cyanidin-3-O-glucoside decreased the levels of intracellular reactive oxygen species generated by UVB treatment. Cyanidin-3-O-glucoside also decreased the UVB-augmented levels of the DNA damage indicators phospho-p53 and phospho-ATM/ATR. In addition, cyanidin-3-O-glucoside protected keratinocytes from UVB-induced injury by overturning the disruption of mitochondrial membrane potential and reversing apoptosis. The expression of anti-apoptotic protein B-cell lymphoma 2 (Bcl-2) was attenuated in UVB-exposed cells but restored in UVB/cyanidin-3-O-glucoside-treated cells. Furthermore, expression of the proapoptotic proteins Bcl-2-associated X (Bax) and the key apoptosis executer cleaved caspase-3 were increased in UVB-irradiated cells and decreased in UVB/cyanidin-3-O-glucoside-treated cells. For these reasons, the results demonstrate that cyanidin-3-O-glucoside protects human keratinocytes against UVB-induced oxidative stress and apoptosis. Our study provides a theoretical basis for the use of cyanidin-3-O-glucoside in the fight against light damage. PMID:27656146

  18. Protective Effect of Cyanidin-3-O-Glucoside against Ultraviolet B Radiation-Induced Cell Damage in Human HaCaT Keratinocytes

    PubMed Central

    Hu, Yunfeng; Ma, Yuetang; Wu, Shi; Chen, Tianfeng; He, Yong; Sun, Jianxia; Jiao, Rui; Jiang, Xinwei; Huang, Yadong; Deng, Liehua; Bai, Weibin

    2016-01-01

    Ultraviolet radiation is the major environmental harmful factor that has emotional impact on human skin. The aim of the present study was to determine the mechanism of protection of cyanidin-3-O-glucoside against ultraviolet B (UVB)-induced damage to human HaCaT keratinocytes. Our results show that cyanidin-3-O-glucoside decreased the levels of intracellular reactive oxygen species generated by UVB treatment. Cyanidin-3-O-glucoside also decreased the UVB-augmented levels of the DNA damage indicators phospho-p53 and phospho-ATM/ATR. In addition, cyanidin-3-O-glucoside protected keratinocytes from UVB-induced injury by overturning the disruption of mitochondrial membrane potential and reversing apoptosis. The expression of anti-apoptotic protein B-cell lymphoma 2 (Bcl-2) was attenuated in UVB-exposed cells but restored in UVB/cyanidin-3-O-glucoside-treated cells. Furthermore, expression of the proapoptotic proteins Bcl-2-associated X (Bax) and the key apoptosis executer cleaved caspase-3 were increased in UVB-irradiated cells and decreased in UVB/cyanidin-3-O-glucoside-treated cells. For these reasons, the results demonstrate that cyanidin-3-O-glucoside protects human keratinocytes against UVB-induced oxidative stress and apoptosis. Our study provides a theoretical basis for the use of cyanidin-3-O-glucoside in the fight against light damage.

  19. Protective Effect of Cyanidin-3-O-Glucoside against Ultraviolet B Radiation-Induced Cell Damage in Human HaCaT Keratinocytes.

    PubMed

    Hu, Yunfeng; Ma, Yuetang; Wu, Shi; Chen, Tianfeng; He, Yong; Sun, Jianxia; Jiao, Rui; Jiang, Xinwei; Huang, Yadong; Deng, Liehua; Bai, Weibin

    2016-01-01

    Ultraviolet radiation is the major environmental harmful factor that has emotional impact on human skin. The aim of the present study was to determine the mechanism of protection of cyanidin-3-O-glucoside against ultraviolet B (UVB)-induced damage to human HaCaT keratinocytes. Our results show that cyanidin-3-O-glucoside decreased the levels of intracellular reactive oxygen species generated by UVB treatment. Cyanidin-3-O-glucoside also decreased the UVB-augmented levels of the DNA damage indicators phospho-p53 and phospho-ATM/ATR. In addition, cyanidin-3-O-glucoside protected keratinocytes from UVB-induced injury by overturning the disruption of mitochondrial membrane potential and reversing apoptosis. The expression of anti-apoptotic protein B-cell lymphoma 2 (Bcl-2) was attenuated in UVB-exposed cells but restored in UVB/cyanidin-3-O-glucoside-treated cells. Furthermore, expression of the proapoptotic proteins Bcl-2-associated X (Bax) and the key apoptosis executer cleaved caspase-3 were increased in UVB-irradiated cells and decreased in UVB/cyanidin-3-O-glucoside-treated cells. For these reasons, the results demonstrate that cyanidin-3-O-glucoside protects human keratinocytes against UVB-induced oxidative stress and apoptosis. Our study provides a theoretical basis for the use of cyanidin-3-O-glucoside in the fight against light damage. PMID:27656146

  20. Protective Effect of Cyanidin-3-O-Glucoside against Ultraviolet B Radiation-Induced Cell Damage in Human HaCaT Keratinocytes.

    PubMed

    Hu, Yunfeng; Ma, Yuetang; Wu, Shi; Chen, Tianfeng; He, Yong; Sun, Jianxia; Jiao, Rui; Jiang, Xinwei; Huang, Yadong; Deng, Liehua; Bai, Weibin

    2016-01-01

    Ultraviolet radiation is the major environmental harmful factor that has emotional impact on human skin. The aim of the present study was to determine the mechanism of protection of cyanidin-3-O-glucoside against ultraviolet B (UVB)-induced damage to human HaCaT keratinocytes. Our results show that cyanidin-3-O-glucoside decreased the levels of intracellular reactive oxygen species generated by UVB treatment. Cyanidin-3-O-glucoside also decreased the UVB-augmented levels of the DNA damage indicators phospho-p53 and phospho-ATM/ATR. In addition, cyanidin-3-O-glucoside protected keratinocytes from UVB-induced injury by overturning the disruption of mitochondrial membrane potential and reversing apoptosis. The expression of anti-apoptotic protein B-cell lymphoma 2 (Bcl-2) was attenuated in UVB-exposed cells but restored in UVB/cyanidin-3-O-glucoside-treated cells. Furthermore, expression of the proapoptotic proteins Bcl-2-associated X (Bax) and the key apoptosis executer cleaved caspase-3 were increased in UVB-irradiated cells and decreased in UVB/cyanidin-3-O-glucoside-treated cells. For these reasons, the results demonstrate that cyanidin-3-O-glucoside protects human keratinocytes against UVB-induced oxidative stress and apoptosis. Our study provides a theoretical basis for the use of cyanidin-3-O-glucoside in the fight against light damage.

  1. Arabidopsis thaliana β-glucosidase BGLU15 attacks flavonol 3-O-β-glucoside-7-O-α-rhamnosides.

    PubMed

    Roepke, Jonathon; Bozzo, Gale G

    2015-01-01

    Kaempferol and quercetin 3-O-β-glucoside-7-O-α-rhamnoside (K3G7R and Q3G7R, respectively) are major flavonol bisglycosides accumulating in Arabidopsis thaliana with synergistic abiotic stresses (i.e., nitrogen deficiency and low temperature, NDLT). However, these molecules disappear rapidly during recovery from NDLT. Typically, catabolism of related chemicals relies on β-glucosidase (BGLU) action. Evidence for flavonol 3-O-β-glucoside-7-O-α-rhamnoside BGLU activity is provided here. Major losses of Q3G7R and K3G7R coincided with an approximate 250% induction in flavonol 3-O-β-glucoside-7-O-α-rhamnoside BGLU activity within 2days of NDLT recovery relative to plants cultured under nitrogen sufficiency and high temperature (NSHT, control). QTOF-MS/MS established the product of Q3G7R hydrolysis in the presence of Arabidopsis cell free extracts was quercetin 7-O-α-rhamnoside. A phylogenetic analysis of the Arabidopsis glycoside hydrolase family 1 identified BGLU15 (At2g44450) and five other members that cluster with Fabaceae hydrolases known to attack isoflavones and isoflavonoids, which are structurally somewhat related to flavonol 3-O-β-glucoside-7-O-α-rhamnosides. Real time quantitative PCR analysis established a 300% higher expression of BGLU15 within 1day of the recovery from NDLT relative to control plants; lower or negligible changes in expression were evident for the remaining BGLUs. Recombinant thioredoxin-His6-tagged mature BGLU15 protein was expressed in Escherichia coli and purified to homogeneity. A comparison of a wide spectrum of β-glucosides showed that recombinant BGLU15 preferentially hydrolyses the 3-O-β-glucosides of flavonols, but does not attack quercetin 3-O-α-rhamnoside, quercetin 3-O-β-galactoside and rutin. BGLU15 displayed the highest catalytic efficiency for Q3G7R and K3G7R yielding their respective 7-O-rhamnosides as products; flavonol 3-O-glucosides were also attacked, albeit with lower efficiency. Together, it appears the

  2. Engineering of glucoside acceptors for the regioselective synthesis of beta-(1-->3)-disaccharides with glycosynthases.

    PubMed

    Marton, Zsuzanna; Tran, Vinh; Tellier, Charles; Dion, Michel; Drone, Jullien; Rabiller, Claude

    2008-11-24

    Glycosynthase mutants obtained from Thermotogamaritima were able to catalyze the regioselective synthesis of aryl beta-D-Galp-(1-->3)-beta-D-Glcp and aryl beta-D-Glcp-(1-->3)-beta-D-Glcp in high yields (up to 90 %) using aryl beta-D-glucosides as acceptors. The need for an aglyconic aryl group was rationalized by molecular modeling calculations, which have emphasized a high stabilizing interaction of this group by stacking with W312 of the enzyme. Unfortunately, the deprotection of the aromatic group of the disaccharides was not possible without partial hydrolysis of the glycosidic bond. The replacement of aryl groups by benzyl ones could offer the opportunity to deprotect the anomeric position under very mild conditions. Assuming that benzyl acceptors could preserve the stabilizing stacking, benzyl beta-d-glucoside firstly assayed as acceptor resulted in both poor yields and poor regioselectivity. Thus, we decided to undertake molecular modeling calculations in order to design which suitable substituted benzyl acceptors could be used. This study resulted in the choice of 2-biphenylmethyl beta-D-glucopyranoside. This choice was validated experimentally, since the corresponding beta-(1-->3) disaccharide was obtained in good yields and with a high regioselectivity. At the same time, we have shown that phenyl 1-thio-beta-D-glucopyranoside was also an excellent substrate leading to similar results as those obtained with the O-phenyl analogue. The NBS deprotection of the S-phenyl group afforded the corresponding disaccharide quantitatively.

  3. Enhanced production of β-glucosides by in-situ UDP-glucose regeneration.

    PubMed

    Huang, Fong-Chin; Hinkelmann, Jens; Hermenau, Alexandra; Schwab, Wilfried

    2016-04-20

    Glycosyltransferase (GT)-mediated methodology is recognized as one of the most practical approaches for large-scale production of glycosides. However, GT enzymes require a sugar nucleotide as donor substrate that must be generated in situ for preparative applications by recycling of the nucleotide moiety, e.g. by sucrose synthase (SUS). Three plant GT genes CaUGT2, VvGT14a, and VvGT15c and the fungal SbUGTA1 were successfully co-expressed with GmSUS from soybean in Escherichia coli BL21 and W cells. In vitro, the crude protein extracts prepared from four GT genes and GmSUS co-expressing cells were able to convert several small molecules to the corresponding glucosides, when sucrose and UDP were supplied. In addition, GmSUS was able to enhance the glucosylation efficiency and reduced the amount of supplying UDP-glucose. In the biotransformation system, co-expression of VvGT15c with GmSUS also improved the glucosylation of geraniol and enhanced the resistance of the cells against the toxic terpenol. GT-EcW and GTSUS-EcW cells tolerated up to 2mM geraniol and converted more than 99% of the substrate into the glucoside at production rates exceeding 40μgml(-1)h(-1). The results confirm that co-expression of SUS allows in situ regeneration of UDP-sugars and avoids product inhibition by UDP. PMID:26912290

  4. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside.

    PubMed

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-α) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables.

  5. Glucosylation of Steviol and Steviol-Glucosides in Extracts from Stevia rebaudiana Bertoni

    PubMed Central

    Shibata, Hitoshi; Sonoke, Satoru; Ochiai, Hideo; Nishihashi, Hideji; Yamada, Masaharu

    1991-01-01

    To evaluate and characterize stevioside biosynthetic pathway in Stevia rebaudiana Bertoni cv Houten, two enzyme fractions that catalyze glucosylation of steviol (ent-13-hydroxy kaur-16-en-19-oic acid) and steviol-glucosides (steviol-13-O-glucopyranoside, steviolbioside and stevioside), utilizing UDP-glucose as the glucose donor, were prepared from the soluble extracts of S. rebaudiana leaves. Enzyme fraction I, passed through DEAE-Toyopearl equilibrated with 50 millimolar K-phosphate pH 7.5, catalyzed the glucosylation to steviol and 19-O-methylsteviol, but not to iso-steviol and 13-O-methylsteviol, indicating that 13-hydroxyl group of the steviol skeleton is glucosylated first from UDP-glucose to produce steviol-13-O-glucopyranoside. Enzyme fraction II, eluted from the DEAE-Toyopearl column with 0.15 molar KCI, catalyzed the glucose transfer from UDP-glucose to steviol-13-O-glucopyranoside, steviolbioside and stevioside, but not to rubusoside (13, 19-di-O-glucopyranoside) and rebaudioside A. The reaction products glucosylated from steviol-13-O-glucopyranoside, steviolbioside and stevioside were identified to be steviolbioside, stevioside and rebaudioside A, respectively. These results indicate that in the steviol-glucoside biosynthetic pathway, steviol-13-O-glucopyranoside produced from the steviol glucosylation is successively glucosylated to steviolbioside, then to stevioside producing rebaudioside A. PMID:16667943

  6. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside

    PubMed Central

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-α) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables. PMID:26113868

  7. Effects on Liver Lipid Metabolism of the Naturally Occurring Dietary Flavone Luteolin-7-glucoside.

    PubMed

    Sá, Carla; Oliveira, Ana Rita; Machado, Cátia; Azevedo, Marisa; Pereira-Wilson, Cristina

    2015-01-01

    Disruptions in whole-body lipid metabolism can lead to the onset of several pathologies such as nonalcoholic fatty liver disease (NAFLD) and cardiovascular diseases (CVDs). The present study aimed at elucidating the molecular mechanisms behind the lipid-lowering effects of the flavone luteolin-7-glucoside (L7G) which we previously showed to improve plasma lipid profile in rats. L7G is abundant in plant foods of Mediterranean diet such as aromatic plants used as herbs. Results show that dietary supplementation with L7G for one week induced the expression of peroxisome proliferator-activated receptor-alpha (PPAR-α) and of its target gene carnitine palmitoyl transferase 1 (CPT-1) in rat liver. L7G showed a tendency to decrease the hepatic expression of sterol regulatory element-binding protein-1 (SREBP-1), without affecting fatty acid synthase (FAS) protein levels. Although SREBP-2 and LDLr mRNA levels did not change, the expression of HMG CoA reductase (HMGCR) was significantly repressed by L7G. L7G also inhibited this enzyme's in vitro activity in a dose dependent manner, but only at high and not physiologically relevant concentrations. These results add new evidence that the flavone luteolin-7-glucoside may help in preventing metabolic diseases and clarify the mechanisms underlying the beneficial health effects of diets rich in fruits and vegetables. PMID:26113868

  8. Indoline Amide Glucosides from Portulaca oleracea: Isolation, Structure, and DPPH Radical Scavenging Activity.

    PubMed

    Jiao, Ze-Zhao; Yue, Su; Sun, Hong-Xiang; Jin, Tian-Yun; Wang, Hai-Na; Zhu, Rong-Xiu; Xiang, Lan

    2015-11-25

    A polyamide column chromatography method using an aqueous ammonia mobile phase was developed for large-scale accumulation of water-soluble indoline amide glucosides from a medicinal plant, Portulaca oleracea. Ten new [oleraceins H, I, K, L, N, O, P, Q, R, S (1-10)] and four known [oleraceins A-D (11-14)] indoline amide glucosides were further purified and structurally characterized by various chromatographic and spectroscopic methods. The DPPH radical scavenging activities of oleraceins K (5) and L (6), with EC50 values of 15.30 and 16.13 μM, respectively, were twice that of a natural antioxidant, vitamin C; the EC50 values of the 12 other indoline amides, which ranged from 29.05 to 43.52 μM, were similar to that of vitamin C. Structure-activity relationships indicated that the DPPH radical scavenging activities of these indoline amides correlate with the numbers and positions of the phenolic hydroxy groups. PMID:26562741

  9. Red clover Trifolium pratense L. phytoestrogens: UV-B radiation increases isoflavone yield, and postharvest drying methods change the glucoside conjugate profiles.

    PubMed

    Swinny, Ewald E; Ryan, Ken G

    2005-10-19

    Isoflavone extracts of red clover Trifolium pratense L. (cv. Pawera) with dissimilar glucoside conjugate profiles were obtained by employing different postharvest drying methods. The most prominent isoflavones found were formononetin and biochanin A and their corresponding glucosides and malonyl glucoside esters. Postharvest freeze drying inhibited the conversion of the glycosides to the aglycones, while vacuum drying allowed for maximum conversion of the glycosides to their corresponding aglycones. Air drying produced a low level of the aglycones formononetin and biochanin A, and oven drying promoted decarboxylation of the malonyl glucosides to the acetyl glucosides. Exposure to enhanced UV-B radiation resulted in an increase in total formononetin and biochanin A isoflavone levels, indicating that harvest during a period of high ambient UV-B radiation may be appropriate for maximum yield. The levels of caffeic acid and flavonols also increased by about 40 and 250%, respectively, on exposure to enhanced UV-B radiation.

  10. Experiments with Plasmas Produced by Potassium-Seeded Cyanogen Oxygen Flames for Study of Radio Transmission at Simulated Reentry Vehicle Plasma Conditions

    NASA Technical Reports Server (NTRS)

    Huber, Paul W.; Gooderum, Paul B.

    1961-01-01

    A method for the chemical production of an ionized gas stream for application to radio transmission studies is described. Involved is the combustion of gaseous cyanogen and oxygen with the addition of vaporized potassium in some cases to further increase the ionization. Experiments are described in which a 3-inch-diameter subsonic free jet at atmospheric pressure is used, and the results are presented. The plasma obtained by using this method is sufficient to simulate plasma conditions expected for reentering hypersonic vehicles. The unseeded plasma stream temperature is indicated to be about 4,200 K, with the degree of ionization indicated to be that expected from thermal equilibrium considerations. Measurements of radio-signal loss due to the unseeded flame plasma are presented for microwaves of 8 to 20 kmc transmitted through the stream and for a dipole transmitting model of 219.5 mc immersed in the stream. Favorable comparison of these results with the simple plane-wave signal-attenuation theory was obtained. In the case of a 9.4-kmc microwave signal of 30-kw peak power, the preliminary indication is that the plasma characteristics were not changed due to this strong signal. Comparison of a simplified concept of radio-signal attenuation due to plasmas is made with some hypersonic reentry vehicle signal-loss data. Other areas of plasma research using this method for the transmission problem are indicated.

  11. Purification of labeled cyanogen bromide peptides of the alpha polypeptide from sodium ion and potassium ion activated adenosinetriphosphatase modified with N-(/sup 3/H)ethylmaleimide

    SciTech Connect

    Le, D.T.

    1986-05-06

    Sodium ion and potassium ion activated adenosinetriphosphatase, isolated from canine kidney, was reacted with N-(/sup 3/H)ethylmaleimide while it was poised in three different conformations, ostensibly E2-P, E2, and E1, respectively. These assignments were made from a consideration of the particular concentrations of ligands in the respective alkylation mixtures. After a 30-min reaction, the remaining enzymatic activity was found to vary among these three different samples from 90 to 30% of that of unalkylated controls. In all cases, the alpha polypeptide was purified and subjected to digestion with cyanogen bromide, and in each digest the same two distinct radioactive peptides were identified and purified by gel filtration on a column of Sephadex LH-60. The incorporation of N-(/sup 3/H)ethylmaleimide into one of these two peptides correlated closely with enzymatic inactivation, while the incorporation into the other was most extensive when the portion of the active site to which ATP binds was unoccupied. Alkylation of the residue within the latter peptide, however, does not result in inactivation of the enzyme. Both peptides were further purified by high-pressure liquid chromatography, and their amino-terminal sequences were determined by manual dansyl Edman or solid-phase techniques. The peptide containing the sulfhydryl protected by ATP has, as its amino terminus, the lysine that reacts exclusively with fluoresceinyl 5'-isothiocyanate.

  12. Isolation of high-salinity-tolerant bacterial strains, Enterobacter sp., Serratia sp., Yersinia sp., for nitrification and aerobic denitrification under cyanogenic conditions.

    PubMed

    Mpongwana, N; Ntwampe, S K O; Mekuto, L; Akinpelu, E A; Dyantyi, S; Mpentshu, Y

    2016-01-01

    Cyanides (CN(-)) and soluble salts could potentially inhibit biological processes in wastewater treatment plants (WWTPs), such as nitrification and denitrification. Cyanide in wastewater can alter metabolic functions of microbial populations in WWTPs, thus significantly inhibiting nitrifier and denitrifier metabolic processes, rendering the water treatment processes ineffective. In this study, bacterial isolates that are tolerant to high salinity conditions, which are capable of nitrification and aerobic denitrification under cyanogenic conditions, were isolated from a poultry slaughterhouse effluent. Three of the bacterial isolates were found to be able to oxidise NH(4)-N in the presence of 65.91 mg/L of free cyanide (CN(-)) under saline conditions, i.e. 4.5% (w/v) NaCl. The isolates I, H and G, were identified as Enterobacter sp., Yersinia sp. and Serratia sp., respectively. Results showed that 81% (I), 71% (G) and 75% (H) of 400 mg/L NH(4)-N was biodegraded (nitrification) within 72 h, with the rates of biodegradation being suitably described by first order reactions, with rate constants being: 4.19 h(-1) (I), 4.21 h(-1) (H) and 3.79 h(-1) (G), respectively, with correlation coefficients ranging between 0.82 and 0.89. Chemical oxygen demand (COD) removal rates were 38% (I), 42% (H) and 48% (G), over a period of 168 h with COD reduction being highest at near neutral pH. PMID:27148718

  13. Freezing and melting behavior of an octyl β-D-glucoside-water binary system--inhibitory effect of octyl β-D-glucoside on ice crystal formation.

    PubMed

    Ogawa, Shigesaburo; Asakura, Kouichi; Osanai, Shuichi

    2012-12-21

    Phase transition behavior of lyotropic liquid crystals of an octyl β-D-glucoside (OG)-water binary system during ice freezing and melting was studied by differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Not the thermotropic, but the lyotropic phase transition due to the change of OG concentration during ice freezing and melting was observed. The concentration-temperature phase diagram of the binary system was constructed. Melting temperature of ice, T(m), lyotropic phase transition temperature, T(tr), and glass transition temperatures of unfrozen phases in the absence and presence of ice, T(g) and T(g)', were shown in the phase diagram. The phase diagram indicated that the OG aqueous system was concentrated to ca. 90-92 wt% by ice freezing and exhibited glass transition at T(g)'. An observation of the concentration-gradient specimen by the cryo-POM showed the evidence of the inhibitory effects of OG on nucleation and growth of ice crystals in the extremely high OG concentration system in which the lamellar liquid crystalline phase was formed. This study provided the importance of the influence of concentration change by ice freezing on the behaviour of the sugar-based surfactant-water system under low temperature conditions.

  14. Two novel aromatic glucosides, marylaurencinosides D and E, from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'.

    PubMed

    Yoshikawa, Kazuko; Okahuji, Mariko; Iseki, Kanako; Ito, Takuya; Asakawa, Yoshinori; Kawano, Sachiko; Hashimoto, Toshihiro

    2014-04-01

    Two novel aromatic glucosides, named marylaurencinosides D (1) and E (2), were isolated from the fresh flowers of Cymbidium Great Flower 'Marylaurencin'. In addition, eight known aromatic compounds (3-10) were isolated. These structures were determined on the basis of NMR experiments as well as chemical evidence.

  15. Flavonoid C-glucosides Derived from Flax Straw Extracts Reduce Human Breast Cancer Cell Growth In vitro and Induce Apoptosis

    PubMed Central

    Czemplik, Magdalena; Mierziak, Justyna; Szopa, Jan; Kulma, Anna

    2016-01-01

    Flax straw of flax varieties that are grown for oil production is a by product which represents a considerable biomass source. Therefore, its potential application for human use is of high interest. Our research has revealed that flax straw is rich in flavonoid C-glucosides, including vitexin, orientin, and isoorientin. The objective of this study was to evaluate the cytotoxicity and possible proapoptotic effect of flax straw derived C-glucosides of flavonoids in the human breast adenocarcinoma cell line (MCF-7). The effects of flax straw derived flavonoid C-glucosides on cell proliferation of MCF-7 cells were evaluated by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and sulforhodamine B assays. The expression of apoptosis-related genes was assessed by real-time PCR. Our data revealed that flax C-glucosides as well as pure compounds are cytotoxic toward MCF-7 cells and inhibit their proliferation. Moreover, the induction of apoptosis was correlated with the changes in the mRNA level of pro-apoptotic genes. Increased expression of bax and caspase-7, -8, and -9 and decreased mRNA expression of bcl-2 was observed, whereas the mRNA levels of p53 and mdm2 were not altered. These results clearly demonstrated that flax straw metabolites effectively induced growth inhibition and apoptosis in human breast adenocarcinoma cells.

  16. A UDP-glucosyltransferase functions in both acylphloroglucinol glucoside and anthocyanin biosynthesis in strawberry (Fragaria × ananassa).

    PubMed

    Song, Chuankui; Zhao, Shuai; Hong, Xiaotong; Liu, Jingyi; Schulenburg, Katja; Schwab, Wilfried

    2016-03-01

    Physiologically active acylphloroglucinol (APG) glucosides were recently found in strawberry (Fragaria sp.) fruit. Although the formation of the APG aglycones has been clarified, little is known about APG glycosylation in plants. In this study we functionally characterized ripening-related glucosyltransferase genes in Fragaria by comprehensive biochemical analyses of the encoded proteins and by a RNA interference (RNAi) approach in vivo. The allelic proteins UGT71K3a/b catalyzed the glucosylation of diverse hydroxycoumarins, naphthols and flavonoids as well as phloroglucinols, enzymatically synthesized APG aglycones and pelargonidin. Total enzymatic synthesis of APG glucosides was achieved by co-incubation of recombinant dual functional chalcone/valerophenone synthase and UGT71K3 proteins with essential coenzyme A esters and UDP-glucose. An APG glucoside was identified in strawberry fruit which has not yet been reported in other plants. Suppression of UGT71K3 activity in transient RNAi-silenced fruits led to a loss of pigmentation and a substantial decrease of the levels of various APG glucosides and an anthocyanin. Metabolite analyses of transgenic fruits confirmed UGT71K3 as a UDP-glucose:APG glucosyltransferase in planta. These results provide the foundation for the breeding of fruits with improved health benefits and for the biotechnological production of bioactive natural products. PMID:26859691

  17. A UDP-glucosyltransferase functions in both acylphloroglucinol glucoside and anthocyanin biosynthesis in strawberry (Fragaria × ananassa).

    PubMed

    Song, Chuankui; Zhao, Shuai; Hong, Xiaotong; Liu, Jingyi; Schulenburg, Katja; Schwab, Wilfried

    2016-03-01

    Physiologically active acylphloroglucinol (APG) glucosides were recently found in strawberry (Fragaria sp.) fruit. Although the formation of the APG aglycones has been clarified, little is known about APG glycosylation in plants. In this study we functionally characterized ripening-related glucosyltransferase genes in Fragaria by comprehensive biochemical analyses of the encoded proteins and by a RNA interference (RNAi) approach in vivo. The allelic proteins UGT71K3a/b catalyzed the glucosylation of diverse hydroxycoumarins, naphthols and flavonoids as well as phloroglucinols, enzymatically synthesized APG aglycones and pelargonidin. Total enzymatic synthesis of APG glucosides was achieved by co-incubation of recombinant dual functional chalcone/valerophenone synthase and UGT71K3 proteins with essential coenzyme A esters and UDP-glucose. An APG glucoside was identified in strawberry fruit which has not yet been reported in other plants. Suppression of UGT71K3 activity in transient RNAi-silenced fruits led to a loss of pigmentation and a substantial decrease of the levels of various APG glucosides and an anthocyanin. Metabolite analyses of transgenic fruits confirmed UGT71K3 as a UDP-glucose:APG glucosyltransferase in planta. These results provide the foundation for the breeding of fruits with improved health benefits and for the biotechnological production of bioactive natural products.

  18. Flavonoid C-glucosides Derived from Flax Straw Extracts Reduce Human Breast Cancer Cell Growth In vitro and Induce Apoptosis

    PubMed Central

    Czemplik, Magdalena; Mierziak, Justyna; Szopa, Jan; Kulma, Anna

    2016-01-01

    Flax straw of flax varieties that are grown for oil production is a by product which represents a considerable biomass source. Therefore, its potential application for human use is of high interest. Our research has revealed that flax straw is rich in flavonoid C-glucosides, including vitexin, orientin, and isoorientin. The objective of this study was to evaluate the cytotoxicity and possible proapoptotic effect of flax straw derived C-glucosides of flavonoids in the human breast adenocarcinoma cell line (MCF-7). The effects of flax straw derived flavonoid C-glucosides on cell proliferation of MCF-7 cells were evaluated by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and sulforhodamine B assays. The expression of apoptosis-related genes was assessed by real-time PCR. Our data revealed that flax C-glucosides as well as pure compounds are cytotoxic toward MCF-7 cells and inhibit their proliferation. Moreover, the induction of apoptosis was correlated with the changes in the mRNA level of pro-apoptotic genes. Increased expression of bax and caspase-7, -8, and -9 and decreased mRNA expression of bcl-2 was observed, whereas the mRNA levels of p53 and mdm2 were not altered. These results clearly demonstrated that flax straw metabolites effectively induced growth inhibition and apoptosis in human breast adenocarcinoma cells. PMID:27630565

  19. Flavonoid C-glucosides Derived from Flax Straw Extracts Reduce Human Breast Cancer Cell Growth In vitro and Induce Apoptosis.

    PubMed

    Czemplik, Magdalena; Mierziak, Justyna; Szopa, Jan; Kulma, Anna

    2016-01-01

    Flax straw of flax varieties that are grown for oil production is a by product which represents a considerable biomass source. Therefore, its potential application for human use is of high interest. Our research has revealed that flax straw is rich in flavonoid C-glucosides, including vitexin, orientin, and isoorientin. The objective of this study was to evaluate the cytotoxicity and possible proapoptotic effect of flax straw derived C-glucosides of flavonoids in the human breast adenocarcinoma cell line (MCF-7). The effects of flax straw derived flavonoid C-glucosides on cell proliferation of MCF-7 cells were evaluated by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and sulforhodamine B assays. The expression of apoptosis-related genes was assessed by real-time PCR. Our data revealed that flax C-glucosides as well as pure compounds are cytotoxic toward MCF-7 cells and inhibit their proliferation. Moreover, the induction of apoptosis was correlated with the changes in the mRNA level of pro-apoptotic genes. Increased expression of bax and caspase-7, -8, and -9 and decreased mRNA expression of bcl-2 was observed, whereas the mRNA levels of p53 and mdm2 were not altered. These results clearly demonstrated that flax straw metabolites effectively induced growth inhibition and apoptosis in human breast adenocarcinoma cells. PMID:27630565

  20. Antidiabetic and antioxidative effects of Annona squamosa leaves are possibly mediated through quercetin-3-O-glucoside.

    PubMed

    Panda, Sunanda; Kar, Anand

    2007-01-01

    Present investigation was made to reveal the involvement of a quercetin in the antidiabetic and antiperoxidative effects of Annona squamosa leaf extract. Quercetin-3-O-glucoside (characterized by UV, IR, MS and NMR analyses) was isolated from Annona squamosa leaves and examined for its potential to regulate alloxan-induced hyperglycemia and lipid peroxidation (LPO) in rats. While in alloxan treated animals, an increase in the concentration of serum glucose with a parallel decrease in insulin level was observed, administration of 15 mg/kg/day of isolated quercetin-3-O-glucoside for 10 consecutive days to the hyperglycemic animals reversed these effects and simultaneously inhibited the activity of hepatic glucose-6-phosphatase. It further decreased the hepatic and renal LPO with a concomitant increase in the activities of antioxidative enzymes, such as catalase (CAT) and superoxide dismutase (SOD) and in glutathione (GSH) content, indicating its safe and antiperoxidative effects. These findings suggest the potential of quercetin-3-O-glucoside in the amelioration of diabetes mellitus and tissue lipid peroxidation. It also appears that the antidiabetic effects of A. squamosa leaf extract is possibly mediated through the insulin stimulating and/or free radical scavenging properties of its active constituent, quercetin-3-O-glucoside. PMID:18997283

  1. Synthesis and biological evaluation of novel dioxa-bicycle C-aryl glucosides as SGLT2 inhibitors.

    PubMed

    Yan, Qi; Ding, Ning; Li, Yingxia

    2016-02-01

    A series of novel C-aryl glucosides containing dioxa-bicycle were synthesized and evaluated for inhibition activity against hSGLT2. Among the compounds tested, compound 6a showed moderate SGLT2 inhibition activities at 700 nM. The results could benefit the discovery of new SGLT2 inhibitors. PMID:26735747

  2. In vitro anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca

    PubMed Central

    Behbahani, M.; Sayedipour, S.; Pourazar, A.; Shanehsazzadeh, M.

    2014-01-01

    Previously, we reported that the kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca showed potent anti-HSV activity. In the present study the anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside are investigated at different concentrations (100, 50, 25 and 10 μg/ml) using HIV-1 p24 Antigen kit. Real-time Polymerase chain reaction (RT-PCR) assay was also used for quantification of full range of virus load observed in treated and untreated cells. According to the results of RT- PCR, tested compounds at a concentration of 100 μg/ml exerted potent inhibitory effect. Time of drug addition experiments demonstrated that these compounds exerted their inhibitory effects on the early stage of HIV infection. The results also showed potent anti-HIV-1 reverse transcriptase activity. Antiviral activity of kaempferol-7-O-glucoside was more pronounced than that of kaempferol. These findings demonstrate that kaempferol-7-O-glucoside could be considered as a new potential drug candidate for the treatment of HIV infection which requires further assessments. PMID:26339261

  3. In vitro anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca.

    PubMed

    Behbahani, M; Sayedipour, S; Pourazar, A; Shanehsazzadeh, M

    2014-01-01

    Previously, we reported that the kaempferol and kaempferol-7-O-glucoside isolated from Securigera securidaca showed potent anti-HSV activity. In the present study the anti-HIV-1 activities of kaempferol and kaempferol-7-O-glucoside are investigated at different concentrations (100, 50, 25 and 10 μg/ml) using HIV-1 p24 Antigen kit. Real-time Polymerase chain reaction (RT-PCR) assay was also used for quantification of full range of virus load observed in treated and untreated cells. According to the results of RT- PCR, tested compounds at a concentration of 100 μg/ml exerted potent inhibitory effect. Time of drug addition experiments demonstrated that these compounds exerted their inhibitory effects on the early stage of HIV infection. The results also showed potent anti-HIV-1 reverse transcriptase activity. Antiviral activity of kaempferol-7-O-glucoside was more pronounced than that of kaempferol. These findings demonstrate that kaempferol-7-O-glucoside could be considered as a new potential drug candidate for the treatment of HIV infection which requires further assessments. PMID:26339261

  4. Flavonoid C-glucosides Derived from Flax Straw Extracts Reduce Human Breast Cancer Cell Growth In vitro and Induce Apoptosis.

    PubMed

    Czemplik, Magdalena; Mierziak, Justyna; Szopa, Jan; Kulma, Anna

    2016-01-01

    Flax straw of flax varieties that are grown for oil production is a by product which represents a considerable biomass source. Therefore, its potential application for human use is of high interest. Our research has revealed that flax straw is rich in flavonoid C-glucosides, including vitexin, orientin, and isoorientin. The objective of this study was to evaluate the cytotoxicity and possible proapoptotic effect of flax straw derived C-glucosides of flavonoids in the human breast adenocarcinoma cell line (MCF-7). The effects of flax straw derived flavonoid C-glucosides on cell proliferation of MCF-7 cells were evaluated by 3-[4,5-dimethylthiazol-2-yl]-2,5-diphenyl-tetrazolium bromide (MTT) and sulforhodamine B assays. The expression of apoptosis-related genes was assessed by real-time PCR. Our data revealed that flax C-glucosides as well as pure compounds are cytotoxic toward MCF-7 cells and inhibit their proliferation. Moreover, the induction of apoptosis was correlated with the changes in the mRNA level of pro-apoptotic genes. Increased expression of bax and caspase-7, -8, and -9 and decreased mRNA expression of bcl-2 was observed, whereas the mRNA levels of p53 and mdm2 were not altered. These results clearly demonstrated that flax straw metabolites effectively induced growth inhibition and apoptosis in human breast adenocarcinoma cells.

  5. Absorption of toxic beta-glucosides produced by plants and their effect on tissue trehalases from insects.

    PubMed

    Silva, Maria C P; Terra, Walter R; Ferreira, Clélia

    2006-03-01

    Trehalases present in body wall, Malpighian tubules, fat body, midgut and haemolymph from Tenebrio molitor (Coleoptera), Musca domestica (Diptera), Spodoptera frugiperda and Diatraea saccharalis (Lepidoptera) were assayed in the presence and absence of toxic beta-glucosides produced by plants or their aglycones. The glucosides used were phlorizin, amygdalin, prunasin and the aglycone mandelonitrile. In addition, T. molitor and S. frugiperda trehalases were assayed with and without esculin. More than 60% of total trehalase activity was found in the midgut of these insects. As a rule, trehalases present in each insect were inhibited by at least two of the glucosides. Prunasin was the best inhibitor in tissues with highest trehalase activity. S. frugiperda beta-glucosidases were not able to hydrolyze esculin. Nevertheless, their larval midguts absorb the intact glucoside that is recovered from the fat body, Malpighian tubules and mainly from haemolymph. Mature larvae fed on a diet containing 3 mM (0.1%) esculin have 0.2 mM esculin in their haemolymph, and weigh 60% of control larvae. In vitro, haemolymph trehalase activity is abolished by 0.5 mM esculin. This inhibition may play a role in the decrease of body weight and in animal survival. S. frugiperda larvae reared in 0.1% amygdalin-containing diet present higher trehalase activity in tissues than the larvae reared in 0.1% esculin-containing diet. Higher trehalase activity should be the reason why the S. frugiperda development is not impaired by 1% dietary amygdalin, in contrast to what is observed when insects are reared in 0.1% esculin. The data suggest that many plant beta-glucosides are toxic because they inhibit trehalase, a key enzyme controlling glucose availability in insects.

  6. Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.

    PubMed

    Opitz, Sebastian E W; Jensen, Søren R; Müller, Caroline

    2010-02-01

    In this study, the larval sequestration abilities and defense effectiveness of four sawfly species of the genus Athalia (Hymenoptera: Tenthredinidae) that feed as larvae either on members of the Brassicaceae or Plantaginaceae were investigated. Brassicaceae are characterized by glucosinolates (GLSs), whereas Plantaginaceae contain iridoid glucosides (IGs) as characteristic secondary compounds. Athalia rosae and A. liberta feed on members of the Brassicaceae. Larvae of A. rosae sequester aromatic and aliphatic GLSs of Sinapis alba in their hemolymph, as shown previously, but no indolic GLSs; A. liberta larvae with a narrower host range sequester aliphatic as well as indolic GLSs from their host plant Alliaria petiolata. Larvae of A. circularis and A. cordata are specialized on members of the Plantaginaceae. Athalia circularis utilizes mainly Veronica beccabunga as host plant, whereas A. cordata feeds additionally on Plantago lanceolata. Both sawfly species sequester the IGs aucubin and catalpol. In V. beccabunga, catalpol esters and carboxylated IGs also occur. The high catalpol concentrations in hemolymph of A. circularis can only be explained by a metabolization of catalpol esters and subsequent uptake of the resulting catalpol. The carboxylated IGs of the plant are excreted. The IG-sequestering sawfly species are able to accumulate much higher glucoside concentrations in their hemolymph than the GLS-sequestering species, and the concentration of IGs in hemolymph increases constantly during larval development. The defensive effectiveness of hemolymph that contains GLSs or IGs and of the respective glucosides was tested in feeding-bioassays against a potential predator, the ant Myrmica rubra (Hymenoptera: Formicidae). Hemolymph of IG-sequestering cryptic A. cordata larvae has a higher deterrence potential than hemolymph of the GLS-sequestering conspicuous A. rosae larvae. The results show that glucoside sequestration is widespread in the genus Athalia, but that the

  7. Potential applications of glucosyltransferases in terpene glucoside production: impacts on the use of aroma and fragrance.

    PubMed

    Schwab, Wilfried; Fischer, Thilo C; Giri, Ashok; Wüst, Matthias

    2015-01-01

    The detection of glucoconjugated forms of monoterpene alcohols in rose petals in the late 1960s opened the new field of nonvolatile aroma precursors in flavor research. It is now well established that odorless glycosides represent a significant pool of aroma precursors in plants where they act as preformed but inactivated defense or attractive chemicals. Technical improvements in the separation and identification of plant secondary metabolites have provided a multitude of chemical structures, but functional characterization of glycosyltransferases that catalyze their formation lags behind. As technical efforts and costs for DNA sequencing dramatically dropped during the last decade, the number of plant genome sequences increased significantly, thus providing opportunities to functionally characterize the glycosyltransferase gene families in plants. These studies yielded the first glycosyltransferase genes that encode efficient biocatalysts for the production of monoterpene glucosides. They have applications in the food, feed, chemical, cosmetic, and pharmaceutical industries as slow release aroma chemicals. PMID:25431013

  8. New polyacetylene glucosides from the florets of Carthamus tinctorius and their weak anti-inflammatory activities.

    PubMed

    He, Jun; Shen, Yi; Jiang, Jian-Shuang; Yang, Ya-Nan; Feng, Zi-Ming; Zhang, Pei-Cheng; Yuan, Shao-Peng; Hou, Qi

    2011-09-27

    Eight new linear polyacetylene glucosides (1-8), containing two C(10)-, one C(13)- and five C(14)-acetylenes, together with three known polyacetylenes (9-11) were isolated from the florets of Carthamus tinctorius L. Their structures were elucidated by means of spectroscopic methods and chemical evidence. The absolute configurations of compounds 3-9 were confirmed by Snatzke and Gerards's method, observing the induced circular dichroism after addition of dirhodium tetrakis (trifluoroacetate) [Rh(2)(OCOCF(3))(4)] in CHCl(3). All the isolated compounds (1-11) were also tested for inhibitory activities against LPS-induced NO production in murine macrophages and just showed weak activities at concentrations of 1×10(-5)M.

  9. Synthesis, characterisation and antioxidant features of procyanidin B4 and malvidin-3-glucoside stearic acid derivatives.

    PubMed

    Cruz, Luis; Fernandes, Virgínia C; Araújo, Paula; Mateus, Nuno; de Freitas, Victor

    2015-05-01

    The acylation of procyanidin B4 with a saturated fatty acid chloride containing 18 carbon atoms was studied in order to obtain procyanidin B4 3-O-di-stearic acid conjugate. This compound was structurally characterised by mass spectrometry and 1D and 2D NMR techniques. Derivatization of malvidin-3-glucoside using stearoyl chloride in acetonitrile was also performed yielding mono-, di- and tri-stearic ester derivatives. The novel derivatives obtained revealed significant antioxidant activity, although lower than the respective precursors. However, the chemical modification of anthocyanins and procyanidins (water soluble pigments) to more lipophilic compounds has the advantage of increased bioavailability in biological matrices, and to potentiate their application in food matrices and cosmetic products.

  10. Sesquiterpene lactone glucosides and alkyl glycosides from the fruit of cumin.

    PubMed

    Takayanagi, Tomomi; Ishikawa, Toru; Kitajima, Junichi

    2003-06-01

    From the polar portion of the methanolic extract of cumin (fruit of Cuminum cyminum L.), two sesquiterpenoid glucosides, cuminoside A and B, and two alkyl glycosides were isolated together with five known compounds. Their structures were established as (1S,5S,6S,10S)-10-hydroxyguaia-3,7(11)-dien-12,6-olide beta-D-glucopyranoside, (1R,5R,6S,7S,9S,10R,11R)-1,9-dihydroxyeudesm-3-en-12,6-olide 9-O-beta-D-glucopyranoside, methyl beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside and ethane-1,2-diol 1-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside, respectively.

  11. Benzoxazinoids-cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae).

    PubMed

    Baumeler, A; Hesse, M; Werner, C

    2000-01-01

    An improved method of sample preparation and simultaneous HPLC separation was developed that allowed the separation of 2,4-dihydroxy-1,4-benzoxazine-3(4H)-one (DIBOA), 2,4-dihydroxy-7-methoxy-1,4-benzoxazine-3(4H)-one (DIMBOA), 2-hydroxy-1,4-benzoxazine-3(2H)-one (HBOA), 2-hydroxy-7-methoxy-1,4-benzoxazine-3(2H)-one (HMBOA) and their corresponding glucosides as well as the benzoxazolinones BOA and MBOA. The amount and distribution of these compounds was determined in the roots of Aphelandra squarrosa and A. fuscopunctata plants. There is a significant difference in the amount and distribution of this substance class in the two species analyzed. The results are discussed in relation to their function as defence compounds and allelochemicals.

  12. Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans.

    PubMed

    Lang, Roman; Klade, Stefan; Beusch, Anja; Dunkel, Andreas; Hofmann, Thomas

    2015-12-01

    Sensory-guided fractionation of a roasted coffee beverage revealed a highly polar, bitter-tasting subfraction, from which the furokaurane glucoside mozambioside was isolated and identified in its chemical structure by means of HDMS and NMR spectra. Sensory evaluation revealed a bitter taste recognition threshold of 60 (± 10) μmol/L. UPLC-HDMS quantitation of raw coffee beans showed that Arabica coffees contained 396-1188 nmol/g mozambioside, whereas only traces (<5 nmol/g) were detected in Robusta coffees, thus suggesting that mozambioside can be used as an analytical marker for Arabica coffee. Roasted Arabica contained a substantially reduced concentration (232 ± 37 nmol/g), indicating partial degradation of mozambioside during coffee roasting. Mozambioside was nearly quantitatively extracted into the aqueous brew during coffee-making (86-98%).

  13. Synthesis and antimicrobial activity of 6-triazolo-6-deoxy eugenol glucosides.

    PubMed

    de Souza, Thiago Belarmino; Raimundo, Paulo Otávio Botelho; Andrade, Saulo Fernandes; Hipólito, Taciane Maira Magalhães; Silva, Naiara Chaves; Dias, Amanda Latercia Tranches; Ikegaki, Masaharu; Rocha, Raissa Prado; Coelho, Luiz Felipe Leomil; Veloso, Marcia Paranho; Carvalho, Diogo Teixeira; Dias, Danielle Ferreira

    2015-06-17

    A new series of 1,2,3-triazole eugenol glucosides were synthesized. The new compound structures were confirmed by MS, (1)H NMR and (13)C NMR. All of the synthesized compounds were screened for antimicrobial and cytotoxic activity. Five compounds exerted significant activity against the Gram-negative bacteria Salmonella typhimurium with low IC50 values (49.73-68.53 μΜ), and seven compounds were active against the Gram-positive bacteria Micrococcus luteus (42.89-210.94 μM). In vitro cytotoxicity on mouse spleen cells was also evaluated. One compound bearing a phenyl substituent at the triazole ring showed good activity against Salmonella typhimurium (49.73 μM) and low toxicity to normal cells (CC50=157.83 μM). Thus, the compounds herein can be considered for further modification for improving their antibacterial activity or obtaining novel antibacterial drug candidates.

  14. Mozambioside Is an Arabica-Specific Bitter-Tasting Furokaurane Glucoside in Coffee Beans.

    PubMed

    Lang, Roman; Klade, Stefan; Beusch, Anja; Dunkel, Andreas; Hofmann, Thomas

    2015-12-01

    Sensory-guided fractionation of a roasted coffee beverage revealed a highly polar, bitter-tasting subfraction, from which the furokaurane glucoside mozambioside was isolated and identified in its chemical structure by means of HDMS and NMR spectra. Sensory evaluation revealed a bitter taste recognition threshold of 60 (± 10) μmol/L. UPLC-HDMS quantitation of raw coffee beans showed that Arabica coffees contained 396-1188 nmol/g mozambioside, whereas only traces (<5 nmol/g) were detected in Robusta coffees, thus suggesting that mozambioside can be used as an analytical marker for Arabica coffee. Roasted Arabica contained a substantially reduced concentration (232 ± 37 nmol/g), indicating partial degradation of mozambioside during coffee roasting. Mozambioside was nearly quantitatively extracted into the aqueous brew during coffee-making (86-98%). PMID:26585544

  15. New fatty acid, aromatic ester and monoterpenic benzyl glucoside from the fruits of Withania coagulans Dunal.

    PubMed

    Ali, Abuzer; Jameel, Mohammad; Ali, Mohammed

    2015-01-01

    The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections in the indigenous system of medicine. Phytochemical investigation of the methanolic extract of W. coagulans fruits led to the isolation of a new fatty acid, an aromatic ester and a monoterpenic benzyl glucoside characterised as n-octatriacont-17-enoic acid (3), geranilan-10-olyl dihydrocinnamoate (4) and geranilan-8-oic acid-10-olyl salicyloxy-2-O-β-D-glucofuranosyl-(6″→1‴)-O-β-D-glucofuranosyl-6‴-n-octadec-9‴',11‴'-dienoate (5) along with two known fatty acids, n-dotriacont-21-enoic acid (1) and n-tetratriacontanoic acid (2). The structures of isolated phytoconstituents were established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means.

  16. Decyl glucoside as a corrosion inhibitor for magnesium-air battery

    NASA Astrophysics Data System (ADS)

    Deyab, M. A.

    2016-09-01

    In this research, the effects of decyl glucoside (DG) on the corrosion inhibition and battery performance of Mg-air battery have been investigated. Chemical and electrochemical techniques have been used to evaluate the corrosion rate and inhibitor efficiency. Mg surface has been characterized with scanning electron microscopy (SEM) and infrared spectroscopy (FTIR). A significant reduction in the corrosion rate of Mg in battery electrolyte (3.5% NaCl solution) has been observed in the presence of DG surfactant. Maximum inhibition efficiency (>94%) is achieved at critical micelle concentration of DG surfactant (CMC = 2.5 mM). The presence of DG surfactant increases the activation energy of the corrosion reaction. Physisorption mechanism has been suggested for the inhibition action of DG surfactant. The Mg-air battery containing DG surfactant offers higher operating voltage, discharge capacity and anodic utilization than in its absence.

  17. Isolation of new flavan-3-ol and lignan glucoside from Loropetalum chinense and their antimicrobial activities.

    PubMed

    Zhang, Qinghua; Fan, Dan; Xiong, Bingjian; Kong, Lingbao; Zhu, Xiangdong

    2013-10-01

    Phytochemical and antimicrobial activity study on the ethanol extract of the leaves and stems of Loropetalum chinense led to the isolation of a new flavan-3-ol compounds, 8-[1-(3,4-dihydroxyphenyl)-3-methoxy-3-oxopropyl]-catechin (loropetaliside A) (1) and a new lignan glucoside, 1-(5-hydroxy-3-methoxyphenyl)-2-(2-β-glucopyranosyl-4-hydroxy-5-(1-(E)propen-3-ol)-phenyl)-propane-3-ol (loropetaliside B) (3) and several known compounds manglieside D (2), quercetin (4), kaempferol-3-O-D-glucopyranoside (5), quercetin-3-O-β-L-rhamnoside (6) and tiliroside (7). Their structures were elucidated on the basis of extensive spectroscopic analysis.

  18. Stability studies of ascorbic acid 2-glucoside in cosmetic lotion using surface response methodology.

    PubMed

    Huang, Wen-Ying; Lee, Pei-Chi; Huang, Ling-Kuei; Lu, Li-Ping; Liao, Wayne C

    2013-03-15

    Ascorbic acid 2-glucoside (AA-2G) has been widely used in cream and lotion types of cosmetic products. Thus, the degradation of AA-2G caused by the temperature change and pH variation was very critical for determining the bio-functionality of cosmetics. Response surface methodology (RSM) was introduced to study the influence of temperature and pH on the stability of AA-2G. The optimal condition of retaining AA-2G with the highest stability was determined to be 55.3°C and pH 6.4. The antioxidative activities of AA-2G including DPPH and ABTS free radical scavenging activities, metal chelating activity, and reducing ability were also determined. AA-2G was a good ascorbic acid derivative which could be used in cosmetic products as an active ingredient.

  19. Occurrence of deoxynivalenol and deoxynivalenol-3-glucoside in hard red spring wheat grown in the USA.

    PubMed

    Simsek, Senay; Ovando-Martínez, Maribel; Ozsisli, Bahri; Whitney, Kristin; Ohm, Jae-Bom

    2013-12-18

    Deoxynivalenol (DON) is a mycotoxin found in wheat that is infected with Fusarium fungus. DON may also be converted to a type of "masked mycotoxin", named deoxynivalenol-3-glucoside (D3G), as a result of detoxification of the plant. In this study, DON and D3G were measured using gas chromatographic (GC) and liquid chromatography-mass spectrometry (LC-MS) in wheat samples collected during 2011 and 2012 in the USA. Results indicate that the growing region had a significant effect on the DON and D3G (p < 0.0001). There was a positive correlation between both methods (GC and LC-MS) used for determination of DON content. DON showed a significant and positive correlation with D3G during 2011. Overall, DON production had an effect on D3G content and kernel damage, and was dependent on environmental conditions during Fusarium infection.

  20. Some aspects of the inhibitory activity of hypolaetin-8-glucoside in acute inflammation.

    PubMed

    Villar, A; Gascó, M A; Alcaraz, M J

    1987-07-01

    Hypolaetin-8-glucoside (H-8-G) has been examined for its mode of action in several models of acute inflammation. Its anti-inflammatory activity in carrageenan-induced inflammation of the rat hind-paw is not affected either by adrenalectomy or by phentolamine given with propranolol. H-8-G and its aglycone, hypolaetin, did not antagonize the actions of histamine, 5-hydroxytryptamine (5-HT), bradykinin or prostaglandin E2 (PGE2) on various smooth muscle preparations in-vitro, but protected erythrocytes from heat-induced lysis. The glycoside was more potent than troxerutin on capillary permeability increased by histamine and exerted inhibitory effects on protein exudation, leucocyte migration and beta-glucuronidase activity in the carrageenan air pouch, thereby showing some difference from indomethacin. These results are discussed in relation to the features of non-steroidal anti-inflammatory drugs (NSAID) and flavonoid anti-inflammatory actions.

  1. Molecular cloning and characterization of genistein 4'-O-glucoside specific glycosyltransferase from Bacopa monniera.

    PubMed

    Ruby; Santosh Kumar, R J; Vishwakarma, Rishi K; Singh, Somesh; Khan, Bashir M

    2014-07-01

    Health related benefits of isoflavones such as genistein are well known. Glycosylation of genistein yields different glycosides like genistein 7-O-glycoside (genistin) and genistein 4'-O-glycoside (sophoricoside). This is the first report on isolation, cloning and functional characterization of a glycosyltransferase specific for genistein 4'-O-glucoside from Bacopa monniera, an important Indian medicinal herb. The glycosyltransferase from B. monniera (UGT74W1) showed 49% identity at amino acid level with the glycosyltransferases from Lycium barbarum. The UGT74W1 sequence contained all the conserved motifs present in plant glycosyltransferases. UGT74W1 was cloned in pET-30b (+) expression vector and transformed into E. coli. The molecular mass of over expressed protein was found to be around 52 kDa. Functional characterization of the enzyme was performed using different substrates. Product analysis was done using LC-MS and HPLC, which confirmed its specificity for genistein 4'-O-glucoside. Immuno-localization studies of the UGT74W1 showed its localization in the vascular bundle. Spatio-temporal expression studies under normal and stressed conditions were also performed. The control B. monniera plant showed maximum expression of UGT74W1 in leaves followed by roots and stem. Salicylic acid treatment causes almost tenfold increase in UGT74W1 expression in roots, while leaves and stem showed decrease in expression. Since salicylic acid is generated at the time of injury or wound caused by pathogens, this increase in UGT74W1 expression under salicylic acid stress might point towards its role in defense mechanism.

  2. Molecular cloning and characterization of genistein 4'-O-glucoside specific glycosyltransferase from Bacopa monniera.

    PubMed

    Ruby; Santosh Kumar, R J; Vishwakarma, Rishi K; Singh, Somesh; Khan, Bashir M

    2014-07-01

    Health related benefits of isoflavones such as genistein are well known. Glycosylation of genistein yields different glycosides like genistein 7-O-glycoside (genistin) and genistein 4'-O-glycoside (sophoricoside). This is the first report on isolation, cloning and functional characterization of a glycosyltransferase specific for genistein 4'-O-glucoside from Bacopa monniera, an important Indian medicinal herb. The glycosyltransferase from B. monniera (UGT74W1) showed 49% identity at amino acid level with the glycosyltransferases from Lycium barbarum. The UGT74W1 sequence contained all the conserved motifs present in plant glycosyltransferases. UGT74W1 was cloned in pET-30b (+) expression vector and transformed into E. coli. The molecular mass of over expressed protein was found to be around 52 kDa. Functional characterization of the enzyme was performed using different substrates. Product analysis was done using LC-MS and HPLC, which confirmed its specificity for genistein 4'-O-glucoside. Immuno-localization studies of the UGT74W1 showed its localization in the vascular bundle. Spatio-temporal expression studies under normal and stressed conditions were also performed. The control B. monniera plant showed maximum expression of UGT74W1 in leaves followed by roots and stem. Salicylic acid treatment causes almost tenfold increase in UGT74W1 expression in roots, while leaves and stem showed decrease in expression. Since salicylic acid is generated at the time of injury or wound caused by pathogens, this increase in UGT74W1 expression under salicylic acid stress might point towards its role in defense mechanism. PMID:24664316

  3. The underlying toxicological mechanism of chemical mixtures: A case study on mixture toxicity of cyanogenic toxicants and aldehydes to Photobacterium phosphoreum

    SciTech Connect

    Tian, Dayong; Lin, Zhifen; Zhou, Xianghong; Yin, Daqiang

    2013-10-15

    Intracellular chemical reaction of chemical mixtures is one of the main reasons that cause synergistic or antagonistic effects. However, it still remains unclear what the influencing factors on the intracellular chemical reaction are, and how they influence on the toxicological mechanism of chemical mixtures. To reveal this underlying toxicological mechanism of chemical mixtures, a case study on mixture toxicity of cyanogenic toxicants and aldehydes to Photobacterium phosphoreum was employed, and both their joint effects and mixture toxicity were observed. Then series of two-step linear regressions were performed to describe the relationships between joint effects, the expected additive toxicities and descriptors of individual chemicals (including concentrations, binding affinity to receptors, octanol/water partition coefficients). Based on the quantitative relationships, the underlying joint toxicological mechanisms were revealed. The result shows that, for mixtures with their joint effects resulting from intracellular chemical reaction, their underlying toxicological mechanism depends on not only their interaction with target proteins, but also their transmembrane actions and their concentrations. In addition, two generic points of toxicological mechanism were proposed including the influencing factors on intracellular chemical reaction and the difference of the toxicological mechanism between single reactive chemicals and their mixtures. This study provided an insight into the understanding of the underlying toxicological mechanism for chemical mixtures with intracellular chemical reaction. - Highlights: • Joint effects of nitriles and aldehydes at non-equitoxic ratios were determined. • A novel descriptor, ligand–receptor interaction energy (E{sub binding}), was employed. • Quantitative relationships for mixtures were developed based on a novel descriptor. • The underlying toxic mechanism was revealed based on quantitative relationships. • Two

  4. Metabolism of Monoterpenes : Early Steps in the Metabolism of d-Neomenthyl-beta-d-Glucoside in Peppermint (Mentha piperita) Rhizomes.

    PubMed

    Croteau, R; Sood, V K; Renstrøm, B; Bhushan, R

    1984-11-01

    Previous studies have shown that the monoterpene ketone l-[G-(3)H] menthone is reduced to the epimeric alcohols l-menthol and d-neomenthol in leaves of flowering peppermint (Mentha piperita L.), and that a portion of the menthol is converted to menthyl acetate while the bulk of the neomenthol is transformed to neomenthyl-beta-d-glucoside which is then transported to the rhizome (Croteau, Martinkus 1979 Plant Physiol 64: 169-175). Analysis of the disposition of l-[G-(3)H]menthone applied to midstem leaves of intact flowering plants allowed the kinetics of synthesis and transport of the monoterpenyl glucoside to be determined, and gave strong indication that the glucoside was subsequently metabolized in the rhizome. Studies with d-[G-(3)H]neomenthyl-beta-d-glucoside as substrate, using excised rhizomes or rhizome segments, confirmed the hydrolysis of the glucoside as an early step in metabolism at this site, and revealed that the terpenoid moiety was further converted to a series of ether-soluble, methanol-soluble, and water-soluble products. Studies with d-[G-(3)H]neomenthol as the substrate, using excised rhizomes, showed the subsequent metabolic steps to involve oxidation of the alcohol back to menthone, followed by an unusual lactonization reaction in which oxygen is inserted between the carbonyl carbon and the carbon bearing the isopropyl group, to afford 3,4-menthone lactone. The conversion of menthone to the lactone, and of the lactone to more polar products, were confirmed in vivo using l-[G-(3)H]menthone and l-[G-(3)H]-3,4-menthone lactone as substrates. Additional oxidation products were formed in vivo via the desaturation of labeled neomenthol and/or menthone, but none of these transformations appeared to lead to ring opening of the p-menthane skeleton. Each step in the main reaction sequence, from hydrolysis of neomenthyl glucoside to lactonization of menthone, was demonstrated in cell-free extracts from the rhizomes of flowering mint plants. The

  5. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate

    PubMed Central

    Schmeitzl, Clemens; Warth, Benedikt; Fruhmann, Philipp; Michlmayr, Herbert; Malachová, Alexandra; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf; Adam, Gerhard

    2015-01-01

    Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-β-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-β-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-β-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives. PMID:26274975

  6. The Metabolic Fate of Deoxynivalenol and Its Acetylated Derivatives in a Wheat Suspension Culture: Identification and Detection of DON-15-O-Glucoside, 15-Acetyl-DON-3-O-Glucoside and 15-Acetyl-DON-3-Sulfate.

    PubMed

    Schmeitzl, Clemens; Warth, Benedikt; Fruhmann, Philipp; Michlmayr, Herbert; Malachová, Alexandra; Berthiller, Franz; Schuhmacher, Rainer; Krska, Rudolf; Adam, Gerhard

    2015-08-12

    Deoxynivalenol (DON) is a protein synthesis inhibitor produced by the Fusarium species, which frequently contaminates grains used for human or animal consumption. We treated a wheat suspension culture with DON or one of its acetylated derivatives, 3-acetyl-DON (3-ADON), 15-acetyl-DON (15-ADON) and 3,15-diacetyl-DON (3,15-diADON), and monitored the metabolization over a course of 96 h. Supernatant and cell extract samples were analyzed using a tailored LC-MS/MS method for the quantification of DON metabolites. We report the formation of tentatively identified DON-15-O-β-D-glucoside (D15G) and of 15-acetyl-DON-3-sulfate (15-ADON3S) as novel deoxynivalenol metabolites in wheat. Furthermore, we found that the recently identified 15-acetyl-DON-3-O-β-D-glucoside (15-ADON3G) is the major metabolite produced after 15-ADON challenge. 3-ADON treatment led to a higher intracellular content of toxic metabolites after six hours compared to all other treatments. 3-ADON was exclusively metabolized into DON before phase II reactions occurred. In contrast, we found that 15-ADON was directly converted into 15-ADON3G and 15-ADON3S in addition to metabolization into deoxynivalenol-3-O-β-D-glucoside (D3G). This study highlights significant differences in the metabolization of DON and its acetylated derivatives.

  7. Overexpression of the UGT73C6 alters brassinosteroid glucoside formation in Arabidopsis thaliana

    PubMed Central

    2011-01-01

    Background Brassinosteroids (BRs) are signaling molecules that play essential roles in the spatial regulation of plant growth and development. In contrast to other plant hormones BRs act locally, close to the sites of their synthesis, and thus homeostatic mechanisms must operate at the cellular level to equilibrate BR concentrations. Whilst it is recognized that levels of bioactive BRs are likely adjusted by controlling the relative rates of biosynthesis and by catabolism, few factors, which participate in these regulatory events, have as yet been identified. Previously we have shown that the UDP-glycosyltransferase UGT73C5 of Arabidopsis thaliana catalyzes 23-O-glucosylation of BRs and that glucosylation renders BRs inactive. This study identifies the closest homologue of UGT73C5, UGT73C6, as an enzyme that is also able to glucosylate BRs in planta. Results In a candidate gene approach, in which homologues of UGT73C5 were screened for their potential to induce BR deficiency when over-expressed in plants, UGT73C6 was identified as an enzyme that can glucosylate the BRs CS and BL at their 23-O-positions in planta. GUS reporter analysis indicates that UGT73C6 shows over-lapping, but also distinct expression patterns with UGT73C5 and YFP reporter data suggests that at the cellular level, both UGTs localize to the cytoplasm and to the nucleus. A liquid chromatography high-resolution mass spectrometry method for BR metabolite analysis was developed and applied to determine the kinetics of formation and the catabolic fate of BR-23-O-glucosides in wild type and UGT73C5 and UGT73C6 over-expression lines. This approach identified novel BR catabolites, which are considered to be BR-malonylglucosides, and provided first evidence indicating that glucosylation protects BRs from cellular removal. The physiological significance of BR glucosylation, and the possible role of UGT73C6 as a regulatory factor in this process are discussed in light of the results presented. Conclusion

  8. Skin absorption and metabolism of a new vitamin E prodrug, delta-tocopherol-glucoside: in vitro evaluation in human skin models.

    PubMed

    Mavon, Alain; Raufast, Véronique; Redoulès, Daniel

    2004-11-24

    The aim of this study was to investigate the cutaneous penetration and metabolism of the new vitamin E prodrug delta-tocopherol glucoside (delta-TG), as compared to those of common vitamin E acetate, in vitro, both in reconstituted human epidermis and in viable human skin. Better diffusion was observed with alpha-tocopherol acetate (alpha-TAc) than with delta-tocopherol glucoside in both skin models, at 0.1% and 0.05% in a myritol solution; however, no metabolism was detected with alpha-tocopherol acetate. In all conditions tested (two skin models, two concentrations, three test times, and compartmental analysis) the delta-tocopherol glucoside was metabolized into free tocopherol. In the reconstituted human epidermis, after 18 h, over 90% of the delta-tocopherol glucoside was bioconverted. In the viable human skin, the extent of metabolism was about 20%, with 0.12 and 0.10 microg/cm2 of delta-tocopherol glucoside in the stratum corneum and epidermis, respectively. After topical application, the delta-tocopherol glucoside had a considerable reservoir effect, associated with gradual delivery of free tocopherol. The use of this gluco-conjugated vitamin E at a low concentration shows the capability of the skin to metabolize the prodrug in a slow and prolonged manner, making this gluco-conjugated vitamin E an excellent candidate for continuous reinforcement of antioxidants in the skin.

  9. Purification of the labeled cyanogen bromide peptides of the. cap alpha. polypeptide from sodium and potassium ion-activated adenosinetriphosphatase modified with N-(/sup 3/H)ethylmaleimide

    SciTech Connect

    Le, D.T.

    1985-01-01

    Sodium and potassium ion-activated adenosinetriphosphatase, isolated from canine kidney, was reacted with N-(/sup 3/H)ethylmaleimide under three different conditions, defined by particular concentrations of ligands for the enzyme, such that after the same amount of time the remaining activity of then enzyme varied from 90% to 30%. The conformation of the enzyme also differed among the three conditions. In all cases, the ..cap alpha..-polypeptide was purified and subjected to cyanogen bromide digestion. Two distinct, radioactive peptides were separated by gel filtration of the cyanogen bromide digest on a column of Sephadex LH-60 equilibrated with 95% ethanol: 88% formic acid:4:1. One of the radioactive peptides was shown to contain the sulfhydryl residue whose reaction with N-ethylmaleimide inactivates the enzyme. The other radioactive peptide contained a sulfhydryl residue that seems to react with N-ethylmaleimide only when the binding site for ATP is not occupied. Alkylation of this residue, however, does not result in inactivation of enzyme. Both peptides were purified further by high-pressure liquid chromatography, and their amino-terminal sequences were determined by the manual dansyl-Edman or solid-phase techniques. The peptide containing the sulfhydryl protected by ATP has, as its amino terminus, the lysine that reacts exclusively with fluorescein-5'-isothiocyanate.

  10. Cool-cultivated red leaf lettuce accumulates cyanidin-3-O-(6″-O-malonyl)-glucoside and caffeoylmalic acid.

    PubMed

    Becker, Christine; Klaering, Hans-Peter; Kroh, Lothar W; Krumbein, Angelika

    2014-03-01

    Cultivating lettuce in greenhouses at low temperatures improves its CO2-balance and may increase its content of flavonoid glycosides and phenolic acids. We cultivated 5weeks old red leaf lettuce seedlings at 20/15°C (day/night) or 12/7°C until plants reached comparable growth stages: small heads were harvested after 13 (warm) and 26 (cool)days, while mature heads were harvested after 26 (warm) or 52 (cool)days. Additionally, some plants were cultivated first cool then warm and vice versa (39days). Cool-cultivated small heads had higher concentrations of cyanidin-3-O-(6″-O-malonyl)-glucoside and caffeoylmalic acid than warm-cultivated ones but we detected no differences concerning quercetin and luteolin glycosides or di-O-caffeoyltartaric and 5-O-caffeoylquinic acid. Regarding mature heads, there were only differences concerning cyanidin-3-O-(6″-O-malonyl)-glucoside. We therefore suggest that only cyanidin-3-O-(6″-O-malonyl)-glucoside was truly responsive to temperatures alone. Previously reported contrasting effects may rather be due to comparison of different growth stages or interactive effects with radiation.

  11. Hydrolysis of aromatic β-glucosides by non-pathogenic bacteria confers a chemical weapon against predators.

    PubMed

    Sonowal, Robert; Nandimath, Krithi; Kulkarni, Sucheta S; Koushika, Sandhya P; Nanjundiah, Vidyanand; Mahadevan, S

    2013-07-01

    Bacteria present in natural environments such as soil have evolved multiple strategies to escape predation. We report that natural isolates of Enterobacteriaceae that actively hydrolyze plant-derived aromatic β-glucosides such as salicin, arbutin and esculin, are able to avoid predation by the bacteriovorous amoeba Dictyostelium discoideum and nematodes of multiple genera belonging to the family Rhabditidae. This advantage can be observed under laboratory culture conditions as well as in the soil environment. The aglycone moiety released by the hydrolysis of β-glucosides is toxic to predators and acts via the dopaminergic receptor Dop-1 in the case of Caenorhabditis elegans. While soil isolates of nematodes belonging to the family Rhabditidae are repelled by the aglycone, laboratory strains and natural isolates of Caenorhabditis sp. are attracted to the compound, mediated by receptors that are independent of Dop-1, leading to their death. The β-glucosides-positive (Bgl(+)) bacteria that are otherwise non-pathogenic can obtain additional nutrients from the dead predators, thereby switching their role from prey to predator. This study also offers an evolutionary explanation for the retention by bacteria of 'cryptic' or 'silent' genetic systems such as the bgl operon. PMID:23677347

  12. Synthesis of α - mangostin-D-glucoside in supercritical carbon dioxide media.

    PubMed

    Zarena, A S; Sankar, Kadimi Udaya

    2015-10-01

    α-Mangostin, the major xanthone constituent of mangoteen fruit pericarp, has several important pharmaceutical application but its bioavailability is restricted due to its insolubility in water. Herein, we synthesized water soluble α-mangostin-D-glucoside by glycosylation of α-mangostin at hydroxyl group; using amyloglucosidase (3.2.1.3) catalyzed reaction in supercritical carbon dioxide (SC-CO2) media. Response surface methodology (RSM) based on a five-variable central composite rotatable design involving 32 experiments was used to determine the effect of pressure (80-160 bar), temperature (35-75 °C), enzyme concentration (15-45 mg), buffer pH (4.0-8.0) and buffer volume (1.0-5.0 mL). Experimental data fitted the second-order polynomial equation as indicated by R(2) value of 0.94. The optimal enzymatic conversion within the experimental range of the variables reached 20.3 % at a pressure of 120 bar, temperature of 55 °C, enzyme concentration of 30 mg, buffer volume of 3 mL and pH 6.0 which is well matched with the predictive yield.

  13. Furofuran Lignan Glucosides with Estrogen-Inhibitory Properties from the Bangladeshi Medicinal Plant Terminalia citrina.

    PubMed

    Muhit, Md Abdul; Umehara, Kaoru; Mori-Yasumoto, Kanami; Noguchi, Hiroshi

    2016-05-27

    Extracts from the leaves of the Bangladeshi medicinal plant Terminalia citrina were prepared, and 13 new furofuran lignan glucosides, terminalosides A-K (1-4, 6-12), 2-epiterminaloside D (5), and 6-epiterminaloside K (13), were characterized using various spectroscopic techniques. Twelve of the isolates were found to contain rare tetraoxygenated aryl groups in their structures. Analysis of the NMR chemical shifts for the oxymethine signals in the furofuran ring suggested a pragmatic approach to determining the relative configuration of these compounds. The ECD and NOESY spectroscopic data obtained allowed for the deduction of the absolute configurations and conformations of the compounds. The isolates were tested for their estrogenic/antiestrogenic activity using the MCF-7 and T47D estrogen-responsive human breast cancer cell lines. Terminalosides B (2) and G (8) exhibited inhibitory effects for both cell lines, and estradiol-enhanced cell proliferation was suppressed by 90% at concentrations lower than 10 μM. Terminaloside E (6) showed inhibitory activity against the T47D cell line, whereas terminalosides C (3), F (7), and I (10) and 6-epiterminaloside K (13) displayed antiestrogenic activity against MCF-7 cells. PMID:27110635

  14. Prophylactic Efficacy of Quercetin 3-β-O-d-Glucoside against Ebola Virus Infection.

    PubMed

    Qiu, Xiangguo; Kroeker, Andrea; He, Shihua; Kozak, Robert; Audet, Jonathan; Mbikay, Majambu; Chrétien, Michel

    2016-09-01

    Ebola outbreaks occur on a frequent basis, with the 2014-2015 outbreak in West Africa being the largest one ever recorded. This outbreak has resulted in over 11,000 deaths in four African countries and has received international attention and intervention. Although there are currently no approved therapies or vaccines, many promising candidates are undergoing clinical trials, and several have had success in promoting recovery from Ebola. However, these prophylactics and therapeutics have been designed and tested only against the same species of Ebola virus as the one causing the current outbreak. Future outbreaks involving other species would require reformulation and possibly redevelopment. Therefore, a broad-spectrum alternative is highly desirable. We have found that a flavonoid derivative called quercetin 3-β-O-d-glucoside (Q3G) has the ability to protect mice from Ebola even when given as little as 30 min prior to infection. Furthermore, we have demonstrated that this compound targets the early steps of viral entry. Most promisingly, antiviral activity against two distinct species of Ebola virus was seen. This study serves as a proof of principle that Q3G has potential as a prophylactic against Ebola virus infection.

  15. Prophylactic Efficacy of Quercetin 3-β-O-d-Glucoside against Ebola Virus Infection.

    PubMed

    Qiu, Xiangguo; Kroeker, Andrea; He, Shihua; Kozak, Robert; Audet, Jonathan; Mbikay, Majambu; Chrétien, Michel

    2016-09-01

    Ebola outbreaks occur on a frequent basis, with the 2014-2015 outbreak in West Africa being the largest one ever recorded. This outbreak has resulted in over 11,000 deaths in four African countries and has received international attention and intervention. Although there are currently no approved therapies or vaccines, many promising candidates are undergoing clinical trials, and several have had success in promoting recovery from Ebola. However, these prophylactics and therapeutics have been designed and tested only against the same species of Ebola virus as the one causing the current outbreak. Future outbreaks involving other species would require reformulation and possibly redevelopment. Therefore, a broad-spectrum alternative is highly desirable. We have found that a flavonoid derivative called quercetin 3-β-O-d-glucoside (Q3G) has the ability to protect mice from Ebola even when given as little as 30 min prior to infection. Furthermore, we have demonstrated that this compound targets the early steps of viral entry. Most promisingly, antiviral activity against two distinct species of Ebola virus was seen. This study serves as a proof of principle that Q3G has potential as a prophylactic against Ebola virus infection. PMID:27297486

  16. Glucosidic pathways of glycogen breakdown and glucose production by muscle from postexercised frogs.

    PubMed

    Fournier, P A; Guderley, H

    1993-11-01

    Muscle and body glucose in frogs increases markedly during the initial hour of recovery after strenuous exercise. The liver is not the major source responsible for this accumulation. This is indicated by the stability of liver glycogen levels after exercise and by the observation that hepatectomized and normal frogs accumulate similar amounts of glucose in their muscles and body during recovery. The renal contribution cannot account for this increase in body glucose. Most of the glucose that accumulates in the body after exercise has a muscular origin, as indicated by the facts that two-thirds of the body glucose is found in muscle and that the intracellular levels of muscle glucose are much higher than those of the plasma. The glucose that accumulates outside muscle may also have a muscular origin. The glucosidic pathways of glycogen breakdown are the only metabolic avenue with sufficient capacity to account for the amount of glucose accumulated in muscle during the first hour of recovery. These results indicate that the ability of an isolated preparation of frog muscle to liberate glucose during recovery from exercise (Fournier et al. J. Biol. Chem. 267: 8234-8238, 1992) is not an artifactual metabolic curiosity but rather a metabolic reality that takes place in vivo. Glucose accumulation during recovery is thought to facilitate the metabolic transition of frog carbohydrate metabolism from a catabolic state, characteristic of exercise, to an anabolic one. PMID:8238616

  17. Investigation of coco-glucoside as a novel intestinal permeation enhancer in rat models.

    PubMed

    Aguirre, Tanira A S; Rosa, Mónica; Guterres, Sílvia S; Pohlmann, Adriana R; Coulter, Ivan; Brayden, David J

    2014-11-01

    Due to instability in the GI tract and low intestinal permeability, peptides invariably have oral bioavailabilities below 1% and this has prevented the development of oral formulations. A mild plant-derived naturalalkyl polyglycoside (APG), coco-glucoside (CG), was studied for its capacity to enable rat intestinal permeation of the paracellular sugar marker, fluorescein isothiocyanate-dextran 4000 (FD4), across isolated rat jejunal and colonic mucosae mounted in Ussing chambers, as well as the polypeptide, salmon calcitonin (sCT) following intra-intestinal instillations in rats. 0.1% (w/v) CG enabled a 2.9-fold increase in the apparent permeability coefficient (Papp) of FD4 over the basal Papp across colonic mucosae, but it was without effect in jejunal mucosae. In situ intestinal instillations revealed that although sCT was absorbed across rat colonic loops to a greater extent than jejunal, CG still improved sCT absolute bioavailability(F) from both segments. Histopathology of rat intestinal mucosae following exposure to CG indicated only minor perturbation with adequate maintenance of secretory function. High content analysis(HCA) on Caco-2 showed that acute and chronic exposure to a range of concentrations of CG did not cause sub-lethal damage at concentrations at which it was effective as an enhancer. Overall, CG increased bioavailability of sCT across rat jejunal and colonic loops without indication of tissue damage. Thus, CG has potential as a safe and effective intestinal enhancer for oral delivery of proteins and peptides.

  18. Protective effects of luteolin-7-glucoside against liver injury caused by carbon tetrachloride in rats.

    PubMed

    Qiusheng, Zheng; Xiling, Sun; Xubo; Meng, Song; Changhai, Wang

    2004-04-01

    Ixeris chinensis (Thunb.) Nakai has been used as a Chinese folk medicine; the information on the physiological and biochemical functions of the compounds extracted from I. chinensis is still scanty. We investigated the effects of luteolin -7-glucoside (LUTG) isolated from I. chinensis against liver injury caused by carbon tetrachloride (CCl4). CCl4 significantly increased the enzyme activities of glutamic pyruvic transaminase (GPT) and glutamic oxaloacetic transaminase (GOT) in blood serum, as well as the level of malondialdehyde (MDA) and 8-hydroxydeoxyguanosine (8-OHdG) in liver tissue, and decreased the levels of reduced glutathione (GSH). Pretreatment with LUTG was not only able to suppress the elevation of GPT, GOT, MDA and 8-OHdG, and inhibit the reduction of GSH in a dose-dependent manner in vivo, but also reduce the damage of hepatocytes in vitro. On the other hand, we also found LUTG has strong antioxidant activity against reactive oxygen species (ROS) in vitro in a concentration-dependent manner. The hepatoprotective activity of LUTG was possibly due to its antioxidant properties, acting as scavengers of ROS. These results obtained in vivo and in vitro suggest that LUTG had protective effects against hepatic oxidative injury induced by chemicals. Further studies on the pharmaceutical functions and immunological responses of LUTG may help in the development of a clinical application.

  19. Effects of iriflophenone 3-C-β-glucoside on fasting blood glucose level and glucose uptake

    PubMed Central

    Pranakhon, Ratree; Aromdee, Chantana; Pannangpetch, Patchareewan

    2015-01-01

    Background: One of the biological activities of agar wood (Aquilaria sinensis Lour., Thymelaeaceae), is anti-hyperglycemic activity. The methanolic extract (ME) was proven to possess the fasting blood glucose activity in rat and glucose uptake transportation by rat adipocytes. Objective: To determine the decreasing fasting blood glucose level of constituents affordable for in vivo test. If the test was positive, the mechanism which is positive to the ME, glucose transportation, will be performed. Materials and Methods: The ME was separated by column chromatography and identified by spectroscopic methods. Mice was used as an animal model (in vivo), and rat adipocytes were used for the glucose transportation activity (in vitro). Result: Iriflophenone 3-C-β-glucoside (IPG) was the main constituent, 3.17%, and tested for the activities. Insulin and the ME were used as positive controls. The ME, IPG and insulin lowered blood glucose levels by 40.3, 46.4 and 41.5%, respectively, and enhanced glucose uptake by 152, 153, and 183%, respectively. Conclusion: These findings suggest that IPG is active in lowering fasting blood glucose with potency comparable to that of insulin. PMID:25709215

  20. The iridoid glucoside, antirrhinoside, from Antirrhinum majus L. has differential effects on two generalist insect herbivores.

    PubMed

    Beninger, Clifford W; Cloutier, Renée R; Grodzinski, Bernard

    2008-05-01

    The iridoid glucoside, antirrhinoside, is constitutively distributed throughout Antirrhinum majus L. in a manner consistent with its possible role as an allelochemical, but there is no evidence that it has a defensive function with respect to insect herbivory. To address this question, two generalist herbivores, Lymantria dispar L. (gypsy moth) and Trichoplusia ni Hübner (cabbage looper) were chosen for feeding trials on excised whole leaves of A. majus and in artificial diet assays. In leaf excision feeding trials, fourth instar gypsy moth rejected, without sampling, the leaves of A. majus regardless of what node the leaf was excised from. In contrast, fourth instar cabbage looper readily fed on the excised leaves, and antirrhinoside was not found in their bodies or feces (frass) as determined by thin layer and high-pressure liquid chromatography. In the leaf and diet assays, a second major leaf iridoid in A. majus, antirrhide, was found in both cabbage looper and gypsy moth frass. In diet feeding assays, the growth of gypsy moth and cabbage looper were not inhibited by methanol extracts, iridoid fractions, or pure antirrhinoside at concentrations of 0.6% in diet, but cabbage looper growth was enhanced. At an antirrhinoside concentration of 3.3% in diet, gypsy moth growth was reduced, whereas cabbage looper growth again increased significantly relative to the control. It is likely that antirrhinoside functions as defense against herbivory for one generalist insect herbivore but also, at low concentrations, enhances the growth of another. PMID:18414950

  1. PLS-Prediction and Confirmation of Hydrojuglone Glucoside as the Antitrypanosomal Constituent of Juglans Spp.

    PubMed

    Ellendorff, Therese; Brun, Reto; Kaiser, Marcel; Sendker, Jandirk; Schmidt, Thomas J

    2015-05-29

    Naphthoquinones (NQs) occur naturally in a large variety of plants. Several NQs are highly active against protozoans, amongst them the causative pathogens of neglected tropical diseases such as human African trypanosomiasis (sleeping sickness), Chagas disease and leishmaniasis. Prominent NQ-producing plants can be found among Juglans spp. (Juglandaceae) with juglone derivatives as known constituents. In this study, 36 highly variable extracts were prepared from different plant parts of J. regia, J. cinerea and J. nigra. For all extracts, antiprotozoal activity was determined against the protozoans Trypanosoma cruzi, T. brucei rhodesiense and Leishmania donovani. In addition, an LC-MS fingerprint was recorded for each extract. With each extract's fingerprint and the data on in vitro growth inhibitory activity against T. brucei rhodesiense a Partial Least Squares (PLS) regression model was calculated in order to obtain an indication of compounds responsible for the differences in bioactivity between the 36 extracts. By means of PLS, hydrojuglone glucoside was predicted as an active compound against T. brucei and consequently isolated and tested in vitro. In fact, the pure compound showed activity against T. brucei at a significantly lower cytotoxicity towards mammalian cells than established antiprotozoal NQs such as lapachol.

  2. Analysis of Deoxynivalenol and Deoxynivalenol-3-glucoside in Hard Red Spring Wheat Inoculated with Fusarium Graminearum

    PubMed Central

    Ovando-Martínez, Maribel; Ozsisli, Bahri; Anderson, James; Whitney, Kristin; Ohm, Jae-Bom; Simsek, Senay

    2013-01-01

    Deoxynivalenol (DON) is a mycotoxin affecting wheat quality. The formation of the “masked” mycotoxin deoxinyvalenol-3-glucoside (D3G) results from a defense mechanism the plant uses for detoxification. Both mycotoxins are important from a food safety point of view. The aim of this work was to analyze DON and D3G content in inoculated near-isogenic wheat lines grown at two locations in Minnesota, USA during three different years. Regression analysis showed positive correlation between DON content measured with LC and GC among wheat lines, locality and year. The relationship between DON and D3G showed a linear increase until a certain point, after which the DON content and the D3G increased. Wheat lines having higher susceptibility to Fusarium showed the opposite trend. ANOVA demonstrated that the line and location have a greater effect on variation of DON and D3G than do their interaction among years. The most important factor affecting DON and D3G was the growing location. In conclusion, the year, environmental conditions and location have an effect on the D3G/DON ratio in response to Fusarium infection. PMID:24351715

  3. pH-dependent interaction of rhodopsin with cyanidin-3-glucoside. 1. Structural aspects.

    PubMed

    Yanamala, Naveena; Tirupula, Kalyan C; Balem, Fernanda; Klein-Seetharaman, Judith

    2009-01-01

    Anthocyanins are a class of natural compounds common in flowers and vegetables. Because of the increasing preference of consumers for food containing natural colorants and the demonstrated beneficial effects of anthocyanins on human health, it is important to decipher the molecular mechanisms of their action. Previous studies indicated that the anthocyanin cyanidin-3-glucoside (C3G) modulates the function of the photoreceptor rhodopsin. In this paper, we show using selective excitation (1)H NMR spectroscopy that C3G binds to rhodopsin. Ligand resonances broaden upon rhodopsin addition and rhodopsin resonances exhibit chemical shift changes as well as broadening effects in specific resonances, in an activation state-dependent manner. Furthermore, dark-adapted and light-activated states of rhodopsin show preferences for different C3G species. Molecular docking studies of the flavylium cation, quinoidal base, carbinol pseudobase and chalcone forms of C3G to models of the dark, light-activated and opsin structures of rhodopsin also support this conclusion. The results provide new insights into anthocyanin-protein interactions and may have relevance for the enhancement of night vision by this class of compounds. This work is also the first report of the study of ligand binding to a full-length membrane receptor in detergent micelles by (1)H NMR spectroscopy. Such studies were previously hampered by the presence of detergent micelle resonances, a problem overcome by the selective excitation approach. PMID:19192199

  4. Effect of heat/pressure on cyanidin-3-glucoside ethanol model solutions

    NASA Astrophysics Data System (ADS)

    Corrales, M.; Lindauer, R.; Butz, P.; Tauscher, B.

    2008-07-01

    The stability of cyanidin-3-glucoside (Cy3gl) in 50% ethanol model solutions under heat/pressure treatments was investigated. Cy3gl was rapidly degraded when solutions were subjected to a heat/pressure treatment. The higher the pressure and the temperature used, the higher the degradation. Moreover, the degradation was increased according to increasing holding times. Parallel to the degradation of Cy3gl several hydrolytic products were formed and identified by LC-DAD/ESI-MS. The degradation of Cy3gl was well fitted to a first order reaction (R=0.99). This study pointed out the rate of susceptibility of Cy3gl in model solutions to degrade when exposed to a heat/pressure treatment and the trigger effect of high hydrostatic pressure to hydrolyse Cy3gl. By contrast, the degradation of anthocyanins in a food matrix (red grape extract solutions) was negligible after a heat/pressure process at 600MPa, 70°C during 1h (P >0.05).

  5. Cyanidin 3-glucoside improves diet-induced metabolic syndrome in rats.

    PubMed

    Bhaswant, Maharshi; Fanning, Kent; Netzel, Michael; Mathai, Michael L; Panchal, Sunil K; Brown, Lindsay

    2015-12-01

    Increased consumption of dark-coloured fruits and vegetables may mitigate metabolic syndrome. This study has determined the changes in metabolic parameters, and in cardiovascular and liver structure and function, following chronic administration of either cyanidin 3-glucoside (CG) or Queen Garnet plum juice (QG) containing cyanidin glycosides to rats fed either a corn starch (C) or a high-carbohydrate, high-fat (H) diet. Eight to nine-week-old male Wistar rats were randomly divided into six groups for 16-week feeding with C, C with CG or QG, H or H with CG or QG. C or H were supplemented with CG or QG at a dose of ∼ 8 mg/kg/day cyanidin glycosides from week 8 to 16. H rats developed signs of metabolic syndrome including visceral adiposity, impaired glucose tolerance, hypertension, cardiovascular remodelling, increased collagen deposition in left ventricle, non-alcoholic fatty liver disease, increased plasma liver enzymes and increased inflammatory cell infiltration in the heart and liver. Both CG and QG reversed these cardiovascular, liver and metabolic signs. However, no intact anthocyanins or common methylated/conjugated metabolites could be detected in the plasma samples and plasma hippuric acid concentrations were unchanged. Our results suggest CG is the most likely mediator of the responses to QG but that further investigation of the pharmacokinetics of oral CG in rats is required.

  6. Degradation kinetics of malvidin-3-glucoside and malvidin-3,5-diglucoside exposed to microwave treatment.

    PubMed

    Zhao, Mengyao; Li, Yuan; Xu, Xiayang; Wu, Jihong; Liao, Xiaojun; Chen, Fang

    2013-01-16

    Understanding the factors that contribute to the degradation of bioactive compounds during microwave treatment is meaningful for the practical application of this novel technology. The influence of microwave power, energy density, temperature, pH value, and initial concentration of anthocyanins (Acys) on the degradation behavior of malvidin-3-glucoside (Mv-3-glu) and malvidin-3,5-diglucoside (Mv-3,5-diglu) was investigated in this study. Results showed that the degradation of both Acys was accelerated with the increase of microwave power, energy density, temperature, pH value, and initial concentration of Acys. The degradation process of both Acys followed the first-order kinetics model (R² > 0.94), whereas the relationship between Acys degradation and energy density fitted to the logistic model well (R² > 0.98). In addition, Mv-3-glu was more susceptible to the microwave treatment than Mv-3,5-diglu. Compared with heating in a 98 ± 2 °C water bath, both Acys degraded more rapidly under microwave treatment at 100 °C, indicating the occurrence of microwave effect. The results provide a guide for the scientific application of microwave treatment.

  7. Proanthocyanidin profile of cowpea (Vigna unguiculata) reveals catechin-O-glucoside as the dominant compound.

    PubMed

    Ojwang, Leonnard O; Yang, Liyi; Dykes, Linda; Awika, Joseph

    2013-08-15

    Proanthocyanidin (PA) profile and content can have important nutritional and health implications on plant foods. Six diverse cowpea phenotypes (black, red, green, white, light-brown and golden-brown) were investigated for PA composition using normal-phase HPLC and reversed-phase UPLC-TQD-MS. Catechin and (epi)afzelechin were the major flavan-3-ol units. Unusual composition was observed in all cowpea phenotypes with significant degrees of glycosylation in the monomers and dimers. The PA content of cowpea (dry basis) ranged between 2.2 and 6.3 mg/g. Monomeric flavan-3-ols were the largest group of PA (36-69%) in cowpea, with catechin-7-O-glucoside accounting for most (about 88%) of the monomers. The oligomers with degree of polymerization (DP) 2-4 ranged from 0.41 to 1.3 mg/g (15-20%), whereas DP>10 polymers accounted for only 13.5% of PA. Future studies that highlight the impact of the unusual cowpea PA profile on nutritional and bioactive properties of this important legume are warranted.

  8. Protective effects of luteolin-7-glucoside against liver injury caused by carbon tetrachloride in rats.

    PubMed

    Qiusheng, Zheng; Xiling, Sun; Xubo; Meng, Song; Changhai, Wang

    2004-04-01

    Ixeris chinensis (Thunb.) Nakai has been used as a Chinese folk medicine; the information on the physiological and biochemical functions of the compounds extracted from I. chinensis is still scanty. We investigated the effects of luteolin -7-glucoside (LUTG) isolated from I. chinensis against liver injury caused by carbon tetrachloride (CCl4). CCl4 significantly increased the enzyme activities of glutamic pyruvic transaminase (GPT) and glutamic oxaloacetic transaminase (GOT) in blood serum, as well as the level of malondialdehyde (MDA) and 8-hydroxydeoxyguanosine (8-OHdG) in liver tissue, and decreased the levels of reduced glutathione (GSH). Pretreatment with LUTG was not only able to suppress the elevation of GPT, GOT, MDA and 8-OHdG, and inhibit the reduction of GSH in a dose-dependent manner in vivo, but also reduce the damage of hepatocytes in vitro. On the other hand, we also found LUTG has strong antioxidant activity against reactive oxygen species (ROS) in vitro in a concentration-dependent manner. The hepatoprotective activity of LUTG was possibly due to its antioxidant properties, acting as scavengers of ROS. These results obtained in vivo and in vitro suggest that LUTG had protective effects against hepatic oxidative injury induced by chemicals. Further studies on the pharmaceutical functions and immunological responses of LUTG may help in the development of a clinical application. PMID:15125574

  9. The iridoid glucoside, antirrhinoside, from Antirrhinum majus L. has differential effects on two generalist insect herbivores.

    PubMed

    Beninger, Clifford W; Cloutier, Renée R; Grodzinski, Bernard

    2008-05-01

    The iridoid glucoside, antirrhinoside, is constitutively distributed throughout Antirrhinum majus L. in a manner consistent with its possible role as an allelochemical, but there is no evidence that it has a defensive function with respect to insect herbivory. To address this question, two generalist herbivores, Lymantria dispar L. (gypsy moth) and Trichoplusia ni Hübner (cabbage looper) were chosen for feeding trials on excised whole leaves of A. majus and in artificial diet assays. In leaf excision feeding trials, fourth instar gypsy moth rejected, without sampling, the leaves of A. majus regardless of what node the leaf was excised from. In contrast, fourth instar cabbage looper readily fed on the excised leaves, and antirrhinoside was not found in their bodies or feces (frass) as determined by thin layer and high-pressure liquid chromatography. In the leaf and diet assays, a second major leaf iridoid in A. majus, antirrhide, was found in both cabbage looper and gypsy moth frass. In diet feeding assays, the growth of gypsy moth and cabbage looper were not inhibited by methanol extracts, iridoid fractions, or pure antirrhinoside at concentrations of 0.6% in diet, but cabbage looper growth was enhanced. At an antirrhinoside concentration of 3.3% in diet, gypsy moth growth was reduced, whereas cabbage looper growth again increased significantly relative to the control. It is likely that antirrhinoside functions as defense against herbivory for one generalist insect herbivore but also, at low concentrations, enhances the growth of another.

  10. Eriodictyol-7-O-glucoside activates Nrf2 and protects against cerebral ischemic injury

    SciTech Connect

    Jing, Xu; Ren, Dongmei; Wei, Xinbing; Shi, Huanying; Zhang, Xiumei; Perez, Ruth G.; Lou, Haiyan; Lou, Hongxiang

    2013-12-15

    Stroke is a complex disease that may involve oxidative stress-related pathways in its pathogenesis. The nuclear factor erythroid-2-related factor 2/antioxidant response element (Nrf2/ARE) pathway plays an important role in inducing phase II detoxifying enzymes and antioxidant proteins and thus has been considered a potential target for neuroprotection in stroke. The aim of the present study was to determine whether eriodictyol-7-O-glucoside (E7G), a novel Nrf2 activator, can protect against cerebral ischemic injury and to understand the role of the Nrf2/ARE pathway in neuroprotection. In primary cultured astrocytes, E7G increased the nuclear localization of Nrf2 and induced the expression of the Nrf2/ARE-dependent genes. Exposure of astrocytes to E7G provided protection against oxygen and glucose deprivation (OGD)-induced oxidative insult. The protective effect of E7G was abolished by RNA interference-mediated knockdown of Nrf2 expression. In vivo administration of E7G in a rat model of focal cerebral ischemia significantly reduced the amount of brain damage and ameliorated neurological deficits. These data demonstrate that activation of Nrf2/ARE signaling by E7G is directly associated with its neuroprotection against oxidative stress-induced ischemic injury and suggest that targeting the Nrf2/ARE pathway may be a promising approach for therapeutic intervention in stroke. - Highlights: • E7G activates Nrf2 in astrocytes. • E7G stimulates expression of Nrf2-mediated cytoprotective proteins in astrocytes. • E7G protects astrocytes against OGD-induced cell death and apoptosis. • The neuroprotective effect of E7G involves the Nrf2/ARE pathway. • E7G protects rats against cerebral ischemic injury.

  11. Dispersion of Vesicles Composed of Industrially Produced Alkyl (Oligo) Glucoside Using Diol-Boron Complexation.

    PubMed

    Aikawa, Tatsuo; Asano, Yuuka; Kondo, Takeshi; Yuasa, Makoto

    2016-07-01

    Alkyl (oligo)glucosides (AOG) are known to be environmentally compatible amphiphiles whose commercial applicability should be broadened. The present paper describes the preparation of molecular assemblies of industrially produced AOG, which is a mixture composed of different length of alkyl chains (C9-C12) with oligoglucoside moiety with a few (1-3) of glucose units. It was also described that regulation of the dispersibility of the molecular assemblies prepared by diol-boron complexation between the sugar moiety on AOG and boric acid in a dispersion medium. The molecular assembly of AOG was successfully formed by mixing AOG and cholesterols (CH). When using a suitable amount of CH (20-40 mol% with respect to AOG), the molecular assembly formed a vesicle structure. The dispersion ability of the resulting vesicle was dependent on both the boric acid concentration and pH of the dispersion medium. The light-scattering and ζ-potential measurements revealed that high concentrations (≥10 mM) of boric acid improved dispersibility the vesicles. In contrast, the vesicle agglomerated at low concentrations of boric acid (1-7.5 mM). In the absence of boric acid in dispersion medium, the vesicles were completely agglomerated. The optimum pH range for vesicle dispersion was found to be from neutral to basic (7.4-10.1). The (11)B NMR study revealed that borate ester formation occurred between boric acid and the diol of the sugar moiety on AOG vesicle. The present data suggest that borate ester formation that occurred on the surface of the vesicle provided negative charge to the vesicles, contributing to their dispersion via repulsive forces. PMID:27321117

  12. Phenylethanoid glucosides from in vitro propagated plants and callus cultures of Plantago lanceolata.

    PubMed

    Budzianowska, Anna; Skrzypczak, Lutosława; Budzianowski, Jaromir

    2004-09-01

    The well-known medicinal plant Plantago lanceolata L. (ribwort plantain) was effectively propagated by direct organogenesis from segments of leaves and roots using MS medium supplemented with IAA (11.42 microM), kinetin (9.29 microM) for multiplication and IAA (5.71 microM) for rooting. The plantlets were successfully hardened (80 %) and transferred to field cultivation (100 %). Two lines of callus tissue, derived from leaves and roots, were obtained on MS medium without NH (4)NO (3) and supplemented with 2,4-D (4.52 microM) and kinetin ( 0.46 microM). From plant materials--leaf rosettes from in vitro, leaves from plants in field cultivation obtained by micropropagation, root-derived callus and leaf-derived callus--sixteen phenylethanoid glucosides representing nine different structures were isolated and identified by spectral methods (1D and 2D NMR) as known for the species: lavandulifolioside ( 1), plantamajoside ( 2,) acteoside ( 3); new for the species: leucosceptoside A ( 4), martynoside ( 5), desrhamnosylisoacteoside ( 6), plantainoside D ( 7), desrhamnosylacteoside ( 8) and - 2-(4-hydroxyphenyl)ethyl beta- D-glucopyranosyl-(1-->3)-4- O- trans- and cis- p-coumaroyl-beta- D-glucopyranoside ( 9)--the latter also being found for the first time in nature and named lancetoside. Only plantamajoside ( 2) and acteoside ( 3) were common to all plant materials, the former was the main constituent of calli (1.19 - 2.84 % of dry weight), while the latter was the main constituent of the leaves (1.78 - 10.43 % of dry weight). Flavonoids were present only in plants of field cultivation. PMID:15386192

  13. Trihydroxybenzoic acid glucoside as a global skin color modulator and photo-protectant

    PubMed Central

    Chajra, Hanane; Redziniak, Gérard; Auriol, Daniel; Schweikert, Kuno; Lefevre, Fabrice

    2015-01-01

    Background 3,4,5-Trihydroxybenzoic acid glucoside (THBG), a molecule produced by an original biocatalysis-based technology, was assessed in this study with respect to its skin photoprotective capacity and its skin color control property on Asian-type skin at a clinical level and on skin explant culture models. Methods The double-blinded clinical study was done in comparison to a vehicle by the determination of objective color parameters thanks to recognized quantitative and qualitative analysis tools, including Chroma-Meter, VISIA-CR™, and SIAscope™. Determination of L* (brightness), a* and b* (green–red and blue–yellow chromaticity coordinates), individual typology angle, and C* (chroma) and h* (hue angle) parameters using a Chroma-Meter demonstrated that THBG is able to modify skin color while quantification of ultraviolet (UV) spots by VISIA-CR™ confirmed its photoprotective effect. The mechanism of action of THBG molecule was determined using explant skin culture model coupled to histological analysis (epidermis melanin content staining). Results We have demonstrated that THBG was able to modulate significantly several critical parameters involved in skin color control such as L* (brightness), a* (redness), individual typology angle (pigmentation), and hue angle (yellowness in this study), whereas no modification occurs on b* and C* parameters. We have demonstrated using histological staining that THBG decrease epidermis melanin content under unirradiated and irradiated condition. We also confirmed that THBG molecule is not a sunscreen agent. Conclusion This study demonstrated that THBG controls skin tone via the inhibition of melanin synthesis as well as the modulation of skin brightness, yellowness, and redness. PMID:26648748

  14. The Flavonoid Luteolin, but Not Luteolin-7-O-Glucoside, Prevents a Transthyretin Mediated Toxic Response

    PubMed Central

    Pokrzywa, Malgorzata; Walfridsson, Malin; Sauer-Eriksson, A. Elisabeth; Olofsson, Anders

    2015-01-01

    Transthyretin (TTR) is a homotetrameric plasma protein with amyloidogenic properties that has been linked to the development of familial amyloidotic polyneuropathy (FAP), familial amyloidotic cardiomyopathy, and senile systemic amyloidosis. The in vivo role of TTR is associated with transport of thyroxine hormone T4 and retinol-binding protein. Loss of the tetrameric integrity of TTR is a rate-limiting step in the process of TTR amyloid formation, and ligands with the ability to bind within the thyroxin binding site (TBS) can stabilize the tetramer, a feature that is currently used as a therapeutic approach for FAP. Several different flavonoids have recently been identified that impair amyloid formation. The flavonoid luteolin shows therapeutic potential with low incidence of unwanted side effects. In this work, we show that luteolin effectively attenuates the cytotoxic response to TTR in cultured neuronal cells and rescues the phenotype of a Drosophila melanogaster model of FAP. The plant-derived luteolin analogue cynaroside has a glucoside group in position 7 of the flavone A-ring and as opposed to luteolin is unable to stabilize TTR tetramers and thus prevents a cytotoxic effect. We generated high-resolution crystal-structures of both TTR wild type and the amyloidogenic mutant V30M in complex with luteolin. The results show that the A-ring of luteolin, in contrast to what was previously suggested, is buried within the TBS, consequently explaining the lack of activity from cynaroside. The flavonoids represent an interesting group of drug candidates for TTR amyloidosis. The present investigation shows the potential of luteolin as a stabilizer of TTR in vivo. We also show an alternative orientation of luteolin within the TBS which could represent a general mode of binding of flavonoids to TTR and is of importance concerning the future design of tetramer stabilizing drugs. PMID:26020516

  15. Orcinol glucoside produces antidepressant effects by blocking the behavioural and neuronal deficits caused by chronic stress.

    PubMed

    Ge, Jin-Fang; Gao, Wen-Chao; Cheng, Wen-Ming; Lu, Wei-Li; Tang, Jie; Peng, Lei; Li, Ning; Chen, Fei-Hu

    2014-01-01

    This study focused on the antidepressant potential of orcinol glucoside (OG) and its possible mechanisms of action. We established a depressed rat model using 3 consecutive weeks of chronic unpredictable mild stress (CUMS). The antidepressant-like effect of OG was revealed using the sucrose preference test, the open field test, the forced swimming test (FST), and the tail suspension test (TST). The activity of the hypothalamic-pituitary-adrenal (HPA) axis was evaluated by detecting the serum corticosterone (CORT) concentrations and mRNA expression of corticotrophin-releasing hormone (CRH) in the hypothalamus. The protein expression levels of brain-derived neurotrophic factor (BDNF) and total phosphorylated-ERK1/2 were detected by western blot. The results showed that OG treatment (1.5, 3, or 6mg/kg) alleviated the depression-like behaviour of rats under CUMS, as indicated by the increased sucrose preference and the decreased immobility in both the FST and TST, although the rearing frequency in the open field test increased only in the group that received the lowest dose (1.5mg/kg OG). Rats that received OG treatment exhibited reduced serum CORT levels and CRH mRNA expression in the hypothalamus, suggesting that the hyperactivity of the HPA axis in CUMS rats was reversed by OG treatment. Moreover, OG treatment upregulated the protein levels of BDNF and phosphorylated-ERK1/2 in the hippocampus, even above control levels. Our findings suggest that OG improved depressive behaviour in CUMS rats by downregulating HPA axis hyperactivity and increasing BDNF expression and ERK1/2 phosphorylation in the hippocampus. PMID:23838013

  16. The flavonoid luteolin, but not luteolin-7-O-glucoside, prevents a transthyretin mediated toxic response.

    PubMed

    Iakovleva, Irina; Begum, Afshan; Pokrzywa, Malgorzata; Walfridsson, Malin; Sauer-Eriksson, A Elisabeth; Olofsson, Anders

    2015-01-01

    Transthyretin (TTR) is a homotetrameric plasma protein with amyloidogenic properties that has been linked to the development of familial amyloidotic polyneuropathy (FAP), familial amyloidotic cardiomyopathy, and senile systemic amyloidosis. The in vivo role of TTR is associated with transport of thyroxine hormone T4 and retinol-binding protein. Loss of the tetrameric integrity of TTR is a rate-limiting step in the process of TTR amyloid formation, and ligands with the ability to bind within the thyroxin binding site (TBS) can stabilize the tetramer, a feature that is currently used as a therapeutic approach for FAP. Several different flavonoids have recently been identified that impair amyloid formation. The flavonoid luteolin shows therapeutic potential with low incidence of unwanted side effects. In this work, we show that luteolin effectively attenuates the cytotoxic response to TTR in cultured neuronal cells and rescues the phenotype of a Drosophila melanogaster model of FAP. The plant-derived luteolin analogue cynaroside has a glucoside group in position 7 of the flavone A-ring and as opposed to luteolin is unable to stabilize TTR tetramers and thus prevents a cytotoxic effect. We generated high-resolution crystal-structures of both TTR wild type and the amyloidogenic mutant V30M in complex with luteolin. The results show that the A-ring of luteolin, in contrast to what was previously suggested, is buried within the TBS, consequently explaining the lack of activity from cynaroside. The flavonoids represent an interesting group of drug candidates for TTR amyloidosis. The present investigation shows the potential of luteolin as a stabilizer of TTR in vivo. We also show an alternative orientation of luteolin within the TBS which could represent a general mode of binding of flavonoids to TTR and is of importance concerning the future design of tetramer stabilizing drugs. PMID:26020516

  17. Plant growth inhibition by cis-cinnamoyl glucosides and cis-cinnamic acid.

    PubMed

    Hiradate, Syuntaro; Morita, Sayaka; Furubayashi, Akihiro; Fujii, Yoshiharu; Harada, Jiro

    2005-03-01

    Spiraea thunbergii Sieb. contains 1-O-cis-cinnamoyl-beta-D-glucopyranose (CG) and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose (BCG) as major plant growth inhibiting constituents. In the present study, we determined the inhibitory activity of CG and BCG on root elongation of germinated seedlings of lettuce (Lactuca sativa), pigweed (Amaranthus retroflexus), red clover (Trifolium pratense), timothy (Phleum pratense), and bok choy (Brassica rapa var chinensis) in comparison with that of two well-known growth inhibitors, 2,4-dichlorophenoxyacetic acid (2,4-D) and (+)-2-cis-4-trans-abscisic acid (cis-ABA), as well as two related chemicals of CG and BCG, cis-cinnamic acid (cis-CA) and trans-cinnamic acid (trans-CA). The EC50 values for CG and BCG on lettuce were roughly one-half to one-quarter of the value for cis-ABA. cis-Cinnamic acid, which is a component of CG and BCG, possessed almost the same inhibitory activity of CG and BCG, suggesting that the essential chemical structure responsible for the inhibitory activity of CG and BCG is cis-CA. The cis-stereochemistry of the methylene moiety is apparently needed for high inhibitory activity, as trans-CA had an EC50 value roughly 100 times that of CG, BCG, and cis-CA. Growth inhibition by CG, BCG, and cis-CA was influenced by the nature of the soil in the growing medium: alluvial soil preserved the bioactivity, whereas volcanic ash and calcareous soils inhibited bioactivity. These findings indicate a potential role of cis-CA and its glucosides as allelochemicals for use as plant growth regulators in agricultural fields.

  18. Potential role for gut microbiota in cell wall digestion and glucoside detoxification in Tenebrio molitor larvae.

    PubMed

    Genta, Fernando A; Dillon, Rod J; Terra, Walter R; Ferreira, Clélia

    2006-06-01

    Tenebrio molitor larvae were successfully reared free of cultivatable gut lumen bacteria, yeasts and fungi using two approaches; aseptic rearing from surface sterilized eggs and by feeding larvae with antibiotic-containing food. Insects were reared on a rich-nutrient complete diet or a nutrient-poor refractory diet. A comparison of digestive enzyme activities in germ free and conventional insects containing a gut microbiota did not reveal gross differences in enzymes that degrade cell walls from bacteria (lysozyme), fungi (chitinase and laminarinase) and plants (cellulase and licheninase). This suggested that microbial-derived enzymes are not an essential component of the digestive process in this insect. However, more detailed analysis of T. molitor midgut proteins using an electrophoretic separation approach showed that some digestive enzymes were absent and others were newly expressed in microbiota-free larvae. Larvae reared in antibiotic-containing refractory wheat bran diet performed poorly in comparison with controls. The addition of saligenin, the aglycone of the plant glucoside salicin, has more deleterious effects on microbiota-free larvae than on the conventionally reared larvae, suggesting a detoxifying role of midgut microbiota. Analysis of the volatile organic compounds released from the faecal pellets of the larvae shows key differences in the profiles from conventionally reared and aseptically reared larvae. Pentadecene is a semiochemical commonly found in other beetle species. Here we demonstrate the absence of pentadecene from aseptically reared larvae in contrast to its presence in conventionally reared larvae. The results are discussed in the light of the hypothesis that microbial products play subtle roles in the life of the insect, they are involved in the digestion of refractory food, detoxification of secondary plant compounds and modify the volatile profiles of the insect host.

  19. Plant growth inhibition by cis-cinnamoyl glucosides and cis-cinnamic acid.

    PubMed

    Hiradate, Syuntaro; Morita, Sayaka; Furubayashi, Akihiro; Fujii, Yoshiharu; Harada, Jiro

    2005-03-01

    Spiraea thunbergii Sieb. contains 1-O-cis-cinnamoyl-beta-D-glucopyranose (CG) and 6-O-(4'-hydroxy-2'-methylene-butyroyl)-1-O-cis-cinnamoyl-beta-D-glucopyranose (BCG) as major plant growth inhibiting constituents. In the present study, we determined the inhibitory activity of CG and BCG on root elongation of germinated seedlings of lettuce (Lactuca sativa), pigweed (Amaranthus retroflexus), red clover (Trifolium pratense), timothy (Phleum pratense), and bok choy (Brassica rapa var chinensis) in comparison with that of two well-known growth inhibitors, 2,4-dichlorophenoxyacetic acid (2,4-D) and (+)-2-cis-4-trans-abscisic acid (cis-ABA), as well as two related chemicals of CG and BCG, cis-cinnamic acid (cis-CA) and trans-cinnamic acid (trans-CA). The EC50 values for CG and BCG on lettuce were roughly one-half to one-quarter of the value for cis-ABA. cis-Cinnamic acid, which is a component of CG and BCG, possessed almost the same inhibitory activity of CG and BCG, suggesting that the essential chemical structure responsible for the inhibitory activity of CG and BCG is cis-CA. The cis-stereochemistry of the methylene moiety is apparently needed for high inhibitory activity, as trans-CA had an EC50 value roughly 100 times that of CG, BCG, and cis-CA. Growth inhibition by CG, BCG, and cis-CA was influenced by the nature of the soil in the growing medium: alluvial soil preserved the bioactivity, whereas volcanic ash and calcareous soils inhibited bioactivity. These findings indicate a potential role of cis-CA and its glucosides as allelochemicals for use as plant growth regulators in agricultural fields. PMID:15898503

  20. Total glucosides of paeony for rheumatoid arthritis: a protocol for a systematic review

    PubMed Central

    Luo, Jing; Jin, Di-Er; Yang, Guo-Yan; Zhang, Ying-Ze; Wang, Jian-Ming; Kong, Wei-Ping; Tao, Qing-Wen

    2016-01-01

    Introduction Total glucosides of paeony (TGP) is a natural plant extract, which is widely used in China for treating rheumatoid arthritis (RA). Many relevant randomised controlled trials (RCTs) of TGP for RA are available, but they have not been systematically reviewed. This systematic review aims to examine the effectiveness and safety of TGP in patients with RA. Methods and analyses We will search for RCTs of TGP in the treatment of RA, performed up until February 2016, in PubMed, Embase, Cochrane Central Register of Controlled Trials, and four Chinese databases (Chinese Biomedical Database, China National Knowledge Infrastructure, Wanfang Database and Chinese Scientific Journal Database). Trial registers and reference lists of retrieved articles will also be searched to identify potential articles. RCTs comparing TGP with placebo, no treatment, or disease-modifying antirheumatic drugs for patients with RA will be retrieved. The primary outcomes will be disease improvement and disease remission. The secondary outcomes will be surrogate outcomes, symptoms, adverse effects, and quality of life. Two reviewers will independently extract data on participants, interventions, comparisons, outcomes, etc. The methodological quality of each included study will be evaluated using the Cochrane risk of bias tool, and the strength of evidence on prespecified outcomes will be assessed in accordance with the GRADE (Grading of Recommendations Assessment, Development and Evaluation) approach. Review Manager 5.3 software will be used for data analyses. Meta-analyses will be performed if the data are sufficiently homogeneous, both statistically and clinically. Possible publication bias will also be checked using funnel plots once the number of included studies is sufficient. Ethics and dissemination Ethics approval is not required, as this study will not involve patients. The results of this study will be submitted to a peer-reviewed journal for publication, to inform both clinical

  1. Luteolin and luteolin-7-O-glucoside strengthen antioxidative potential through the modulation of Nrf2/MAPK mediated HO-1 signaling cascade in RAW 264.7 cells.

    PubMed

    Song, Young Sun; Park, Chung Mu

    2014-03-01

    It has been understood that glycosidic forms of flavonoids were hydrolyzed by gut bacteria and absorbed as aglycones. However, several reports suggested that glycosides were partly absorbed without hydrolysis and remained biologically active. In this study, we evaluated the antioxidative potential of luteolin and luteolin-7-O-glucoside, glycosidic form of luteolin, against the oxidative damage and compared their antioxidative mechanisms in RAW 264.7 cells. Heme oxygenase-1 (HO-1), one of the phase II enzymes showing an antioxidative activity, was potently induced by luteolin and luteolin-7-O-glucoside treatment, which was in accordance with the translocated nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) into nucleus. Moreover, luteolin and the luteolin-7-O-glucoside activated HO-1 expression by p38 and c-Jun NH2-terminal kinase (JNK) regulation. In order to identify the antioxidation potential by HO-1, tert-butyl hydroperoxide (t-BHP)-induced oxidative damage was applied and ameliorated by luteolin and the luteolin-7-O-glucoside treatment in a dose dependent manner, which was confirmed by HO-1 selective inhibitor and inducer, tin protoporphyrin (SnPP) and cobalt protoporphyrin (CoPP), respectively. Consequently, luteolin and luteolin-7-O-glucoside potently strengthen the HO-1-mediated antioxidative potential through the modulation of the Nrf2/MAPK signaling pathways.

  2. Luteolin and luteolin-7-O-glucoside strengthen antioxidative potential through the modulation of Nrf2/MAPK mediated HO-1 signaling cascade in RAW 264.7 cells.

    PubMed

    Song, Young Sun; Park, Chung Mu

    2014-03-01

    It has been understood that glycosidic forms of flavonoids were hydrolyzed by gut bacteria and absorbed as aglycones. However, several reports suggested that glycosides were partly absorbed without hydrolysis and remained biologically active. In this study, we evaluated the antioxidative potential of luteolin and luteolin-7-O-glucoside, glycosidic form of luteolin, against the oxidative damage and compared their antioxidative mechanisms in RAW 264.7 cells. Heme oxygenase-1 (HO-1), one of the phase II enzymes showing an antioxidative activity, was potently induced by luteolin and luteolin-7-O-glucoside treatment, which was in accordance with the translocated nuclear factor-erythroid 2 p45-related factor 2 (Nrf2) into nucleus. Moreover, luteolin and the luteolin-7-O-glucoside activated HO-1 expression by p38 and c-Jun NH2-terminal kinase (JNK) regulation. In order to identify the antioxidation potential by HO-1, tert-butyl hydroperoxide (t-BHP)-induced oxidative damage was applied and ameliorated by luteolin and the luteolin-7-O-glucoside treatment in a dose dependent manner, which was confirmed by HO-1 selective inhibitor and inducer, tin protoporphyrin (SnPP) and cobalt protoporphyrin (CoPP), respectively. Consequently, luteolin and luteolin-7-O-glucoside potently strengthen the HO-1-mediated antioxidative potential through the modulation of the Nrf2/MAPK signaling pathways. PMID:24361407

  3. Comparison of nano and conventional liquid chromatographic methods for the separation of (+)-catechin-ethyl-malvidin-3-glucoside diastereoisomers.

    PubMed

    Kučera, Lukáš; Fanali, Salvatore; Aturki, Zeineb; Pospíšil, Tomáš; Bednář, Petr

    2016-01-01

    Nano-liquid chromatography and conventional HPLC were used for the separation of diastereomers of (+)-catechin-ethyl-malvidin-3-glucoside. Those bridged anthocyanin dyes were obtained by reaction of (+)-catechin with malvidin-3-glucoside in the presence of acetaldehyde. Both diastereomers were isolated with semipreparative chromatography and their structures were confirmed by nuclear magnetic resonance and mass spectrometry. In-laboratory prepared capillary columns packed with fully porous particles Chromosphere C18, dp=3μm, core-shell particles Kinetex C18, dp=2.6μm (100μm i.d.) and monolithic column Chromolith CapRod (100μm i.d.) were used for the separation of (+)-catechin, malvidin-3-glucoside and both diastereomers. Chromosphere C18 stationary phase provided the best chromatographic performance. Mobile phase containing water:acetonitrile (80:20) acidified with trifluoroacetic acid (0.1%, v/v/v) was used in an isocratic elution mode with a flow rate of 360nLmin(-1). Separation of studied compounds was achieved in less than 7min under optimized conditions. The nano-liquid chromatographic method and a conventional HPLC one using the same fully porous particles (Chromosphere C18, 3μm, 100mm×4.6mm) were compared providing higher separation efficiency with the first analytical method and similar selectivity. A better peak symmetry and higher resolution of the studied diastereomers was achieved by conventional chromatography. Nevertheless, nano-liquid chromatography appeared to be useful for the separation of complex anthocyanin dyes and can be utilized for their analysis in plant and food micro-samples. The developed method was used for analysis of red wine grape pomace. PMID:26433264

  4. Effect of Multiple Dietary Supplement Containing Lutein, 
Astaxanthin, Cyanidin-3-Glucoside, and DHA on Accommodative Ability

    PubMed Central

    Kono, Keiko; Shimizu, Yoshiki; Takahashi, Satomi; Matsuoka, Sayuri; Yui, Kei

    2014-01-01

    Objective The study aimed to verify that ingestion of multiple dietary supplement containing lutein, astaxanthin, cyanidin-3-glucoside and docosahexaenoic acid (DHA) would improve accommodative ability of aged and older subjects who were aware of eye strain on a daily basis. Methods A randomized double-blind placebo-controlled parallel group comparison study was conducted for 48 participants aged 45 to 64 years who complained of eye strain. The subjects took multiple dietary supplement containing 10 mg of lutein, 20 mg of bilberry extract and 26.5 mg of black soybean hull extract (a total of 2.3 mg of cyanidin-3-glucoside in both extracts), 4 mg of astaxanthin, and 50 mg of DHA (test supplement) or placebo for four consecutive weeks. Near-point accommodation (NPA) and subjective symptoms were evaluated both before and after four weeks’ intake. Results The variation of the NPA of both eyes from baseline to 4 weeks’ post-intake in the test supplement group was significantly higher than in the placebo group (1.321±0.394 diopter (D) in the test supplement group and 0.108±0.336 D in the placebo group, p=0.023). The multiple dietary supplement group showed improvement in the NPA. Regarding subjective symptoms, significant improvement of “stiff shoulders or neck” and “blurred vision” was also found in the test supplement group compared to the placebo group (p<0.05). There were no safety concerns in this study. Conclusion This study shows that multiple dietary supplement containing lutein, astaxanthin, cyanidin-3-glucoside, and DHA has effect to improve accommodative ability and subjective symptoms related to eye fatigue.

  5. Application of amylomaltase for the synthesis of salicin-α-glucosides as efficient anticoagulant and anti-inflammatory agents.

    PubMed

    Rudeekulthamrong, Prakarn; Kaulpiboon, Jarunee

    2016-09-01

    The focus of this study was the synthesis of α-glucosyl derivatives of salicin by a transglucosylation reaction. The reaction was catalyzed by recombinant amylomaltase using tapioca starch as a glucosyl donor. Several reaction parameters, such as the enzyme-substrate concentrations, pH, temperature and incubation time, were optimized. Using the optimum conditions, at least three products with retention times (Rt) of 6.2, 9.2 and 14.1 were observed. The maximum yield of glucosylated salicin derivatives was 63% (w/w) of the total products. The structures of the glucosylated salicin derivatives were confirmed to be salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside through a combination of enzyme treatments, mass spectrometry and NMR analyses. The glycosidic bond between glucose units consisted of an α-1,4-configuration. The water solubility of salicin-α-D-glucopyranoside, salicin-α-D-maltopyranoside and salicin-α-D-maltotriopyranoside was 3-, 5- and 8-fold higher, respectively, than that of salicin, whereas their relative sweetness values were lower than that of sucrose. Interestingly, the long-chain salicin-α-D-glucosides showed greater anticoagulant and anti-inflammatory activities than salicin. In addition, the synthesized salicin-α-D-glucosides were able to tolerate acidic and high temperature conditions, but not α-glucosidase or human digestive enzymes. Therefore, these salicin-α-D-glucosides should be applied by the injection route to achieve greater bioavailability than is possible by the oral route. PMID:27394039

  6. Chronic Exposure to Dietary Sterol Glucosides is Neurotoxic to Motor Neurons and Induces an ALS-PDC Phenotype

    PubMed Central

    Tabata, R. C.; Wilson, J. M. B.; Ly, P.; Zwiegers, P.; Kwok, D.; Van Kampen, J. M.; Cashman, N.; Shaw, C. A.

    2008-01-01

    Epidemiological studies of the Guamanian variants of amyotrophic lateral sclerosis (ALS) and parkinsonism, amyotrophic lateral sclerosis-parkinsonism dementia complex (ALS-PDC), have shown a positive correlation between consumption of washed cycad seed flour and disease occurrence. Previous in vivo studies by our group have shown that the same seed flour induces ALS and PDC phenotypes in out bred adult male mice. In vitro studies using isolated cycad compounds have also demonstrated that several of these are neurotoxic, specifically, a number of water insoluble phytosterol glucosides of which β-sitosterol β-d-glucoside (BSSG) forms the largest fraction. BSSG is neurotoxic to motor neurons and other neuronal populations in culture. The present study shows that an in vitro hybrid motor neuron (NSC-34) culture treated with BSSG undergoes a dose-dependent cell loss. Surviving cells show increased expression of HSP70, decreased cytosolic heavy neurofilament expression, and have various morphological abnormalities. CD-1 mice fed mouse chow pellets containing BSSG for 15 weeks showed motor deficits and motor neuron loss in the lumbar and thoracic spinal cord, along with decreased glutamate transporter labelling, and increased glial fibrillary acid protein reactivity. Other pathological outcomes included increased caspase-3 labelling in the striatum and decreased tyrosine-hydroxylase labelling in the striatum and substantia nigra. C57BL/6 mice fed BSSG-treated pellets for 10 weeks exhibited progressive loss of motor neurons in the lumbar spinal cord that continued to worsen even after the BSSG exposure ended. These results provide further support implicating sterol glucosides as one potential causal factor in the motor neuron pathology previously associated with cycad consumption and ALS-PDC. PMID:18196479

  7. Identification of delta7 phytosterols and phytosteryl glucosides in the wood and bark of several Acacia species.

    PubMed

    Freire, Carmen S R; Coelho, Dora S C; Santos, Nuno M; Silvestre, Armando J D; Pascoal Neto, Carlos

    2005-03-01

    The wood and bark of four Acacia species growing in Portugal, namely, A. longifolia, A. dealbata, A. melanoxylon, and A. retinodes, were investigated for their sterol content. The lipids fractions of the different wood and bark samples were isolated, and the sterols were identified and quantified by GC-MS. Two delta7 sterols, specifically, spinasterol and dihydrospinasterol, were the main sterols found in considerable amounts, particularly in wood tissues (more than 0.5 g/kg of dry wood in the case of A. melanoxylon and A. retinodes). The corresponding unusual steryl glucosides were also identified in significant amounts in the wood and bark extracts. PMID:15957259

  8. A study of transglucosylation kinetic in an enzymatic synthesis of benzyl alcohol glucoside by α-glucosidase from S. cerevisiae

    NASA Astrophysics Data System (ADS)

    Pavlović, M.; Dimitrijević, A.; Trbojević, J.; Milosavić, N.; Gavrović-Jankulović, M.; Bezbradica, D.; Veličković, D.

    2013-12-01

    α-1,4-Glucosidase from Saccharomyces cerevisiae is an enzyme which is widely used in synthesis of different drugs. Glucosidase inhibitors are studied as potential drugs for prevention of HIV and diabetes. For understanding of these processes it is very important to have insights in the transglucosylation activity of this enzyme. In this paper the kinetics of transglucosylation reaction catalyzed by this enzyme in the synthesis of benzyl alcohol glucoside was studied and all relevant kinetic constants for this system are found. It was shown one additional property of transglycosylation reactions catalyzed by glycosidases—inhibition by both, glucose acceptor and glucose donor, and mechanisms for these inhibitions were proposed.

  9. LC determination of luteolin-7-O-β-D-glucoside and apigenin-7-O-β-D-glucoside in rat plasma after administration of Humulus scandens extract and its application to pharmacokinetic studies.

    PubMed

    Chen, Zaixing; Ying, Xixiang; Meng, Shu; Zhu, Xu; Jiang, Hong; Cao, Qishen; Wang, Lin; Meng, Fanhao

    2012-01-01

    The present study was to investigate the pharmacokinetics of luteolin-7-O-β-D-glucoside (LGL) and apigenin-7-O-β-D-glucoside (AGL) in rat plasma after intravenous administration of the Humulus scandens extract (HSE). A simple and accurate high-performance liquid chromatographic (HPLC) method was successfully developed for simultaneous determination of LGL and AGL in rat plasma after the plasma protein was precipitated with methanol. HPLC analysis was performed on a C₁₈ column with UV detection at 350 nm and a mobile phase of methanol-0.2% phosphoric acid (1 : 1, v/v). Calibration curves of LGL and AGL were linear over the concentration range of 0.16-20.0 and 0.06-7.20 µg mL⁻¹, respectively. The accuracy and precision of the two analytes at low, medium and high concentrations were within the range of -3.4% to 8.1%. The relative standard deviations (RSDs) of the intra- and inter-day precisions were less than 11.7% and 10.0%, respectively. The extraction recoveries (n = 5) varied from 91.9% to 104.1% for LGL and from 92.6% to 109.3% for AGL. The method was fully validated and successfully applied to a pharmacokinetic study of LGL and AGL in rat plasma after the intravenous administration of HSE. PMID:21756194

  10. Occurrence and fate of the norsesquiterpene glucoside ptaquiloside (PTA) in soils

    NASA Astrophysics Data System (ADS)

    Zaccone, Claudio; Cavoski, Ivana; Costi, Roberta; Sarais, Giorgia; Caboni, Pierluigi; Miano, Teodoro M.; Lattanzio, Vincenzo

    2014-05-01

    The bracken fern Pteridium aquilinum (L.) Kuhn, one of the most common plant species on Earth, produces a wide range of secondary metabolites including the norsesquiterpene glucoside ptaquiloside (PTA). This bracken constituent causes acute poisoning, blindness and cancer in animals, and can be transferred to man when bracken is utilized as food. Also milk from cows eating bracken is thought to be the vector for the transfer of PTA to humans, as well as PTA-contaminated drinking waters. Although some studies on the effect of growth conditions and soil properties on the production and mobility of PTA have been carried out (mainly in the North of Europe), results are sometimes conflicting and further investigations are needed. The aim of the present work is to study the occurrence and the fate of PTA in soils showing different physico-chemical features, collected in different pedoclimatic areas (from the South of Italy), but having the extensive ("wild") livestock farming as common denominator. The PTA content was determined in both soil and fern samples by GC-MS; both the extraction protocol and recovery were previously tested through incubation studies. Soils samples were also characterizes from the physical and chemical point of view (pH, EC, texture, total carbonates, cation exchange capacity, organic C, total N, available nutrients and heavy metal concentration) in order to correlate the possible influence of soil parameters on PTA production, occurrence and mobility. PTA concentration in soil samples was always

  11. Metabolism of monoterpenes: early steps in the metabolism of d-neomenthyl-. beta. -D-glucoside in peppermint (Mentha piperita) rhizomes

    SciTech Connect

    Croteau, R.; Sood, V.K.; Renstroem, B.; Bhushan, R.

    1984-11-01

    Previous studies have shown that the monoterpene ketone l-(G-/sup 3/H) menthone is reduced to the epimeric alcohols l-menthol and d-neomenthol in leaves of flowering peppermint (Mentha piperita L.), and that a portion of the menthol is converted to methyl acetate while the bulk of the neomenthol is transformed to neomenthyl-..beta..-D-glucoside which is then transported to the rhizome. Analysis of the disposition of l-(G)/sup 3/H)menthone applied to midstem leaves of intact flowering plants allowed the kinetics of synthesis and transport of the monoterpenyl glucoside to be determined, and gave strong indication that the glucoside was subsequently metabolized in the rhizome. Studies with d-(G-/sup 3/H)neomenthyl-..beta..-D-glucoside as substrate, using excised rhizomes or rhizome segments, confirmed the hydrolysis of the glucoside as an early step in metabolism at this site, and revealed that the terpenoid moiety was further converted to a series of ether-soluble, methanol-soluble, and water-soluble products. The conversion of menthone to the lactone, and of the lactone to more polar products, were confirmed in vivo using l-(G-/sup 3/H)menthone and l-(G-/sup 3/H)-3,4-menthone lactone as substrates. Additional oxidation products were formed in vivo via the desaturation of labeled neomenthol and/or menthone, but none of these transformations appeared to lead to ring opening of the p-menthane skeleton. Each step in the main reaction sequence, from hydrolysis of neomenthyl glucoside to lactonization of menthone, was demonstrated in cell-free extracts from the rhizomes of flowering mint plants. The lactomization step is of particular significance in providing a means of cleaving the p-methane ring to afford an acyclic carbon skeleton that can be further degraded by modifications of the well-known ..beta..-oxidation sequence. 41 references, 3 figures, 1 table.

  12. A novel anti-inflammatory compound, artonkin-4'-O-glucoside, from the leaves of Artocarpus tonkinensis suppresses experimentally induced arthritis.

    PubMed

    Dang, D T N; Eriste, E; Liepinsh, E; Trinh, T T; Erlandsson-Harris, H; Sillard, R; Larsson, P

    2009-02-01

    Artocarpus tonkinenesis (Moraceae) has been used in Vietnamese traditional medicine for the treatment of backache and joint diseases since many 100 years. We have previously shown that a crude extract of A. tonkinensis elicited anti-inflammatory effects in rat collagen-induced arthritis (CIA), with significant improvement of disease symptoms. However, the pharmacological basis of the bioactivity of A. tonkinensis extract is not known. In the present study, we have isolated four individual active components from A. tonkinensis extract by reverse phase high-pressure liquid chromatography. The structures of the compounds were determined by nuclear magnetic resonance (NMR) spectroscopy and mass spectrometry and their biological effects investigated. A novel biologically active flavonoid glucoside (5-hydroxy-8-hydroxymethyl-8-methyl-2-[4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-8H-pyrano[3,2-g]chromen-4-one) with an average molecular mass of 514.49 Da was isolated.We have named the compound artonkin-4'-O-glucoside. The name 'artonkin' for the novel flavonoid part of the compound was coined from the Latin name of its source Artocarpus tonkinensis. The three other active flavonoid glucosides isolated and characterized were alphitonin-4-O-beta-D-glucoside, maesopsin-4-O-beta-D-glucoside and kaempherol-3-O-beta-D-glucoside. All four compounds were found to cause anti-inflammatory effect with different potencies. The anti-inflammatory effects demonstrated in the rat model of arthritis correlate well with the inhibition of mitogen-induced T-cell proliferation. Furthermore, the compounds inhibit production of cytokines, such as tumour necrosis factor-a and interferon-c, in mitogen-stimulated T cells in a concentration-dependent manner. We postulate that the isolated flavonoids suppress T-cell proliferation as well as cytokine expression and thereby contribute to an amelioration of arthritis severity in CIA.

  13. Occurrence of different trichothecenes and deoxynivalenol-3-β-D-glucoside in naturally and artificially contaminated Danish cereal grains and whole maize plants.

    PubMed

    Rasmussen, P H; Nielsen, K F; Ghorbani, F; Spliid, N H; Nielsen, G C; Jørgensen, L N

    2012-08-01

    Fusarium mycotoxins such as deoxynivalenol (DON) can occur in cereals conjugated to glucose and probably also to other sugars. These conjugates, which are often referred to as "masked mycotoxins", will not be detected with routine analytical techniques. Furthermore, it is suspected that the parent toxin may again be released after hydrolysis in the digestive tracts of animals and humans. Today, our knowledge of the occurrence of these compounds in cereal grains is limited. In this paper, a LC-MS/MS method for the simultaneous determination of DON, deoxynivalenol-3-β-D-glucoside (DON-3-glucoside), 3 acetyl-DON, nivalenol, fusarenon-X, diacetoxyscirpenol, HT-2 toxin, and T-2 toxin in naturally (n = 48) and artificially (n = 30) contaminated cereal grains (wheat, barley, oat, rye triticale) is reported. The method has also been applied to whole fresh maize plant intended for production of maize silage (n = 10). The samples were collected from the harvest years 2006-2010, The results show that DON-3-glucoside and DON co-occurred in cereal grains and, especially in several of the highly contaminated samples, the concentration of the glucoside can be relatively high, corresponding to over 37 % of the DON concentration. The DON-3-glucoside levels in both the naturally and in the artificially grain inoculated with Fusarium were second only to DON, and were generally higher than those of the other tested trichothecenes, which were found at low concentrations in most samples, in many cases even below the detection limit of the method. This argues for the importance of taking DON-3-glucoside into account in the ongoing discussion within the European Community concerning exposure re-evaluations for setting changed values for the tolerable intake for DON. Our results indicate that, in the naturally contaminated grains and in the Fusarium infested cereal grains (winter and spring wheat, oat, triticale), the concentration level of DON-3-glucoside is positively

  14. Crotocascarins I-K: Crotofolane-Type Diterpenoids, Crotocascarin γ, Isocrotofolane Glucoside and Phenolic Glycoside from the Leaves of Croton cascarilloides.

    PubMed

    Kawakami, Susumu; Matsunami, Katsuyoshi; Otsuka, Hideaki; Inagaki, Masanori; Takeda, Yoshio; Kawahata, Masatoshi; Yamaguchi, Kentaro

    2015-01-01

    From the 1-BuOH-soluble fraction of a methanol (MeOH) extract of the leaves of Croton cascarilloides, crotofolanes: crotocascarins I-K, nor-crotofolane: crotocascarin γ, isocrotofolane glucoside and phenolic glycoside were isolated by a combination of various separation techniques. Their structures were elucidated mainly from the NMR spectroscopic evidence. The structure of crotocascarin K was first elucidated by spectroscopic analysis and then was confirmed by X-ray crystallographic analysis. Its absolute structure was finally determined by the modified Mosher's method. Isocrotofolane glucoside was found to possess a new skeleton, however, its absolute structure remains to be determined.

  15. In vitro evaluation of the effects of protein-polyphenol-polysaccharide interactions on (+)-catechin and cyanidin-3-glucoside bioaccessibility.

    PubMed

    Oliveira, Ana; Pintado, Manuela

    2015-11-01

    The bioaccessibility of cyanidin-3-glucoside and (+)-catechin in model solutions when β-lactoglobulin (β-LG) and pectin/chitosan are present was investigated using an in vitro model simulating gastrointestinal conditions. In the mouth, the free cyanidin content increased (+) 90 and 14% while the (+)-catechin content decreased (-) 23 and 13%, respectively for mixtures with -pectin and -β-LG-pectin. Under gastric conditions, the cyanidin content decreased 85 and 28% for mixtures with -pectin and -β-LG-pectin. On the contrary, after gastric digestion, (+)-catechin bioaccessibility increased and exhibited values similar to the original samples for all the systems tested. The transition to the intestinal environment induced a significant alteration on both polyphenols and this effect was more marked for cyanidin. Systems with pectin allowed obtaining a higher content of bioaccessible cyanidin. The gastric conditions promoted an increase in the antioxidant capacity, followed by a decrease of it in the intestine. The free (+)-catechin and cyanidin-3-glucoside contents decreased when exposed to the gastrointestinal tract conditions. However, when incorporated in food matrix components, the gastrointestinal tract may act positively on the extraction of polyphenols, since they are progressively released from protein and polysaccharide bonds, being available for the absorption and to exert their biological effects.

  16. [Effect of algorithms for calibration set selection on quantitatively determining asiaticoside content in Centella total glucosides by near infrared spectroscopy].

    PubMed

    Zhan, Xue-yan; Zhao, Na; Lin, Zhao-zhou; Wu, Zhi-sheng; Yuan, Rui-juan; Qiao, Yan-jiang

    2014-12-01

    The appropriate algorithm for calibration set selection was one of the key technologies for a good NIR quantitative model. There are different algorithms for calibration set selection, such as Random Sampling (RS) algorithm, Conventional Selection (CS) algorithm, Kennard-Stone(KS) algorithm and Sample set Portioning based on joint x-y distance (SPXY) algorithm, et al. However, there lack systematic comparisons between two algorithms of the above algorithms. The NIR quantitative models to determine the asiaticoside content in Centella total glucosides were established in the present paper, of which 7 indexes were classified and selected, and the effects of CS algorithm, KS algorithm and SPXY algorithm for calibration set selection on the accuracy and robustness of NIR quantitative models were investigated. The accuracy indexes of NIR quantitative models with calibration set selected by SPXY algorithm were significantly different from that with calibration set selected by CS algorithm or KS algorithm, while the robustness indexes, such as RMSECV and |RMSEP-RMSEC|, were not significantly different. Therefore, SPXY algorithm for calibration set selection could improve the predicative accuracy of NIR quantitative models to determine asiaticoside content in Centella total glucosides, and have no significant effect on the robustness of the models, which provides a reference to determine the appropriate algorithm for calibration set selection when NIR quantitative models are established for the solid system of traditional Chinese medcine.

  17. [Effect of algorithms for calibration set selection on quantitatively determining asiaticoside content in Centella total glucosides by near infrared spectroscopy].

    PubMed

    Zhan, Xue-yan; Zhao, Na; Lin, Zhao-zhou; Wu, Zhi-sheng; Yuan, Rui-juan; Qiao, Yan-jiang

    2014-12-01

    The appropriate algorithm for calibration set selection was one of the key technologies for a good NIR quantitative model. There are different algorithms for calibration set selection, such as Random Sampling (RS) algorithm, Conventional Selection (CS) algorithm, Kennard-Stone(KS) algorithm and Sample set Portioning based on joint x-y distance (SPXY) algorithm, et al. However, there lack systematic comparisons between two algorithms of the above algorithms. The NIR quantitative models to determine the asiaticoside content in Centella total glucosides were established in the present paper, of which 7 indexes were classified and selected, and the effects of CS algorithm, KS algorithm and SPXY algorithm for calibration set selection on the accuracy and robustness of NIR quantitative models were investigated. The accuracy indexes of NIR quantitative models with calibration set selected by SPXY algorithm were significantly different from that with calibration set selected by CS algorithm or KS algorithm, while the robustness indexes, such as RMSECV and |RMSEP-RMSEC|, were not significantly different. Therefore, SPXY algorithm for calibration set selection could improve the predicative accuracy of NIR quantitative models to determine asiaticoside content in Centella total glucosides, and have no significant effect on the robustness of the models, which provides a reference to determine the appropriate algorithm for calibration set selection when NIR quantitative models are established for the solid system of traditional Chinese medcine. PMID:25881421

  18. In vitro evaluation of the effects of protein-polyphenol-polysaccharide interactions on (+)-catechin and cyanidin-3-glucoside bioaccessibility.

    PubMed

    Oliveira, Ana; Pintado, Manuela

    2015-11-01

    The bioaccessibility of cyanidin-3-glucoside and (+)-catechin in model solutions when β-lactoglobulin (β-LG) and pectin/chitosan are present was investigated using an in vitro model simulating gastrointestinal conditions. In the mouth, the free cyanidin content increased (+) 90 and 14% while the (+)-catechin content decreased (-) 23 and 13%, respectively for mixtures with -pectin and -β-LG-pectin. Under gastric conditions, the cyanidin content decreased 85 and 28% for mixtures with -pectin and -β-LG-pectin. On the contrary, after gastric digestion, (+)-catechin bioaccessibility increased and exhibited values similar to the original samples for all the systems tested. The transition to the intestinal environment induced a significant alteration on both polyphenols and this effect was more marked for cyanidin. Systems with pectin allowed obtaining a higher content of bioaccessible cyanidin. The gastric conditions promoted an increase in the antioxidant capacity, followed by a decrease of it in the intestine. The free (+)-catechin and cyanidin-3-glucoside contents decreased when exposed to the gastrointestinal tract conditions. However, when incorporated in food matrix components, the gastrointestinal tract may act positively on the extraction of polyphenols, since they are progressively released from protein and polysaccharide bonds, being available for the absorption and to exert their biological effects. PMID:26289110

  19. Structure elucidation of Sch 20562, a glucosidic cyclic dehydropeptide lactone--the major component of W-10 antifungal antibiotic.

    PubMed

    Afonso, A; Hon, F; Brambilla, R

    1999-04-01

    A novel bacterium designated as Aeromonas sp. W-10 produces the antibiotic W-10 complex which comprises of two major and several minor components. The two major components from this complex, Sch 20562 (1) and Sch 20561 (1a), are of biological interest in view of their potent antifungal activity. The chemical degradation studies utilized for the assignment of structure 1 for Sch 20562 are described here. Some of the noteworthy diversity of structural features in this glucosidic cyclic dehydrononapeptide lactone 1 are: an N-terminal (D)-beta-hydroxymyristyl unit, three D-amino acid units, two (E)-alpha-aminocrotonyl units, and an O-alpha-D-glucosyl-N-methyl-L-allo-threonine unit. The structure determination of 1 utilized the selective cleavage of the dehydropeptide units by ozonolysis to form fragments that were sequenced by mass spectrometry. The stereochemistry of the amino acid units were assigned by isolation of the free amino acids from the hydrolysates of the fragments. The stereochemistry of the alpha-aminocrotonyl units and the glucosidic linkage were assigned by nmr spectroscopy and molecular rotation data.

  20. Non-water miscible ionic liquid improves biocatalytic production of geranyl glucoside with Escherichia coli overexpressing a glucosyltransferase.

    PubMed

    Schmideder, Andreas; Priebe, Xenia; Rubenbauer, Mark; Hoffmann, Thomas; Huang, Fong-Chin; Schwab, Wilfried; Weuster-Botz, Dirk

    2016-09-01

    Whole cells of Escherichia coli overexpressing a glucosyltransferase from Vitis vinifera were used for the glucosylation of geraniol to geranyl glucoside. A high cell density cultivation process for the production of whole-cell biocatalysts was developed, gaining a dry cell mass concentration of up to 67.6 ± 1.2 g L(-1) and a glucosyltransferase concentration of up to 2.7 ± 0.1 g protein L(-1) within a process time of 48 h. Whole-cell batch biotransformations in milliliter-scale stirred-tank bioreactors showed highest conversion of geraniol at pH 7.0 although the pH optimum of the purified glucosyltransferase was at pH 8.5. The biocatalytic batch process performance was improved significantly by the addition of a water-immiscible ionic liquid (N-hexylpyridinium bis(trifluoromethylsulfonyl)imid) for in situ substrate supply. The so far highest final geranyl glucoside concentration (291 ± 9 mg L(-1)) and conversion (71 ± 2 %) reported for whole-cell biotransformations of geraniol were achieved with 5 % (v/v) of the ionic liquid. PMID:27142377

  1. High-resolution MALDI mass spectrometry imaging of gallotannins and monoterpene glucosides in the root of Paeonia lactiflora

    PubMed Central

    Li, Bin; Bhandari, Dhaka Ram; Römpp, Andreas; Spengler, Bernhard

    2016-01-01

    High-resolution atmospheric-pressure scanning microprobe matrix-assisted laser desorption/ionization mass spectrometry imaging (AP-SMALDI MSI) at 10 μm pixel size was performed to unravel the spatio-chemical distribution of major secondary metabolites in the root of Paeonia lactiflora. The spatial distributions of two major classes of bioactive components, gallotannins and monoterpene glucosides, were investigated and visualized at the cellular level in tissue sections of P. lactiflora roots. Accordingly, other primary and secondary metabolites were imaged, including amino acids, carbohydrates, lipids and monoterpenes, indicating the capability of untargeted localization of metabolites by using high-resolution MSI platform. The employed AP-SMALDI MSI system provides significant technological advancement in the visualization of individual molecular species at the cellular level. In contrast to previous histochemical studies of tannins using unspecific staining reagents, individual gallotannin species were accurately localized and unequivocally discriminated from other phenolic components in the root tissues. High-quality ion images were obtained, providing significant clues for understanding the biosynthetic pathway of gallotannins and monoterpene glucosides and possibly helping to decipher the role of tannins in xylem cells differentiation and in the defence mechanisms of plants, as well as to investigate the interrelationship between tannins and lignins. PMID:27796322

  2. Turning the 'mustard oil bomb' into a 'cyanide bomb': aromatic glucosinolate metabolism in a specialist insect herbivore.

    PubMed

    Stauber, Einar J; Kuczka, Petrissa; van Ohlen, Maike; Vogt, Birgit; Janowitz, Tim; Piotrowski, Markus; Beuerle, Till; Wittstock, Ute

    2012-01-01

    Plants have evolved a variety of mechanisms for dealing with insect herbivory among which chemical defense through secondary metabolites plays a prominent role. Physiological, behavioural and sensorical adaptations to these chemicals provide herbivores with selective advantages allowing them to diversify within the newly occupied ecological niche. In turn, this may influence the evolution of plant metabolism giving rise to e.g. new chemical defenses. The association of Pierid butterflies and plants of the Brassicales has been cited as an illustrative example of this adaptive process known as 'coevolutionary armsrace'. All plants of the Brassicales are defended by the glucosinolate-myrosinase system to which larvae of cabbage white butterflies and related species are biochemically adapted through a gut nitrile-specifier protein. Here, we provide evidence by metabolite profiling and enzyme assays that metabolism of benzylglucosinolate in Pieris rapae results in release of equimolar amounts of cyanide, a potent inhibitor of cellular respiration. We further demonstrate that P. rapae larvae develop on transgenic Arabidopsis plants with ectopic production of the cyanogenic glucoside dhurrin without ill effects. Metabolite analyses and fumigation experiments indicate that cyanide is detoxified by β-cyanoalanine synthase and rhodanese in the larvae. Based on these results as well as on the facts that benzylglucosinolate was one of the predominant glucosinolates in ancient Brassicales and that ancient Brassicales lack nitrilases involved in alternative pathways, we propose that the ability of Pierid species to safely handle cyanide contributed to the primary host shift from Fabales to Brassicales that occured about 75 million years ago and was followed by Pierid species diversification.

  3. Turning the 'mustard oil bomb' into a 'cyanide bomb': aromatic glucosinolate metabolism in a specialist insect herbivore.

    PubMed

    Stauber, Einar J; Kuczka, Petrissa; van Ohlen, Maike; Vogt, Birgit; Janowitz, Tim; Piotrowski, Markus; Beuerle, Till; Wittstock, Ute

    2012-01-01

    Plants have evolved a variety of mechanisms for dealing with insect herbivory among which chemical defense through secondary metabolites plays a prominent role. Physiological, behavioural and sensorical adaptations to these chemicals provide herbivores with selective advantages allowing them to diversify within the newly occupied ecological niche. In turn, this may influence the evolution of plant metabolism giving rise to e.g. new chemical defenses. The association of Pierid butterflies and plants of the Brassicales has been cited as an illustrative example of this adaptive process known as 'coevolutionary armsrace'. All plants of the Brassicales are defended by the glucosinolate-myrosinase system to which larvae of cabbage white butterflies and related species are biochemically adapted through a gut nitrile-specifier protein. Here, we provide evidence by metabolite profiling and enzyme assays that metabolism of benzylglucosinolate in Pieris rapae results in release of equimolar amounts of cyanide, a potent inhibitor of cellular respiration. We further demonstrate that P. rapae larvae develop on transgenic Arabidopsis plants with ectopic production of the cyanogenic glucoside dhurrin without ill effects. Metabolite analyses and fumigation experiments indicate that cyanide is detoxified by β-cyanoalanine synthase and rhodanese in the larvae. Based on these results as well as on the facts that benzylglucosinolate was one of the predominant glucosinolates in ancient Brassicales and that ancient Brassicales lack nitrilases involved in alternative pathways, we propose that the ability of Pierid species to safely handle cyanide contributed to the primary host shift from Fabales to Brassicales that occured about 75 million years ago and was followed by Pierid species diversification. PMID:22536404

  4. Observation of T-2 Toxin and HT-2 Toxin Glucosides from Fusarium sporotrichioides by Liquid Chromatography Coupled to Tandem Mass Spectrometry (LC-MS/MS)

    PubMed Central

    Busman, Mark; Poling, Stephen M.; Maragos, Chris M.

    2011-01-01

    The trichothecenes produced by solid and liquid cultures of Fusarium sporotrichioides were evaluated with high performance liquid chromatography-tandem mass spectrometry (LC-MS/MS). Along with the expected T-2 toxin HT-2 toxin and neosolaniol, two additional compounds were detected, which had ions 162 m/z higher than those in the mass spectra of T-2 toxin or HT-2 toxin. Fragmentation behavior of these two compounds was similar to that of T-2 toxin and HT-2 toxin. Based on LC-MS/MS behavior, it is proposed that the two compounds are T-2 toxin 3-O-glucoside and HT-2 toxin 3-O-glucoside. Production of the two glucosides was measured in kernels from wheat and oat inoculated with F. sporotrichiodes, as well as in cultures grown in liquid media and on cracked corn or rice. Production of glucosides in wheat and oats suggest that they may also be present in naturally contaminated cereals. PMID:22295176

  5. A Versatile Family 3 Glycoside Hydrolase from Bifidobacterium adolescentis Hydrolyzes β-Glucosides of the Fusarium Mycotoxins Deoxynivalenol, Nivalenol, and HT-2 Toxin in Cereal Matrices.

    PubMed

    Michlmayr, Herbert; Varga, Elisabeth; Malachova, Alexandra; Nguyen, Nhung Thi; Lorenz, Cindy; Haltrich, Dietmar; Berthiller, Franz; Adam, Gerhard

    2015-08-01

    Glycosylation plays a central role in plant defense against xenobiotics, including mycotoxins. Glucoconjugates of Fusarium toxins, such as deoxynivalenol-3-O-β-d-glucoside (DON-3G), often cooccur with their parental toxins in cereal-based food and feed. To date, only limited information exists on the occurrence of glucosylated mycotoxins and their toxicological relevance. Due to a lack of analytical standards and the requirement of high-end analytical instrumentation for their direct determination, hydrolytic cleavage of β-glucosides followed by analysis of the released parental toxins has been proposed as an indirect determination approach. This study compares the abilities of several fungal and recombinant bacterial β-glucosidases to hydrolyze the model analyte DON-3G. Furthermore, substrate specificities of two fungal and two bacterial (Lactobacillus brevis and Bifidobacterium adolescentis) glycoside hydrolase family 3 β-glucosidases were evaluated on a broader range of substrates. The purified recombinant enzyme from B. adolescentis (BaBgl) displayed high flexibility in substrate specificity and exerted the highest hydrolytic activity toward 3-O-β-d-glucosides of the trichothecenes deoxynivalenol (DON), nivalenol, and HT-2 toxin. A Km of 5.4 mM and a Vmax of 16 μmol min(-1) mg(-1) were determined with DON-3G. Due to low product inhibition (DON and glucose) and sufficient activity in several extracts of cereal matrices, this enzyme has the potential to be used for indirect analyses of trichothecene-β-glucosides in cereal samples.

  6. Determination of citrus limonoid glucosides by high performance liquid chromatography coupled to post-column reaction with Ehrlich’s Reagent

    Technology Transfer Automated Retrieval System (TEKTRAN)

    A method for the identification and quantification of citrus limonoid glucosides in juices based upon high performance liquid chromatography (HPLC) separation coupled to post-column reaction with Ehrlichs’s reagent has been developed. This method utilizes a phenyl stationary phase and an isocratic ...

  7. Application of ESI/MS, CID/MS and tandem MS/MS to the fragmentation study of eriodictyol 7-O-glucosyl-(1-->2)-glucoside and luteolin 7-O-glucosyl-(1-->2)-glucoside

    NASA Astrophysics Data System (ADS)

    Es-Safi, Nour-Eddine; Kerhoas, Lucien; Einhorn, Jacques; Ducrot, Paul-Henri

    2005-12-01

    A mass spectrometric method based on the combined use of positive and negative electrospray ionization, collision-induced dissociation and tandem mass spectrometry has been applied to the structural characterization of the eriodictyol 7-O-glucosyl-(1-->2)-glucoside and luteolin 7-O-glucosyl-(1-->2)-glucoside. The low-energy product ion mass spectrum of [M + H]+ and [M - H]- ions showed extensive fragmentation of the diglucose moiety, loss of the glycan residue, and fragmentation of the aglycon units that permit characterization of the interglycosidic linkage and the substituents in the A- and B-rings. Both glycosides were shown to yield the 0,2X00,2X1 ion which can be considered as characteristic of the 1-->2 interglycosidic linkage in the glucoglucoside adducts, since it can not be formed in the case of other interglycosidic types. In the case of the eriodictyol diglucoside the 1, 3 fragmentation of the C-ring was observed before those involving the carbohydrates thus allowing the position determination of the diglucoside moiety on the A-ring. In the negative ion mode only the luteolin diglucoside was shown to undergo collision-induced homolytic and heterolytic cleavages of the O-glycosidic bond producing the aglycone radical-anion [Y0-H]-- and Y0- product ions, while this was not observed in the case of eriodictyol glycoside. CID MS/MS analysis of the sodiated molecules gave complementary informations for the structural characterization of the studied compounds. The B2+ fragment which is useful for establishing that the terminal carbohydrate unit is linked to another carbohydrate and not directly to the aglycone was obtained as base peak. This result is of analytical value for the differentiation of O-diglycosyl and di-O-glycosyl flavonoids.

  8. Identification of rice Os4BGlu13 as a β-glucosidase which hydrolyzes gibberellin A4 1-O-β-d-glucosyl ester, in addition to tuberonic acid glucoside and salicylic acid derivative glucosides.

    PubMed

    Hua, Yanling; Ekkhara, Watsamon; Sansenya, Sompong; Srisomsap, Chantragan; Roytrakul, Sittiruk; Saburi, Wataru; Takeda, Ryosuke; Matsuura, Hideyuki; Mori, Haruhide; Ketudat Cairns, James R

    2015-10-01

    Gibberellin 1-O-β-d-glucose ester hydrolysis activity has been detected in rice seedling extracts, but no enzyme responsible for this activity has ever been purified and identified. Therefore, gibberellin A4 glucosyl ester (GA4-GE) β-d-glucosidase activity was purified from ten-day rice seedling stems and leaves. The family 1 glycoside hydrolase Os4BGlu13 was identified in the final purification fraction. The Os4BGlu13 cDNA was amplified from rice seedlings and expressed as an N-terminal thioredoxin-tagged fusion protein in Escherichia coli. The purified recombinant Os4BGlu13 protein (rOs4BGlu13) had an optimum pH of 4.5, for hydrolysis of p-nitrophenyl β-d-glucopyranoside (pNPGlc), which was the best substrate identified, with a kcat/Km of 637 mM(-1) s(-1). rOs4BGlu13 hydrolyzed helicin best among natural glycosides tested (kcat/Km of 74.4 mM(-1) s(-1)). Os4BGlu13 was previously designated tuberonic acid glucoside (TAG) β-glucosidase (TAGG), and here the kcat/Km of rOsBGlu13 for TAG was 6.68 mM(-1) s(-1), while that for GA4-GE was 3.63 mM(-1) s(-1) and for salicylic acid glucoside (SAG) is 0.88 mM(-1) s(-1). rOs4BGlu13 also hydrolyzed oligosaccharides, with preference for short β-(1 → 3)-linked over β-(1 → 4)-linked glucooligosaccharides. The enzymatic data suggests that Os4BGlu13 may contribute to TAG, SAG, oligosaccharide and GA4-GE hydrolysis in the rice plant, although helicin or a similar compound may be its primary target.

  9. Identification, amounts, and kinetics of extraction of C-glucosidic ellagitannins during wine aging in oak barrels or in stainless steel tanks with oak chips.

    PubMed

    Jourdes, Michaël; Michel, Julien; Saucier, Cédric; Quideau, Stéphane; Teissedre, Pierre-Louis

    2011-09-01

    The C-glucosidic ellagitannins are found in wine as a result of its aging in oak barrels or in stainless steel tanks with oak chips. Once dissolved in this slightly acidic solution, the C-glucosidic ellagitannins vescalagin can react with nucleophilic entities present in red wine, such as ethanol, catechin, and epicatechin, to generate condensed hybrid products such as the β-1-O-ethylvescalagin and the flavano-ellagitannins (acutissimin A/B and epiacutissimin A/B), respectively. During this study, we first monitored the extraction kinetic and the evolution of the eight major oak-derived C-glucosidic ellagitannins in red wines aged in oak barrels or in stainless steel tank with oak chips. Their extraction rates appeared to be faster during red wine aging in stainless steel tanks with oak chips. However, their overall concentrations in wines were found higher in the wine aged in barrels. The formation rates of the vescalagin-coupled derivatives were also estimated for the first time under both red wine aging conditions (i.e., oak barrels or stainless steel tanks with oak chips). As observed for the oak-native C-glucosidic ellagitannins, the concentrations of these vescalagin derivatives were higher in the red wine aged in oak barrels than in stainless steel tanks with oak chips. Despite these differences, their relative composition was similar under both red wine aging conditions. Finally, the impact of the oak chips size and toasting level on the C-glucosidic ellagitannins concentration in wine was also investigated.

  10. Isolation of cyanidin 3-glucoside from blue honeysuckle fruits by high-speed counter-current chromatography.

    PubMed

    Chen, Liang; Xin, Xiulan; Lan, Rong; Yuan, Qipeng; Wang, Xiaojie; Li, Ye

    2014-01-01

    Blue honeysuckle fruits are rich in anthocyanins with many beneficial effects such as reduction of the risk of cardiovascular diseases, diabetes and cancers. High-speed counter-current chromatography (HSCCC) was used for the separation of anthocyanin on a preparative scale from blue honeysuckle fruit crude extract with a biphasic solvent system composed of tert-butyl methyl ether/n-butanol/acetonitrile/water/trifluoroacetic acid (2:2:1:5:0.01, v/v) for the first time in this paper. Each injection of 100 mg crude extract yielded 22.8 mg of cyanidin 3-glucoside (C3G) at 98.1% purity. The compound was identified by means of electro-spray ionisation mass (ESI/MS) and (1)H and (13)C nuclear magnetic resonance (NMR) spectra.

  11. The corrected structure of depressoside, an antioxidative iridoid glucoside extracted from the flowers of Gentiana urnula Harry Sm.

    PubMed

    Kusakari, Ken; Fukuhara, Tadao; Motoyama, Akira; Ochiai, Nobuhiko; Watanabe, Takashi; Sugimoto, Yukihiro

    2016-01-01

    Three known iridoid glucosides (gentiournoside A, gentiournoside E and depressoside) were isolated from the flowers of Gentiana urnula Harry Sm. through activity-guided fractionations with a 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. All three compounds exhibited excellent DPPH radical scavenging activities (IC50: 10-20 μmol L(-1)) comparable to that of ascorbic acid and Trolox. However, examination of the NMR data revealed that the reported chemical structure of depressoside, previously isolated from the leaves of G. depressa, needed correcting due to incorrect elucidation around C-7 of the iridane skeleton, and was corrected to 6-β-(2,3-dihydroxyphenyl)-D-glucosyl 7-O-(2,3-dihydroxybenzoyl)-loganate. Depressoside exhibited a much higher scavenging activity against superoxide radicals (IC50: 45.5 μmol L(-1)) than the other two extracted compounds (IC50: more than 900 μmol L(-1)) due to the crucial presence of a pyrogallyl unit.

  12. Protection of cyanidin-3-glucoside against oxidative stress induced by acrylamide in human MDA-MB-231 cells.

    PubMed

    Song, Jian; Zhao, Mengyao; Liu, Xin; Zhu, Yuchen; Hu, Xiaosong; Chen, Fang

    2013-08-01

    Acrylamide (AA) occurs in many cooked starchy foods and has caused widespread concern as a possible carcinogen. In the present study, we investigate the intervention of AA toxicity in MDA-MB-231 cells pretreated with cyanidin-3-glucoside (Cy-3-glu). Compared to the cells treated with AA, Cy-3-glu significantly inhibited AA-induced cytotoxicity, reduced reactive oxygen species (ROS) generation, recovered glutathione (GSH) depletion and decreased the activities of glutathione peroxidase (GPx) and glutathione S-transferase (GST). Moreover, the expression of GPx1, GSTP1 and gamma-glutamyl cysteine synthase (γ-GCS) were enhanced, and cytochrome P450 2E1 (CYP2E1) expression was inhibited by the pretreatment of Cy-3-glu. Cy-3-glu presents the protective role against oxidative stress induced by AA in MDA-MB-231 cells.

  13. Validated HPLC method for simultaneous estimation of khellol glucoside, khellin and visnagin in Ammi visnaga L. fruits and pharmaceutical preparations.

    PubMed

    Badr, Jihan M; Hadad, Ghada M; Nahriry, Khaled; Hassanean, Hashem A

    2015-01-01

    Tea bags including fruits of Ammi visnaga L. are used in Egypt as remedy for the treatment of kidney stones. Our study focuses on developing simple and rapid method utilising HPLC for quantitative estimation of khellol glucoside (KG), khellin (KH) and visnagin (VS) simultaneously. Their concentrations were determined in A. visnaga L. fruits at different developmental stages and in pharmaceutical formulations together with following up them during shelf life. Separation was accomplished using HPLC. Perfect resolution between KG, KH and VS was possible through using a mobile phase consisting of water:methanol:tetrahydrofuran (50:45:5, v/v/v). Peaks were detected at 245 nm. The suggested method for the determination of KG, KH and VS was successful in determining the analytes of interest without any interference of other compounds and matrix. All validation parameters were satisfactory and the procedure was relatively easy and fast as extracts are evaluated without previous steps of purification.

  14. CTG-loaded liposomes as an approach for improving the intestinal absorption of asiaticoside in Centella Total Glucosides.

    PubMed

    Wang, Jiayu; Ma, Changhua; Guo, Chengjie; Yuan, Ruijuan; Zhan, Xueyan

    2016-07-25

    Centella Total Glucosides (CTG),obtained from Centella asiatica (L.), have been shown to possess a multitude of pharmacological activities, however, oral administeration of CTG failed to fulfill their therapeutic potentials due to the low bioavailability. In this study, the author prepared the liposomes encapsulated CTG using the ethanol injection method in order to enhance their intestinal absorption. The average particle size and the polydispersityindex(PDI) of CTG-loaded liposome in a batch are 137.0nm and 0.283, and the CTG-loaded amounts in CTG-loaded liposomes were 0.177mgmL(-1) and the zeta potential of CTG-loaded lipsomes is -21.2mV. The TEM images of CTG-loaded lipsomes showed that CTG-loaded liposomes are round and maintain high structural integrity, and their DSC thermograms indicated that CTG might be incorporated into the aqueous phase of DPPC to become more stable. The everted rat gut sac model was used to study the absorption characteristic of CTG-loaded solution in rat intestines. The cumulative absorption amount (Q) and the cumulative absorption percentage (P%) of asiaticoside in the CTG-loaded liposome was significantly higher than that in CTG (P<0.05), both the steady-state infiltration rate (Jss, μgcm(-2)s(-1)) and the permeability coefficient (Papp, cms(-1)) of asiaticoside in CTG-loaded liposomes were significantly higher than those in CTG (P<0.05), which revealed that the liposomes encapsulated CTG can promote the absorption of asiaticoside in the ileum of the rats by enhancing its transmembrane permeability. The above study will provide the experimental evidence and a reference for the development of the oral dosage forms of Centella total glucosides.

  15. cDNA cloning, heterologous expressions, and functional characterization of malonyl-coenzyme a:anthocyanidin 3-o-glucoside-6"-o-malonyltransferase from dahlia flowers.

    PubMed

    Suzuki, Hirokazu; Nakayama, Toru; Yonekura-Sakakibara, Keiko; Fukui, Yuko; Nakamura, Noriko; Yamaguchi, Masa-Atsu; Tanaka, Yoshikazu; Kusumi, Takaaki; Nishino, Tokuzo

    2002-12-01

    In the flowers of important ornamental Compositae plants, anthocyanins generally carry malonyl group(s) at their 3-glucosyl moiety. In this study, for the first time to our knowledge, we have identified a cDNA coding for this 3-glucoside-specific malonyltransferase for anthocyanins, i.e. malonyl-coenzyme A:anthocyanidin 3-O-glucoside-6"-O-malonyltransferase, from dahlia (Dahlia variabilis) flowers. We isolated a full-length cDNA (Dv3MaT) on the basis of amino acid sequences specifically conserved among anthocyanin acyltransferases of the versatile plant acyltransferase family. Dv3MaT coded for a protein of 460 amino acids. Quantitative real-time PCR analyses of Dv3MaT showed that the transcript was present in accordance with the distribution of 3MaT activities and the anthocyanin accumulation pattern in the dahlia plant. The Dv3MaT cDNA was expressed in Escherichia coli, and the recombinant enzyme was purified to homogeneity and characterized. The recombinant Dv3MaT catalyzed the regiospecific transfer of the malonyl group from malonyl-coenzyme A (K(m), 18.8 microM) to pelargonidin 3-O-glucoside (K(m), 46.7 microM) to produce pelargonidin 3-O-6"-O-malonylglucoside with a k(cat) value of 7.3 s(-1). The other enzymatic profiles of the recombinant Dv3MaT were closely related to those of native anthocyanin malonyltransferase activity in the extracts of dahlia flowers. Dv3MaT cDNA was introduced into petunia (Petunia hybrida) plants whose red floral color is exclusively provided by cyanidin 3-O-glucoside and 3,5-O-diglucoside. Thirteen transgenic lines of petunia were found to produce malonylated products of these anthocyanins (11-63 mol % of total anthocyanins in the flower). The spectral stability of cyanidin 3-O-6"-O-malonylglucoside at the pHs of intracellular milieus of flowers was significantly higher than that of cyanidin 3-O-glucoside. Moreover, 6"-O-malonylation of cyanidin 3-O-glucoside effectively prevented the anthocyanin from attack of beta

  16. Genome wide association mapping for leaf

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Cyanogenic glucosides are natural compounds found in over 1,000 species of angiosperms that produce HCN and are deemed undesirable for agricultural use. However, these compounds are important components of primary defensive mechanisms of many plant species. One of the best-studied cyanogenic gluco...

  17. In vitro and in vivo study of cucurbitacins-type triterpene glucoside from Citrullus colocynthis growing in Saudi Arabia against hepatocellular carcinoma.

    PubMed

    Ayyad, Seif-Eldin N; Abdel-Lateff, Ahmed; Alarif, Walied M; Patacchioli, Francesca R; Badria, Farid A; Ezmirly, Saleh T

    2012-03-01

    Chromatographic investigation of fruits obtained from Citrullus colocynthis, growing in Saudi Arabia, led to isolation of two compounds; Cucurbitacin E glucoside (Cu E, 1), and Cucurbitacin I glucoside (Cu I, 2). The chemical structures of 1 and 2, were elucidated by spectroscopic analyses include; 1D ((1)H and (13)C) and 2D (COSY, HMQC and HMBC) NMR and ESI-MS spectroscopy. The in vitro cytotoxic activity against hepatoma cell line (HepG2) and mice-bearing tumor of Ehrlich's ascites carcinoma (EAC) of the compounds were estimated. Both compounds had potent inhibitory activity on HepG2 with IC(50) 3.5 and 2.8 nmol/mL, respectively. In addition to these activities, the in vivo study employing EAC, showed the capability of both compounds to prolong the survival time, life span and normalize the biochemical parameters of the infected mice with EAC.

  18. Enzymic synthesis of alpha- and beta-D-glucosides of 1-deoxynojirimycin and their glycosidase inhibitory activities.

    PubMed

    Asano, N; Oseki, K; Kaneko, E; Matsui, K

    1994-05-20

    1-Deoxynojirimycin (1) is a potent inhibitor of mammalian and rice alpha-glucosidase. Several glucosides of 1 were synthesized by use of the native and immobilized enzyme and their effect on various enzymes was investigated. Transglucosylation reactions using rice alpha-glucosidase, yeast alpha- and beta-glucosidases purified from Rhodotorula lactosa were performed with maltose or cellobiose as a glucose donor and N-(benzyloxycarbonyl)-1-deoxynojirimycin (2) as an acceptor. The transglucosylation reaction using native rice alpha-glucosidase afforded 3-O-alpha-D-glucopyranosyl-N-(benzyloxycarbonyl)-1-deoxynojirimycin (4), 4-O-alpha-D-glucopyranosyl-N-(benzyloxycarbonyl)-1-deoxynojirimycin (5), and 2-O-alpha-D-glucopyranosyl-N-(benzyloxycarbonyl)-1-deoxynojirimycin (3) in yields of 40, 13, and 2%, respectively, after 30 min. The transglucosylation reaction using immobilized rice alpha-glucosidase was similar to that using the native enzyme. In the system using native yeast alpha-glucosidase, 3, 5, and 4 were formed in yields of 34, 13, and 6%, respectively, after 15 h. The immobilization of yeast alpha-glucosidase caused a significant decrease in transglucosylation activity. Yeast beta-glucosidase showed a high transglucosylation activity and incubation with the reaction system afforded 2-O-beta-D-glucopyranosyl-N-(benzyloxycarbonyl)-1-deoxynojirimycin (6) and 4-O-beta-D-glucopyranosyl-N-(benzyloxycarbonyl)-1-deoxynojirimycin (7) in yields of 69 and 3%, respectively, after 3 h. The transglucosylation reaction using immobilized yeast beta-glucosidase preferentially afforded 6 in a yield of 73% after 3 h. After removal of N-benzyloxycarbonyl group from the product glucosides, their glycosidase inhibitory activities were measured. 3-O-alpha-D-Glucopyranosyl-1-deoxynojirimycin (9) retained the potent inhibition of 1 against rat intestinal sucrase activity and was more effective than 1 against rice alpha-glucosidase. 4-O-alpha-D-Glucopyranosyl-1-deoxynojirimycin (10

  19. Enhanced catalytic efficiency in quercetin-4'-glucoside hydrolysis of Thermotoga maritima β-glucosidase A by site-directed mutagenesis.

    PubMed

    Sun, Huihui; Xue, Yemin; Lin, Yufei

    2014-07-16

    Te-BglA and Tm-BglA are glycoside hydrolase family 1 β-glucosidases from Thermoanaerobacter ethanolicus JW200 and Thermotoga maritima, respectively, with 53% sequence identity. However, Te-BglA could more effectively hydrolyze isoflavone glucosides to their aglycones than could Tm-BglA, possibly due to the difference in amino acid residues around their glycone binding pockets. Site-directed mutagenesis was used to replace the amino acid residues of Tm-BglA with the corresponding residues of Te-BglA, generating three single mutants (F221L, N223L, and G224T), as well as the corresponding three double mutants (F221L/N223L, F221L/G224T, and N223L/G224T) and one triple mutant (F221L/N223L/G224T). The seven mutants have been purified, characterized, and compared to the wild-type Tm-BglA. The effects of the mutations on kinetics, enzyme activity, and substrate specificity were determined. All mutants showed pH-activity curves narrower on the basic side and wider on the acid side and had similar optimal pH and stability at pH 6.5-8.3. They were more stable up to 85 °C, but G224T displayed higher optimal temperature than Tm-BglA. Seven mutants indicated an obvious increase in catalytic efficiency toward p-nitrophenyl β-D-glucopyranoside (pNPG) but an increase or not change in K(m). All mutants showed a decrease in catalytic efficiency of isoflavonoid glycosides and were not changed for F221L and lost for N223L in enzymatic hydrolysis on quercetin glucosides. Contrarily, G224T resulted in a dramatic increase conversion of Q4' (35.5%) and Q3,4' (28.6%) in accord with an increased turnover number (k(cat), 1.4×) and catalytic efficiency (k(cat)/K(m), 2.2×) as well as a decrease in K(m) (0.24) for Q4'. Modeling showed that G224T mutation at position 224 may enhance the interaction between G224T and 5-OH and 3-OH on the quercetin backbone of Q4'.

  20. Dianthosaponins G-I, triterpene saponins, an anthranilic acid amide glucoside and a flavonoid glycoside from the aerial parts of Dianthus japonicus and their cytotoxicity.

    PubMed

    Kanehira, Yuka; Kawakami, Susumu; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2016-10-01

    Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of the aerial parts of Dianthus japonicus afforded three further triterpene glycosyl estsers, termed dianthosaponins G-I, an anthranilic acid amide glucoside and a C-glycosyl flavonoid along with one known triterpene saponin. Their structures were elucidated from spectroscopic evidence. The cytotoxicity of the isolated compounds toward A549 cells was evaluated.

  1. Dianthosaponins G-I, triterpene saponins, an anthranilic acid amide glucoside and a flavonoid glycoside from the aerial parts of Dianthus japonicus and their cytotoxicity.

    PubMed

    Kanehira, Yuka; Kawakami, Susumu; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki

    2016-10-01

    Extensive isolation work on the 1-BuOH-soluble fraction of a MeOH extract of the aerial parts of Dianthus japonicus afforded three further triterpene glycosyl estsers, termed dianthosaponins G-I, an anthranilic acid amide glucoside and a C-glycosyl flavonoid along with one known triterpene saponin. Their structures were elucidated from spectroscopic evidence. The cytotoxicity of the isolated compounds toward A549 cells was evaluated. PMID:27351981

  2. A flavonoid 3-O-glucoside:2″-O-glucosyltransferase responsible for terminal modification of pollen-specific flavonols in Arabidopsis thaliana

    PubMed Central

    Yonekura-Sakakibara, Keiko; Nakabayashi, Ryo; Sugawara, Satoko; Tohge, Takayuki; Ito, Takuya; Koyanagi, Misuzu; Kitajima, Mariko; Takayama, Hiromitsu; Saito, Kazuki

    2014-01-01

    Flavonol 3-O-diglucosides with a 1→2 inter-glycosidic linkage are representative pollen-specific flavonols that are widely distributed in plants, but their biosynthetic genes and physiological roles are not well understood. Flavonoid analysis of four Arabidopsis floral organs (pistils, stamens, petals and calyxes) and flowers of wild-type and male sterility 1 (ms1) mutants, which are defective in normal development of pollen and tapetum, showed that kaempferol/quercetin 3-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosides accumulated in Arabidopsis pollen. Microarray data using wild-type and ms1 mutants, gene expression patterns in various organs, and phylogenetic analysis of UDP-glycosyltransferases (UGTs) suggest that UGT79B6 (At5g54010) is a key modification enzyme for determining pollen-specific flavonol structure. Kaempferol and quercetin 3-O-glucosyl-(1→2)-glucosides were absent from two independent ugt79b6 knockout mutants. Transgenic ugt79b6 mutant lines transformed with the genomic UGT79B6 gene had the same flavonoid profile as wild-type plants. Recombinant UGT79B6 protein converted kaempferol 3-O-glucoside to kaempferol 3-O-glucosyl-(1→2)-glucoside. UGT79B6 recognized 3-O-glucosylated/galactosylated anthocyanins/flavonols but not 3,5- or 3,7-diglycosylated flavonoids, and prefers UDP-glucose, indicating that UGT79B6 encodes flavonoid 3-O-glucoside:2″-O-glucosyltransferase. A UGT79B6-GUS fusion showed that UGT79B6 was localized in tapetum cells and microspores of developing anthers. PMID:24916675

  3. Retargeting a maize β-glucosidase to the vacuole--evidence from intact plants that zeatin-O-glucoside is stored in the vacuole.

    PubMed

    Kiran, Nagavalli S; Benková, Eva; Reková, Alena; Dubová, Jaroslava; Malbeck, Jiří; Palme, Klaus; Brzobohatý, Břetislav

    2012-07-01

    Cytokinin (CK) activity is regulated by the complex interplay of their metabolism, transport, stability and cellular/tissue localization. O-glucosides of zeatin-type CKs are postulated to be storage and/or transport forms. Active CK levels are determined in part by their differential distribution of CK metabolites across different subcellular compartments. We have previously shown that overexpressing chloroplast-localized Zm-p60.1, a maize β-glucosidase capable of releasing active cytokinins from their O- and N3-glucosides, perturbs CK homeostasis in transgenic tobacco. We obtained tobacco (Nicotiana tabacum L., cv Petit Havana SR1) plants overexpressing a recombinant Zm-p60.1 that is targeted to the vacuole. The protein is correctly processed and localized to the vacuole. When grown on medium containing exogenous zeatin, transgenic seedlings rapidly accumulate fresh weight due to ectopic growths at the base of the hypocotyl. The presence of the enzyme in these ectopic structures is shown by histochemical staining. CK quantification reveals that these transgenic seedlings are unable to accumulate zeatin-O-glucoside to levels similar to those observed in the wild type. When crossed with tobacco overexpressing the zeatin-O-glucosyltransferase gene from Phaseolus, the vacuolar variant shows an almost complete reversion in the root elongation assay. This is the first evidence from intact plants that the vacuole is the storage organelle for CK O-glucosides and that they are available to attack by Zm-p60.1. We propose the use of Zm-p60.1 as a robust molecular tool that exploits the reversibility of O-glucosylation and enables delicate manipulations of active CK content at the cellular level.

  4. Resistance of glucose-6-phosphate dehydrogenase deficiency to malaria: effects of fava bean hydroxypyrimidine glucosides on Plasmodium falciparum growth in culture and on the phagocytosis of infected cells.

    PubMed

    Ginsburg, H; Atamna, H; Shalmiev, G; Kanaani, J; Krugliak, M

    1996-07-01

    The balanced polymorphism of glucose-6-phosphate dehydrogenase deficiency (G6PD-) is believed to have evolved through the selective pressure of malarial combined with consumption of fava beans. The implicated fava bean constituents are the hydroxypyrimidine glucosides vicine and convicine, which upon hydrolysis of their beta-O-glucosidic bond, became protein pro-oxidants. In this work we show that the glucosides inhibit the growth of Plasmodium falciparum, increase the hexose-monophosphate shunt activity and the phagocytosis of malaria-infected erythrocytes. These activities are exacerbated in the presence of beta-glucosidase, implicating their pro-oxidant aglycones in the toxic effect, and are more pronounced in infected G6PD- erythrocytes. These results suggest that G6PD- infected erythrocytes are more susceptible to phagocytic cells, and that fava bean pro-oxidants are more efficiently suppressing parasite propagation in G6PD- erythrocytes, either by directly affecting parasite growth, or by means of enhanced phagocytic elimination of infected cells. The present findings could account for the relative resistance of G6PD- bearers to falciparum malaria, and establish a link between dietary habits and malaria in the selection of the G6PD- genotype.

  5. Resistance of glucose-6-phosphate dehydrogenase deficiency to malaria: effects of fava bean hydroxypyrimidine glucosides on Plasmodium falciparum growth in culture and on the phagocytosis of infected cells.

    PubMed

    Ginsburg, H; Atamna, H; Shalmiev, G; Kanaani, J; Krugliak, M

    1996-07-01

    The balanced polymorphism of glucose-6-phosphate dehydrogenase deficiency (G6PD-) is believed to have evolved through the selective pressure of malarial combined with consumption of fava beans. The implicated fava bean constituents are the hydroxypyrimidine glucosides vicine and convicine, which upon hydrolysis of their beta-O-glucosidic bond, became protein pro-oxidants. In this work we show that the glucosides inhibit the growth of Plasmodium falciparum, increase the hexose-monophosphate shunt activity and the phagocytosis of malaria-infected erythrocytes. These activities are exacerbated in the presence of beta-glucosidase, implicating their pro-oxidant aglycones in the toxic effect, and are more pronounced in infected G6PD- erythrocytes. These results suggest that G6PD- infected erythrocytes are more susceptible to phagocytic cells, and that fava bean pro-oxidants are more efficiently suppressing parasite propagation in G6PD- erythrocytes, either by directly affecting parasite growth, or by means of enhanced phagocytic elimination of infected cells. The present findings could account for the relative resistance of G6PD- bearers to falciparum malaria, and establish a link between dietary habits and malaria in the selection of the G6PD- genotype. PMID:8710417

  6. Comparative abilities and optimal conditions for beta-glycosidase enzymes to hydrolyse the glucuronide, glucoside, and N-acetylglucosaminide conjugates of bile acids.

    PubMed

    Momose, T; Maruyama, J; Iida, T; Goto, J; Nambara, T

    1997-08-01

    Enzymatic hydrolyses were described for three variants of glycosidic conjugated bile acids with one beta-glucuronidase (Helix pomatia), three beta-glucosidase (almonds, sweet almonds, and Escherichia coli), and four beta-N-acetylglucosaminidase (jack beans, bovine kidney, human placenta, and Diplococcus pneumoniae) preparations. The substrates include the beta-glucuronide, beta-glucoside, and beta-N-acetylglucosaminide conjugates of bile acids related to hyodeoxycholic, murideoxycholic, chenodeoxycholic, and ursodeoxycholic acids possessing a sugar moiety at position C-3, C-6 or C-7. The comparative abilities and optimal conditions for the beta-glycosidases to catalyze the hydrolyses of the substrates were clarified by changing pHs and incubation times. Hydrolysis rates of the bile acid glycosides with beta-glycosidase treatments were influenced by both the source of the enzyme preparations and the conjugated position of a sugar moiety in the substrates, and the 3-glucoside and 3-N-acetylglucosaminide conjugates were usually hydrolyzed more efficiently than their corresponding 6- and 7-analogs. Escherichia coli and jack bean enzymes were chosen to hydrolyse the glucosidic and N-acetylglucosaminidic conjugated bile acids, respectively. PMID:9300125

  7. Luteolin and luteolin-7-O-glucoside from dandelion flower suppress iNOS and COX-2 in RAW264.7 cells.

    PubMed

    Hu, Chun; Kitts, David D

    2004-10-01

    Both reactive oxygen- and nitrogen-derived reactive species play important roles in physiological and pathophysiological conditions. Flavones, luteolin and luteolin-7-O-glucoside along with a rich plant source of both flavones, namely dandelion (Taraxacum officinale) flower extract were studied for antioxidant activity in different in vitro model systems. In this current study, luteolin and luteolin-7-O-glucoside at concentrations lower than 20 microM, significantly (p < 0.05) suppressed the productions of nitric oxide and prostaglandin E2 (PGE2) in bacterial lipopolysaccharide activated-mouse macrophage RAW264.7 cells without introducing cytotoxicity. The inhibitory effects were further attributed to the suppression of both inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein expression, and not reduced enzymatic activity. Similar suppression for both inducible enzymes was also found with the presence of dandelion flower extract, specifically, the ethyl acetate fraction of dandelion flower extract which contained 10% luteolin and luteolin-7-O-glucoside. PMID:15543940

  8. Deoxynivalenol & Deoxynivalenol-3-Glucoside Mitigation through Bakery Production Strategies: Effective Experimental Design within Industrial Rusk-Making Technology

    PubMed Central

    Generotti, Silvia; Cirlini, Martina; Malachova, Alexandra; Sulyok, Michael; Berthiller, Franz; Dall’Asta, Chiara; Suman, Michele

    2015-01-01

    In the scientific field, there is a progressive awareness about the potential implications of food processing on mycotoxins especially concerning thermal treatments. High temperatures may cause, in fact, transformation or degradation of these compounds. This work is aimed to study the fate of mycotoxins during bakery processing, focusing on deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON3Glc), along the chain of industrial rusk production. Starting from naturally contaminated bran, we studied how concentrations of DON and DON3Glc are influenced by modifying ingredients and operative conditions. The experiments were performed using statistical Design of Experiment (DoE) schemes to synergistically explore the relationship between mycotoxin reduction and the indicated processing transformation parameters. All samples collected during pilot plant experiments were analyzed with an LC-MS/MS multimycotoxin method. The obtained model shows a good fitting, giving back relevant information in terms of optimization of the industrial production process, in particular suggesting that time and temperature in baking and toasting steps are highly relevant for minimizing mycotoxin level in rusks. A reduction up to 30% for DON and DON3Glc content in the finished product was observed within an acceptable technological range. PMID:26213969

  9. Flavonol Glucoside and Antioxidant Enzyme Biosynthesis Affected by Mycorrhizal Fungi in Various Cultivars of Onion (Allium cepa L.).

    PubMed

    Mollavali, Mohanna; Bolandnazar, Saheb Ali; Schwarz, Dietmar; Rohn, Sascha; Riehle, Peer; Zaare Nahandi, Fariborz

    2016-01-13

    The objective of this study was to investigate the impact of mycorrhizal symbiosis on qualitative characteristics of onion (Allium cepa L.). For this reason, five onion cultivars with different scale color and three different strains of arbuscular mycorrhizal fungi (Diversispora versiformis, Rhizophagus intraradices, Funneliformis mosseae) were used. Red cultivars, mainly 'Red Azar-shahr', showed the highest content in vitamin C, flavonols, and antioxidant enzymes. Mycorrhizal inoculation increased total phenolic, pyruvic acid, and vitamin C of onion plants. Considerable increase was observed in quercetin-4'-O-monoglucoside and isorhamnetin-4'-O-monoglucoside content in plants inoculated with Diversispora versiformis, but quercetin-3,4'-O-diglucoside was not significantly influenced. Analyses for phenylalanine ammonia-lyase (PAL) and antioxiodant enzyme activities such as polyphenol oxidase (PPO), catalase (CAT), and peroxidase (POD) revealed that all except PPO were enhanced by mycorrhizal inoculation. Overall, these findings suggested that mycorrhizal inoculation influenced biosynthesis of flavonol glucosides and antioxidant enzymes by increasing nutrient uptake or by induction of the plant defense system. PMID:26694086

  10. Characterization of intermolecular interaction between cyanidin-3-glucoside and bovine serum albumin: spectroscopic and molecular docking methods.

    PubMed

    Shi, Jie-hua; Wang, Jing; Zhu, Ying-yao; Chen, Jun

    2014-08-01

    The intermolecular interaction between cyanidin-3-glucoside (Cy-3-G) and bovine serum albumin (BSA) was investigated using fluorescence, circular dichroism and molecular docking methods. The experimental results revealed that the fluorescence quenching of BSA at 338 nm by Cy-3-G resulted from the formation of Cy-3-G-BSA complex. The number of binding sites (n) for Cy-3-G binding on BSA was approximately equal to 1. The experimental and molecular docking results revealed that after binding Cy-3-G to BSA, Cy-3-G is closer to the Tyr residue than the Trp residue, the secondary structure of BSA almost not change, the binding process of Cy-3-G with BSA is spontaneous, and Cy-3-G can be inserted into the hydrophobic cavity of BSA (site II') in the binding process of Cy-3-G with BSA. Moreover, based on the sign and magnitude of the enthalpy and entropy changes (ΔH(0)  = - 29.64 kcal/mol and ΔS(0)  = - 69.51 cal/mol K) and the molecular docking results, it can be suggested that the main interaction forces of Cy-3-G with BSA are Van der Waals and hydrogen bonding interactions.

  11. Anti-human rhinovirus 2 activity and mode of action of quercetin-7-glucoside from Lagerstroemia speciosa.

    PubMed

    Song, Jae Hyoung; Park, Kwi Sung; Kwon, Dur Han; Choi, Hwa Jung

    2013-04-01

    Human rhinoviruses (HRVs) are a major cause of the common cold, but there is currently, no registered clinically effective antiviral chemotherapeutic agent for treatment of diseases caused by HRVs. In this study, we examined the antiviral activity of quercetin 7-glucoside (Q7G) from Lagerstroemia speciosa against human rhinovirus 2 (HRV2) using a cytopathic effect (CPE) reduction method. Furthermore, to elucidate the action of Q7G on HRV2 multiplication in more detail, we investigated the effect of Q7G on the infection cycle of HRV2 through time-of-addition study, reverse transcription-polymerase chain reaction analysis, and effects of Q7G on the infectivity of HRV2 particles. Q7G potently showed anti-HRV2 activity by reducing the formation of a visible CPE. Q7G also inhibited virus replication in the initial stage of virus infection by indirect interaction with virus particles, and ribavirin had a relative weaker efficacy compared to Q7G. Therefore, these data suggest that Q7G exerted its anti-HRV2 effect via the inhibition of virus replication in the early stage and these findings provide important information for the utilization of Q7G for HRV2 treatment.

  12. Facile preparation of water soluble curcuminoids extracted from turmeric (Curcuma longa L.) powder by using steviol glucosides.

    PubMed

    Nguyen, Thi Thanh Hanh; Si, Jinbeom; Kang, Choongil; Chung, Byoungsang; Chung, Donghwa; Kim, Doman

    2017-01-01

    Curcuminoids from rhizomes of Curcuma longa possess various biological activities. However, low aqueous solubility and consequent poor bioavailability of curcuminoids are major limitations to their use. In this study, curcuminoids extracted from turmeric powder using stevioside (Ste), rebaudioside A (RebA), or steviol glucosides (SG) were solubilized in water. The optimum extraction condition by Ste, RebA, or SG resulted in 11.3, 9.7, or 6.7mg/ml water soluble curcuminoids. Curcuminoids solubilized in water showed 80% stability at pH from 6.0 to 10.0 after 1week of storage at 25°C. The particle sizes of curcuminoids prepared with Ste, RebA, and SG were 110.8, 95.7, and 32.7nm, respectively. The water soluble turmeric extracts prepared with Ste, RebA, and SG showed the 2,2-diphenyl-1-picrylhydrazyl radical scavenging (SC50) activities of 127.6, 105.4, and 109.8μg/ml, and the inhibition activities (IC50) against NS2B-NS3(pro) from dengue virus type IV of 14.1, 24.0 and 15.3μg/ml, respectively. PMID:27507487

  13. Stability, Antioxidant Capacity and Degradation Kinetics of Pelargonidin-3-glucoside Exposed to Ultrasound Power at Low Temperature.

    PubMed

    Sun, Jianxia; Mei, Zhouxiong; Tang, Yajuan; Ding, Lijun; Jiang, Guichuan; Zhang, Chi; Sun, Aidong; Bai, Weibin

    2016-01-01

    As an alternative preservation method to thermal treatment, ultrasound is a novel non-thermal processing technology that can significantly avoid undesirable nutritional changes. However, recently literature indicated that anthocyanin degradation occurred when high amplitude ultrasound was applied to juice. This work mainly studied the effect of ultrasound on the stability and antioxidant capacity of pelargonidin-3-glucoside (Pg-3-glu) and the correlation between anthocyanin degradation and •OH generation in a simulated system. Results indicated that the spectral intensities of Pg-3-glu decreased with increasing ultrasound power (200-500 W) and treatment time (0-60 min). The degradation trend was consistent with first-order reaction kinetics (R² > 0.9100). Further study showed that there was a good linear correlation between Pg-3-glu degradation and •OH production (R² = 0.8790), which indicated the important role of •OH in the degradation of anthocyanin during ultrasound exposure. Moreover, a decrease in the antioxidant activity of solution(s) containing Pg-3-glu as evaluated by the DPPH and FRAP methods was observed after ultrasound treatment. PMID:27563863

  14. In-vivo absorption of pinocembrin-7-O-β-D-glucoside in rats and its in-vitro biotransformation

    PubMed Central

    Guo, Wei-Wei; Qiu, Feng; Chen, Xiao-Qing; Ba, Yin-Ying; Wang, Xing; Wu, Xia

    2016-01-01

    Pinocembrin-7-O-β-D-glucoside (PCBG), a flavonoid isolated from Penthorum chinense Pursh., has significant liver-protecting effects. The pharmacokinetics of PCBG and its major metabolite pinocembrin (PCB) in rats were investigated in this study. A sensitive and accurate UPLC-MS/MS method was developed and validated for the simultaneous quantitative determination of PCBG and PCB in rat plasma after oral and intravenous administration of PCBG. After intravenous administration, PCBG was the main form in plasma. In contrast, after oral administration, the concentration of PCB was about 4-fold higher than that of PCBG, indicating that PCBG was metabolized to PCB. We also investigated the biotransformation of PCBG in vitro in order to understand whether the pH and the intestinal flora of gastrointestinal tract could affect the metabolism of PCBG. PCBG was incubated in rat plasma, liver homogenization, gastrointestial contents, liver microsomes (RLM) and hepatocytes in vitro. The data showed that PCB was quickly formed in the gastrointestinal incubation but PCBG was converted to PCB gradually in other incubations. The results indicated that the majority of PCBG was converted to its aglycone PCB in digestive system after oral administration, and PCB could be the active ingredient in the body. PMID:27378517

  15. Flavonol Glucoside and Antioxidant Enzyme Biosynthesis Affected by Mycorrhizal Fungi in Various Cultivars of Onion (Allium cepa L.).

    PubMed

    Mollavali, Mohanna; Bolandnazar, Saheb Ali; Schwarz, Dietmar; Rohn, Sascha; Riehle, Peer; Zaare Nahandi, Fariborz

    2016-01-13

    The objective of this study was to investigate the impact of mycorrhizal symbiosis on qualitative characteristics of onion (Allium cepa L.). For this reason, five onion cultivars with different scale color and three different strains of arbuscular mycorrhizal fungi (Diversispora versiformis, Rhizophagus intraradices, Funneliformis mosseae) were used. Red cultivars, mainly 'Red Azar-shahr', showed the highest content in vitamin C, flavonols, and antioxidant enzymes. Mycorrhizal inoculation increased total phenolic, pyruvic acid, and vitamin C of onion plants. Considerable increase was observed in quercetin-4'-O-monoglucoside and isorhamnetin-4'-O-monoglucoside content in plants inoculated with Diversispora versiformis, but quercetin-3,4'-O-diglucoside was not significantly influenced. Analyses for phenylalanine ammonia-lyase (PAL) and antioxiodant enzyme activities such as polyphenol oxidase (PPO), catalase (CAT), and peroxidase (POD) revealed that all except PPO were enhanced by mycorrhizal inoculation. Overall, these findings suggested that mycorrhizal inoculation influenced biosynthesis of flavonol glucosides and antioxidant enzymes by increasing nutrient uptake or by induction of the plant defense system.

  16. Spectrophotometric study of the copigmentation of malvidin 3-O-glucoside with p-coumaric, vanillic and syringic acids.

    PubMed

    Malaj, Naim; De Simone, Bruna Clara; Quartarolo, Angelo Domenico; Russo, Nino

    2013-12-15

    Anthocyanins are a natural source of pigments in plants and their processed food products have become attractive and excellent candidates to replace the synthetic colourants due to their characteristic intense colours and associated health benefits. The intermolecular copigmentation between anthocyanins and other colourless compounds has been reported to be an important way to enhance and stabilise the colour intensity of aqueous solutions. In the present work we report the equilibrium constant, stoichiometric ratio and the thermodynamic parameters (ΔG°, ΔH° and ΔS°) related to the intermolecular copigmentation reactions of the anthocyanin malvidin 3-O-glucoside with one hydroxycinnamic acid (p-coumaric acid) and two O-methylated hydroxybenzoic acids (vanillic and syringic acid). Different factors which affect their interactions such as copigment concentration, pH and temperature of the medium are examined at two pH levels (pH=2.50 and 3.65) corresponding to those of the major food mediums where these reactions take place (fruit juices, wine, jams etc.).

  17. Isolation of a flavonoid, apigenin 7-O-glucoside, from Mentha longifolia (L.) Hudson subspecies longifolia and its genotoxic potency.

    PubMed

    Gulluce, Medine; Orhan, Furkan; Yanmis, Derya; Arasoglu, Tulin; Guvenalp, Zuhal; Demirezer, Lutfiye Omur

    2015-09-01

    Mentha is a medicinal and aromatic plant belonging to the Lamiaceae family, which is widely used in food, flavor, cosmetic and pharmaceutical industries. Recently, it has been found that the use of Mentha as a pharmaceutical source is based on its phytochemical constituents that have far been identified as tannins, saponins, phenolic acids and flavonoids. This study was designed to evaluate the mutagenic and antimutagenic activities of apigenin 7-O-glucoside (A7G), a flavonoid isolated from Mentha longifolia (L.) Hudson subspecies longifolia (ML). The possible antimutagenic potential of A7G was examined against mutagens ethyl methanesulfonate and acridine in an eukaryotic cell system Saccharomyces cerevisiae and sodium azide in Salmonella typhimurium TA1535 and 9-aminoacridine in S. typhimurium TA1537. According to our findings, any concentrations of the A7G used did not show mutagenic activity but exerted strong antimutagenic activities at tested concentrations. The inhibition rates for the Ames test ranged from 27.2% (S. typhimurium TA1535: 0.4 μM/plate) to 91.1% (S. typhimurium TA1537: 0.2 μM/plate) and for the yeast deletion assay from 4% to 57.7%. This genotoxicological study suggests that a flavonoid from ML owing to antimutagenic properties is of great pharmacological importance and might be beneficial to industries producing food additives, cosmetics and pharmaceuticals products.

  18. Binding of the alkaloid aristololactam-β-D-glucoside and daunomycin to human hemoglobin: spectroscopy and calorimetry studies.

    PubMed

    Das, Abhi; Suresh Kumar, Gopinatha

    2016-01-01

    The interaction of the plant alkaloid aristololactam-β-D-glucoside (ADG) and the anticancer agent daunomycin (DAN) with human hemoglobin was studied by different spectroscopic and calorimetric methods. The binding affinity values of ADG and DAN, estimated from spectroscopic experiments, were 3.79 × 10(4) and 6.68 × 10(4) M(-1), respectively. From circular dichroism, 3D fluorescence, and FTIR studies it was observed that, DAN induced stronger conformational changes than ADG in the protein. From synchronous fluorescence spectroscopy results, a pronounced shift in the maximum emission wavelength of tyrosine residues was observed in both cases suggesting that the drugs changed the polarity around tyrosine residues with marginal change around the tryptophan residues. The thermodynamics of the binding interaction analyzed using microcalorimetry presented single binding events that were exothermic in nature in both cases. The binding was driven by large positive standard molar entropy changes with small favorable enthalpy contributions. Negative heat capacity changes in both cases are correlated to the involvement of significant hydrophobic forces in the complexation process. The affinity of DAN to Hb was higher than that of ADG. PMID:26065442

  19. The inhibitory effect and mechanism of luteolin 7-glucoside on rat aortic vascular smooth muscle cell proliferation.

    PubMed

    Kim, Tack-Joong; Kim, Jin-Ho; Jin, Yong-Ri; Yun, Yeo-Pyo

    2006-01-01

    The abnormal proliferation of aortic vascular smooth muscle cells (VSMCs) plays a central role in the pathogenesis of atherosclerosis and restenosis after angioplasty and possibly also in the development of hypertension. The present study was designed to examine the inhibitory effects and the mechanism of luteolin 7-glucoside (L7G) on the platelet-derived growth factor (PDGF)-BB-induced proliferation of VSMCs. L7G significantly inhibited the PDGF-BB-induced proliferation and the DNA synthesis of the VSMCs in a concentration-dependent manner. Pre-incubation of the VSMCs with L7G significantly inhibited the PDGF-BB-induced extracellular signal-regulated kinase 1/2 (ERK1/2), Akt and the phospholipase C (PLC)-gamma1 activation. However, L7G had almost no affect on the phosphorylation of PDGF-beta receptor tyrosine kinase, which was induced by PDGF-BB. These results suggest that L7G inhibits the PDGF-BB-induced proliferation of VSMCs via the blocking of PLC-gamma1, Akt, and ERK1/2 phosphorylation.

  20. Ursolic acid and luteolin-7-glucoside improve lipid profiles and increase liver glycogen content through glycogen synthase kinase-3.

    PubMed

    Azevedo, Marisa F; Camsari, Cagri; Sá, Carla M; Lima, Cristovao F; Fernandes-Ferreira, Manuel; Pereira-Wilson, Cristina

    2010-06-01

    In the present study, two phytochemicals - ursolic acid (UA) and luteolin-7-glucoside (L7G) - were assessed in vivo in healthy rats regarding effects on plasma glucose and lipid profile (total cholesterol, HDL and LDL), as well as liver glycogen content, in view of their importance in the aetiology of diabetes and associated complications. Both UA and L7G significantly decreased plasma glucose concentration. UA also significantly increased liver glycogen levels accompanied by phosphorylation of glycogen synthase kinase-3 (GSK3). The increase in glycogen deposition induced by UA (mediated by GSK3) could have contributed to the lower plasma glucose levels observed. Both compounds significantly lowered total plasma cholesterol and low-density lipoprotein levels, and, in addition, UA increased plasma high-density lipoprotein levels. Our results show that UA particularly may be useful in preventable strategies for people at risk of developing diabetes and associated cardiovascular complications by improving plasma glucose levels and lipid profile, as well as by promoting liver glycogen deposition.

  1. ABCC1, an ATP Binding Cassette Protein from Grape Berry, Transports Anthocyanidin 3-O-Glucosides[W][OA

    PubMed Central

    Francisco, Rita Maria; Regalado, Ana; Ageorges, Agnès; Burla, Bo J.; Bassin, Barbara; Eisenach, Cornelia; Zarrouk, Olfa; Vialet, Sandrine; Marlin, Thérèse; Chaves, Maria Manuela; Martinoia, Enrico; Nagy, Réka

    2013-01-01

    Accumulation of anthocyanins in the exocarp of red grapevine (Vitis vinifera) cultivars is one of several events that characterize the onset of grape berry ripening (véraison). Despite our thorough understanding of anthocyanin biosynthesis and regulation, little is known about the molecular aspects of their transport. The participation of ATP binding cassette (ABC) proteins in vacuolar anthocyanin transport has long been a matter of debate. Here, we present biochemical evidence that an ABC protein, ABCC1, localizes to the tonoplast and is involved in the transport of glucosylated anthocyanidins. ABCC1 is expressed in the exocarp throughout berry development and ripening, with a significant increase at véraison (i.e., the onset of ripening). Transport experiments using microsomes isolated from ABCC1-expressing yeast cells showed that ABCC1 transports malvidin 3-O-glucoside. The transport strictly depends on the presence of GSH, which is cotransported with the anthocyanins and is sensitive to inhibitors of ABC proteins. By exposing anthocyanin-producing grapevine root cultures to buthionine sulphoximine, which reduced GSH levels, a decrease in anthocyanin concentration is observed. In conclusion, we provide evidence that ABCC1 acts as an anthocyanin transporter that depends on GSH without the formation of an anthocyanin-GSH conjugate. PMID:23723325

  2. Long Chain Fatty Acid Acylated Derivatives of Quercetin-3-O-Glucoside as Antioxidants to Prevent Lipid Oxidation

    PubMed Central

    Warnakulasuriya, Sumudu N.; Ziaullah; Rupasinghe, H.P. Vasantha

    2014-01-01

    Flavonoids have shown promise as natural plant-based antioxidants for protecting lipids from oxidation. It was hypothesized that their applications in lipophilic food systems can be further enhanced by esterification of flavonoids with fatty acids. Quercetin-3-O-glucoside (Q3G) was esterified individually with six selected long chain fatty acids: stearic acid (STA), oleic acid (OLA), linoleic acid (LNA), α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and decosahexaenoic acid (DHA), using Candida antarctica B lipase as the biocatalyst. The antioxidant activity of esterified flavonoids was evaluated using lipid oxidation model systems of poly-unsaturated fatty acids-rich fish oil and human low density lipoprotein (LDL), in vitro. In the oil-in-water emulsion, Q3G esters exhibited 50% to 100% inhibition in primary oxidation and 30% to 75% inhibition in secondary oxidation. In bulk oil, Q3G esters did not provide considerable protection from lipid oxidation; however, Q3G demonstrated more than 50% inhibition in primary oxidation. EPA, DHA and ALA esters of Q3G showed significantly higher inhibition in Cu2+- and peroxyl radical-induced LDL oxidation in comparison to Q3G. PMID:25384198

  3. Effects of baking on cyanidin-3-glucoside content and antioxidant properties of black and yellow soybean crackers.

    PubMed

    Slavin, Margaret; Lu, Yingjian; Kaplan, Nicholas; Yu, Liangli Lucy

    2013-11-15

    Black soybean is a potential functional food ingredient with high anthocyanin content, but the ability to maintain anthocyanin content under dry heat processing has not been reported. This study investigated the effects of soybean seed coat colour and baking time-temperature combinations on the extractable antioxidant properties of a soy cracker food model. Crackers prepared with black soybeans had significantly higher TPC, total isoflavones, and peroxyl, hydroxyl, and ABTS(+) radical scavenging abilities than their yellow counterparts, at all time-temperature combinations. Cyanidin-3-glucoside (C3G) was detected only in black soybean crackers, and all baking treatments significantly decreased C3G. The greatest losses occurred at the low temperature×long time and high temperature×short time, the smallest loss with moderate temperature×short/medium time. The high temperature treatment altered phenolic acid and isoflavone profiles; however, total isoflavones were unaffected. Overall results suggest that moderate baking temperature at minimal time may best preserve anthocyanin and other phenolics in baked black soybean crackers.

  4. Facile preparation of water soluble curcuminoids extracted from turmeric (Curcuma longa L.) powder by using steviol glucosides.

    PubMed

    Nguyen, Thi Thanh Hanh; Si, Jinbeom; Kang, Choongil; Chung, Byoungsang; Chung, Donghwa; Kim, Doman

    2017-01-01

    Curcuminoids from rhizomes of Curcuma longa possess various biological activities. However, low aqueous solubility and consequent poor bioavailability of curcuminoids are major limitations to their use. In this study, curcuminoids extracted from turmeric powder using stevioside (Ste), rebaudioside A (RebA), or steviol glucosides (SG) were solubilized in water. The optimum extraction condition by Ste, RebA, or SG resulted in 11.3, 9.7, or 6.7mg/ml water soluble curcuminoids. Curcuminoids solubilized in water showed 80% stability at pH from 6.0 to 10.0 after 1week of storage at 25°C. The particle sizes of curcuminoids prepared with Ste, RebA, and SG were 110.8, 95.7, and 32.7nm, respectively. The water soluble turmeric extracts prepared with Ste, RebA, and SG showed the 2,2-diphenyl-1-picrylhydrazyl radical scavenging (SC50) activities of 127.6, 105.4, and 109.8μg/ml, and the inhibition activities (IC50) against NS2B-NS3(pro) from dengue virus type IV of 14.1, 24.0 and 15.3μg/ml, respectively.

  5. Five furofuranone lignan glucosides from Terminalia citrina inhibit in vitro E2-enhanced breast cancer cell proliferation.

    PubMed

    Muhit, Md Abdul; Umehara, Kaoru; Noguchi, Hiroshi

    2016-09-01

    Five new polyalkoxylated furofuranone lignan glucosides, terminalosides L-P (1-5), were isolated from EtOAc extracts of the leaves of Terminalia citrina, a Bangladeshi medicinal plant. The structures of the isolates were deduced primarily by NMR spectroscopy, and four of the isolates were found to contain rare tetraoxygenated aryl groups in their structures. The absolute configurations and conformations of the furofuranone ring were confirmed by ECD spectroscopy. All of the isolates were evaluated for their estrogenic and/or antiestrogenic properties using two estrogen responsive breast cancer cell lines, T47D and MCF-7. At a concentration of 10nM, terminaloside L (1) suppressed E2-enhanced T47D cell proliferation by 90%, while terminaloside M (2) showed 90% antiestrogenic activity against MCF-7 cells. Compared to 2, the antiestrogenic activity of terminaloside O (4) and P (5) was weak, possibly due to the different attachment positions of the sugar moiety that they share in common. This is the first report of furofuranone lignans from any Terminalia species, and also of their antiestrogenic activity. PMID:27425446

  6. Analysis of deoxynivalenol and deoxynivalenol-3-glucosides content in Canadian spring wheat cultivars inoculated with Fusarium graminearum.

    PubMed

    Amarasinghe, Chami C; Simsek, Senay; Brûlé-Babel, Anita; Fernando, W G Dilantha

    2016-07-01

    Contamination of wheat grains with Fusarium mycotoxins and their modified forms is an important issue in wheat industry. The objective of this study was to analyse the deoxynivalenol (DON) and deoxynivalenol-3-glucosides (D3G) content in Canadian spring wheat cultivars grown in two locations, inoculated with a mixture of 3-acetyldeoxynivalenol (3-ADON)-producing Fusarium graminearum strains and a mixture of 15-acetlyldeoxynivalenol (15-ADON)-producing F. graminearum strains. According to the analysis of variance, significant differences were observed among the cultivars for Fusarium head blight (FHB) disease index, Fusarium-damaged kernel percentage (%FDK), DON content and D3G content. When the effect of chemotype was considered, significant differences were observed for FHB disease index, FDK percentage and DON content. The D3G content and D3G/DON ratio were not significantly different between the chemotypes, except for D3G content at the Winnipeg location. The Pearson correlation coefficient between DON and D3G was 0.84 and 0.77 at Winnipeg and Carman respectively. The highest D3G/DON ratio was observed in cultivars Carberry (44%) in Carman and CDC Kernen (63.8%) in Winnipeg. The susceptible cultivars showed lower D3G/DON ratio compared with the cultivars rated as moderately resistant and intermediate. The current study indicated that Canadian spring cultivars produce D3G upon Fusarium infection.

  7. Deoxynivalenol & Deoxynivalenol-3-Glucoside Mitigation through Bakery Production Strategies: Effective Experimental Design within Industrial Rusk-Making Technology.

    PubMed

    Generotti, Silvia; Cirlini, Martina; Malachova, Alexandra; Sulyok, Michael; Berthiller, Franz; Dall'Asta, Chiara; Suman, Michele

    2015-07-24

    In the scientific field, there is a progressive awareness about the potential implications of food processing on mycotoxins especially concerning thermal treatments. High temperatures may cause, in fact, transformation or degradation of these compounds. This work is aimed to study the fate of mycotoxins during bakery processing, focusing on deoxynivalenol (DON) and deoxynivalenol-3-glucoside (DON3Glc), along the chain of industrial rusk production. Starting from naturally contaminated bran, we studied how concentrations of DON and DON3Glc are influenced by modifying ingredients and operative conditions. The experiments were performed using statistical Design of Experiment (DoE) schemes to synergistically explore the relationship between mycotoxin reduction and the indicated processing transformation parameters. All samples collected during pilot plant experiments were analyzed with an LC-MS/MS multimycotoxin method. The obtained model shows a good fitting, giving back relevant information in terms of optimization of the industrial production process, in particular suggesting that time and temperature in baking and toasting steps are highly relevant for minimizing mycotoxin level in rusks. A reduction up to 30% for DON and DON3Glc content in the finished product was observed within an acceptable technological range.

  8. Behaviour of cyanidin-3-glucoside, β-lactoglobulin and polysaccharides nanoparticles in bulk and oil-in-water interfaces.

    PubMed

    Oliveira, Ana; Ruiz-Henestrosa, Víctor M Pizones; von Staszewski, Mariana; Pilosof, Ana M R; Pintado, Manuela

    2015-11-01

    Particle size distributions as well the interfacial and rheological properties of the films at the oil/water interface were used to study the effect of the interacting system between β-lactoglobulin, cyanidin-3-glucoside and pectin or chitosan in buffer solutions. The particles obtained were smaller with cy-3-gluc-β-lg-pectin and had reduced polydispersity with cy-3-gluc-β-lg-chitosan. Based on time dependent surface pressure results, β-lg-pectin mixtures showed a slower increase at the beginning of the measurement, while β-lg-chitosan mixtures showed no differences with β-lg alone. Contrarily, dilatational properties increased for ternary chitosan mixtures, but they remained similar to the pure protein in ternary pectin mixtures. Cy-3-gluc interfacial properties were reduced by the presence of pectin and chitosan. The interactions between cy-3-gluc and the biopolymers that have been selected in the present work resulted in a lower content of free polyphenol, reduced antioxidant properties as well as free β-lg. The impact of this effect was more relevant when pectin was used. PMID:26256371

  9. A new monoterpene glucoside and complete assignments of dihydroflavonols of Pulicaria jaubertii: potential cytotoxic and blood pressure lowering activity.

    PubMed

    Ragab, Ehab A; Raafat, Mohamed

    2016-06-01

    One new monoterpene glucoside and five dihydroflavonols were isolated for the first time from the aerial parts of Pulicaria jaubertii and identified as p-menthane-2-O-β-D-glucopyranoside [1], dihydroquercetin (taxifolin) [2], 7,3'-di-O-methyltaxifolin [3], 3'-O-methyltaxifolin [4], 7-O-methyltaxifolin (padmatin) [5] and 7-O-methyl-dihydrokampferol (7-O-methylaromadenderin) [6]. The structures of these compounds were unambiguously assigned on the basis of NMR spectroscopic data ((1)H, (13)C, DEPT, HSQC, HMBC) and MS analysis. 2D-NMR methods required revision of assignments of H-6 and H-8 for dihydroflavonol compounds. Possible cytotoxic activity as well as blood pressure (BP) lowering activity were tested. The alcoholic extract showed cytotoxic activity against prostate carcinoma (PC-3), breast carcinoma (MCF-7) and hepatocellular carcinoma (HepG-2) human cell lines with IC50 19.1, 20.0 and 24.1 μg, respectively. The higher dose levels of the alcoholic extract significantly reduced normal BP of rats in a dose-dependent manner.

  10. Differentiation of flavonol glucoside and galactoside isomers combining chemical isopropylidenation with liquid chromatography-mass spectrometry analysis.

    PubMed

    de Souza, Lauro M; Dartora, Nessana; Scoparo, Camila T; Gorin, Philip A J; Iacomini, Marcello; Sassaki, Guilherme L

    2016-05-20

    Flavonol glycosides are important components of leaves from vascular plants. A lot of isomers of these compounds are produced by plants, making their analysis very difficult and causing many structural misinterpretations. Galactosides and glucosides as mono- or oligosaccharides yield many diastereoisomers, hindering the analysis by mass spectrometry. In order to enable the mass spectrometric distinctions of these isomers, in this work we combine an isopropylidene based chemical derivatization with liquid chromatography with multiple-stage mass spectrometry (LC-MS(n)) analysis. The isomers of flavonol triglycosides, after the reaction, yielded products with different molecular weight, therefore, they were no longer isomers, allowing their identification by MS(1) analysis. However, to the 4 isomers of flavonol diglycosides, only one yielded, after isopropylidenation, a product with different molecular weight. To the other 3 species, the incorporation of 2 isopropylidene groups retained them in the isomeric form. For such species, chromatographic separation and MS(n) detection targeting the lithium adducts of 3,4-O-isopropylidene-galactosyl or 4,6-O-isopropylidene-glucosyl residues (m/z 209.099) provided specific MS profile. PMID:27109198

  11. The inhibitory effect and mechanism of luteolin 7-glucoside on rat aortic vascular smooth muscle cell proliferation.

    PubMed

    Kim, Tack-Joong; Kim, Jin-Ho; Jin, Yong-Ri; Yun, Yeo-Pyo

    2006-01-01

    The abnormal proliferation of aortic vascular smooth muscle cells (VSMCs) plays a central role in the pathogenesis of atherosclerosis and restenosis after angioplasty and possibly also in the development of hypertension. The present study was designed to examine the inhibitory effects and the mechanism of luteolin 7-glucoside (L7G) on the platelet-derived growth factor (PDGF)-BB-induced proliferation of VSMCs. L7G significantly inhibited the PDGF-BB-induced proliferation and the DNA synthesis of the VSMCs in a concentration-dependent manner. Pre-incubation of the VSMCs with L7G significantly inhibited the PDGF-BB-induced extracellular signal-regulated kinase 1/2 (ERK1/2), Akt and the phospholipase C (PLC)-gamma1 activation. However, L7G had almost no affect on the phosphorylation of PDGF-beta receptor tyrosine kinase, which was induced by PDGF-BB. These results suggest that L7G inhibits the PDGF-BB-induced proliferation of VSMCs via the blocking of PLC-gamma1, Akt, and ERK1/2 phosphorylation. PMID:16491846

  12. Ursolic acid and luteolin-7-glucoside improve lipid profiles and increase liver glycogen content through glycogen synthase kinase-3.

    PubMed

    Azevedo, Marisa F; Camsari, Cagri; Sá, Carla M; Lima, Cristovao F; Fernandes-Ferreira, Manuel; Pereira-Wilson, Cristina

    2010-06-01

    In the present study, two phytochemicals - ursolic acid (UA) and luteolin-7-glucoside (L7G) - were assessed in vivo in healthy rats regarding effects on plasma glucose and lipid profile (total cholesterol, HDL and LDL), as well as liver glycogen content, in view of their importance in the aetiology of diabetes and associated complications. Both UA and L7G significantly decreased plasma glucose concentration. UA also significantly increased liver glycogen levels accompanied by phosphorylation of glycogen synthase kinase-3 (GSK3). The increase in glycogen deposition induced by UA (mediated by GSK3) could have contributed to the lower plasma glucose levels observed. Both compounds significantly lowered total plasma cholesterol and low-density lipoprotein levels, and, in addition, UA increased plasma high-density lipoprotein levels. Our results show that UA particularly may be useful in preventable strategies for people at risk of developing diabetes and associated cardiovascular complications by improving plasma glucose levels and lipid profile, as well as by promoting liver glycogen deposition. PMID:20127879

  13. Rice bran extract containing acylated steryl glucoside fraction decreases elevated blood LDL cholesterol level in obese Japanese men.

    PubMed

    Ito, Yukihiko; Nakashima, Yuri; Matsuoka, Sayuri

    2015-01-01

    People who frequently consume whole grains show a lower incidence of arteriosclerotic disease than people who consume primarily refined grains. We examined whether or not rice bran extract containing the acylated steryl glucosides (ASG) fraction decreases blood LDL cholesterol levels in obese Japanese men with high blood levels of LDL cholesterol. The study utilized a randomized, double-blind design. A total of 51 subjects were randomly allocated to either a rice bran extract containing ASG fraction (RB-ASG) group or a placebo group. Subjects in the RB-ASG group received 30-50 mg/day of RB-ASG, and the placebo group took 9 capsules/day for 12 weeks. Before and after intake, height, weight, body fat percentage, systolic and diastolic blood pressure were measured, blood was collected, and visceral fat area, subcutaneous fat area, and abdominal circumference were determined based on umbilical computed tomography. Percentage decreases in blood LDL cholesterol, non-HDL cholesterol, LDL/HDL ratio, abdominal circumference and subcutaneous fat area were significantly better in the RB-ASG group than in the placebo group. These findings suggest that RB-ASG fraction may reduce blood LDL cholesterol levels and the risk of arteriosclerosis in obese Japanese men with high LDL cholesterol levels.

  14. Glass transition behavior of octyl β-D-glucoside and octyl β-D-thioglucoside/water binary mixtures.

    PubMed

    Ogawa, Shigesaburo; Asakura, Kouichi; Osanai, Shuichi

    2010-11-22

    The lyotropic behavior and glass-forming properties of octyl β-D-glucoside (C8Glu) and octyl β-D-thioglucoside (C8SGlu)/water binary mixtures were evaluated using differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). The results clearly indicate that the mixture forms a glass in the supercooling state of liquid crystalline phases such as cubic, lamellar, and smectic. The glass transition temperature (T(g)) of the mixture was strongly dependent on solute concentration, with a higher concentration correlating with a higher T(g). The experimental T(g) was consistent with the predicted value calculated using the Couchman-Karasz equation in both the C8Glu and C8SGlu/water mixtures. The change of heat capacity at T(g) showed the two bending points under variation of concentrations. And the highest temperature of phase transition from lamellar to isotropic solution was observed at around 50% molar concentration. It was expected that non-percolated state of water existed in extremely higher concentration ranges.

  15. In-vivo absorption of pinocembrin-7-O-β-D-glucoside in rats and its in-vitro biotransformation.

    PubMed

    Guo, Wei-Wei; Qiu, Feng; Chen, Xiao-Qing; Ba, Yin-Ying; Wang, Xing; Wu, Xia

    2016-01-01

    Pinocembrin-7-O-β-D-glucoside (PCBG), a flavonoid isolated from Penthorum chinense Pursh., has significant liver-protecting effects. The pharmacokinetics of PCBG and its major metabolite pinocembrin (PCB) in rats were investigated in this study. A sensitive and accurate UPLC-MS/MS method was developed and validated for the simultaneous quantitative determination of PCBG and PCB in rat plasma after oral and intravenous administration of PCBG. After intravenous administration, PCBG was the main form in plasma. In contrast, after oral administration, the concentration of PCB was about 4-fold higher than that of PCBG, indicating that PCBG was metabolized to PCB. We also investigated the biotransformation of PCBG in vitro in order to understand whether the pH and the intestinal flora of gastrointestinal tract could affect the metabolism of PCBG. PCBG was incubated in rat plasma, liver homogenization, gastrointestial contents, liver microsomes (RLM) and hepatocytes in vitro. The data showed that PCB was quickly formed in the gastrointestinal incubation but PCBG was converted to PCB gradually in other incubations. The results indicated that the majority of PCBG was converted to its aglycone PCB in digestive system after oral administration, and PCB could be the active ingredient in the body. PMID:27378517

  16. Determination of the relative contribution of quercetin and its glucosides to the antioxidant capacity of onion by cyclic voltammetry and spectrophotometric methods.

    PubMed

    Zielinska, Danuta; Wiczkowski, Wieslaw; Piskula, Mariusz Konrad

    2008-05-28

    This paper describes the use of cyclic voltammetry (CV), spectrophotometric methods [Trolox equivalent antioxidant capacity (TEAC), peroxyl radical trapping capacity (PRTC), DPPH radical scavenging activity (RSA), and Folin-Ciocalteu reagent (FCR) reducing capacity], and photochemiluminescence (PCL) for the measurement of the antioxidant capacity of onion var. Sochaczewska and var. Szalotka. The antioxidant and reducing activity of the dominant onion flavonoids quercetin (Q), quercetin-3- O-beta-glucoside (Q3G), quercetin-4'- O-beta-glucoside (Q4'G), and quercetin-3,4'-di- O-beta-glucoside (Q3,4'G) were determined by spectrophotometric (TEAC and PRTC) and CV methods, respectively. The contribution of quercetin and its glucosides to the antioxidant capacity of onion was calculated in consequence of the qualitative and quantitative analysis of onion flavonoids by high-performance liquid chromatography-ultraviolet-mass spectrometry. The dominant forms of quercetin in the onion var. Sochaczewska and Szalotka included Q4'G (61 and 54%), Q3,4'G (37 and 44%), Q3G (1.4 and 1.1%), and free quercetin (1.1 and 0.7%), respectively. The CV experiment showed the highest reducing activity of Q while Q3G, Q4'G, and Q3,4'G exhibited about 68, 51, and 30% of the reducing power noted for Q. The order of the reducing activity of onion flavonoids was confirmed by their free radical scavenging activity and evaluated by TEAC and PRTC assays as follows: Q > Q3G > Q4'G > Q3,4'G. The Q4'G and Q3,4'G showed poor antioxidant activity under both applied spectrophotometric assays but still exhibited reducing activity based on CV experiments. The reducing capacity of onions determined by CV method was twice higher than the antioxidant capacity formed by water-soluble compounds (ACW) evaluated by PCL, and it was about 50% higher than PRTC and DPPH RSA results and the converted FCR reducing capacity. In contrast, the reducing capacity of onions determined by the CV method was 3-fold and about four

  17. Total Glucosides of Paeony Promote Intestinal Motility in Slow Transit Constipation Rats through Amelioration of Interstitial Cells of Cajal

    PubMed Central

    Zhu, Feiye; Xu, Shan; Zhang, Yongsheng; Chen, Fangming; Ji, Jinjun; Xie, Guanqun

    2016-01-01

    Objectives Using an atropine-diphenoxylate-induced slow transit constipation (STC) model, this study explored the effects of the total glucosides of paeony (TGP) in the treatment of STC and the possible mechanisms. Study Design A prospective experimental animal study. Methods The constipation model was set up in rats with an oral gavage of atropine-diphenoxylate and then treated with the TGP. The volume and moisture content of the faeces were observed and the intestinal kinetic power was evaluated. Meanwhile, the colorimetric method and enzyme linked immunosorbent assay (ELISA) were employed to determine the changes of nitric oxide (NO), nitric oxide synthase (NOS), vasoative intestinal peptide (VIP) and the P substance (SP) in the serum, respectively. The protein expressions of c-kit and stem cell factor (SCF) were assessed by immunohistochemical analysis and western blot, respectively, and the mRNA level of c-kit was measured by a reverse transcription polymerase chain reaction (RT-PCR). Results The TGP attenuated STC responses in terms of an increase in the fecal volume and moisture content, an enhancement of intestinal transit rate and the reduction of NO, NOS and VIP in the serum. In addition, the c-kit, a labeling of interstitial cells of Cajal (ICC) increased at both protein and mRNA levels. SCF, which serves as a ligand of c-kit also increased at protein level. Conclusion The analysis of our data indicated that the TGP could obviously attenuate STC through improving the function of ICC and blocking the inhibitory neurotransmitters such as NO, NOS and VIP. PMID:27478893

  18. Deglycosylation is a key step in biotransformation and lifespan effects of quercetin-3-O-glucoside in Caenorhabditis elegans.

    PubMed

    Dueñas, Montserrat; Surco-Laos, Felipe; González-Manzano, Susana; González-Paramás, Ana M; Gómez-Orte, Eva; Cabello, Juan; Santos-Buelga, Celestino

    2013-10-01

    Due to their purported healthful activities, quercetin and other flavonoids are being increasingly proposed as nutraceuticals. Quercetin occurs in food as glycosides; however, most assays on its activity have been performed with the aglycone, despite glycosylation deeply affects compound bioavailability. In this work, the uptake and lifespan effects of quercetin-3-O-glucoside (Q3Glc) and quercetin have been assessed in Caenorhabditis elegans. Q3Glc was taken up by this nematode in a concentration-dependent manner and rapidly deglycosylated to quercetin, which was accumulated in the worm and partially biotransformed to conjugated metabolites. Significant mean lifespan extension up to 23% compared to controls was observed in wild type worms cultivated in the presence of low concentrations of Q3Glc (10 μM and 25 μM), whereas exposure to greater concentrations of Q3Glc (50-200 μM) caused a reduction in mean and maximum lifespan compared with the control. By contrast, treatment of klo-1 and klo-2 mutant worms lacking β-glucosidase activity with 200 μM of Q3Glc led to extended mean lifespan (up to 39%), similar to quercetin aglycone at the same concentration levels. In those mutants, Q3Glc was accumulated without important deglycosylation to quercetin was produced. Taken together, these findings indicated that Q3Glc was taken up by the nematode in greater extent than quercetin, and that deglycosylation and subsequent aglycone accumulation in the worm appeared as key points to explain the observed lifespan effects. The obtained results also suggested that facilitated absorption should be more important for the uptake of quercetin derivatives than passive diffusion.

  19. Charge Transfer Dynamics of Highly Efficient Cyanidin-3-O- Glucoside Sensitizer for Dye-Sensitized Solar Cells

    NASA Astrophysics Data System (ADS)

    Prima, E. C.; Yuliarto, B.; Suyatman; Dipojono, H. K.

    2016-08-01

    This paper reports the novel efficiency achievement of black rice-based natural dye- sensitized solar cells. The higher dye concentration, the longer dye extraction as well as dye immersion onto a TiO2 film, and the co-adsorption addition are key strategies for improved-cell performance compared to the highest previous achievement. The black rice dye containing 1.38 mM cyanidin-3-O-glucoside has been extracted without purification for 3 weeks at dark condition and room temperature. The anatase TiO2 photoanode was dipped into dye solution within 4 days. Its electrode was firmly sealed to be a cell and was filled by I-/I3- electrolyte using vacuum technique. As a result, the overall solar-to-energy conversion efficiency was 1.49% at AM 1.5 illumination (100 mW.cm-2). The voltametric analysis has reported the interfacial electronic band edges of TiO2-Dye-Electrolyte. Furthermore, electrochemical impedance spectroscopy has shown the kinetic of interfacial electron transfer dynamics among TiO2-dye-electrolyte. The cell has the transfer resistance (Rt) of 12.5 ω, the recombination resistance (Rr) of 266.8 ω, effective electron diffusion coefficients (Dn) of 1.4 × 10-3 cm2/s, Dye-TiO2 effective electron transfer (τd) of 26.6 μs, effective diffusion length (Ln)of 33.78 μm, chemical capacitance (Cμ) of 12.43 μF, and electron lifetime (τn) of 3.32 ms.

  20. Cyanidin-3-glucoside isolated from mulberry fruit protects pancreatic β-cells against oxidative stress-induced apoptosis.

    PubMed

    Lee, Jong Seok; Kim, Young Rae; Song, In Gyu; Ha, Suk-Jin; Kim, Young Eon; Baek, Nam-In; Hong, Eock Kee

    2015-02-01

    The extract obtained from berries contains high amounts of anthocyanins, and this extract is used as a phytotherapeutic agent for different types of diseases. In this study, we examined the cytoprotective effects of cyanidin-3-glucoside (C3G) isolated from mulberry fruit against pancreatic β-cell apoptosis caused by hydrogen peroxide (H2O2)-induced oxidative stress. The MIN6 pancreatic β-cells were used to investigate the cytoprotective effects of C3G on the oxidative stress-induced apoptosis of cells. Cell viability was examined by MTT assay and lipid peroxidation was assayed by thiobarbituric acid (TBA) reaction. Immunofluorescence staining, flow cytometry and western blot analysis were also used to determine apoptosis and the expression of proteins associated with apoptosis. Our results revealed that H2O2 increased the rate of apoptosis by stimulating various pro-apoptotic processes, such as the generation of intracellular reactive oxygen species (ROS), lipid peroxidation, DNA fragmentation and caspase-3 activation. However, C3G reduced the H2O2-induced cell death in the MIN6N pancreatic β-cells. In addition, we confirmed that H2O2 activated mitogen-activated protein kinases (MAPKs), such as extracellular signal-regulated kinase (ERK), c-Jun NH2-terminal kinase (JNK) and p38 MAPK. C3G inhibited the phosphorylation of ERK and p38 without inducing the phosphorylation of JNK. Furthermore, C3G regulated the intrinsic apoptotic pathway-associated proteins, such as proteins belonging to the Bcl-2 family, cytochrome c and caspase-3. Taken together, our results suggest that C3G isolated from mulberry fruit has potential for use as a phytotherapeutic agent for the prevention of diabetes by preventing oxidative stress-induced β-cell apoptosis.

  1. A Validated HPLC Method for Simultaneous Determination of Caffeoyl Phenylethanoid Glucosides and Flavone 8-C-glycosides in Haberlea rhodopensis.

    PubMed

    Zheleva-Dimitrova, Dimitrina; Nedialkov, Paraskev; Giresser, Ulrich

    2016-06-01

    A HPLC-UV method for analysis of the main compounds: caffeoyl phenylethanoid glucosides myconoside (1) and paucifloside (2) and flavone 8-C-glycosides: hispidulin 8-C-β-galactopyranoside (3), hispidulin 8-C-(2"-O-syringoyl-β-glucopyranoside) (4), hispidulin 8-C-(6-O-acetyl-β-glucopyranoside) (5) and hispidulin 8-C-(6-O-acetyl-2"-O-syringoyl--glucopyranoside) (6) in Haberlea rhodopensis leaves was developed and validated. Compound 3 was isolated for the first time from the title species. Ultrasound extraction with 80% methanol at room temperature allowed a good recovery of analytes (from 87.2 % for 1 to 109.8 % for 3) and the precision of the entire procedure was between 1.6% and 6.9%. The subsequent HPLC separation and quantification was achieved using a Hypersil ODS C18 column and UV detection at 280 nm. The mobile phase comprised methanol and 0.1 % o-phosphoric acid, and gradient elution mode was applied. The detection limits ranged from 0.042 μg/mL (6) to 0.18 μg/mL (5). The total amount in leaves of the assayed phenolic compounds was 374.2 mg/g. Myconoside was found to be the dominant compound in H. rhodopensis extract (332.2 ± 0.7 mg/g dw) and reached up to 88.8% of the analyzed mixture in leaves, while the total content of flavone C-glycosides was 17.1 mg/g dw. PMID:27534117

  2. The human fecal microbiota metabolizes deoxynivalenol and deoxynivalenol-3-glucoside and may be responsible for urinary deepoxy-deoxynivalenol.

    PubMed

    Gratz, Silvia W; Duncan, Gary; Richardson, Anthony J

    2013-03-01

    Deoxynivalenol (DON) is a potent mycotoxin produced by Fusarium molds and affects intestinal nutrient absorption and barrier function in experimental and farm animals. Free DON and the plant metabolite DON-3-β-d-glucoside (D3G) are frequently found in wheat and maize. D3G is stable in the upper human gut, but some human intestinal bacteria release DON from D3G in vitro. Furthermore, some bacteria derived from animal digestive systems degrade DON to a less toxic metabolite, deepoxy-deoxynivalenol (DOM-1). The metabolism of D3G and DON by the human microbiota has not been fully assessed. We therefore conducted in vitro batch culture experiments assessing the activity of the human fecal microbiota to release DON from D3G. We also studied detoxification of DON to DOM-1 by the microbiota and its potential effect on urinary DON excretion in humans. Fecal slurry from five volunteers was spiked with DON or D3G and incubated anaerobically (from 1 h to 7 days), and mycotoxins were extracted into acetonitrile. Mycotoxins were detected in fecal extracts and urine by liquid chromatography-tandem mass spectrometry (LC-MS/MS). The fecal microbiota released DON from D3G very efficiently, with hydrolysis peaking after 4 to 6 h. The fecal microbiota from one volunteer transformed DON to DOM-1. Urine from the same volunteer also contained DOM-1 (4.7% of DON), whereas DOM-1 was not detectable in urine from other volunteers. Our results confirm that the fecal microbiota releases DON from its glycosylated form, hence increasing the toxic burden in exposed individuals. Furthermore, this is first evidence that the human fecal microbiota of one volunteer detoxifies DON, resulting in the appearance of DOM-1 in urine.

  3. Deoxynivalenol, deoxynivalenol-3-glucoside, and enniatins: the major mycotoxins found in cereal-based products on the Czech market.

    PubMed

    Malachova, Alexandra; Dzuman, Zbynek; Veprikova, Zdenka; Vaclavikova, Marta; Zachariasova, Milena; Hajslova, Jana

    2011-12-28

    Fusarium toxins, Alternaria toxins, and ergot alkaloids represent common groups of mycotoxins that can be found in cereals grown under temperate climatic conditions. Because most of them are chemically and thermally stable, these toxic fungal secondary metabolites might be transferred from grains into the final products. To get information on the commensurate contamination of various cereal-based products collected from the Czech retail market in 2010, the occurrence of "traditional" mycotoxins such as groups of A and B trichothecenes and zearalenone, less routinely determined Alternaria toxins (alternariol, alternariol monomethyl ether and altenuene), ergot alkaloids (ergosine, ergocryptine, ergocristine, and ergocornine) and "emerging" mycotoxins (enniatins A, A1, B, and B1 and beauvericin) were monitored. In a total 116 samples derived from white flour and mixed flour, breakfast cereals, snacks, and flour, only trichothecenes A and B and enniatins were found. Deoxynivalenol was detected in 75% of samples with concentrations ranging from 13 to 594 μg/kg, but its masked form, deoxynivalenol-3-β-d-glucoside, has an even higher incidence of 80% of samples, and concentrations ranging between 5 and 72 μg/kg were detected. Nivalenol was found only in three samples at levels of 30 μg/kg. For enniatins, all of the samples investigated were contaminated with at least one of four target enniatins. Enniatin A was detected in 97% of samples (concentration range of 20-2532 μg/kg) followed by enniatin B with an incidence in 91% of the samples (concentration range of 13-941 μg/kg) and enniatin B1 with an incidence of 80% in the samples tested (concentration range of 8-785 μg/kg). Enniatin A1 was found only in 44% of samples at levels ranging between 8 and 851 μg/kg.

  4. Plant Food Delphinidin-3-Glucoside Significantly Inhibits Platelet Activation and Thrombosis: Novel Protective Roles against Cardiovascular Diseases

    PubMed Central

    Yang, Yan; Shi, Zhenyin; Reheman, Adili; Jin, Joseph W.; Li, Conglei; Wang, Yiming; Andrews, Marc C.; Chen, Pingguo; Zhu, Guangheng; Ling, Wenhua; Ni, Heyu

    2012-01-01

    Delphinidin-3-glucoside (Dp-3-g) is one of the predominant bioactive compounds of anthocyanins in many plant foods. Although several anthocyanin compounds have been reported to be protective against cardiovascular diseases (CVDs), the direct effect of anthocyanins on platelets, the key players in atherothrombosis, has not been studied. The roles of Dp-3-g in platelet function are completely unknown. The present study investigated the effects of Dp-3-g on platelet activation and several thrombosis models in vitro and in vivo. We found that Dp-3-g significantly inhibited human and murine platelet aggregation in both platelet-rich plasma and purified platelets. It also markedly reduced thrombus growth in human and murine blood in perfusion chambers at both low and high shear rates. Using intravital microscopy, we observed that Dp-3-g decreased platelet deposition, destabilized thrombi, and prolonged the time required for vessel occlusion. Dp-3-g also significantly inhibited thrombus growth in a carotid artery thrombosis model. To elucidate the mechanisms, we examined platelet activation markers via flow cytometry and found that Dp-3-g significantly inhibited the expression of P-selectin, CD63, CD40L, which reflect platelet α- and δ-granule release, and cytosol protein secretion, respectively. We further demonstrated that Dp-3-g downregulated the expression of active integrin αIIbβ3 on platelets, and attenuated fibrinogen binding to platelets following agonist treatment, without interfering with the direct interaction between fibrinogen and integrin αIIbβ3. We found that Dp-3-g reduced phosphorylation of adenosine monophosphate-activated protein kinase, which may contribute to the observed inhibitory effects on platelet activation. Thus, Dp-3-g significantly inhibits platelet activation and attenuates thrombus growth at both arterial and venous shear stresses, which likely contributes to its protective roles against thrombosis and CVDs. PMID:22624015

  5. Total glucosides of peony ameliorates Sjögren's syndrome by affecting Th1/Th2 cytokine balance

    PubMed Central

    WU, GUOLIN; WU, NAYUAN; LI, TIANYI; LU, WENWEN; YU, GUOYOU

    2016-01-01

    The present study aimed to investigate the molecular mechanisms underlying the effects of total glucosides of peony (TGP) in the treatment of Sjögren's syndrome (SS). A total of 40 mice with SS were evenly assigned into four groups, including: Control group; TGP group, receiving 1 mg TGP daily; hydroxychloroquine (HCQ) group, receiving 0.25 mg HCQ daily; and a combined group, receiving 1 mg TGP and 0.25 mg HCQ daily. After 8 weeks, quantitative polymerase chain reaction and an enzyme-linked immunosorbent assay were used to detect the levels of interferon-γ (IFN-γ), interleukin-4 (IL-4), Fas and FasL in each group of mice. In addition, immunohistochemical analysis was used to determine the expression levels of IFN-γ and IL-4. IFN-γ, IL-4, Fas and FasL levels were significantly increased in the control group compared with the other three groups (P<0.05). Furthermore, the expression levels of these factors were reduced in the combined group in comparison with the HCQ group (P<0.05). The ratios of IFN-γ to IL-4 were decreased in the TGP and combined groups compared with the control group (P<0.05). The present results indicate that TGP ameliorates SS by affecting the Th1/Th2 cytokine balance and decreasing the expression levels of IFN-γ, IL-4, Fas and FasL. Therefore, TGP may represent a potential novel therapeutic agent for the treatment of SS. PMID:26998049

  6. A semiquinone glucoside derivative provides protection to male reproductive system of the mice against gamma radiation toxicity.

    PubMed

    Patel, Dev Dutt; Bansal, Deen Dayal; Mishra, Saurabh; Arora, Rajesh; Sharma, Rakesh Kumar; Jain, Swatantra Kumar; Kumar, Raj

    2014-05-01

    Present investigation was carried out to evaluate the radioprotective efficacy of a novel Semiquinone glucoside derivative (SQGD), isolated from Bacillus sp. INM-1, in the male reproductive system of BALB/c mice. Animals were administered 50 mg/kg b.wt. (i.p.) SQGD 2 h before whole body γ-irradiation (10 Gy). Radiation-induced cellular toxicity and its modulation by SQGD pretreatment was evaluated in the mice testes by quantitative histological and protein expression analysis. SQGD pretreatment protects irradiated mice from radiation-induced testicular atrophy and germ cells degeneration, which may lead to emptiness of seminiferous tubules. Significant decrease in P53 and P21((Cip/WAF-1)) expression was observed in the irradiated mice pretreated (2 h) by SQGD at 6 h compared with only irradiated mice. However, contrary to P53, expressions of P21 at latter time, that is, 24-72 h was found to be increased significantly in the irradiated mice pretreated by SQGD. Significant increase in the intact PARP-1 protein expression were observed in the testes of the mice pretreated by SQGD 2 h before irradiation at 24-72 h compared with the only irradiated mice, whereas significant increase in PARP-1 cleaved fragment was noticed at 24 h. Similarly, significant increase in NF-kB and BCL-2/BAX expressions ratio was noticed in SQGD-treated mice (± irradiation) compared with irradiated mice, suggested a role of SQGD in the activation of prosurvival signaling in the testicular germinal cells population of the irradiated mice and thus contributed to protection against lethal γ-irradiation.

  7. Purfication and properties of a specific isoflavone 7-O-glucoside-6''-malonate malonyestrase from roots of chickpea (Cicer arietinum L.).

    PubMed

    Hinderer, W; Köster, J; Barz, W

    1986-08-01

    Protein extracts from roots of chickpea (Cicer arietinum L.) plants contained high esterase activity hydrolyzing malonate hemiesters of isoflavone 7-O-glucosides. Using 5,7-dihydroxy-4'-methoxyisoflavone (biochanin A) 7-O-glucoside-6"-malonate as a substrate, a specific malonylesterase was purified about 700-fold to near homogeneity. The purified enzyme possesses an extremely low enzyme activity with synthetic esterase substrates. Various putative nonspecific esterases, as tested with alpha-naphthylacetate, were removed during enzyme purification. The malonylesterase demonstrated a very high molecular mass in gel chromatography and in sedimentation analyses with sucrose gradients (greater than or equal to 2 X 10(6)). Analytical sodium dodecyl sulfate-polyacrylamide gel electrophoresis pointed to a single subunit of 32,000. The catalyzed reaction showed a pH optimum at 7.5 and a temperature optimum between 30 and 35 degrees C. The apparent Km for biochanin A 7-O-glucoside-6"-malonate was (4.2 +/- 1.2) X 10(-4) M. The malonylesterase was insensitive to the esterase inhibitors eserine and neostigmine (10(-3) M) as well as phenylmethylsulfonyl fluoride, paraoxon, and diisopropylfluorophosphate (10(-4) M). On the other hand enzyme activity was totally inhibited by Hg2+ ions (10(-5) M) and p-hydroxymercuribenzoate (10(-4) M), whereas iodoacetamide (10(-6)-10(-4) M) inhibited only partially. Di- and tricarboxylic acids strongly stimulated enzyme activity at 10(-2) M. These properties indicate that the malonylesterase from chickpea roots greatly differs from other known esterases. The possible biological function of the specific malonylesterase is discussed in relation to isoflavone conjugate metabolism in chickpea.

  8. A Novel Sinorhizobium meliloti Operon Encodes an α-Glucosidase and a Periplasmic-Binding-Protein-Dependent Transport System for α-Glucosides

    PubMed Central

    Willis, Laura B.; Walker, Graham C.

    1999-01-01

    The most abundant carbon source transported into legume root nodules is photosynthetically produced sucrose, yet the importance of its metabolism by rhizobia in planta is not yet known. To identify genes involved in sucrose uptake and hydrolysis, we screened a Sinorhizobium meliloti genomic library and discovered a segment of S. meliloti DNA which allows Ralstonia eutropha to grow on the α-glucosides sucrose, maltose, and trehalose. Tn5 mutagenesis localized the required genes to a 6.8-kb region containing five open reading frames which were named agl, for α-glucoside utilization. Four of these (aglE, aglF, aglG, and aglK) appear to encode a periplasmic-binding-protein-dependent sugar transport system, and one (aglA) appears to encode an α-glucosidase with homology to family 13 of glycosyl hydrolases. Cosmid-borne agl genes permit uptake of radiolabeled sucrose into R. eutropha cells. Analysis of the properties of agl mutants suggests that S. meliloti possesses at least one additional α-glucosidase as well as a lower-affinity transport system for α-glucosides. It is possible that the Fix+ phenotype of agl mutants on alfalfa is due to these additional functions. Loci found by DNA sequencing to be adjacent to aglEFGAK include a probable regulatory gene (aglR), zwf and edd, which encode the first two enzymes of the Entner-Doudoroff pathway, pgl, which shows homology to a gene encoding a putative phosphogluconolactonase, and a novel Rhizobium-specific repeat element. PMID:10400573

  9. Biological Activities of 2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-Glucoside in Antiaging and Antiaging-Related Disease Treatments.

    PubMed

    Ling, Shuang; Xu, Jin-Wen

    2016-01-01

    2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG) is active component of the Chinese medicinal plant Polygonum multiflorum Thunb. (THSG). Pharmacological studies have demonstrated that THSG exhibits numerous biological functions in treating atherosclerosis, lipid metabolism, vascular and cardiac remodeling, vascular fibrosis, cardiac-cerebral ischemia, learning and memory disorders, neuroinflammation, Alzheimer and Parkinson diseases, diabetic complications, hair growth problems, and numerous other conditions. This review focuses on the biological effects of THSG in antiaging and antiaging-related disease treatments and discusses its molecular mechanisms. PMID:27413420

  10. Biological Activities of 2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-Glucoside in Antiaging and Antiaging-Related Disease Treatments

    PubMed Central

    2016-01-01

    2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG) is active component of the Chinese medicinal plant Polygonum multiflorum Thunb. (THSG). Pharmacological studies have demonstrated that THSG exhibits numerous biological functions in treating atherosclerosis, lipid metabolism, vascular and cardiac remodeling, vascular fibrosis, cardiac-cerebral ischemia, learning and memory disorders, neuroinflammation, Alzheimer and Parkinson diseases, diabetic complications, hair growth problems, and numerous other conditions. This review focuses on the biological effects of THSG in antiaging and antiaging-related disease treatments and discusses its molecular mechanisms. PMID:27413420

  11. Human lens coloration and aging. Evidence for crystallin modification by the major ultraviolet filter, 3-hydroxy-kynurenine O-beta-D-glucoside.

    PubMed

    Hood, B D; Garner, B; Truscott, R J

    1999-11-12

    The human lens becomes increasingly yellow with age and thereby reduces our perception of blue light. This coloration is associated with lens proteins (crystallins), but its molecular basis was unknown. Here we show that the coloration occurs because of the interaction of crystallins with a UV filter compound, 3-hydroxykynurenine glucoside (3-OHKG). Crystallin modification results from deamination of the 3-OHKG amino acid side chain, yielding an unsaturated ketone that is susceptible to nucleophilic attack by cysteine, histidine, and lysine residues. This novel protein modification contributes to age-related lens coloration and may play a role in human nuclear cataractogenesis. PMID:10551806

  12. Survey of deoxynivalenol and its conjugates deoxynivalenol-3-glucoside and 3-acetyl-deoxynivalenol in 374 beer samples.

    PubMed

    Varga, Elisabeth; Malachova, Alexandra; Schwartz, Heidi; Krska, Rudolf; Berthiller, Franz

    2013-01-01

    Beer is one of the most popular beverages worldwide. Malted cereal grains are among the basic ingredients and hence mycotoxin contamination might occur. Previous studies reported the presence of the Fusarium mycotoxins deoxynivalenol (DON) and 3-acetyl-deoxynivalenol (3ADON), as well as of the masked mycotoxin deoxynivalenol-3-glucoside (D3G) in beer. In the present survey, 374 beer samples from 38 countries with a focus on Austrian (156) and German (64) beers were analysed for the presence of D3G, DON and 3ADON. Beers were assigned to the following six categories: pale (217), wheat (46), dark (47), bock (20), nonalcoholic beers (19) and shandies (25). In total, 348 and 289 beers (93 and 77%, respectively) contained D3G and DON at the levels above the limit of detection, whereas 3ADON was not detected in any of the samples. Average concentrations of all beers were 6.9 µg L(-1) for D3G and 8.4 µg L(-1) in the case of DON. Nonalcoholic beers and shandies showed the lowest contaminations, 1.5 and 3.2 µg L(-1) for D3G and 2.7 and 4.4 µg L(-1) for DON, respectively. In bock beers characterised by a higher gravity, a significant trichothecene load of 14.8 µg L(-1) D3G and 12.4 µg L(-1) DON was found. The highest contamination (81 µg L(-1) D3G, 89 µg L(-1) DON) was detected in a pale beer from Austria, underlining the importance of this study for food safety. The molar D3G to DON ratio ranged between 0.11 and 1.25 and was 0.56 on average. Concluding, the average contamination of beer is not of toxicological concern for moderate beer drinkers. However, in the case of heavy beer drinkers, beer consumption may considerably contribute to the overall intake of DON, which might even lead to exceeding the maximum tolerable limits established for this Fusarium toxin.

  13. Evaluation of ozonation technique for pesticide residue removal and its effect on ascorbic acid, cyanidin-3-glucoside, and polyphenols in apple (Malus domesticus) fruits.

    PubMed

    Swami, Saurabh; Muzammil, Raunaq; Saha, Supradip; Shabeer, Ahammed; Oulkar, Dasharath; Banerjee, Kaushik; Singh, Shashi Bala

    2016-05-01

    Ozonated water dip technique was evaluated for the detoxification of six pesticides, i.e., chlorpyrifos, cypermethrin, azoxystrobin, hexaconazole, methyl parathion, and chlorothalonil from apple fruits. Results revealed that ozonation was better than washing alone. Ozonation for 15 min decreased residues of the test pesticides in the range of from 26.91 to 73.58%, while ozonation for 30 min could remove the pesticide residues by 39.39-95.14 % compared to 19.05-72.80 % by washing. Cypermethrin was the least removed pesticide by washing as well as by ozonation. Chlorothalonil, chlorpyrifos, and azoxystrobin were removed up to 71.45-95.14 % in a 30-min ozonation period. In case of methyl parathion removal, no extra advantage could be obtained by ozonation. The HPLC analysis indicated that ozonation also affected adversely the ascorbic acid and cyanidin-3-glucoside content of apples. However, 11 polyphenols studied showed a mixed trend. Gallic acid, 3,4-dihydroxybenzoic acid, catechin, epicatechin, p-coumaric acid, quercetin-3-O-glucoside, quercetin, and kaempferol were found to decrease while syringic acid, rutin, and resveratrol were found to increase in 30-min ozonation.

  14. Evaluation of ozonation technique for pesticide residue removal and its effect on ascorbic acid, cyanidin-3-glucoside, and polyphenols in apple (Malus domesticus) fruits.

    PubMed

    Swami, Saurabh; Muzammil, Raunaq; Saha, Supradip; Shabeer, Ahammed; Oulkar, Dasharath; Banerjee, Kaushik; Singh, Shashi Bala

    2016-05-01

    Ozonated water dip technique was evaluated for the detoxification of six pesticides, i.e., chlorpyrifos, cypermethrin, azoxystrobin, hexaconazole, methyl parathion, and chlorothalonil from apple fruits. Results revealed that ozonation was better than washing alone. Ozonation for 15 min decreased residues of the test pesticides in the range of from 26.91 to 73.58%, while ozonation for 30 min could remove the pesticide residues by 39.39-95.14 % compared to 19.05-72.80 % by washing. Cypermethrin was the least removed pesticide by washing as well as by ozonation. Chlorothalonil, chlorpyrifos, and azoxystrobin were removed up to 71.45-95.14 % in a 30-min ozonation period. In case of methyl parathion removal, no extra advantage could be obtained by ozonation. The HPLC analysis indicated that ozonation also affected adversely the ascorbic acid and cyanidin-3-glucoside content of apples. However, 11 polyphenols studied showed a mixed trend. Gallic acid, 3,4-dihydroxybenzoic acid, catechin, epicatechin, p-coumaric acid, quercetin-3-O-glucoside, quercetin, and kaempferol were found to decrease while syringic acid, rutin, and resveratrol were found to increase in 30-min ozonation. PMID:27098519

  15. Molecular Cloning and Biochemical Characterization of a Recombinant Sterol 3-O-Glucosyltransferase from Gymnema sylvestre R.Br. Catalyzing Biosynthesis of Steryl Glucosides

    PubMed Central

    Sangwan, Rajender Singh; Asha; Mishra, B. N.; Sangwan, Neelam S.

    2014-01-01

    Gymnema sylvestre R.Br., a pharmacologically important herb vernacularly called Gur-Mar (sugar eliminator), is widely known for its antidiabetic action. This property of the herb has been attributed to the presence of bioactive triterpene glycosides. Although some information regarding pharmacology and phytochemical profiles of the plant are available, no attempts have been made so far to decipher the biosynthetic pathway and key enzymes involved in biosynthesis of steryl glucosides. The present report deals with the identification and catalytic characterization of a glucosyltransferase, catalyzing biosynthesis of steryl glycosides. The full length cDNA (2572 bp) contained an open reading frame of 2106 nucleotides that encoded a 701 amino acid protein, falling into GT-B subfamily of glycosyltransferases. The GsSGT was expressed in Escherichia coli and biochemical characterization of the recombinant enzyme suggested its key role in the biosynthesis of steryl glucosides with catalytic preference for C-3 hydroxyl group of sterols. To our knowledge, this pertains to be the first report on cloning and biochemical characterization of a sterol metabolism gene from G. sylvestre R.Br. catalyzing glucosylation of a variety of sterols of biological origin from diverse organisms such as bacteria, fungi, and plants. PMID:25250339

  16. Biochemical Characterization of a Recombinant UDP-glucosyltransferase from Rice and Enzymatic Production of Deoxynivalenol-3-O-β-D-glucoside.

    PubMed

    Michlmayr, Herbert; Malachová, Alexandra; Varga, Elisabeth; Kleinová, Jana; Lemmens, Marc; Newmister, Sean; Rayment, Ivan; Berthiller, Franz; Adam, Gerhard

    2015-07-21

    Glycosylation is an important plant defense mechanism and conjugates of Fusarium mycotoxins often co-occur with their parent compounds in cereal-based food and feed. In case of deoxynivalenol (DON), deoxynivalenol-3-O-β-D-glucoside (D3G) is the most important masked mycotoxin. The toxicological significance of D3G is not yet fully understood so that it is crucial to obtain this compound in pure and sufficient quantities for toxicological risk assessment and for use as an analytical standard. The aim of this study was the biochemical characterization of a DON-inactivating UDP-glucosyltransferase from rice (OsUGT79) and to investigate its suitability for preparative D3G synthesis. Apparent Michaelis constants (Km) of recombinant OsUGT79 were 0.23 mM DON and 2.2 mM UDP-glucose. Substrate inhibition occurred at DON concentrations above 2 mM (Ki = 24 mM DON), and UDP strongly inhibited the enzyme. Cu2+ and Zn2+ (1 mM) inhibited the enzyme completely. Sucrose synthase AtSUS1 was employed to regenerate UDP-glucose during the glucosylation reaction. With this approach, optimal conversion rates can be obtained at limited concentrations of the costly co-factor UDP-glucose. D3G can now be synthesized in sufficient quantity and purity. Similar strategies may be of interest to produce β-glucosides of other toxins.

  17. Biochemical Characterization of a Recombinant UDP-glucosyltransferase from Rice and Enzymatic Production of Deoxynivalenol-3-O-β-d-glucoside

    PubMed Central

    Michlmayr, Herbert; Malachová, Alexandra; Varga, Elisabeth; Kleinová, Jana; Lemmens, Marc; Newmister, Sean; Rayment, Ivan; Berthiller, Franz; Adam, Gerhard

    2015-01-01

    Glycosylation is an important plant defense mechanism and conjugates of Fusarium mycotoxins often co-occur with their parent compounds in cereal-based food and feed. In case of deoxynivalenol (DON), deoxynivalenol-3-O-β-d-glucoside (D3G) is the most important masked mycotoxin. The toxicological significance of D3G is not yet fully understood so that it is crucial to obtain this compound in pure and sufficient quantities for toxicological risk assessment and for use as an analytical standard. The aim of this study was the biochemical characterization of a DON-inactivating UDP-glucosyltransferase from rice (OsUGT79) and to investigate its suitability for preparative D3G synthesis. Apparent Michaelis constants (Km) of recombinant OsUGT79 were 0.23 mM DON and 2.2 mM UDP-glucose. Substrate inhibition occurred at DON concentrations above 2 mM (Ki = 24 mM DON), and UDP strongly inhibited the enzyme. Cu2+ and Zn2+ (1 mM) inhibited the enzyme completely. Sucrose synthase AtSUS1 was employed to regenerate UDP-glucose during the glucosylation reaction. With this approach, optimal conversion rates can be obtained at limited concentrations of the costly co-factor UDP-glucose. D3G can now be synthesized in sufficient quantity and purity. Similar strategies may be of interest to produce β-glucosides of other toxins. PMID:26197338

  18. C-Aryl Glucosides with Substituents at the Distal Aryl Ring as Sodium-Dependent Glucose Cotransporter Inhibitors for the Treatment of Diabetes Mellitus.

    PubMed

    Wang, Xuekun; Li, Ying; Yang, Baowei; Li, Zheng; Huang, Wenlong; Qian, Hai

    2015-08-01

    A series of novel C-aryl glucosides with various substituents at the distal aryl ring have been synthesized and evaluated for hypoglycemic effect in normal and diabetic mice and in type 2 diabetic rats. The results indicated that introduction of electron-donating group at the distal aryl ring could improve glucose tolerance in normal mice, whereas introduction of electron-withdrawing group at this position could deteriorate. The urinary glucose excretion was significantly increased after glucose (3 g/kg) administration in normal mice with the treatment of 13c. Moreover, compound 13c could reduce fed blood glucose levels in a dose-dependent manner in type 2 diabetic rats, showed a remarkable antihyperglycemic effect with 2 weeks of treatment in diabetic mice, and might be a promising drug candidate for the treatment of diabetes mellitus.

  19. Fluorescence Up-Conversion Studies of [2,2'-Bipyridyl]-3,3'-diol in Octyl-β-d-glucoside and Other Micellar Aggregates.

    PubMed

    Satpathi, Sagar; Gavvala, Krishna; Hazra, Partha

    2015-12-24

    In this present work, excited state double proton transfer dynamics (ESIDPT) of 2,2'-bipyridyl-3,3'-diol (BP(OH)2) molecules has been probed in a nontoxic, biocompatible sugar surfactant assembly, namely, octyl-β-d-glucoside (OBG) micelle with the help of steady state and fluorescence up-conversion techniques. Moreover, the ultrafast double proton transfer dynamics in conventional micelles (SDS, CTAB) and bile salts aggregates have been probed and compared. Interestingly, in all these supramolecular aggregates, the ESIDPT dynamics is found to follow sequential pathway; however, the time-scale of proton transfer dynamics varies from 11 to 30 ps. This difference in proton transfer time scale in different supramolecular aggregates has been explained in terms of accessibility of water molecules in the vicinity of probe.

  20. The color expression of copigmentation between malvidin-3-O-glucoside and three phenolic aldehydes in model solutions: The effects of pH and molar ratio.

    PubMed

    Zhang, Bo; He, Fei; Zhou, Pan-Pan; Liu, Yue; Duan, Chang-Qing

    2016-05-15

    Copigmentation was investigated in model solutions between the anthocyanin malvidin-3-O-glucoside and three phenolic aldehydes (vanillic, syringic and coniferyl aldehydes) as a function of the pH and the pigment/copigment molar ratio. Tristimulus colorimetry was applied to evaluate the chromatic variations induced by copigmentation process. The results indicated that the greatest magnitude of copigmentation was obtained at pH 3.0 and molar ratio of 1:100, being significantly higher with coniferyl aldehyde, followed by syringic and vanillic aldehydes. The equilibrium constant (K) and Gibbs free energies (ΔG°) determined here show a spontaneous exothermic reaction. Theoretical calculations (ΔGbinding, ΔE) specified the relative arrangement of the pigment and copigment molecules within the complexes. In addition, an atoms in molecules (AIM) analysis was used to explore the main driving forces contributing to the formation of copigmentation complexes. PMID:26775964

  1. Higenamine 4'-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor.

    PubMed

    Kato, Eisuke; Inagaki, Yosuke; Kawabata, Jun

    2015-07-01

    Hypoglycemic effect is an efficient means to modulate elevated blood glucose levels in patients with diabetes. We found that the extract of lotus plumule (the germ of Nelumbo nucifera Gaertn. seed) showed potent glucose uptake enhancement activity against L6 myotubes, which results in a hypoglycemic effect. This activity was further investigated, and an active constituent was identified as a single bioactive compound, higenamine 4'-O-β-d-glucoside. Mechanistic studies employing phosphatidylinositol 3-kinase (PI3K) inhibitor, AMP-activated protein kinase (AMPK) inhibitor, or adrenergic receptor antagonist showed that the compound induced its activity through β2-adrenergic receptor. Patients with type II diabetes mellitus frequently develop insulin resistance. Owing to the differences between the mechanism of action of insulin and of the isolated compound, the compound or lotus plumule itself may have the possibility of modulating blood glucose levels in insulin-resistant patients effectively. PMID:25943853

  2. Higenamine 4'-O-β-d-glucoside in the lotus plumule induces glucose uptake of L6 cells through β2-adrenergic receptor.

    PubMed

    Kato, Eisuke; Inagaki, Yosuke; Kawabata, Jun

    2015-07-01

    Hypoglycemic effect is an efficient means to modulate elevated blood glucose levels in patients with diabetes. We found that the extract of lotus plumule (the germ of Nelumbo nucifera Gaertn. seed) showed potent glucose uptake enhancement activity against L6 myotubes, which results in a hypoglycemic effect. This activity was further investigated, and an active constituent was identified as a single bioactive compound, higenamine 4'-O-β-d-glucoside. Mechanistic studies employing phosphatidylinositol 3-kinase (PI3K) inhibitor, AMP-activated protein kinase (AMPK) inhibitor, or adrenergic receptor antagonist showed that the compound induced its activity through β2-adrenergic receptor. Patients with type II diabetes mellitus frequently develop insulin resistance. Owing to the differences between the mechanism of action of insulin and of the isolated compound, the compound or lotus plumule itself may have the possibility of modulating blood glucose levels in insulin-resistant patients effectively.

  3. Phenylalanine ammonia lyase functions as a switch directly controlling the accumulation of calycosin and calycosin-7-O-beta-D-glucoside in Astragalus membranaceus var. mongholicus plants.

    PubMed

    Pan, Haiyun; Wang, Yuguo; Zhang, Yongfeng; Zhou, Tongshui; Fang, Changming; Nan, Peng; Wang, Xiaoqiang; Li, Xiaobing; Wei, Yinlong; Chen, Jiakuan

    2008-01-01

    Previously it had been shown that calycosin and calycosin-7-O-beta-D-glucoside (CGs) accumulate in whole plants, mainly in leaves, of Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao (A. mongholicus) plants in response to low temperature. In this work, it was demonstrated that the influences of different conditions on CGs biosynthesis, by examining the changes in CGs content, as well as the expression of related genes, including phenylalanine ammonia lyase (PAL1), cinnamic acid 4-hydroxylase (C4H), chalcone synthase (CHS), chalcone reductase (CHR), chalcone isomerase (CHI), isoflavone synthase (IFS), and isoflavone 3'-hydroxylase (I3'H). The seven gene mRNAs accumulated in leaves of A. mongholicus upon exposure to low temperature in a light-dependent manner, though they exhibited different expression patterns. Transcriptions of CHS, CHR, CHI, IFS, and I3'H of the calycosin-7-O-beta-D-glucoside pathway were all up-regulated when plants were transferred from 16 degrees C to 2 degrees C or 25 degrees C or from 2 degrees C (kept for 24 h) to 25 degrees C. However, fluctuations in temperature influenced differently the transcriptions of PAL1 and C4H of the general phenylpropanoid pathway in leaves. Moreover, the amount of PAL1 expression changed sharply up and down, consistent with the variation of the content of CGs. PAL enzyme activity appears to be the limiting factor in determining the CGs levels. The inhibitor of PAL enzyme, L-alpha-aminooxy-beta-phenylpropionic acid, almost entirely shut down CGs accumulation at low temperature. All these results confirmed that PAL1, as a smart gene switch, directly controls the accumulation of CGs in A. mongholicus plants, in a light-dependent manner, during low temperature treatment.

  4. Analgesic and antiinflammatory effects of mollic acid glucoside, a 1 alpha-hydroxycycloartenoid saponin extractive from Combretum molle R. Br. ex G. Don (Combretaceae) leaf.

    PubMed

    Ojewole, John A O

    2008-01-01

    The analgesic and antiinflammatory properties of mollic acid glucoside (MAG), a 1 alpha-hydroxycycloartenoid extract from Combretum molle leaf, have been investigated in mice and rats. The effects of graded doses of mollic acid glucoside (MAG, 5-80 mg/kg i.p.) were examined against thermally- and chemically-induced nociceptive pain in mice. Furthermore, the effects of graded doses of the plant extract (MAG, 5-80 mg/kg p.o.) were also investigated on rat paw oedema induced by subplantar injections of fresh egg albumin (0.5 mg/kg). Morphine (MPN, 10 mg/kg i.p.) and diclofenac (DIC, 100 mg/kg i.p.) were used as reference analgesic and antiinflammatory agents for comparison, respectively. Like DIC (100 mg/kg i.p.) and MPN (10 mg/kg i.p.), MAG (5-80 mg/kg i.p.) produced dose-dependent, significant (p < 0.05-0.001) analgesic effects against thermally and chemically induced nociceptive pain in mice. The extractive (MAG, 5-80 mg/kg i.p.) also significantly reduced (p < 0.05-0.001) rat paw oedema induced by subplantar injections of fresh egg albumin in a dose-related fashion. However, the extract (MAG, 5-80 mg/kg i.p.) was found to be less potent than diclofenac (DIC) as an analgesic or antiinflammatory agent. Experimental evidence obtained from this laboratory animal study indicates that the Combretum molle leaf extractive (MAG) possesses analgesic and antiinflammatory properties, and thus lend pharmacological credence to the folkloric, ethnomedical uses of the plant's leaf in the management, control and/or treatment of painful, arthritic and other inflammatory conditions in some rural communities of southern Africa.

  5. Simultaneous determination of major type B trichothecenes and deoxynivalenol-3-glucoside in animal feed and raw materials using improved DSPE combined with LC-MS/MS.

    PubMed

    Zhao, Zhiyong; Rao, Qinxiong; Song, Suquan; Liu, Na; Han, Zheng; Hou, Jiafa; Wu, Aibo

    2014-07-15

    A simple and reliable method for simultaneous determination of deoxynivalenol-3-glucoside and major type B trichothecenes (deoxynivalenol, nivalenol, fusarenon X, 3-acetyldeoxynivalenol, 15-acetyldeoxynivalenol and deepoxy-deoxynivalenol) in animal feed and raw materials has been developed and validated in this study. The method was based on an improved dispersive solid-phase extraction (DSPE) followed by analysis using high performance liquid chromatography coupled to tandem mass spectrometry (HPLC-MS/MS). Also, matrix-matched calibration curve (R(2)>0.99) was employed to minimize matrix effects and ensure accurate quantification. The recoveries during sample preparation process (including extraction and clean-up) ranged from 79.03% to 118.39%, with intra-day and inter-day relative standard deviation lower than 20% for all the analytes. The limit of quantification ranged from 5.0 μg/kg for deoxynivalenol to 13.6 μg/kg for fusarenon X. The validated method was successfully applied to the analysis of animal feed and corn. The pilot study showed that 37 out of 41 samples were contaminated with deoxynivalenol-3-glucoside at the levels of 6.0-121.0 μg/kg. Most of the type B trichothecenes were also found with the exception of fusarenon X, at the contaminated levels of 10.0-1,382 μg/kg. To the best of our knowledge, this was the first scientific report on the co-occurrence of masked deoxynivalenol and type B trichothecenes in animal feed and raw materials.

  6. Natural Variation in Maize Aphid Resistance Is Associated with 2,4-Dihydroxy-7-Methoxy-1,4-Benzoxazin-3-One Glucoside Methyltransferase Activity[C][W

    PubMed Central

    Meihls, Lisa N.; Handrick, Vinzenz; Glauser, Gaetan; Barbier, Hugues; Kaur, Harleen; Haribal, Meena M.; Lipka, Alexander E.; Gershenzon, Jonathan; Buckler, Edward S.; Erb, Matthias; Köllner, Tobias G.; Jander, Georg

    2013-01-01

    Plants differ greatly in their susceptibility to insect herbivory, suggesting both local adaptation and resistance tradeoffs. We used maize (Zea mays) recombinant inbred lines to map a quantitative trait locus (QTL) for the maize leaf aphid (Rhopalosiphum maidis) susceptibility to maize Chromosome 1. Phytochemical analysis revealed that the same locus was also associated with high levels of 2-hydroxy-4,7-dimethoxy-1,4-benzoxazin-3-one glucoside (HDMBOA-Glc) and low levels of 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one glucoside (DIMBOA-Glc). In vitro enzyme assays with candidate genes from the region of the QTL identified three O-methyltransferases (Bx10a-c) that convert DIMBOA-Glc to HDMBOA-Glc. Variation in HDMBOA-Glc production was attributed to a natural CACTA family transposon insertion that inactivates Bx10c in maize lines with low HDMBOA-Glc accumulation. When tested with a population of 26 diverse maize inbred lines, R. maidis produced more progeny on those with high HDMBOA-Glc and low DIMBOA-Glc. Although HDMBOA-Glc was more toxic to R. maidis than DIMBOA-Glc in vitro, BX10c activity and the resulting decline of DIMBOA-Glc upon methylation to HDMBOA-Glc were associated with reduced callose deposition as an aphid defense response in vivo. Thus, a natural transposon insertion appears to mediate an ecologically relevant trade-off between the direct toxicity and defense-inducing properties of maize benzoxazinoids. PMID:23898034

  7. Quercetin 7-O-glucoside suppresses nitrite-induced formation of dinitrosocatechins and their quinones in catechin/nitrite systems under stomach simulating conditions.

    PubMed

    Morina, Filis; Takahama, Umeo; Yamauchi, Ryo; Hirota, Sachiko; Veljovic-Jovanovic, Sonja

    2015-01-01

    Foods of plant origin contain flavonoids. In the adzuki bean, (+)-catechin, quercetin 3-O-rutinoside (rutin), and quercetin 7-O-β-D-glucopyranoside (Q7G) are the major flavonoids. During mastication of foods prepared from the adzuki bean, the flavonoids are mixed with saliva and swallowed into the stomach. Here we investigated the interactions between Q7G and (+)-catechin at pH 2, which may proceed in the stomach after the ingestion of foods prepared from the adzuki bean. Q7G reacted with nitrous acid producing nitric oxide (˙NO) and a glucoside of 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone. (+)-Catechin reacted with nitrous acid producing ˙NO and 6,8-dinitrosocatechin. The production of the dinitrosocatechin was partly suppressed by Q7G, and the suppression resulted in the enhancement of Q7G oxidation. 6,8-Dinitrosocatechin reacted further with nitrous acid generating the o-quinone, and the quinone formation was effectively suppressed by Q7G. In the flavonoids investigated, the suppressive effect decreased in the order Q7G≈quercetin>kaempferol>quercetin 4'-O-glucoside>rutin. Essentially the same results were obtained when (-)-epicatechin was used instead of (+)-catechin. The results indicate that nitrous acid-induced formation of 6,8-dinitrosocatechins and the o-quinones can be suppressed by flavonols in the stomach, and that both a hydroxyl group at C3 and ortho-hydroxyl groups in the B-ring are required for efficient suppression.

  8. Expression pattern of NMDA receptors reveals antiepileptic potential of apigenin 8-C-glucoside and chlorogenic acid in pilocarpine induced epileptic mice.

    PubMed

    Aseervatham, G Smilin Bell; Suryakala, U; Doulethunisha; Sundaram, S; Bose, P Chandra; Sivasudha, T

    2016-08-01

    The present study was aimed to evaluate the effect of apigenin 8-C-glucoside (Vitexin) and chlorogenic acid on epileptic mice induced by pilocarpine and explored its possible mechanisms. Intraperitonial administration of pilocarpine (85mg/kg) induced seizure in mice was assessed by behavior observations, which is significantly (p>0.05) reduced by apigenin 8-C-glucoside (AP8CG) (10mg/kg) and chlorogenic acid (CA) (5mg/kg), similar to diazepam. Seizure was accompanied by an imbalance in the levels of Gamma-aminobutyric acid (GABA) and glutamate in the pilocarpine administered group. Moreover, convulsion along with reduced acetylcholinesterase, increased monoamine oxidase and oxidative stress was observed in epileptic mice brain. AP8CG and CA significantly restored back to normal levels even at lower doses. Further, increased lipid peroxidation and nitrite content was also significantly attenuated by AP8CG and CA. However, CA was found to be more effective when compared to AP8CG. In addition, the mRNA expression of N-methyl-d-aspartate receptor (NMDAR), mGluR1 and mGlu5 was significantly (P≤0.05) inhibited by AP8CG and CA in a lower dose. The mRNA expression of GRIK1 did not differ significantly in any of the group and showed a similar pattern of expression. Our result shows that AP8CG and CA selectively inhibit NMDAR, mGluR1 and mGlu5 expression. Modification in the provoked NMDAR calcium response coupled with neuronal death. Hence, these findings underline that the polyphenolics, AP8CG and CA have exerted antiepileptic and neuroprotective activity by suppressing glutamate receptors. PMID:27470339

  9. Assessment of the Therapeutic Effect of Total Glucosides of Peony for Juvenile Idiopathic Arthritis: A Systematic Review and Meta-Analysis

    PubMed Central

    Cai, Yongsong; Yuan, Qiling; Xu, Ke; Zhu, Jialin; Li, Yuanbo; Wu, Xiaoqing; Yang, Le

    2016-01-01

    Juvenile idiopathic arthritis (JIA) is the most common rheumatic disease in children; some clinical trials have reported the effects of total glucosides of peony (TGP) in the treatment of JIA. However, no systematic review has yet been conducted. In this study, we assessed the efficacy and safety in patients with JIA enrolled in randomized controlled trials (RCTs) of TGP. We extracted data for studies searched from 8 electronic databases that were searched and also evaluated the methodological quality of the included studies. We assessed the following outcome measures: overall response rate, pain, tender joint count (TJC), swollen joint count (SJC), duration of morning stiffness (DMS), grip strength (GS), rheumatoid factor (RF), erythrocyte sedimentation rate (ESR), C-reactive protein (CRP), and adverse effects (AEs) in short term (4–8 weeks), intermediate term (9–26 weeks), and long term (>26 weeks). The final analysis showed that TGP acted as a unique nonbiologic disease-modifying antirheumatic drug (nonbiologic DMARD), and its therapeutic effects were safe and efficacious for the treatment of JIA with few AEs. However, more high-quality RCTs are needed to confirm these therapeutic effects. PMID:27525026

  10. Antiproliferative activity of long chain acylated esters of quercetin-3-O-glucoside in hepatocellular carcinoma HepG2 cells

    PubMed Central

    Sudan, Sudhanshu

    2015-01-01

    Despite their strong role in human health, poor bioavailability of flavonoids limits their biological effects in vivo. Enzymatically catalyzed acylation of fatty acids to flavonoids is one of the approaches of increasing cellular permeability and hence, biological activities. In this study, six long chain fatty acid esters of quercetin-3-O-glucoside (Q3G) acylated enzymatically and were used for determining their antiproliferative action in hepatocellular carcinoma cells (HepG2) in comparison to precursor compounds and two chemotherapy drugs (Sorafenib and Cisplatin). Fatty acid esters of Q3G showed significant inhibition of HepG2 cell proliferation by 85 to 90% after 6 h and 24 h of treatment, respectively. The cell death due to these novel compounds was associated with cell-cycle arrest in S-phase and apoptosis observed by DNA fragmentation, fluorescent microscopy and elevated caspase-3 activity and strong DNA topoisomerase II inhibition. Interestingly, Q3G esters showed significantly low toxicity to normal liver cells than Sorafenib (P < 0.05), a chemotherapy drug for hepatocellular carcinoma. Among all, oleic acid ester of Q3G displayed the greatest antiproliferation action and a high potential as an anti-cancer therapeutic. Overall, the results of the study suggest strong antiproliferative action of these novel food-derived compounds in treatment of cancer. PMID:25681471

  11. Palmitate-induced endothelial dysfunction is attenuated by cyanidin-3-O-glucoside through modulation of Nrf2/Bach1 and NF-κB pathways.

    PubMed

    Fratantonio, D; Speciale, A; Ferrari, D; Cristani, M; Saija, A; Cimino, F

    2015-12-15

    Free fatty acids (FFA), commonly elevated in diabetes and obesity, have been shown to impair endothelial functions and cause oxidative stress, inflammation, and insulin resistance. Anthocyanins represent one of the most important and interesting classes of flavonoids and seem to play a role in preventing cardiovascular diseases. Herein, we investigated the in vitro protective effects of cyanidin-3-O-glucoside (C3G) on cell signaling pathways in human umbilical vein endothelial cells (HUVECs) exposed to palmitic acid (PA), the most prevalent saturated FFA in circulation. Our data reported a significant augmentation of free radicals and oxidative stress in HUVECs exposed to PA for 3h, while C3G pretreatment improved intracellular redox status altered by FFA. Moreover, C3G significantly inhibited NF-κB proinflammatory pathway and adhesion molecules induced by PA, and these effects were attributed to the activation of Nrf2/EpRE pathway. In fact, C3G induced Nrf2 nuclear localization and activation of cellular antioxidant and cytoprotective genes at baseline and after PA exposure in endothelial cells. Our data confirm the hypothesis that natural Nrf2 inducers, such as C3G, might be a potential therapeutic strategy to protect vascular system against various stressors preventing several pathological conditions. PMID:26422990

  12. Bioconversion of Cyanidin-3-Rutinoside to Cyanidin-3-Glucoside in Black Raspberry by Crude α-L-Rhamnosidase from Aspergillus Species.

    PubMed

    Lim, Taehwan; Jung, Hana; Hwang, Keum Taek

    2015-11-01

    Cyanidin-3-glucoside (C3G) has been known to be more bioavailable than cyanidin-3- rutinoside (C3R), the most abundant anthocyanin in black raspberry (Rubus occidentalis). The aim of this study was to enhance the bioavailability of anthocyanins in black raspberry by cleaving L-rhamnose in C3R using crude enzyme extracts (CEEs) from Aspergillus usamii KCTC 6956, A. awamori KCTC 60380, A. niger KCCM 11724, A. oryzae KCCM 12698, and A. kawachii KCCM 32819. The enzyme activities of the CEEs were determined by a spectrophotometric method using rho-nitrophenyl-rhamnopyranoside and rho-nitrophenyl-glucopyranoside. The CEE from A. usamii had the highest α-L-rhamnosidase activity with 2.73 U/ml at 60°C, followed by those from A. awamori and A. niger. When bioconversion of C3R to C3G in black raspberry was analyzed by HPLC-DAD, the CEEs from A. usamii and A. awamori hydrolyzed 95.7% and 95.6% of C3R to C3G, respectively, after 2 h incubation. The CEEs from A. kawachii and A. oryzae did not convert C3R to C3G in black raspberry.

  13. Involvement of the GABAergic system in the neuroprotective and sedative effects of acacetin 7-O-glucoside in rodents

    PubMed Central

    Gálvez, Javier; Estrada-Reyes, Rosa; Benítez-King, Gloria; Araujo, Gabriela; Orozco, Sandra; Fernández-Mas, Rodrigo; Almazán, Salvador; Calixto, Eduardo

    2015-01-01

    Abstract Purpose: Characterization of sedative, possible anticonvulsant, and protective effects of Acacetin-7-O-glucoside (7-ACAG). Methods: 7-ACAG was separated and its purity was analyzed. Its sedative and anti-seizure effects (1, 10, 20, and 40 mg/kg) were evaluated in male mice. Synaptic responses were acquired from area CA1 of hippocampal slices obtained from male Wistar rats. Rats were subjected to stereotaxic surgeries to allow Electroencephalographic (EEG) recordings. Functional recovery was evaluated by measuring the time rats spent in completing the motor task. Then the rats were subjected to right hemiplegia and administered 7-ACAG (40 mg/kg) 1 h or 24 h after surgery. Brains of each group of rats were prepared for histological analysis. Results: Effective sedative doses of 7-ACAG comprised those between 20 and 40 mg/kg. Latency and duration of the epileptiform crisis were delayed by this flavonoid. 7-ACAG decreased the synaptic response in vitro, similar to Gamma-aminobutyric acid (GABA) effects. The flavonoid facilitated functional recovery. This data was associated with preserved cytoarchitecture in brain cortex and hippocampus. Conclusions: 7-ACAG possesses anticonvulsive and sedative effects. Results suggest that GABAergic activity and neuroprotection are involved in the mechanism of action of 7-ACAG and support this compound’s being a potential drug for treatment of anxiety or post-operative conditions caused by neurosurgeries. PMID:26410208

  14. Analogs of Natural 3-Deoxyanthocyanins: O-Glucosides of the 4′,7-Dihydroxyflavylium Ion and the Deep Influence of Glycosidation on Color

    PubMed Central

    Basílio, Nuno; Al Bittar, Sheiraz; Mora, Nathalie; Dangles, Olivier; Pina, Fernando

    2016-01-01

    3-Deoxyanthocyanidins and their O-β-d-glucosides are natural pigments abundant in black sorghum. O-glycosidation can perturb the acid-base properties of the chromophore and lower its electron density with a large impact on the distribution of colored and colorless forms in aqueous solution. In this work, the influence of O-glycosidation on color is systematically studied from a series of 3-deoxyanthocyanin analogs. The pH- and light-dependent reversible reactions of 7-β-d-glucopyranosyloxy-4′-hydroxyflavylium (P3) and 4′-β-d-glucopyranosyloxy-7-hydroxyflavylium (P5) were completely characterized in mildly acidic solution and compared with the parent aglycone 4′,7-dihydroxyflavylium ion and the O-methylethers of P3 and P5. Except P5, the chalcone forms of the pigments exhibit a high cis-trans isomerization barrier that allows a pseudo-equilibrium involving all species except the trans-chalcone. At equilibrium, only the flavylium cation and trans-chalcone are observed. With all pigments, the colored flavylium ion can be generated by irradiation of the trans-chalcone (photochromism). Glycosidation of C7–OH accelerates hydration and strongly slows down cis-trans isomerization with the pH dependence of the apparent isomerization rate constant shifting from a bell-shaped curve to a sigmoid. The color of P5 is much more stable than that of its regioisomer P3 in near-neutral conditions. PMID:27775619

  15. The Efficacy and Safety of the Combination of Total Glucosides of Peony and Leflunomide for the Treatment of Rheumatoid Arthritis: A Systemic Review and Meta-Analysis

    PubMed Central

    Feng, Zhitao; Xu, Juan; He, Guochao; Cao, Meiqun; Duan, Lihong; Chen, Liguo; Wu, Zhengzhi

    2016-01-01

    Objective. To evaluate the efficacy and safety of the total glucosides of peony (TGP) and leflunomide (LEF) for the treatment of rheumatoid arthritis (RA). Methods. Randomized controlled trials (RCTs) on the efficacy and safety of the combination of TGP and LEF versus LEF alone for the treatment of RA were retrieved by searching PubMed, EMBASE, Cochrane Library, the China National Knowledge Infrastructure database, and Wanfang database. Results. Eight RCTs including 643 RA patients were included in the present meta-analysis. The quality of included studies was poor. The levels of ESR (P < 0.0001), CRP (P < 0.0001), and RF (P < 0.0001) in RA patients who received the combination of TGP and LEF were significantly lower than RA patients who received LEF therapy alone. The pooled results suggest that the combination of TGP and LEF caused less abnormal liver function than LEF alone (P = 0.02). No significant difference in the gastrointestinal discomfort was identified between the combination of TGP and LEF and LEF alone groups (P = 0.18). Conclusion. The combination of TGP and LEF in treatment of RA presented the characteristics of notably decreasing the levels of laboratory indexes and higher safety in terms of liver function. However, this conclusion should be further investigated based on a larger sample size. PMID:27143990

  16. 2,3,5,4′-Tetrahydroxystilbene-2-O-β-glucoside Isolated from Polygoni Multiflori Ameliorates the Development of Periodontitis

    PubMed Central

    Chin, Yu-Tang; Hsieh, Meng-Ti; Lin, Chi-Yu; Kuo, Po-Jan; Yang, Yu-Chen S. H.; Shih, Ya-Jung; Lai, Hsuan-Yu; Cheng, Guei-Yun; Tang, Heng-Yuan; Lee, Chen-Chen; Lee, Sheng-Yang; Wang, Ching-Chiung; Whang-Peng, Jacqueline; Liu, Leroy F.

    2016-01-01

    Periodontitis, a chronic infection by periodontopathic bacteria, induces uncontrolled inflammation, which leads to periodontal tissue destruction. 2,3,5,4′-Tetrahydroxystilbene-2-O-beta-glucoside (THSG), a polyphenol extracted from Polygoni Multiflori, reportedly has anti-inflammatory properties. In this study, we investigated the mechanisms of THSG on the Porphyromonas gingivalis-induced inflammatory responses in human gingival fibroblasts and animal modeling of ligature-induced periodontitis. Human gingival fibroblast cells were treated with lipopolysaccharide (LPS) extracted from P. gingivalis in the presence of resveratrol or THSG to analyze the expression of TNF-α, IL-1β, and IL-6 genes. Increased AMP-activated protein kinase (AMPK) activation and SirT1 expression were induced by THSG. Treatment of THSG decreased the expression of LPS-induced inflammatory cytokines, enhanced AMPK activation, and increased the expression of SirT1. In addition, it suppressed the activation of NF-κB when cells were stimulated with P. gingivalis LPS. The anti-inflammatory effect of THSG and P. Multiflori crude extracts was reproduced in ligature-induced periodontitis animal modeling. In conclusion, THSG inhibited the inflammatory responses of P. gingivalis-stimulated human gingival fibroblasts and ameliorated ligature-induced periodontitis in animal model. PMID:27504055

  17. High Expression of β-Glucosidase in Bifidobacterium bifidum BGN4 and Application in Conversion of Isoflavone Glucosides During Fermentation of Soy Milk.

    PubMed

    You, Hyun Ju; Ahn, Hyung Jin; Kim, Jin Yong; Wu, Qian Qian; Ji, Geun Eog

    2015-04-01

    In spite of the reported probiotic effects, Bifidobacterium bifidum BGN4 (BGN4) showed no β- glucosidase activity and failed to biotransform isoflavone glucosides into the more bioactive aglycones during soy milk fermentation. To develop an isoflavone-biotransforming BGN4, we constructed the recombinant B. bifidum BGN4 strain (B919G) by cloning the structural β- glucosidase gene from B. lactis AD011 (AD011) using the expression vector with the constitutively active promoter 919 from BGN4. As a result, B919G highly expressed β- glucosidase and showed higher β-glucosidase activity and heat stability than the source strain of the β-glucosidase gene, AD011. The biotransformation of daidzin and genistin compounds using the crude enzyme extract from B919G was completed within 4 h, and the bioconversion of daidzin and genistin in soy milk during fermentation with B919G also occurred within 6 h, which was much faster and higher than with AD011. The incorporation of this β-glucosidaseproducing Bifidobacterium strain in soy milk could lead to the production of fermented soy milk with an elevated amount of bioavailable forms of isoflavones as well as to the indigenous probiotic effects of the Bifidobacterium strain.

  18. Development and validation of an HPTLC method for apigenin 7-O-glucoside in chamomile flowers and its application for fingerprint discrimination of chamomile-like materials.

    PubMed

    Guzelmeric, Etil; Vovk, Irena; Yesilada, Erdem

    2015-03-25

    Brewed tea of chamomile flowers (Matricaria recutita L.) (Asteraceae) has been extensively consumed for centuries due to either its pleasant taste or medicinal purposes. On the other hand, the major problem is difficulty in distinguishing the genuine specimen when supplying chamomile through nature-picking. Consequently flowers of other Asteraceae members resembling to chamomile in appearance may frequently be practiced by lay people or marketed in spice shops or bazaars. Evidently detection of such adulterations plays a vital role in terms of public health to avoid risk of toxicity (i.e. pyrazolidin alkaloids) and ineffective treatments (lack or insufficient concentration of the active constituents). This work presents either development and validation of a high performance thin-layer chromatographic (HPTLC) method for apigenin 7-O-glucoside which is one of the active markers in chamomile flowers or its application for the fingerprint discrimination of chamomile-like materials i.e. Anthemis spp., Bellis spp., Chrysanthemum sp. and Tanacetum sp. gathered by local people assuming as chamomile. Separation was performed on the silica gel 60 NH2 F254s HPTLC plates using the developing solvent system of ethyl acetate-formic acid-acetic acid-water (30:1.5:1.5:3, v/v/v/v). The proposed HPTLC method may also be a leading guide for the quality assessment of chamomile tea products on the market.

  19. Validation of a RP-HPLC-DAD Method for Chamomile (Matricaria recutita) Preparations and Assessment of the Marker, Apigenin-7-glucoside, Safety and Anti-Inflammatory Effect.

    PubMed

    Miguel, Felipe Galeti; Cavalheiro, Amanda Henriques; Spinola, Nathália Favaretto; Ribeiro, Diego Luis; Barcelos, Gustavo Rafael Mazzaron; Antunes, Lusânia Maria Greggi; Hori, Juliana Issa; Marquele-Oliveira, Franciane; Rocha, Bruno Alves; Berretta, Andresa Aparecida

    2015-01-01

    Chamomile is a medicinal plant, which presents several biological effects, especially the anti-inflammatory effect. One of the compounds related to this effect is apigenin, a flavonoid that is mostly found in its glycosylated form, apigenin-7-glucoside (APG), in natural sources. However, the affectivity and safety of this glycoside have not been well explored for topical application. In this context, the aim of this work was to develop and validate a reversed-phase high-performance liquid chromatography (RP-HPLC-DAD) method to quantify APG in chamomile preparations. Additionally, the safety and the anti-inflammatory potential of this flavonoid were verified. The RP-HPLC-DAD method was developed and validated with linearity at 24.0-36.0 μg/mL range (r = 0.9994). Intra- and interday precision (RSD) were 0.27-2.66% and accuracy was 98.27-101.21%. The validated method was applied in the analysis of chamomile flower heads, glycolic extract, and Kamillen cream, supporting the method application in the quality control of chamomile preparations. Furthermore, the APG safety was assessed by MTT cytotoxicity assay and mutagenic protocols and the anti-inflammatory activity was confirmed by a diminished TNF-α production showed by mice macrophages treated with APG following LPS treatment. PMID:26421053

  20. Development and validation of an HPTLC method for apigenin 7-O-glucoside in chamomile flowers and its application for fingerprint discrimination of chamomile-like materials.

    PubMed

    Guzelmeric, Etil; Vovk, Irena; Yesilada, Erdem

    2015-03-25

    Brewed tea of chamomile flowers (Matricaria recutita L.) (Asteraceae) has been extensively consumed for centuries due to either its pleasant taste or medicinal purposes. On the other hand, the major problem is difficulty in distinguishing the genuine specimen when supplying chamomile through nature-picking. Consequently flowers of other Asteraceae members resembling to chamomile in appearance may frequently be practiced by lay people or marketed in spice shops or bazaars. Evidently detection of such adulterations plays a vital role in terms of public health to avoid risk of toxicity (i.e. pyrazolidin alkaloids) and ineffective treatments (lack or insufficient concentration of the active constituents). This work presents either development and validation of a high performance thin-layer chromatographic (HPTLC) method for apigenin 7-O-glucoside which is one of the active markers in chamomile flowers or its application for the fingerprint discrimination of chamomile-like materials i.e. Anthemis spp., Bellis spp., Chrysanthemum sp. and Tanacetum sp. gathered by local people assuming as chamomile. Separation was performed on the silica gel 60 NH2 F254s HPTLC plates using the developing solvent system of ethyl acetate-formic acid-acetic acid-water (30:1.5:1.5:3, v/v/v/v). The proposed HPTLC method may also be a leading guide for the quality assessment of chamomile tea products on the market. PMID:25575175

  1. Luteolin-7-glucoside inhibits IL-22/STAT3 pathway, reducing proliferation, acanthosis, and inflammation in keratinocytes and in mouse psoriatic model.

    PubMed

    Palombo, R; Savini, I; Avigliano, L; Madonna, S; Cavani, A; Albanesi, C; Mauriello, A; Melino, G; Terrinoni, A

    2016-01-01

    The epidermis is a dynamic tissue in which keratinocytes proliferate in the basal layer and undergo a tightly controlled differentiation while moving into the suprabasal layers. The balance between keratinocyte proliferation, differentiation, and death is essential, and its perturbation can result in pathological changes. Some common skin diseases, such as psoriasis, are characterized by hyperproliferation accompanied by inflammatory reactions, suggesting that molecules with topical anti-inflammatory and ROS scavenging abilities may be useful for their treatment. Here we investigate the potential of the flavone Luteolin-7-glucoside (LUT-7G) as a treatment for psoriasis. We show that LUT-7G leads to a modification of the cell cycle and the induction of keratinocyte differentiation, with modification of energy, fatty acid, and redox metabolism. LUT-7G treatment also neutralizes the proliferative stimulus induced by the proinflammatory cytokines IL-22 and IL-6 in HEKn. Moreover, in the Imiquimod (IMQ) mouse model of psoriasis, topical administration of LUT-7G leads to a marked reduction of acanthosis and re-expression of epidermal differentiation markers. Dissection of the IL-22 signalling pathway, activated by IMQ treatment, demonstrates that LUT-7G impairs the nuclear translocation of phosphorylated (activated) STAT3, blocking the IL-22 signalling cascade. Thus LUT-7G appears to be a promising compound for the treatment of hyperproliferative and inflammatory skin diseases, such as psoriasis.

  2. Seasonal alteration in amounts of lignans and their glucosides and gene expression of the relevant biosynthetic enzymes in the Forsythia suspense leaf.

    PubMed

    Morimoto, Kinuyo; Satake, Honoo

    2013-01-01

    Lignans of Forsythia spp. are essential components of various Chinese medicines and health diets. However, the seasonal alteration in lignan amounts and the gene expression profile of lignan-biosynthetic enzymes has yet to be investigated. In this study, we have assessed seasonal alteration in amounts of major lignans, such as pinoresinol, matairesinol, and arctigenin, and examined the gene expression profile of pinoresinol/lariciresinol reductase (PLR), pinoresinol-glucosylating enzyme (UGT71A18), and secoisolariciresinol dehydrogenase (SIRD) in the leaf of Forsythia suspense from April to November. All of the lignans in the leaf continuously increased from April to June, reached the maximal level in June, and then decreased. Ninety percent of pinoresinol and matairesinol was converted into glucosides, while approximately 50% of arctigenin was aglycone. PLR was stably expressed from April to August, whereas the PLR expression was not detected from September to November. In contrast, the UGT71A18 expression was found from August to November, but not from April to July. The SIRD expression was prominent from April to May, not detected in June to July, and then increased again from September to November. These expression profiles of the lignan-synthetic enzymes are largely compatible with the alteration in lignan contents. Furthermore, such seasonal lignan profiles are in good agreement with the fact that the Forsythia leaves for Chinese medicinal tea are harvested in June. This is the first report on seasonal alteration in lignans and the relevant biosynthetic enzyme genes in the leaf of Forsythia species. PMID:23832493

  3. Assessment of the Therapeutic Effect of Total Glucosides of Peony for Juvenile Idiopathic Arthritis: A Systematic Review and Meta-Analysis.

    PubMed

    Cai, Yongsong; Yuan, Qiling; Xu, Ke; Zhu, Jialin; Li, Yuanbo; Wu, Xiaoqing; Yang, Le; Qiu, Yusheng; Xu, Peng

    2016-01-01

    Juvenile idiopathic arthritis (JIA) is the most common rheumatic disease in children; some clinical trials have reported the effects of total glucosides of peony (TGP) in the treatment of JIA. However, no systematic review has yet been conducted. In this study, we assessed the efficacy and safety in patients with JIA enrolled in randomized controlled trials (RCTs) of TGP. We extracted data for studies searched from 8 electronic databases that were searched and also evaluated the methodological quality of the included studies. We assessed the following outcome measures: overall response rate, pain, tender joint count (TJC), swollen joint count (SJC), duration of morning stiffness (DMS), grip strength (GS), rheumatoid factor (RF), erythrocyte sedimentation rate (ESR), C-reactive protein (CRP), and adverse effects (AEs) in short term (4-8 weeks), intermediate term (9-26 weeks), and long term (>26 weeks). The final analysis showed that TGP acted as a unique nonbiologic disease-modifying antirheumatic drug (nonbiologic DMARD), and its therapeutic effects were safe and efficacious for the treatment of JIA with few AEs. However, more high-quality RCTs are needed to confirm these therapeutic effects. PMID:27525026

  4. Novel long chain fatty acid derivatives of quercetin-3-O-glucoside reduce cytotoxicity induced by cigarette smoke toxicants in human fetal lung fibroblasts.

    PubMed

    Warnakulasuriya, Sumudu N; Ziaullah; Rupasinghe, H P Vasantha

    2016-06-15

    Smoking has become a global health concern due to its association with many disease conditions, such as chronic obstructive pulmonary disease (COPD), cardiovascular diseases (CVD) and cancer. Flavonoids are plant polyphenolic compounds, studied extensively for their antioxidant, anti-inflammatory, and anti-carcinogenic properties. Quercetin-3-O-glucoside (Q3G) is a flavonoid which is widely found in plants. Six novel long chain fatty acid [stearic acid, oleic acid, linoleic acid, α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA)] derivatives of Q3G were evaluated for their potential in protecting human lung fibroblasts against cytotoxicity induced by selected cigarette smoke toxicants: 4-(methylnitrosoamino)-1-(3-pyridinyl)-1-butanone (NNK), benzo-α-pyrene (BaP), nicotine and chromium (Cr[VI]). Nicotine and Cr[VI] induced toxicity in fibroblasts and reduced the percentage of viable cells, while BaP and NNK did not affect cell viability. The fatty acid derivatives of Q3G provided protection against nicotine- and Cr[VI]-induced cell death and membrane lipid peroxidation. Based on the evaluation of inflammatory markers of cyclooxygenase-2 (COX-2) and prostaglandin E2 (PGE2), the fatty acid derivatives of Q3G were found to be effective in lowering the inflammatory response. Overall, these novel fatty acid esters of Q3G warrant further investigation as potential cytoprotective agents. PMID:27071958

  5. A novel soybean (Glycine max) gene encoding a family 3 β-glucosidase has high isoflavone 7-O-glucoside-hydrolyzing activity in transgenic rice.

    PubMed

    Hsu, Chia-Chen; Wu, Tsung-Meng; Hsu, Yi-Ting; Wu, Chih-Wen; Hong, Chwan-Yang; Su, Nan-Wei

    2015-01-28

    A previous study demonstrated that purified Glycine max β-glucosidase (GmBGL) could hydrolyze glucosyl isoflavone to the aglyconic form. This study reports the cloning and functional characterization of a soybean cDNA encoding the β-glucosidase. GmBGL was isolated by use of a purified soybean N-terminal amino acid sequence and conserved sequences of β-glucosidase genes from other plants. Sequence analysis of GmBGL revealed an open reading frame of 1884 bp encoding a polypeptide of 627 amino acids with a calculated molecular mass of 69 kDa. Phylogenetic analysis classified the GmBGL into the glycosyl hydrolase 3 family. In soybean, the GmBGL transcript was predominantly accumulated in roots and leaves. To examine the enzymatic activity and substrate specificity, GmBGL was ectopically expressed in transgenic rice. Purified GmBGL protein from transgenic rice could catalyze the hydrolysis of genistin and daidzin to produce genistein and daidzein, respectively, which confirmed GmBGL as a functional β-glucosidase with isoflavone glucoside-hydrolyzing activity. This paper reveals that GmBGL is a key enzyme in transforming glucosyl isoflavones to aglycones in soybean, which may help in genetic manipulation of aglycone-rich soybean seeds.

  6. Complexation of bovine β-lactoglobulin with malvidin-3-O-glucoside and its effect on the stability of grape skin anthocyanin extracts.

    PubMed

    He, Zhiyong; Zhu, Haidong; Xu, Mingzhu; Zeng, Maomao; Qin, Fang; Chen, Jie

    2016-10-15

    The binding interaction between bovine β-lactoglobulin and malvidin-3-O-glucoside (MG), the major anthocyanin in grape skin anthocyanin extracts (GSAE), was studied at pH 6.3 using fluorescence, Fourier transform infrared and circular dichroism spectroscopy. The binding constant (KS), binding force and effect of the interaction on the β-lactoglobulin conformation and GSAE stability were investigated. The results indicated that β-lactoglobulin complexed with MG mainly via hydrophobic interaction with KS of 0.67×10(3)M(-)(1) at 297K. The secondary structure of β-lactoglobulin was changed by MG binding, with a decrease in α-helix, turn and random coil and an increase in β-sheet. Bovine whey protein effectively prevented the color fading and degradation of anthocyanin in the GSAE solution during the thermal treatment (80°C/2h), H2O2 oxidation (0.005% H2O2/1h) and photo illumination (5000lx/5d). The whey protein-anthocyanin complexation appeared to have a positive effect on the thermal, oxidation and photo stability of GSAE. PMID:27173557

  7. Phosphorylation of Akt Mediates Anti-Inflammatory Activity of 1-p-Coumaroyl β-D-Glucoside Against Lipopolysaccharide-Induced Inflammation in RAW264.7 Cells

    PubMed Central

    Vo, Van Anh; Lee, Jae-Won; Kim, Ji-Young; Park, Jun-Ho; Lee, Hee Jae; Kim, Sung-Soo; Kwon, Yong-Soo

    2014-01-01

    Hydroxycinnamic acids have been reported to possess numerous pharmacological activities such as antioxidant, anti-inflammatory, and anti-tumor properties. However, the biological activity of 1-p-coumaroyl β-D-glucoside (CG), a glucose ester derivative of p-coumaric acid, has not been clearly examined. The objective of this study is to elucidate the anti-inflammatory action of CG in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells. In the present study, CG significantly suppressed LPS-induced excessive production of pro-inflammatory mediators such as nitric oxide (NO) and PGE2 and the protein expression of iNOS and COX-2. CG also inhibited LPS-induced secretion of pro-inflammatory cytokines, IL-1β and TNF-α. In addition, CG significantly suppressed LPS-induced degradation of IκB. To elucidate the underlying mechanism by which CG exerts its anti-inflammatory action, involvement of various signaling pathways were examined. CG exhibited significantly increased Akt phosphorylation in a concentration-dependent manner, although MAPKs such as Erk, JNK, and p38 appeared not to be involved. Furthermore, inhibition of Akt/PI3K signaling pathway with wortmannin significantly, albeit not completely, abolished CG-induced Akt phosphorylation and anti-inflammatory actions. Taken together, the present study demonstrates that Akt signaling pathway might play a major role in CG-mediated anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells. PMID:24634601

  8. Aortic Remodelling Is Improved by 2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside Involving the Smad3 Pathway in Spontaneously Hypertensive Rats.

    PubMed

    Duan, Ju; Han, Xin; Ling, Shuang; Gan, Woting; Sun, Li; Ni, Rong-Zhen; Xu, Jin-Wen

    2015-01-01

    Hypertension is a common health problem that substantially increases the risk of cardiovascular disease. The condition increases blood pressure, which causes alterations in vascular structure and leads to the development of vascular pathologies. 2,3,5,4'-Tetrahydroxystilbene-2-O-β-D-glucoside (THSG), a resveratrol analogue extracted from a Chinese medicinal plant, has been proven to have numerous vascular protection functions. This study investigated whether THSG can improve vascular remodeling, which has thus far remained unclear. Orally administering THSG to spontaneously hypertensive rats (SHRs) aged 12 weeks for 14 weeks significantly inhibited intima-media thickness in the lower parts of the aortic arch, increased the vascular diastolic rate in response to acetylcholine, and reduced remodelling-related mRNA expression, such as that of ACTA2, CCL3, COL1A2, COL3A1, TIMP1 WISP2, IGFBP1, ECE1, KLF5, MYL1 BMP4, FN1, and PAI-1. Immunofluorescence staining also showed an inhibitory effect similar to that of THSG on PAI-1 protein expression in rat aortas. Results from immunoprecipitation and a Western blot assay showed that THSG inhibited the acetylation of Smad3. A chromatin immunoprecipitation assay showed that THSG prevented Smad3 binding to the PAI-1 proximal promoter in SHR aortas. In conclusion, our results demonstrated that the inhibitory effect of THSG on aortic remodelling involved the deacetylating role of Smad3 with increasing blood flow and with constant blood pressure. PMID:26693246

  9. Seasonal alteration in amounts of lignans and their glucosides and gene expression of the relevant biosynthetic enzymes in the Forsythia suspense leaf.

    PubMed

    Morimoto, Kinuyo; Satake, Honoo

    2013-01-01

    Lignans of Forsythia spp. are essential components of various Chinese medicines and health diets. However, the seasonal alteration in lignan amounts and the gene expression profile of lignan-biosynthetic enzymes has yet to be investigated. In this study, we have assessed seasonal alteration in amounts of major lignans, such as pinoresinol, matairesinol, and arctigenin, and examined the gene expression profile of pinoresinol/lariciresinol reductase (PLR), pinoresinol-glucosylating enzyme (UGT71A18), and secoisolariciresinol dehydrogenase (SIRD) in the leaf of Forsythia suspense from April to November. All of the lignans in the leaf continuously increased from April to June, reached the maximal level in June, and then decreased. Ninety percent of pinoresinol and matairesinol was converted into glucosides, while approximately 50% of arctigenin was aglycone. PLR was stably expressed from April to August, whereas the PLR expression was not detected from September to November. In contrast, the UGT71A18 expression was found from August to November, but not from April to July. The SIRD expression was prominent from April to May, not detected in June to July, and then increased again from September to November. These expression profiles of the lignan-synthetic enzymes are largely compatible with the alteration in lignan contents. Furthermore, such seasonal lignan profiles are in good agreement with the fact that the Forsythia leaves for Chinese medicinal tea are harvested in June. This is the first report on seasonal alteration in lignans and the relevant biosynthetic enzyme genes in the leaf of Forsythia species.

  10. Determination of cyanidin 3-glucoside in rat brain, liver and kidneys by UPLC/MS-MS and its application to a short-term pharmacokinetic study

    PubMed Central

    Fornasaro, Stefano; Ziberna, Lovro; Gasperotti, Mattia; Tramer, Federica; Vrhovšek, Urška; Mattivi, Fulvio; Passamonti, Sabina

    2016-01-01

    Anthocyanins exert neuroprotection in various in vitro and in vivo experimental models. However, no details regarding their brain-related pharmacokinetics are so far available to support claims about their direct neuronal bioactivity as well as to design proper formulations of anthocyanin-based products. To gather this missing piece of knowledge, we intravenously administered a bolus of 668 nmol cyanidin 3-glucoside (C3G) in anaesthetized Wistar rats and shortly after (15 s to 20 min) we collected blood, brain, liver, kidneys and urine samples. Extracts thereof were analysed for C3G and its expected metabolites using UPLC/MS-MS. The data enabled to calculate a set of pharmacokinetics parameters. The main finding was the distinctive, rapid distribution of C3G in the brain, with an apparently constant plasma/brain ratio in the physiologically relevant plasma concentration range (19–355 nM). This is the first report that accurately determines the distribution pattern of C3G in the brain, paving the way to the rational design of future tests of neuroprotection by C3G in animal models and humans. PMID:26965389

  11. Mixtures of n-octyl-beta-D-glucoside and triethylene glycol mono-n-octyl ether: phase behavior and micellar structure near the liquid-liquid phase boundary.

    PubMed

    Santonicola, Gabriella M; Kaler, Eric W

    2005-10-25

    The phase behavior and microstructure of aqueous mixtures of n-octyl-beta-D-glucoside (C8betaG1) and triethylene glycol mono-n-octyl ether (C8E3) is presented. C8betaG1 forms a one-phase micellar solution in water at surfactant concentrations up to 60 wt %, whereas mixtures with C8E3 show a liquid-liquid phase transition at low surfactant concentration. The position of this phase boundary for mixtures can be rationally shifted in the temperature-composition window by altering the ratio of the two surfactants. Small-angle neutron scattering is used to determine the size and shape of the mixed micelles and to characterize the nature of the fluctuations near the cloud point of the micellar solutions. The C8betaG1/C8E3 solutions are characterized by concentration fluctuations that become progressively stronger upon approach to the liquid-liquid phase boundary, whereas micellar growth is negligible. Such observations confirm previous views of the role of the surfactant phase boundary in tuning attractive micellar interactions, which can be used effectively to change the nature and strength of interparticle interactions in colloidal dispersions. Colloidal silica particles were then added to these surfactant mixtures and were found to aggregate at conditions near the cloud point. This finding is relevant to current strategies for protein crystallization.

  12. Luteolin-7-glucoside inhibits IL-22/STAT3 pathway, reducing proliferation, acanthosis, and inflammation in keratinocytes and in mouse psoriatic model.

    PubMed

    Palombo, R; Savini, I; Avigliano, L; Madonna, S; Cavani, A; Albanesi, C; Mauriello, A; Melino, G; Terrinoni, A

    2016-01-01

    The epidermis is a dynamic tissue in which keratinocytes proliferate in the basal layer and undergo a tightly controlled differentiation while moving into the suprabasal layers. The balance between keratinocyte proliferation, differentiation, and death is essential, and its perturbation can result in pathological changes. Some common skin diseases, such as psoriasis, are characterized by hyperproliferation accompanied by inflammatory reactions, suggesting that molecules with topical anti-inflammatory and ROS scavenging abilities may be useful for their treatment. Here we investigate the potential of the flavone Luteolin-7-glucoside (LUT-7G) as a treatment for psoriasis. We show that LUT-7G leads to a modification of the cell cycle and the induction of keratinocyte differentiation, with modification of energy, fatty acid, and redox metabolism. LUT-7G treatment also neutralizes the proliferative stimulus induced by the proinflammatory cytokines IL-22 and IL-6 in HEKn. Moreover, in the Imiquimod (IMQ) mouse model of psoriasis, topical administration of LUT-7G leads to a marked reduction of acanthosis and re-expression of epidermal differentiation markers. Dissection of the IL-22 signalling pathway, activated by IMQ treatment, demonstrates that LUT-7G impairs the nuclear translocation of phosphorylated (activated) STAT3, blocking the IL-22 signalling cascade. Thus LUT-7G appears to be a promising compound for the treatment of hyperproliferative and inflammatory skin diseases, such as psoriasis. PMID:27537526

  13. Malvidin-3-O-β glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats.

    PubMed

    Decendit, Alain; Mamani-Matsuda, Maria; Aumont, Virginie; Waffo-Teguo, Pierre; Moynet, Daniel; Boniface, Katia; Richard, Emmanuel; Krisa, Stéphanie; Rambert, Jérôme; Mérillon, Jean-Michel; Mossalayi, M D

    2013-11-15

    Polyphenolic anthocyanins are major colorful compounds in red fruits, known to prevent cardiovascular and other diseases. Grape polyphenols are a mixture of various molecules and their exact contribution to above bioactivities remains to be clarified. In the present study, we first analyzed the effect of purified grape-derived compounds on human peripheral blood mononuclear cell (PBMC) survival, proliferation, as well as for their ability to inhibit the activation of human normal macrophages. Data indicated that malvidin-3-O-β glucoside (Malβg), the major grape anthocyanin, is bioactive with no toxicity on human PBMC. Malβg decreased the transcription of genes encoding inflammatory mediators, confirmed by the inhibition of TNFα, IL1, IL-6 and iNOS-derived nitric oxide (NO) secretion from activated macrophages. As Malβg also inhibited inflammatory response of rat macrophages, we investigated the anti-inflammatory potential of Malβg in chronic rat adjuvant-induced arthritis (AIA). Malβg significantly diminished inflammatory cachexia and arthritic paw scores in AIA rats at both therapeutic and preventive levels. In vivo effects of Malβg correlated with down-regulation of NO generation from AIA rats' peritoneal macrophages ex vivo. These data indicate that Malβg, major grape anthocyanin, is a potent anti-inflammatory agent in vitro and in vivo, without detectable toxic effect.

  14. Validation of a RP-HPLC-DAD Method for Chamomile (Matricaria recutita) Preparations and Assessment of the Marker, Apigenin-7-glucoside, Safety and Anti-Inflammatory Effect

    PubMed Central

    Miguel, Felipe Galeti; Cavalheiro, Amanda Henriques; Spinola, Nathália Favaretto; Ribeiro, Diego Luis; Barcelos, Gustavo Rafael Mazzaron; Antunes, Lusânia Maria Greggi; Hori, Juliana Issa; Marquele-Oliveira, Franciane; Rocha, Bruno Alves; Berretta, Andresa Aparecida

    2015-01-01

    Chamomile is a medicinal plant, which presents several biological effects, especially the anti-inflammatory effect. One of the compounds related to this effect is apigenin, a flavonoid that is mostly found in its glycosylated form, apigenin-7-glucoside (APG), in natural sources. However, the affectivity and safety of this glycoside have not been well explored for topical application. In this context, the aim of this work was to develop and validate a reversed-phase high-performance liquid chromatography (RP-HPLC-DAD) method to quantify APG in chamomile preparations. Additionally, the safety and the anti-inflammatory potential of this flavonoid were verified. The RP-HPLC-DAD method was developed and validated with linearity at 24.0–36.0 μg/mL range (r = 0.9994). Intra- and interday precision (RSD) were 0.27–2.66% and accuracy was 98.27–101.21%. The validated method was applied in the analysis of chamomile flower heads, glycolic extract, and Kamillen cream, supporting the method application in the quality control of chamomile preparations. Furthermore, the APG safety was assessed by MTT cytotoxicity assay and mutagenic protocols and the anti-inflammatory activity was confirmed by a diminished TNF-α production showed by mice macrophages treated with APG following LPS treatment. PMID:26421053

  15. Protective Effects of Total Glucosides of Paeony on N-nitrosodiethylamine-induced Hepatocellular Carcinoma in Rats via Down-regulation of Regulatory B Cells.

    PubMed

    Song, S S; Yuan, P F; Li, P P; Wu, H X; Ni, W J; Lu, J T; Wei, W

    2015-01-01

    Total glucoside of paeony (TGP), extracted from the root of Paeonia Lactiflora, has been known to show anti-inflammatory, anti-oxidative, hepato-protective and immuno-regulatory activities. The aim of this present study was to determine the anti-tumor effect of TGP against N-nitrosodiethylamine (DEN)-induced hepatocellular carcinoma (HCC) in rats, and to find the related mechanisms. Rat HCC model was established by intragastrically administrating with DEN (8 mg/kg). We found the number of tumor nodules and the index of liver and spleen were increased in the model group compared with the normal group, and was significantly decreased by TGP. Additionally, TGP obviously improved the hepatic pathological lesions induced by DEN, and decreased the elevated levels of serum alanine aminotransferase (ALT), glutamic oxalacetic transaminase (AST), alkaline phosphatase (ALP) and alpha fetoprotein (AFP) by DEN. Moreover, TGP decreased the level of B cell-activating factor (BAFF) and the proportion of IL-10-producing regulatory B cells (Bregs), and the decrease of BAFF by TGP is positively correlated to the decrease of IL-10-producing Bregs by TGP. These results suggest that TGP had a good therapeutic action on DEN-induced HCC rats, which might be due to its down-regulation of Bregs through reducing the level of BAFF. PMID:26207789

  16. Cyanidin 3-O-glucoside reduces Helicobacter pylori VacA-induced cell death of gastric KATO III cells through inhibition of the SecA pathway.

    PubMed

    Kim, Sa-Hyun; Woo, Hyunjun; Park, Min; Rhee, Ki-Jong; Moon, Cheol; Lee, Dongsup; Seo, Woo Duck; Kim, Jong Bae

    2014-01-01

    Two key virulence factors of Helicobacter pylori are the secreted virulent proteins of vacuolating toxin A (VacA) and cytotoxin associated protein A (CagA) which lead to damages of gastric epithelial cells. We previously identified that the cyanidin 3-O-glucoside (C3G) inhibits the secretion of both VacA and CagA. In the current report, we show that C3G inhibits VacA secretion in a dose-dependent manner by inhibiting secretion system subunit protein A (SecA) synthesis. As SecA is involved in translocation of bacterial proteins, we predicted that inhibition of the SecA pathway by C3G should decrease H. pylori-induced cell death. To test this hypothesis, the human gastric cell line KATO III cells were co-cultured with H. pylori 60190 (VacA(+)/CagA(+)) and C3G. We found that C3G treatment caused a decrease in activation of the pro-apoptotic proteins caspase-3/-8 in H. pylori-infected cells leading to a decrease in cell death. Our data suggest that consumption of foods containing anthocyanin may be beneficial in reducing cell damage due to H. pylori infection. PMID:24904230

  17. Cyanidin 3-O-Glucoside Reduces Helicobacter pylori VacA-Induced Cell Death of Gastric KATO III Cells through Inhibition of the SecA Pathway

    PubMed Central

    Kim, Sa-Hyun; Woo, Hyunjun; Park, Min; Rhee, Ki-Jong; Moon, Cheol; Lee, Dongsup; Seo, Woo Duck; Kim, Jong Bae

    2014-01-01

    Two key virulence factors of Helicobacter pylori are the secreted virulent proteins of vacuolating toxin A (VacA) and cytotoxin associated protein A (CagA) which lead to damages of gastric epithelial cells. We previously identified that the cyanidin 3-O-glucoside (C3G) inhibits the secretion of both VacA and CagA. In the current report, we show that C3G inhibits VacA secretion in a dose-dependent manner by inhibiting secretion system subunit protein A (SecA) synthesis. As SecA is involved in translocation of bacterial proteins, we predicted that inhibition of the SecA pathway by C3G should decrease H. pylori-induced cell death. To test this hypothesis, the human gastric cell line KATO III cells were co-cultured with H. pylori 60190 (VacA+/CagA+) and C3G. We found that C3G treatment caused a decrease in activation of the pro-apoptotic proteins caspase-3/-8 in H. pylori-infected cells leading to a decrease in cell death. Our data suggest that consumption of foods containing anthocyanin may be beneficial in reducing cell damage due to H. pylori infection. PMID:24904230

  18. The role of sodium-dependent glucose transporter 1 and glucose transporter 2 in the absorption of cyanidin-3-o-β-glucoside in Caco-2 cells.

    PubMed

    Zou, Tang-Bin; Feng, Dan; Song, Gang; Li, Hua-Wen; Tang, Huan-Wen; Ling, Wen-Hua

    2014-10-01

    Anthocyanins have multiple biological activities of benefit to human health. While a few studies have been conducted to evaluate the bioavailability of anthocyanins, the mechanisms of their absorption mechanism remain ill-defined. In the present study, we investigated the absorption mechanism of cyanidin-3-O-β-glucoside (Cy-3-G) in human intestinal epithelial (Caco-2) cells. Cy-3-G transport was assessed by measuring the absorptive and efflux direction. Inhibition studies were conducted using the pharmacological agents, phloridzin, an inhibitor of sodium-dependent glucose transporter 1 (SGLT1), or phloretin, an inhibitor of glucose transporter 2 (GLUT2). The results showed that phloridzin and phloretin significantly inhibited the absorption of Cy-3-G. In addition, Caco-2 cells transfected with small interfering RNA (siRNA) specific for SGLT1 or GLUT2 showed significantly decreased Cy-3-G absorption. These siRNA transfected cells also showed a significantly decreased rate of transport of Cy-3-G compared with the control group. These findings suggest that Cy-3-G absorption is dependent on the activities of SGLT1 and GLUT2 in the small intestine and that SGLT1 and GLUT2 could be a limiting step for the bioavailability of Cy-3-G. PMID:25314643

  19. Regional intestinal absorption of FITC-dextran 4,400 with nanoparticles based on beta-sitosterol beta-D-glucoside in rats.

    PubMed

    Nakamura, Koji; Takayama, Kozo; Nagai, Tsuneji; Maitani, Yoshie

    2003-02-01

    Nanoparticles (NP) are potential carriers for drug delivery to the targeted intestine. NP based on beta-sitosterol beta-D-glucoside (Sit-G) enhanced the colon-specific absorption of FITC-dextran 4,400 (FD-4), because the concentration-dependent increase of bioavailability appeared in only the colon. In a permeation study, the absorption enhancement in the colon was suppressed in the following conditions: (1) the addition of Sit-G NP to serosa; (2) a permeation study at 4 degrees C; (3) the addition of endocytosis inhibitor, cytochalasin B. NP based on sitosterol, the aglycon of Sit-G, did not increase the FD-4 colonic permeation. The addition of Sit-G NP to the mucosal side induced a decrease of transepithelial resistance (TEER), but this phenomenon was suppressed by an inhibitor of Na(+)-dependent specific glucose transporter, phrolidzin, which did not affect FD-4 permeation. These findings suggested that absorption enhancement by Sit-G NP may not be due to opening of a tight junction, but might be related to endocytosis via glucose residue of Sit-G.

  20. Stimulation of callose synthesis in vivio correlates with changes in intracellular distribution of the callose synthase activator [beta]-Furfuryl-[beta]-Glucoside

    SciTech Connect

    Ohana, P.; Benziman, M.; Delmer, D.P. )

    1993-01-01

    [beta]-Furfuryl-[beta]-glucoside (FG) has been shown to be a specific endogenous activator of higher plant callose synthase. Because glycosides such as FG are usually sequestered in vacuoles, we have proposed that activation of callose synthesis in vivo may involve a change in the compartmentation on FG and Ca[sup 2+], resulting in a synergistic activation of callose synthase. The use of suspension-cultured barley (Hordeum bulbosum L.) cells provides evidence that FG is largely sequestered in the vacuole. Furthermore, conditions that lead to induction of callose synthesis in vivo correspondingly lead to elevation of the cytoplasmic concentration of FG. These conditions include the lowering of cytoplasmic pH or elevation of cytoplasmic Ca[sup 2+]. Oligogalacturonide elicitors have also been reported to cause similar changes in cytoplasmic pH and Ca[sup 2+] concentration, and such an elicitor also causes and elevation in cytoplasmic FG coupled with stimulation of callose synthesis. These results support the concept that a relative redistribution of FG between cytoplasm and vacuole may be one of the components of the signal transduction pathway for elicitation of callose synthase in vivo. 18 refs., 1 fig., 2 tabs.

  1. Hevea Linamarase—A Nonspecific β-Glycosidase 1

    PubMed Central

    Selmar, Dirk; Lieberei, Reinhard; Biehl, Böle; Voigt, Jürgen

    1987-01-01

    In the leaf tissue of the cyanogenic plant Hevea brasiliensis, which contains large amounts of linamarin, there is no specific linamarase. In Hevea leaves only one β-glucosidase is detectable. It is responsible for the cleavage of all β-glucosides and β-galactosides occurring in Hevea leaf tissue, including the cyanogenic glucoside linamarin. Therefore, the enzyme is referred to as a β-glycosidase instead of the term β-glucosidase. This β-glycosidase has a broad substrate spectrum and occurs in multiple forms. These homo-oligomeric forms are interconvertible by dissociation-association processes. The monomer is a single protein of 64 kilodaltons. PMID:16665288

  2. Combining high-performance liquid chromatography with on-line microdialysis sampling for the simultaneous determination of ascorbyl glucoside, kojic acid, and niacinamide in bleaching cosmetics.

    PubMed

    Lin, Cheng-Hui; Wu, Hsin-Lung; Huang, Yeou-Lih

    2007-01-01

    We have used on-line microdialysis sampling coupled with high-performance liquid chromatography and UV-vis detection to simultaneously determine the contents of ascorbyl glucoside (AA-2G), kojic acid (KA), and niacinamide (VitB(3)) in commercial bleaching cosmetics. Our results indicate that AA-2G, KA, and VitB(3) separated well within 4.5 min on a reverse-phase Hypersil Fluophase PFP column when eluting with 0.020 M phosphate buffer solution in 40% (v/v) methanol at pH 5.5. The calibration curves were linear over the ranges 0.068-304, 0.071-284, and 0.024-488 microg mL(-1) for AA-2G, KA, and VitB(3), respectively, with correlation coefficients for the linear regression analyses falling within the range 0.9982-0.9999. The detection limits for AA-2G, KA, and VitB(3) were 0.01, 0.01, and 0.007 microg mL(-1), respectively. The detection wavelength was robust when the levels of the analytes in the samples were high (0.1-2%). The analytes were all detected using ultraviolet light (254 nm). The compounds diffuse through the membrane more readily when KA and VitB(3) are in their molecular forms and AA-2G is ionized. The recoveries were in the range 92-106% with good reproducibility (R.S.D.=3.9-8.7%). We used this procedure to assay six commercially available bleaching cosmetics; our results confirmed not only the precision of the method but also the claims made on the labels of the cosmetics. This approach provides a very simple means to determine the contents of AA-2G, KA, and VitB(3) in various dosages in bleaching cosmetics.

  3. Reversal of multidrug resistance by 5,5’-dimethoxylariciresinol-4-O-β-D-glucoside in doxorubicin-resistant human leukemia K562/DOX

    PubMed Central

    Wang, Tian-Xiao; Shi, Xiao-Yan; Cong, Yue; Wang, Shi-Guang; Wang, Ying-Ying; Zhang, Zhong-Qin

    2013-01-01

    Objective: The objective of this study was to investigate the reversal effects of 5,5’-dimethoxylariciresinol-4’-O-β-D-glucoside (DMAG) extracted from traditional Chinese medicines Mahonia on multidrug resistance (MDR) of human leukemia cells to chemotherapeutic agents. Materials and Methods: MTT(3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay was performed to determine the effect of DMAG on doxorubicin sensitivity to K562/DOX cells. Propidium iodide /Hoechst 33342 double staining assay was used to investigate the effect of DMAG on doxorubicin-induced cellular apoptosis. Intracellular accumulation of doxorubicin and rhodamine 123 assay were performed to evaluate the effect of DMAG on drugs efflux activity of P-glycoprotein. Results: DMAG significantly enhanced the doxorubicin cytotoxicity to K562/DOX cells. In the presence of 1.0 μM of DMAG, the IC50 of doxorubicin decreased from 34.93 ± 1.37 μM to 12.51 ± 1.28 μM. DMAG of 1.0 μM significantly enhanced doxorubicin-induced cell apoptosis in K562/DOX cells and the enhancement was time-dependent. A significant increase in accumulation of doxorubicin in the presence of DMAG was observed. After treatment of the K562/DOX cells for 1 h with 15.0 μM doxorubicin alone, the fluorescence intensity was 33093.12. With the addition of 1.0 μM of DMAG, the fluorescence intensity of doxorubicin was 2.3-fold higher. A significant increase of accumulation of rhodamine 123 in the presence of DMAG was also observed. With the addition of 1.0 μM of DMAG, the fluorescence intensity was increased by 49.11% compared with rhodamine 123 alone. Conclusion: DMAG was shown to effectively enhance chemosensitivity of resistant cells, which makes it might be a suitable candidate for potential MDR-reversing agents. PMID:24347768

  4. Cytotoxicity, Antioxidant and Apoptosis Studies of Quercetin-3-O Glucoside and 4-(β-D-Glucopyranosyl-1→4-α-L-Rhamnopyranosyloxy)-Benzyl Isothiocyanate from Moringa oleifera.

    PubMed

    Maiyo, Fiona C; Moodley, Roshila; Singh, Moganavelli

    2016-01-01

    Moringa oleifera, from the family Moringaceae, is used as a source of vegetable and herbal medicine and in the treatment of various cancers in many African countries, including Kenya. The present study involved the phytochemical analyses of the crude extracts of M.oleifera and biological activities (antioxidant, cytotoxicity and induction of apoptosis in-vitro) of selected isolated compounds. The compounds isolated from the leaves and seeds of the plant were quercetin-3-O-glucoside (1), 4-(β-D-glucopyranosyl-1→4-α-L-rhamnopyranosyloxy)-benzyl isothiocyanate (2), lutein (3), and sitosterol (4). Antioxidant activity of compound 1 was significant when compared to that of the control, while compound 2 showed moderate activity. The cytotoxicity of compounds 1 and 2 were tested in three cell lines, viz. liver hepatocellular carcinoma (HepG2), colon carcinoma (Caco-2) and a non-cancer cell line Human Embryonic Kidney (HEK293), using the MTT cell viability assay and compared against a standard anticancer drug, 5-fluorouracil. Apoptosis studies were carried out using the acridine orange/ethidium bromide dual staining method. The isolated compounds showed selective in vitro cytotoxic and apoptotic activity against human cancer and non-cancer cell lines, respectively. Compound 1 showed significant cytotoxicity against the Caco-2 cell line with an IC50 of 79 μg mL(-1) and moderate cytotoxicity against the HepG2 cell line with an IC50 of 150 μg mL(-1), while compound 2 showed significant cytotoxicity against the Caco- 2 and HepG2 cell lines with an IC50 of 45 μg mL(-1) and 60 μg mL(-1), respectively. Comparatively both compounds showed much lower cytotoxicity against the HEK293 cell line with IC50 values of 186 μg mL(-1) and 224 μg mL(-1), respectively. PMID:26428271

  5. Comparison of Anorectic and Emetic Potencies of Deoxynivalenol (Vomitoxin) to the Plant Metabolite Deoxynivalenol-3-Glucoside and Synthetic Deoxynivalenol Derivatives EN139528 and EN139544

    PubMed Central

    Wu, Wenda; Zhou, Hui-Ren; Bursian, Steven J.; Pan, Xiao; Link, Jane E.; Berthiller, Franz; Adam, Gerhard; Krantis, Anthony; Durst, Tony; Pestka, James J.

    2014-01-01

    The mycotoxin deoxynivalenol (DON) elicits robust anorectic and emetic effects in several animal species. However, less is known about the potential for naturally occurring and synthetic congeners of this trichothecene to cause analogous responses. Here we tested the hypothesis that alterations in DON structure found in the plant metabolite deoxynivalenol-3-glucoside (D3G) and two pharmacologically active synthetic DON derivatives, EN139528 and EN139544, differentially impact their potential to evoke food refusal and emesis. In a nocturnal mouse food consumption model, oral administration with DON, D3G, EN139528, or EN139544 at doses from 2.5 to 10 mg/kg BW induced anorectic responses that lasted up to 16, 6, 6, and 3 h, respectively. Anorectic potency rank orders were EN139544>DON>EN139528>D3G from 0 to 0.5 h but DON>D3G>EN139528>EN139544 from 0 to 3 h. Oral exposure to each of the four compounds at a common dose (2.5 mg/kg BW) stimulated plasma elevations of the gut satiety peptides cholecystokinin and to a lesser extent, peptide YY3–36 that corresponded to reduced food consumption. In a mink emesis model, oral administration of increasing doses of the congeners differentially induced emesis, causing marked decreases in latency to emesis with corresponding increases in both the duration and number of emetic events. The minimum emetic doses for DON, EN139528, D3G, and EN139544 were 0.05, 0.5, 2, and 5 mg/kg BW, respectively. Taken together, the results suggest that although all three DON congeners elicited anorectic responses that mimicked DON over a narrow dose range, they were markedly less potent than the parent mycotoxin at inducing emesis. PMID:25173790

  6. 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside suppresses human colorectal cancer cell metastasis through inhibiting NF-κB activation.

    PubMed

    Lin, Chien-Liang; Hsieh, Shu-Ling; Leung, Wan; Jeng, Jiiang-Huei; Huang, Guan-Cheng; Lee, Chining-Ting; Wu, Chih-Chung

    2016-08-01

    2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (THSG), a major component of Polygonum multiflorum Thunb (He-Shou-Wu), has been reported to exhibit antioxidant and anti-inflammatory effects. However, its anti-metastatic effect against colorectal cancer is still unclear. In this study, cell migration, invasion and adhesion abilities as well as metastasis-associated protein and NF-κB pathway signaling factor expression were analyzed after treating HT-29 cells with THSG. According to the results, the migration and invasiveness of HT-29 cells were reduced after treatment with 5 or 10 mM THSG (p<0.05). Additionally, the levels of matrix metalloproteinase-2 (MMP-2) and phosphorylated VE-cadherin in HT-29 cells were reduced and the transepithelial electrical resistance (TEER) of EA.hy926 endothelial cell monolayers was increased after incubation in THSG for 24 h (p<0.05). Cell adhesion ability and the E-selectin and intercellular adhesion molecule-1 (ICAM-1) protein levels were reduced when EA.hy926 endothelial cells were treated with THSG (p<0.05). In addition, the cytoplasmic phosphorylation of IκB, the nuclear p65 level and the DNA-binding activity of NF-κB were reduced after treating HT-29 or EA.hy926 cells with 5 or 10 mM THSG (p<0.05). These results suggest that THSG inhibits HT-29 cell metastasis by suppressing cell migration, invasion and adhesion. Furthermore, THSG inhibits metastasis-associated protein expression by suppressing NF-κB pathway activation. PMID:27278328

  7. Comparison of anorectic and emetic potencies of deoxynivalenol (vomitoxin) to the plant metabolite deoxynivalenol-3-glucoside and synthetic deoxynivalenol derivatives EN139528 and EN139544.

    PubMed

    Wu, Wenda; Zhou, Hui-Ren; Bursian, Steven J; Pan, Xiao; Link, Jane E; Berthiller, Franz; Adam, Gerhard; Krantis, Anthony; Durst, Tony; Pestka, James J

    2014-11-01

    The mycotoxin deoxynivalenol (DON) elicits robust anorectic and emetic effects in several animal species. However, less is known about the potential for naturally occurring and synthetic congeners of this trichothecene to cause analogous responses. Here we tested the hypothesis that alterations in DON structure found in the plant metabolite deoxynivalenol-3-glucoside (D3G) and two pharmacologically active synthetic DON derivatives, EN139528 and EN139544, differentially impact their potential to evoke food refusal and emesis. In a nocturnal mouse food consumption model, oral administration with DON, D3G, EN139528, or EN139544 at doses from 2.5 to 10 mg/kg BW induced anorectic responses that lasted up to 16, 6, 6, and 3 h, respectively. Anorectic potency rank orders were EN139544>DON>EN139528>D3G from 0 to 0.5 h but DON>D3G>EN139528>EN139544 from 0 to 3 h. Oral exposure to each of the four compounds at a common dose (2.5 mg/kg BW) stimulated plasma elevations of the gut satiety peptides cholecystokinin and to a lesser extent, peptide YY3-36 that corresponded to reduced food consumption. In a mink emesis model, oral administration of increasing doses of the congeners differentially induced emesis, causing marked decreases in latency to emesis with corresponding increases in both the duration and number of emetic events. The minimum emetic doses for DON, EN139528, D3G, and EN139544 were 0.05, 0.5, 2, and 5 mg/kg BW, respectively. Taken together, the results suggest that although all three DON congeners elicited anorectic responses that mimicked DON over a narrow dose range, they were markedly less potent than the parent mycotoxin at inducing emesis.

  8. Long Chain Fatty Acid Esters of Quercetin-3-O-glucoside Attenuate H₂O₂-induced Acute Cytotoxicity in Human Lung Fibroblasts and Primary Hepatocytes.

    PubMed

    Warnakulasuriya, Sumudu N; Ziaullah; Rupasinghe, H P Vasantha

    2016-01-01

    Cellular oxidative stress causes detrimental effects to macromolecules, such as lipids, nucleic acids and proteins, leading to many pathological conditions. Quercetin-3-O-glucoside (Q3G), a glycosylated derivative of quercetin (Q), is a natural polyphenolic compound known to possess antioxidant activity. The hydrophilic/lipophilic nature of an antioxidant molecule is considered as an important factor governing the accessibility to the active sites of oxidative damages in vivo. Six long chain fatty acid esters of Q3G were evaluated with comparison to Q and Q3G, for their cytoprotective activity under H₂O₂-induced oxidative stress using cell culture model systems through cell viability, lipid peroxidation and fluorescence microscopy studies. Pre-incubation of α-linolenic acid (ALA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) esters of Q3G exhibited significantly (p ≤ 0.05) greater cell viability in both human lung fibroblast (WI-38) and human primary hepatocytes upon exposure to H₂O₂ insult when compared to the control. Cytoprotection due to oleic acid and linoleic acid esters of Q3G was observed only in human primary hepatocytes. All the derivatives, Q3G and quercetin showed ability to significantly (p ≤ 0.05) lower production of lipid hydroperoxides under induced oxidative stress, compared to the control. However, ALA and DHA esters of Q3G resulted in significantly lower lipid hydroperoxidation than Q and Q3G. Based on fluorescence microscopy study, H₂O₂-induced apoptosis was attenuated by the fatty acid derivatives of Q3G. The fatty acid derivatives of Q3G possess better cytoprotective effect than Q3G against H₂O₂-induced cytotoxicity in vitro and the concentration should be selected to avoid cytotoxicity. PMID:27058521

  9. Pinoresinol-4,4'-di-O-beta-D-glucoside from Valeriana officinalis root stimulates calcium mobilization and chemotactic migration of mouse embryo fibroblasts.

    PubMed

    Do, Kee Hun; Choi, Young Whan; Kim, Eun Kyoung; Yun, Sung Ji; Kim, Min Sung; Lee, Sun Young; Ha, Jung Min; Kim, Jae Ho; Kim, Chi Dae; Son, Beung Gu; Kang, Jum Soon; Khan, Ikhlas A; Bae, Sun Sik

    2009-06-01

    Lignans are major constituents of plant extracts and have important pharmacological effects on mammalian cells. Here we showed that pinoresinol-4,4'-di-O-beta-D-glucoside (PDG) from Valeriana officinalis induced calcium mobilization and cell migration through the activation of lysophosphatidic acid (LPA) receptor subtypes. Stimulation of mouse embryo fibroblast (MEF) cells with 10 microM PDG resulted in strong stimulation of MEF cell migration and the EC(50) was about 2 microM. Pretreatment with pertussis toxin (PTX), an inhibitor of G(i) protein, completely blocked PDG-induced cell migration demonstrating that PDG evokes MEF cell migration through the activation of the G(i)-coupled receptor. Furthermore, pretreatment of MEF cells with Ki16425 (10 microM), which is a selective antagonist for LPA(1) and LPA(3) receptors, completely blocked PDG-induced cell migration. Likewise, PDG strongly induced calcium mobilization, which was also blocked by Ki16425 in a dose-dependent manner. Prior occupation of the LPA receptor with LPA itself completely blocked PDG-induced calcium mobilization. Finally, PDG-induced MEF cell migration was attenuated by pretreatment with a phosphatidylinositol 3-kinase (PI3K) inhibitor such as LY294002. Cells lacking downstream mediator of PI3K such as Akt1 and Akt2 (DKO cells) showed loss of PDG-induced migration. Re-expression of Akt1 (but not Akt2) completely restored PDG-induced DKO cell migration. Given these results, we conclude that PDG is a strong inducer of cell migration. We suggest that the pharmacological action of PDG may occur through the activation of an LPA receptor whereby activation of PI3K/Akt signaling pathway mediates PDG-induced MEF cell migration.

  10. Total glucosides of paeony attenuate renal tubulointerstitial injury in STZ-induced diabetic rats: role of Toll-like receptor 2.

    PubMed

    Zhang, Wei; Zhao, Li; Su, Shuang-Quan; Xu, Xing-Xin; Wu, Yong-Gui

    2014-01-01

    Accumulating evidence suggested that macrophages induce tubulointerstitial injury. Total glucosides of paeony (TGP), extracted from Paeonia lactiflora, has presented anti-inflammatory activities in diabetic kidney disease. This research will investigate the protective effect of TGP on renal tubulointerstitium and its mechanism in streptozotocin-induced diabetic rats. TGP was administered orally at a dose of 50, 100, and 200 mg·kg(-1)·d(-1) for 8 weeks. Tubulointerstitial injury was quantified, followed by immunohistochemistry analysis of renal α-smooth muscle actin (α-SMA), E-cadherin (E-cad) expression, nuclear factor kappa B (NF-κB)-p-p-65(+), Toll-like receptor (TLR)2(+), and ED-1(+) cell infiltration in renal tubulointerstitium. Renal TLR2(+) macrophages were detected by double immunohistochemical staining. Western blotting was used to detect the TLR2 expression. Histologically, there was marked accumulation of TLR2(+), NF-κB-p-p-65(+), ED-1(+) cells, and ED-1(+)TLR2(+) cells (macrophages) in the diabetic kidney and TGP treatment could alleviate it. Accompanying with that, the tubulointerstitial injury was ameliorated, α-SMA expression was lower, and E-cad expression was higher compared with the diabetic rats. Western blot analysis showed that the expression of TLR2 protein was significantly increased in the kidney of the diabetic rats, whereas TGP treatment reduced it. Our study showed that TGP could prevent renal tubulointerstitium injury in diabetic rats through a mechanism that may be at least partly correlated with suppression of increased macrophage infiltration and the expression of TLR2. PMID:24739281

  11. Isolation, Purification and Characterization of a Novel Steroidal Saponin Cholestanol Glucoside from Lasiodiplodia theobromae that Induces Apoptosis in A549 Cells.

    PubMed

    Valayil, Jinu Mathew; Kuriakose, Gini C; Jayabaskaran, C

    2016-01-01

    Search for novel anticancer lead molecules continues to be a major focus of cancer research due to the limitations of existing drugs such as lack of tumor selectivity, narrow therapeutic index and multidrug resistance of cancer types. Natural molecules often possess better pharmacokinetic traits compared to synthetic molecules as they continually evolve by natural selection process to interact with biological macromolecules. Microbial metabolites constitute nearly half of the pharmaceuticals in market today. Endophytic fungi, owing to its rich chemical diversity, are viewed as attractive sources of novel bioactive compounds. In the present study, we report the purification and characterization of a novel steroidal saponin, cholestanol glucoside (CG) from Saraca asoca endophytic fungus Lasiodiplodia theobromae. The compound was assessed for its cytotoxic potentialities in six human cancer cell lines, A549, PC3, HepG2, U251, MCF7 and OVCAR3. CG exhibited significant cytotoxicities towards A549, PC3 and HepG2 among which A549 cells were most vulnerable to CG treatment. However, CG treatment exhibited negligible cytotoxicity in non malignant human lung fibroblast cell line (WI-38). Induction of cell death by CG treatment in A549 cells was further investigated. CG induced the generation of reactive oxygen species (ROS) and mitochondrial membrane permeability loss followed by apoptotic cell death. Mitochondrial membrane depolarization and apoptotic cell death in CG treated A549 cells were completely blocked in presence of an antioxidant, N-acetyl cysteine (NAC). Hence it could be concluded that CG initiates apoptosis in cancer cells by augmenting the basal oxidative stress and that the generation of intracellular ROS is crucial for the induction of apoptosis. PMID:26338072

  12. Storage behavior of Chionanthus retusus seed and asynchronous development of the radicle and shoot apex during germination in relation to germination inhibitors, including abscisic acid and four phenolic glucosides.

    PubMed

    Chien, Ching-Te; Kuo-Huang, Ling-Long; Shen, Ya-Ching; Zhang, Ruichuan; Chen, Shun-Ying; Yang, Jeng-Chuann; Pharis, Richard P

    2004-09-01

    Studies on seed storage of Chionanthus retusus Lindl. & Paxt. revealed an orthodox behavior, one which showed both desiccation and freezing tolerance. An epicotyl after-ripening dormancy was expressed in C. retusus seeds by slow growth of the shoot apex relative to more rapid growth of the radicle when seeds were germinated at 30/20 degrees C. Although these seeds exhibit radicle protrusion, they must be after-ripened for another 8-10 weeks at 30/20 degrees C in order to obtain normal shoot growth. Removal of the endosperm, however, quickly stimulated cotyledon and shoot emergence without the additional after-ripening. Water-soluble glucoside phenolics, GL-3, Nuzhenide, ligustroside and oleoside dimethyl ester are present at relatively high levels in endosperm of freshly harvested seeds. These glucoside phenolics are excreted from the endosperm during subsequent after-ripening. Embryo and endosperm tissue from seed germinating at 30/20 degrees C (germination being defined by protrusion of the radicle) had a 10 times lower abscisic acid (ABA) content than similar tissues from freshly harvested mature seed. However, no shoot growth occurred even with the 10-fold reduction in ABA and a concomitant increase in endogenous gibberellins A1, A4 and A20. Thus, epicotyl dormancy during the first 8 weeks of after-ripening at 30/20 degrees C may be controlled by factors other than high ABA, i.e., the slow development of the shoot apex following radicle protrusion may be controlled more by high levels of glucoside phenolics than by diminished ABA and elevated GA levels.

  13. Determination of free and glucosidically-bound volatiles in plants. Two case studies: L-menthol in peppermint (Mentha x piperita L.) and eugenol in clove (Syzygium aromaticum (L.) Merr. & L.M.Perry).

    PubMed

    Sgorbini, Barbara; Cagliero, Cecilia; Pagani, Alberto; Sganzerla, Marla; Boggia, Lorenzo; Bicchi, Carlo; Rubiolo, Patrizia

    2015-09-01

    This study arises from both the today's trend towards exploiting plant resources exhaustively, and the wide quantitative discrepancy between the amounts of commercially-valuable markers in aromatic plants and those recovered from the related essential oil. The study addresses the determination of both the qualitative composition and the exhaustive distribution of free and glucosidically-bound L-menthol in peppermint aerial parts (Mentha x piperita L., Lamiaceae) and of eugenol in dried cloves (Syzygium aromaticum (L.) Merr. & L.M.Perry, Myrtaceae), two plants known to provide widely ranging essential oil yields. The two markers were investigated in essential oils and residual hydrodistillation waters, before and after enzymatic hydrolysis. Their amounts were related to those in the headspace taken as reference. The results showed that the difference between marker compound in headspace and in essential oil amounted to 22.8% for L-menthol in peppermint, and 16.5% for eugenol in cloves. The aglycones solubilised in the residual hydrodistillation waters were 7.2% of the headspace reference amount for L-menthol, and 13.3% for eugenol, respectively representing 9.3% and 15.9% of their amounts in the essential oil. The amount of L-menthol from its glucoside in residual hydrodistillation waters was 20.6% of that in the related essential oil, while eugenol from its glucoside accounted for 7.7% of the amount in clove essential oil. The yield of L-menthol, after submitting the plant material to enzymatic hydrolysis before hydrodistillation, increased by 23.1%, and for eugenol the increase was 8.1%, compared to the amount in the respective conventional essential oils. This study also aimed to evaluate the reliability of recently-introduced techniques that are little applied, if at all, in this field. The simultaneous use of high-concentration-capacity sample preparation techniques (SBSE, and HS-SPME and in-solution SPME) to run quali-quantitative analysis without sample

  14. Determination of free and glucosidically-bound volatiles in plants. Two case studies: L-menthol in peppermint (Mentha x piperita L.) and eugenol in clove (Syzygium aromaticum (L.) Merr. & L.M.Perry).

    PubMed

    Sgorbini, Barbara; Cagliero, Cecilia; Pagani, Alberto; Sganzerla, Marla; Boggia, Lorenzo; Bicchi, Carlo; Rubiolo, Patrizia

    2015-09-01

    This study arises from both the today's trend towards exploiting plant resources exhaustively, and the wide quantitative discrepancy between the amounts of commercially-valuable markers in aromatic plants and those recovered from the related essential oil. The study addresses the determination of both the qualitative composition and the exhaustive distribution of free and glucosidically-bound L-menthol in peppermint aerial parts (Mentha x piperita L., Lamiaceae) and of eugenol in dried cloves (Syzygium aromaticum (L.) Merr. & L.M.Perry, Myrtaceae), two plants known to provide widely ranging essential oil yields. The two markers were investigated in essential oils and residual hydrodistillation waters, before and after enzymatic hydrolysis. Their amounts were related to those in the headspace taken as reference. The results showed that the difference between marker compound in headspace and in essential oil amounted to 22.8% for L-menthol in peppermint, and 16.5% for eugenol in cloves. The aglycones solubilised in the residual hydrodistillation waters were 7.2% of the headspace reference amount for L-menthol, and 13.3% for eugenol, respectively representing 9.3% and 15.9% of their amounts in the essential oil. The amount of L-menthol from its glucoside in residual hydrodistillation waters was 20.6% of that in the related essential oil, while eugenol from its glucoside accounted for 7.7% of the amount in clove essential oil. The yield of L-menthol, after submitting the plant material to enzymatic hydrolysis before hydrodistillation, increased by 23.1%, and for eugenol the increase was 8.1%, compared to the amount in the respective conventional essential oils. This study also aimed to evaluate the reliability of recently-introduced techniques that are little applied, if at all, in this field. The simultaneous use of high-concentration-capacity sample preparation techniques (SBSE, and HS-SPME and in-solution SPME) to run quali-quantitative analysis without sample

  15. [Influence of metal ions on stability of 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside contained in Polygoni Multiflori Radix].

    PubMed

    Li, Rui-yu; Feng, Wu-wen; Li, Xiao-fei; Zhang, Ding-kun; Li, Chun-yu; Meng, Ya-kun; Bai, Zhao-fang; Song, Hai-bo; Du, Xiao-xi; Xia, Hou-lin; Wang, Jia-bo; Xiao, Xiao-he

    2016-01-01

    Decoction is one of the most commonly used dosage forms of traditional Chinese medicine. The stability of chemical constituents in decoction is closely related to the clinical efficacy and safety. There were few reports about the influence of metal ions in the stability of chemical constituents in traditional Chinese medicine. However, there is no evidence that metal ions in decoction water need to be controlled. In this study, 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside (THSG), one of the main constituents in Polygoni Multiflori Radix was studied. Ordinary tap water, deionized water, and water containing different metal ions were used to investigate and compare the influence on THSG. The results showed that after storage in a dark place at the room temperature for 10 days, the degradation of THSG was 7% in deionized water, while undetectable in tap water. The content of THSG could be decreased by different kinds of metal ions, and the effect was concentration-dependent. Moreover, Fe3+ and Fe2+ showed the greatest influence at the same concentration; and our study has shown that THSG decreased more than 98% in Fe and Fe2+ solutions at 500 ppm concentration. In the same time we found out p-hydroxybenzaldehyde (molecular weight: 122.036 7) and 2,3,5-trihydroxybenzaldehyde-2-O-glycoside (molecular weight: 316.079 4) were the main degradation products of THSG in tap water and water containing Cu2+, Ca2+, Zn2+, Mg2+ and Al3+. The product of THSG dimer with a water molecule was found in water containing Fe3+ and Fe2+. The above results showed that the metal ions in water could significantly influence the stability of THSG in water, indicating that the clinical efficacy and safety of decoction would be affected if the metal ions in water were not under control. It's suggested that deionized water should be used in the preparation of decoction containing Polygoni Multiflori Radix in the clinic to avoid degradation of THSG. Meanwhile, decoction prepared by tap water

  16. [Influence of metal ions on stability of 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside contained in Polygoni Multiflori Radix].

    PubMed

    Li, Rui-yu; Feng, Wu-wen; Li, Xiao-fei; Zhang, Ding-kun; Li, Chun-yu; Meng, Ya-kun; Bai, Zhao-fang; Song, Hai-bo; Du, Xiao-xi; Xia, Hou-lin; Wang, Jia-bo; Xiao, Xiao-he

    2016-01-01

    Decoction is one of the most commonly used dosage forms of traditional Chinese medicine. The stability of chemical constituents in decoction is closely related to the clinical efficacy and safety. There were few reports about the influence of metal ions in the stability of chemical constituents in traditional Chinese medicine. However, there is no evidence that metal ions in decoction water need to be controlled. In this study, 2,3,5,4'-tetrahydroxy stilbene-2-O-β-D-glucoside (THSG), one of the main constituents in Polygoni Multiflori Radix was studied. Ordinary tap water, deionized water, and water containing different metal ions were used to investigate and compare the influence on THSG. The results showed that after storage in a dark place at the room temperature for 10 days, the degradation of THSG was 7% in deionized water, while undetectable in tap water. The content of THSG could be decreased by different kinds of metal ions, and the effect was concentration-dependent. Moreover, Fe3+ and Fe2+ showed the greatest influence at the same concentration; and our study has shown that THSG decreased more than 98% in Fe and Fe2+ solutions at 500 ppm concentration. In the same time we found out p-hydroxybenzaldehyde (molecular weight: 122.036 7) and 2,3,5-trihydroxybenzaldehyde-2-O-glycoside (molecular weight: 316.079 4) were the main degradation products of THSG in tap water and water containing Cu2+, Ca2+, Zn2+, Mg2+ and Al3+. The product of THSG dimer with a water molecule was found in water containing Fe3+ and Fe2+. The above results showed that the metal ions in water could significantly influence the stability of THSG in water, indicating that the clinical efficacy and safety of decoction would be affected if the metal ions in water were not under control. It's suggested that deionized water should be used in the preparation of decoction containing Polygoni Multiflori Radix in the clinic to avoid degradation of THSG. Meanwhile, decoction prepared by tap water

  17. Cyanidin-3-glucoside inhibits UVB-induced oxidative damage and inflammation by regulating MAP kinase and NF-κB signaling pathways in SKH-1 hairless mice skin

    SciTech Connect

    Pratheeshkumar, Poyil; Son, Young-Ok; Wang, Xin; Divya, Sasidharan Padmaja; Joseph, Binoy; Hitron, John Andrew; Wang, Lei; Kim, Donghern; Yin, Yuanqin; Roy, Ram Vinod; Lu, Jian; Zhang, Zhuo; Wang, Yitao; and others

    2014-10-01

    Skin cancer is one of the most commonly diagnosed cancers in the United States. Exposure to ultraviolet-B (UVB) radiation induces inflammation and photocarcinogenesis in mammalian skin. Cyanidin-3-glucoside (C3G), a member of the anthocyanin family, is present in various vegetables and fruits especially in edible berries, and displays potent antioxidant and anticarcinogenic properties. In this study, we have assessed the in vivo effects of C3G on UVB irradiation induced chronic inflammatory responses in SKH-1 hairless mice, a well-established model for UVB-induced skin carcinogenesis. Here, we show that C3G inhibited UVB-induced skin damage and inflammation in SKH-1 hairless mice. Our results indicate that C3G inhibited glutathione depletion, lipid peroxidation and myeloperoxidation in mouse skin by chronic UVB exposure. C3G significantly decreased the production of UVB-induced pro-inflammatory cytokines, such as IL-6 and TNF-α, associated with cutaneous inflammation. Likewise, UVB-induced inflammatory responses were diminished by C3G as observed by a remarkable reduction in the levels of phosphorylated MAP kinases, Erk1/2, p38, JNK1/2 and MKK4. Furthermore, C3G also decreased UVB-induced cyclooxygenase-2 (COX-2), PGE{sub 2} and iNOS levels, which are well-known key mediators of inflammation and cancer. Treatment with C3G inhibited UVB-induced nuclear translocation of NF-κB and degradation of IκBα in mice skin. Immunofluorescence assay revealed that topical application of C3G inhibited the expression of 8-hydroxy-2′-deoxyguanosine, proliferating cell nuclear antigen, and cyclin D1 in chronic UVB exposed mouse skin. Collectively, these data indicates that C3G can provide substantial protection against the adverse effects of UVB radiation by modulating UVB-induced MAP kinase and NF-κB signaling pathways. - Highlights: • C3G inhibited UVB-induced oxidative damage and inflammation. • C3G inhibited UVB-induced COX-2, iNOS and PGE{sub 2} production. • C3G

  18. Calycosin-7-O-β-d-glucoside attenuates ischemia-reperfusion injury in vivo via activation of the PI3K/Akt pathway

    PubMed Central

    REN, MIN; WANG, XUDONG; DU, GUOQING; TIAN, JIAWEI; LIU, YUJIE

    2016-01-01

    The aim of the present study was to investigate the effects and mechanisms of calycosin-7-O-β-d-glucoside (CG) on ischemia-reperfusion (I/R) injury in vivo. Hemodynamic parameters, including ejection fraction (EF), fractional shortening (FS), left ventricular end-systolic pressure (LVESP) and left ventricular end-diastolic pressure (LVEDP) were monitored using an ultrasound system, and infarct size was measured using Evans blue/tetrazolium chloride double staining. The activities of serum creatine kinase (CK), lactate dehydrogenase (LDH) and superoxide dismutase (SOD), and the levels of malondialdehyde (MDA) were determined to assess the degree of myocardial injury and oxidative stress-induced damage. The protein expression levels of cleaved-caspase-3, cleaved-caspase-9, phosphorylated (p)-phosphatidylinositol 3-kinase (PI3K) p85, PI3K p85, p-Akt and Akt were determined using western blotting. The results demonstrated that pretreatment with high dose (H)-CG markedly improved cardiac function, as evidenced by upregulated EF, FS and LVESP, and downregulated LVEDP. In addition, administration of CG resulted in significant decreases in infarct size in the I/R+low dose-CG and I/R+H-CG groups, compared with the I/R group. The activities of CK and LDH, and the levels of MDA in the I/R+H-CG group were reduced, compared with those in the I/R group, whereas SOD activity was elevated. Treatment with CG inhibited the cleavage and activity of caspase-3 and caspase-9, and enhanced the phosphorylation of PI3K p85 and Akt. Notably, administration of the PI3K inhibitor, LY294002, markedly lowered the levels of p-PI3K p85/p-Akt, and eradicated the inhibitory effects of H-CG on infarct size, myocardial injury and oxidative stress-induced damage. Taken together, the results suggested that CG may alleviate I/R injury by activating the PI3K/Akt signaling pathway. PMID:26648122

  19. The inhibitory effect of luteolin-7-O-glucoside on the formation of pentyl and 7-carboxyheptyl radicals from 13-hydroperoxy-9,11-octadecadienoic acid in the presence of iron(II) ions.

    PubMed

    Iwahashi, Hideo; Akata, Kayo; Sunaga, Atsuko; Tone, Yoshiko; Yamada, Noriko; Iijima, Keiko

    2004-08-01

    A flavone glucoside, luteolin-7-O-glucoside (luteolin-7-G) inhibited the formation of pentyl and 7-carboxyheptyl radicals in the reaction of 13-hydroperoxy-9,11-octadecadienoic (13-HPODE) acid with iron(II) ions. The inhibitory effect of luteolin-7-G was diminished in the presence of EDTA. These results indicated that the inhibitory effects of luteolin-7-G occur partly through the chelation of iron ions. Measurement of visible spectra also showed that luteolin-7-G chelates iron ions. On the other hand, luteolin-7-G did not inhibit the reaction under anaerobic conditions, suggesting that oxygen molecules participate in the inhibition. Oxygen consumption measurements showed that the luteolin-7-G/iron ion complexes react with oxygen molecules in competition with 13-HPODE acid, and free iron ions exclusively react with 13-HPODE acid. The reaction of luteolin-7-G/iron ion complexes with oxygen molecules possibly diminishes the formation of pentyl and 7-carboxyheptyl radicals. PMID:15493461

  20. Rapid separation of cyanidin-3-glucoside and cyanidin-3-rutinoside from crude mulberry extract using high-performance countercurrent chromatography and establishment of a volumetric scale-up process.

    PubMed

    Choi, Soo-Jung; Choi, Janggyoo; Lee, Chang Uk; Yoon, Shin Hee; Bae, Soo Kyung; Chin, Young-Won; Kim, Jinwoong; Yoon, Kee Dong

    2015-06-01

    This study describes the rapid separation of mulberry anthocyanins; namely, cyanidin-3-glucoside and cyanidin-3-rutinoside, using high-performance countercurrent chromatography, and the establishment of a volumetric scale-up process from semi-preparative to preparative-scale. To optimize the separation parameters, biphasic solvent systems composed of tert-butyl methyl ether/n-butanol/acetonitrile/0.01% trifluoroacetic acid, flow rate, sample amount and rotational speed were evaluated for the semi-preparative-scale high-performance countercurrent chromatography. The optimized semi-preparative-scale high-performance countercurrent chromatography parameters (tert-butyl methyl ether/n-butanol/acetonitrile/0.01% trifluoroacetic acid, 1:3:1:5, v/v; flow rate, 4.0 mL/min; sample amount, 200-1000 mg; rotational speed, 1600 rpm) were transferred directly to a preparative-scale (tert-butyl methyl ether/n-butanol/acetonitrile/0.01% trifluoroacetic acid, 1:3:1:5, v/v; flow rate, 28 mL/min; sample amount, 5.0-10.0 g; rotational speed, 1400 rpm) to achieve separation results identical to cyanidin-3-glucoside and cyanidin-3-rutinoside. The separation of mulberry anthocyanins using semi-preparative high-performance countercurrent chromatography and its volumetric scale-up to preparative-scale was addressed for the first time in this report. PMID:25800228

  1. Separation of flavanone enantiomers and flavanone glucoside diastereomers from Balanophora involucrata Hook. f. by capillary electrophoresis and reversed-phase high-performance liquid chromatography on a C18 column.

    PubMed

    Pan, Jianyu; Zhang, Si; Yan, Liushui; Tai, Jiandong; Xiao, Qiang; Zou, Kun; Zhou, Yuan; Wu, Jun

    2008-03-21

    A pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-5-O-beta-d-glucopyranoside (1a, 1b), was successfully separated by RP-C(18) high-performance liquid chromatography from Balanophora involucrata Hook. f. Some other compounds, including a pair of flavanone enantiomers, (2R)- and (2S)-eriodictyol (2a, 2b), and a pair of flavanone glucoside diastereomers, (2R)- and (2S)-eriodictyol-7-O-beta-d-glucopyranoside(3a, 3b), were separated by capillary electrophoresis from the same plant. The absolute configurations at C-2 of 1a and 1b were determined based on their circular dichroism spectra. Enzymatic hydrolysis of 1a and 1b by beta-d-glucosidase afforded (2R)- and (2S)-eriodictyol, respectively, which were used as the authentic standards for co-elution to determine the migration order of the enantiomers, 2a and 2b. We also report the first example of identifying the migration order of 2a and 2b and resolving the separation of 3a and 3b by capillary electrophoresis. In addition, 1a was unambiguously characterized for the first time by NMR spectra.

  2. Evidence on the Molecular Basis of the Ac/ac Adaptive Cyanogenesis Polymorphism in White Clover (Trifolium repens L.)

    PubMed Central

    Olsen, Kenneth M.; Hsu, Shih-Chung; Small, Linda L.

    2008-01-01

    White clover is polymorphic for cyanogenesis, with both cyanogenic and acyanogenic plants occurring in nature. This chemical defense polymorphism is one of the longest-studied and best-documented examples of an adaptive polymorphism in plants. It is controlled by two independently segregating genes: Ac/ac controls the presence/absence of cyanogenic glucosides; and Li/li controls the presence/absence of their hydrolyzing enzyme, linamarase. Whereas Li is well characterized at the molecular level, Ac has remained unidentified. Here we report evidence that Ac corresponds to a gene encoding a cytochrome P450 of the CYP79D protein subfamily (CYP79D15), and we describe the apparent molecular basis of the Ac/ac polymorphism. CYP79D orthologs catalyze the first step in cyanogenic glucoside biosynthesis in other cyanogenic plant species. In white clover, Southern hybridizations indicate that CYP79D15 occurs as a single-copy gene in cyanogenic plants but is absent from the genomes of ac plants. Gene-expression analyses by RT–PCR corroborate this finding. This apparent molecular basis of the Ac/ac polymorphism parallels our previous findings for the Li/li polymorphism, which also arises through the presence/absence of a single-copy gene. The nature of these polymorphisms may reflect white clover's evolutionary origin as an allotetraploid derived from cyanogenic and acyanogenic diploid progenitors. PMID:18458107

  3. Red palm oil-supplemented and biofortified gari on the carotenoid and retinyl palmitate concentrations of triacylglycerol-rich plasma of women

    Technology Transfer Automated Retrieval System (TEKTRAN)

    Boiled biofortified cassava containing ß-carotene (BC) can increase retinyl palmitate (RP) in triacylglycerol (TAG)-rich plasma. Thus, it might alleviate vitamin A deficiency. Cassava requires extensive preparation to decrease its level of cyanogenic glucosides, which can be fatal. Garification ...

  4. Ionic liquids-lithium salts pretreatment followed by ultrasound-assisted extraction of vitexin-4″-O-glucoside, vitexin-2″-O-rhamnoside and vitexin from Phyllostachys edulis leaves.

    PubMed

    Hou, Kexin; Chen, Fengli; Zu, Yuangang; Yang, Lei

    2016-01-29

    An efficient method for the extraction of vitexin, vitexin-4″-O-glucoside, and vitexin-2″-O-rhamnoside from Phyllostachys edulis leaves comprises heat treatment using an ionic liquid-lithium salt mixture (using 1-butyl-3-methylimidazolium bromide as the solvent and lithium chloride as the additive), followed by ultrasound-assisted extraction. To obtain higher extraction yields, the effects of the relevant experimental parameters (including heat treatment temperature and time, relative amounts of 1-butyl-3-methylimidazolium bromide and lithium chloride, power and time of the ultrasound irradiation, and the liquid-solid ratio) are evaluated and response surface methodology is used to optimize the significant factors. The morphologies of the treated and untreated P. edulis leaves are studied by scanning electron microscopy. The improved extraction method proposed provides high extraction yield, good repeatability and precision, and has wide potential applications in the analysis of plant samples. PMID:26763300

  5. Ionic liquids-lithium salts pretreatment followed by ultrasound-assisted extraction of vitexin-4″-O-glucoside, vitexin-2″-O-rhamnoside and vitexin from Phyllostachys edulis leaves.

    PubMed

    Hou, Kexin; Chen, Fengli; Zu, Yuangang; Yang, Lei

    2016-01-29

    An efficient method for the extraction of vitexin, vitexin-4″-O-glucoside, and vitexin-2″-O-rhamnoside from Phyllostachys edulis leaves comprises heat treatment using an ionic liquid-lithium salt mixture (using 1-butyl-3-methylimidazolium bromide as the solvent and lithium chloride as the additive), followed by ultrasound-assisted extraction. To obtain higher extraction yields, the effects of the relevant experimental parameters (including heat treatment temperature and time, relative amounts of 1-butyl-3-methylimidazolium bromide and lithium chloride, power and time of the ultrasound irradiation, and the liquid-solid ratio) are evaluated and response surface methodology is used to optimize the significant factors. The morphologies of the treated and untreated P. edulis leaves are studied by scanning electron microscopy. The improved extraction method proposed provides high extraction yield, good repeatability and precision, and has wide potential applications in the analysis of plant samples.

  6. Identification and Quantification of Oxidoselina-1,3,7(11)-Trien-8-One and Cyanidin-3-Glucoside as One of the Major Volatile and Non-Volatile Low-Molecular-Weight Constituents in Pitanga Pulp

    PubMed Central

    Ehrnhöfer-Ressler, Miriam Margit; Walker, Jessica; Montenegro Brasil, Isabella; Somoza, Veronika

    2015-01-01

    The pulp of pitanga (Eugenia uniflora L.) is used to prepare pitanga juice. However, there are no reports on the identification and quantification of the main constituents in pitanga pulp. The aim of this study was to identify and quantify the major volatile and non-volatile low-molecular-weight constituents of the pulp. Isolation of volatile compounds was performed by solvent-assisted flavor evaporation technique. Characterization of the main volatile and non-volatile constituents was performed by GC-MS, LC-MS and NMR spectroscopy. For quantitative measurements, the main volatile compound needed to be isolated from pitanga pulp to obtain a commercially not available reference standard. Cyanidin-3-glucoside was determined as one of the most abundant non-volatile pulp compound yielding 53.8% of the sum of the intensities of all ions detected by LC-MS. Quantification of cyanidin-3-glucoside in pitanga pulp resulted in a concentration of 344 ± 66.4 μg/mL corresponding to 688 ± 133 μg/g dried pulp and 530 ± 102 μg/g fruit. For the volatile fraction, oxidoselina-1,3,7(11)-trien-8-one was identified as the main volatile pulp constituent (27.7% of the sum of the intensities of all ions detected by GC-MS), reaching a concentration of 89.0 ± 16.9 μg/mL corresponding to 1.34 ± 0.25 μg/g fresh pulp and 1.03 ± 0.19 μg/g fruit. The results provide quantitative evidence for the occurrence of an anthocyanin and an oxygenated sesquiterpene as one of the major volatile and non-volatile low-molecular-weight compounds in pitanga pulp. PMID:26394146

  7. Purification from Fusobacterium mortiferum ATCC 25557 of a 6-phosphoryl-O-alpha-D-glucopyranosyl:6-phosphoglucohydrolase that hydrolyzes maltose 6-phosphate and related phospho-alpha-D-glucosides.

    PubMed Central

    Thompson, J; Gentry-Weeks, C R; Nguyen, N Y; Folk, J E; Robrish, S A

    1995-01-01

    6-Phosphoryl-O-alpha-D-glucopyranosyl:6-phosphoglucohydrolase (6-phospho-alpha-glucosidase) has been purified from Fusobacterium mortiferum ATCC 25557. p-Nitrophenyl-alpha-D-glucopyranoside 6-phosphate (pNP alpha Glc6P) served as the chromogenic substrate for detection and assay of enzyme activity. The O2-sensitive, metal-dependent phospho-alpha-glucosidase was stabilized during purification by inclusion of dithiothreitol and Mn2+ ion in chromatography buffers. Various 6-phosphoryl-O-alpha-linked glucosides, including maltose 6-phosphate, pNP alpha Glc6P, trehalose 6-phosphate, and sucrose 6-phosphate, were hydrolyzed by the enzyme to yield D-glucose 6-phosphate and aglycone moieties in a 1:1 molar ratio. 6-Phospho-alpha-glucosidase (M(r) of approximately 49,000; pI of approximately 4.9) is activated by Fe2+, Mn2+, Co2+, and Ni2+, and the maximum rate of pNP alpha Glc6P hydrolysis occurs at 40 degrees C within the pH range 7.0 to 7.5. The sequence of the first 32 amino acids of 6-phospho-alpha-glucosidase exhibits 67% identity (90% similarity) to that deduced for the N terminus of a putative phospho-beta-glucosidase (designated ORF f212) encoded by glvG in Escherichia coli. Western blots involving highly specific polyclonal antibody against 6-phospho-alpha-glucosidase and spectrophotometric analyses with pNP alpha Glc6P revealed only low levels of the enzyme in glucose-, mannose-, or fructose-grown cells of F. mortiferum. Synthesis of 6-phospho-alpha-glucosidase increased dramatically during growth of the organism on alpha-glucosides, such as maltose, alpha-methylglucoside, trehalose, turanose, and palatinose. PMID:7730284

  8. Influence of biotransformation of luteolin, luteolin 7-O-glucoside, 3',4'-dihydroxyflavone and apigenin by cultured rat hepatocytes on antioxidative capacity and inhibition of EGF receptor tyrosine kinase activity.

    PubMed

    Schlupper, Doreen; Giesa, Sabine; Gebhardt, Rolf

    2006-06-01

    Flavonoids are known as biologically active compounds. Although this has been shown by several in vivo studies, it is still elusive whether their metabolites exert similar activities. Herein we investigated the biotransformation of four different flavonoids, 3',4'-dihydroxyflavone, apigenin, luteolin and luteolin 7-O-glucoside, by cultured rat hepatocytes using a combination of enzymatic deconjugation, HPLC separation and high-resolution mass spectrometry. These flavonoids were chosen because they are active components of many plants, e. g., artichokes. All flavonoids showed rather complex metabolite patterns dominated by phase II metabolites, mainly sulfates, methyl sulfates and methyl glucuronides, but also of combined glucuronide and sulfate conjugates. Phase I metabolism by hydroxylation was rendered likely only for apigenin to form luteolin. When culture media containing the flavonoids and their metabolites were assayed for antioxidative capacity by the DPPH assay, only compounds with hydroxy groups in position 3' and 4' of the B ring were active. Thus, during metabolism of (inactive) apigenin a strong increase in the antioxidative effect was observed while that of the other three flavonoids decreased with time. Determination of EGF receptor tyrosine kinase activity likewise revealed strong inhibition in the presence of a catechol group at ring B. However, in this case the situation was much more complex resulting in a significant increase of the inhibitory activity of 3',4'-dihydroxyflavone and apigenin, but not of luteolin and luteolin 7-O-glucoside during 22 h of incubation. These results show that the biotransformation of flavonoids is very complex and may result not only in a loss but also in a gain of biological activity depending on the individual structural features. PMID:16732514

  9. Identification and Quantification of Oxidoselina-1,3,7(11)-Trien-8-One and Cyanidin-3-Glucoside as One of the Major Volatile and Non-Volatile Low-Molecular-Weight Constituents in Pitanga Pulp.

    PubMed

    Josino Soares, Denise; Pignitter, Marc; Ehrnhöfer-Ressler, Miriam Margit; Walker, Jessica; Montenegro Brasil, Isabella; Somoza, Veronika

    2015-01-01

    The pulp of pitanga (Eugenia uniflora L.) is used to prepare pitanga juice. However, there are no reports on the identification and quantification of the main constituents in pitanga pulp. The aim of this study was to identify and quantify the major volatile and non-volatile low-molecular-weight constituents of the pulp. Isolation of volatile compounds was performed by solvent-assisted flavor evaporation technique. Characterization of the main volatile and non-volatile constituents was performed by GC-MS, LC-MS and NMR spectroscopy. For quantitative measurements, the main volatile compound needed to be isolated from pitanga pulp to obtain a commercially not available reference standard. Cyanidin-3-glucoside was determined as one of the most abundant non-volatile pulp compound yielding 53.8% of the sum of the intensities of all ions detected by LC-MS. Quantification of cyanidin-3-glucoside in pitanga pulp resulted in a concentration of 344 ± 66.4 μg/mL corresponding to 688 ± 133 μg/g dried pulp and 530 ± 102 μg/g fruit. For the volatile fraction, oxidoselina-1,3,7(11)-trien-8-one was identified as the main volatile pulp constituent (27.7% of the sum of the intensities of all ions detected by GC-MS), reaching a concentration of 89.0 ± 16.9 μg/mL corresponding to 1.34 ± 0.25 μg/g fresh pulp and 1.03 ± 0.19 μg/g fruit. The results provide quantitative evidence for the occurrence of an anthocyanin and an oxygenated sesquiterpene as one of the major volatile and non-volatile low-molecular-weight compounds in pitanga pulp.

  10. The cometary flourescence spectrum of cyanogen: A model

    NASA Technical Reports Server (NTRS)

    Kleine, Marvin; Wyckoff, Susan; Wehinger, Peter A.; Peterson, Bruce A.

    1994-01-01

    We present a model to compute flourescence spectra of the stable isotopes of CN in the comae of comets. The effects of collisions are included and shown to be significant as a mechanism secondary to the flourescence process in the calculations. Our computed spectra are compared with high-resolution spectra of the B2 sigma(+)-X2 sigma(+) (0-0) band for comets Halley, Austin, and Levy. This comparison shows that collisonal effects are observable in the CN spectra of relatively high production rate comets, such as Halley and Levy. Moreover, the model confirms that the overall structure of the CN spectra in comets results predominantly from pure flourescence governed by the Swings effect. The primary goal of our model is to provide a methodology to compute accurate rotational line flourescence efficiencies for the stable isotopes of CN: (12)C(14)N, (13)C(14)N, and (12)C(15)N. The flourescence efficiencies are required to convert observed isotope line intensity ratios to isotope abundance ratios of carbons and nitrogen in comets.

  11. Cyanogenic Pseudomonads Influence Multitrophic Interactions in the Rhizosphere

    PubMed Central

    Rudrappa, Thimmaraju; Splaine, Robert E.; Biedrzycki, Meredith L.; Bais, Harsh P.

    2008-01-01

    In the rhizosphere, plant roots cope with both pathogenic and beneficial bacterial interactions. The exometabolite production in certain bacterial species may regulate root growth and other root-microbe interactions in the rhizosphere. Here, we elucidated the role of cyanide production in pseudomonad virulence affecting plant root growth and other rhizospheric processes. Exposure of Arabidopsis thaliana Col-0 seedlings to both direct (with KCN) and indirect forms of cyanide from different pseudomonad strains caused significant inhibition of primary root growth. Further, we report that this growth inhibition was caused by the suppression of an auxin responsive gene, specifically at the root tip region by pseudomonad cyanogenesis. Additionally, pseudomonad cyanogenesis also affected other beneficial rhizospheric processes such as Bacillus subtilis colonization by biofilm formation on A. thaliana Col-0 roots. The effect of cyanogenesis on B. subtilis biofilm formation was further established by the down regulation of important B. subtilis biofilm operons epsA and yqxM. Our results show, the functional significance of pseudomonad cyanogenesis in regulating multitrophic rhizospheric interactions. PMID:18446201

  12. Partial amino acid sequence and mRNA analysis of cytosolic pyridoxine-beta-D-glucoside hydrolase from porcine intestinal mucosa: proposed derivation from the lactase-phlorizin hydrolase gene.

    PubMed

    Tseung, Chi-Wah; McMahon, Laura G; Vázquez, Jorge; Pohl, Jan; Gregory, Jesse F

    2004-05-15

    We have previously identified and purified a novel beta-glucosidase, designated PNGH (pyridoxine-5'-beta-D-glucoside hydrolase), from the cytosolic fraction of pig intestinal mucosal. PNGH catalyses the hydrolysis of PNG (pyridoxine-5'-beta-D-glucoside), a plant derivative of vitamin B6 that exhibits partial nutritional bioavailability in humans and animals. Preliminary amino acid sequence analysis indicated regions of close similarity of PNGH to the precursor form of LPH (lactase-phlorizin hydrolase), the beta-glucosidase localized to the brush-border membrane. We report in the present study amino acid sequence data for PNGH and results of Northern blot analyses, upon which we propose a common genomic origin of PNGH and LPH. Internal Edman sequencing of the PNGH band isolated by SDS/PAGE yielded data for 16 peptides, averaging 10.8 amino acids in length. These peptides from PNGH (approx. 140 kDa) were highly similar to sequences existing over most of the length of the >200 kDa precursor of rabbit LPH; however, we found no PNGH sequences that corresponded to approx. 350 amino acids between positions 463 and 812 of the LPH precursor, a region encoded by exon 7 of the LPH precursor gene (amino acids 568-784), and no sequences that corresponded to regions near the N-terminus. MS analysis of tryptic peptides yielded 25 peptides, averaging 15 amino acids, with masses that matched segments of the rabbit LPH precursor. Northern blot analysis of pig and human small intestinal polyadenylated mRNA using a non-specific LPH cDNA probe showed an expected approx. 6 kb transcript of the LPH precursor, but also an approx. 4 kb transcript that was consistent with the size predicted from the PNGH protein mass. Using a probe specific to the region encoded by exon 7, hybridization occurred only with the 6 kb transcript. Based on these observations, we propose that both PNGH and LPH enzymes have the same genomic origin, but differ in transcriptional and, possibly, post

  13. A Double-Blind, 12-Week Study to Evaluate the Antiaging Efficacy of a Cream Containing the NFκB Inhibitor 4-Hexyl-1, 3-Phenylenediol and Ascorbic Acid-2 Glucoside in Adult Females.

    PubMed

    Roure, Romain; Nollent, Virginie; Dayan, Liliane; Camel, Etienne; Bertin, Christiane

    2016-06-01

    The 5 main physical manifestations of aged skin are wrinkles, uneven tone, brown spots, loss of elasticity, and dryness. One mechanism resulting in these physical manifestations is increased activity of the nuclear factor kappa B (NFκB) protein. This 12-week, double-blind, placebo-controlled, randomized split-face study compared the antiaging effect and safety of a face cream containing 4-Hexyl-1, 3-phenylenediol, an NFκB inhibitor, and ascorbic acid-2 glucoside versus placebo in adult females aged 45-70 years old. Subjects (n=42) applied active treatment or placebo to the same half face twice daily at home for 12 weeks. Clinical evaluation was carried out by a dermatologist. Subjects carried out similar self-grading assessments. Colorimetric measurements analyzed skin color, and biomechanical skin properties were evaluated. Clinical grading showed that most wrinkle parameters were significantly improved after 8 weeks of active treatment compared with baseline and placebo (P≤.05), with improvements maintained after 12 weeks. Only Marionette wrinkles did not show a significant improvement. Brown spots (color intensity/number), overall photodamage, and most complexion parameters improved significantly after 8 and 12 weeks compared with baseline and placebo (P≤.05). Self-grading yielded similar results compared with baseline. Self-grading did not demonstrate improvements with active treatment versus placebo, except for skin firmness at 8 and 12 weeks (P≤.05). A significant difference was seen with active treatment compared with placebo in all colorimetric parameters (L*, b*, and ITA°) after 8 weeks, and in spot coloration (b*) after 12 weeks (P<.05). Improvements in skin elasticity were not significantly different between treatments. Overall tolerability of active treatment was judged as good. In conclusion, a cream containing 4-Hexyl-1, 3-phenylenediol and ascorbic acid-2 glucoside improves the clinical appearance of aged

  14. Partial amino acid sequence and mRNA analysis of cytosolic pyridoxine-beta-D-glucoside hydrolase from porcine intestinal mucosa: proposed derivation from the lactase-phlorizin hydrolase gene.

    PubMed

    Tseung, Chi-Wah; McMahon, Laura G; Vázquez, Jorge; Pohl, Jan; Gregory, Jesse F

    2004-05-15

    We have previously identified and purified a novel beta-glucosidase, designated PNGH (pyridoxine-5'-beta-D-glucoside hydrolase), from the cytosolic fraction of pig intestinal mucosal. PNGH catalyses the hydrolysis of PNG (pyridoxine-5'-beta-D-glucoside), a plant derivative of vitamin B6 that exhibits partial nutritional bioavailability in humans and animals. Preliminary amino acid sequence analysis indicated regions of close similarity of PNGH to the precursor form of LPH (lactase-phlorizin hydrolase), the beta-glucosidase localized to the brush-border membrane. We report in the present study amino acid sequence data for PNGH and results of Northern blot analyses, upon which we propose a common genomic origin of PNGH and LPH. Internal Edman sequencing of the PNGH band isolated by SDS/PAGE yielded data for 16 peptides, averaging 10.8 amino acids in length. These peptides from PNGH (approx. 140 kDa) were highly similar to sequences existing over most of the length of the >200 kDa precursor of rabbit LPH; however, we found no PNGH sequences that corresponded to approx. 350 amino acids between positions 463 and 812 of the LPH precursor, a region encoded by exon 7 of the LPH precursor gene (amino acids 568-784), and no sequences that corresponded to regions near the N-terminus. MS analysis of tryptic peptides yielded 25 peptides, averaging 15 amino acids, with masses that matched segments of the rabbit LPH precursor. Northern blot analysis of pig and human small intestinal polyadenylated mRNA using a non-specific LPH cDNA probe showed an expected approx. 6 kb transcript of the LPH precursor, but also an approx. 4 kb transcript that was consistent with the size predicted from the PNGH protein mass. Using a probe specific to the region encoded by exon 7, hybridization occurred only with the 6 kb transcript. Based on these observations, we propose that both PNGH and LPH enzymes have the same genomic origin, but differ in transcriptional and, possibly, post

  15. Esculetin and esculin (esculetin 6-O-glucoside) occur as inclusions and are differentially distributed in the vacuole of palisade cells in Fraxinus ornus leaves: a fluorescence microscopy analysis.

    PubMed

    Tattini, Massimiliano; Di Ferdinando, Martina; Brunetti, Cecilia; Goti, Andrea; Pollastri, Susanna; Bellasio, Chandra; Giordano, Cristiana; Fini, Alessio; Agati, Giovanni

    2014-11-01

    The location of individual coumarins in leaves of Fraxinus ornus acclimated at full solar irradiance was estimated using their specific UV- and fluorescence spectral features. Using a combination of UV-induced fluorescence and blue light-induced fluorescence of tissues stained with diphenylborinic acid 2-amino-ethylester, in wide field or confocal laser scanning microscopy, we were able to visualize the distribution of esculetin and esculetin 6-O-glucoside (esculin) in palisade cells. Coumarins are not uniformly distributed in the cell vacuole, but accumulate mostly in the adaxial portion of palisade cells. Our study indeed shows, for the first time, that coumarins in palisade cells accumulate as vacuolar inclusions, as previously reported in the pertinent literature only for anthocyanins. Furthermore, esculetin and esculin have a different vacuolar distribution: esculetin largely predominates in the first 15 μm from the adaxial epidermis. This leads to hypothesize for esculetin and esculin different transport mechanisms from the endoplasmic reticulum to the vacuole as well as potentially different roles in photoprotection. Our study open to new experiments aimed at exploring the mechanisms that deliver coumarins to the vacuole using different fluorescence signatures of coumarin aglycones and coumarin glycosides.

  16. Antiasthmatic activity of luteolin-7-O-glucoside from Ailanthus altissima through the downregulation of T helper 2 cytokine expression and inhibition of prostaglandin E2 production in an ovalbumin-induced asthma model.

    PubMed

    Jin, Meihua; Yang, Ju Hye; Lee, Eunkyung; Lu, Yue; Kwon, Soonyoul; Son, Kun Ho; Son, Jong Keun; Chang, Hyeun Wook

    2009-09-01

    Previously, we reported that an ethanol extract of Ailanthus altissima has antiinflammatory activity in an ovalbumin (OVA)-sensitized murine asthmatic model. To determine the biological compounds from this plant, luteolin-7-O-glucoside (L7G) was isolated and its antiasthmatic activity was evaluated in an in vivo murine asthmatic model. L7G (10 to 100 mg/kg, per os (p.o.)) reduced the amount of eosinophil infiltration in bronchoalveolar lavage (BAL) fluid in a dose-dependent manner. In comparison, dexamethasone (5 mg/kg, p.o.), which was used as a positive control, also strongly inhibited the number of infiltrating eosinophils. L7G inhibited both the prostaglandin E(2) (PGE(2)) and serum immunoglobulin E level in BAL fluid in a dose-dependent manner. In addition, L7G inhibited the transcript profiles of interleukin (IL)-4, IL-5, and IL-13 mRNA expression levels in the murine asthma model, as determined using reverse transcription-polymerase chain reaction (RT-PCR). These results suggest that the antiasthmatic activity of L7G in OVA-induced lung inflammation may occur in part via the downregulation of T helper 2 cytokine transcripts as well as the inhibition of PGE(2) production.

  17. TSG (2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside) from the Chinese Herb Polygonum multiflorum Increases Life Span and Stress Resistance of Caenorhabditis elegans

    PubMed Central

    Büchter, Christian; Zhao, Liang; Fritz, Gerhard; Proksch, Peter

    2015-01-01

    2,3,5,4′-Tetrahydroxystilbene-2-O-β-D-glucoside (TSG) was isolated from Polygonum multiflorum, a plant which is traditionally used as an anti-ageing drug. We have analysed ageing-related effects of TSG in the model organism C. elegans in comparison to resveratrol. TSG exerted a high antioxidative capacity both in a cell-free assay and in the nematode. The antioxidative capacity was even higher compared to resveratrol. Presumably due to its antioxidative effects, treatment with TSG decreased the juglone-mediated induction of the antioxidative enzyme SOD-3; the induction of the GST-4 by juglone was diminished slightly. TSG increased the resistance of C. elegans against lethal thermal stress more prominently than resveratrol (50 μM TSG increased mean survival by 22.2%). The level of the ageing pigment lipofuscin was decreased after incubation with the compound. TSG prolongs the mean, median, and maximum adult life span of C. elegans by 23.5%, 29.4%, and 7.2%, respectively, comparable to the effects of resveratrol. TSG-mediated extension of life span was not abolished in a DAF-16 loss-of-function mutant strain showing that this ageing-related transcription factor is not involved in the effects of TSG. Our data show that TSG possesses a potent antioxidative capacity, enhances the stress resistance, and increases the life span of the nematode C. elegans. PMID:26075030

  18. Transcriptional Profiling and Molecular Characterization of Astragalosides, Calycosin, and Calycosin-7-O-β-D-glucoside Biosynthesis in the Hairy Roots of Astragalus membranaceus in Response to Methyl Jasmonate.

    PubMed

    Tuan, Pham Anh; Chung, Eunsook; Thwe, Aye Aye; Li, Xiaohua; Kim, Yeon Bok; Mariadhas, Valan Arasu; Al-Dhabi, Naif Abdullah; Lee, Jai-Heon; Park, Sang Un

    2015-07-15

    We used the next-generation Illumina/Solexa HiSeq2000 platform on RNA analysis to investigate the transcriptome of Astragalus membranaceus hairy roots in response to 100 μM methyl jasmonate (MeJA). In total, 77,758,230 clean reads were assembled into 48,636 transcripts (average length of 1398 bp), which were clustered into 23,658 loci (genes). Of these, 19,940 genes were annotated by BLASTx searches. In addition, DESeq analysis showed that 2127 genes were up-regulated, while 1247 genes were down-regulated by MeJA. Seventeen novel astragaloside (AST) biosynthetic genes and seven novel calycosin and calycosin-7-O-β-D-glucoside (CG) biosynthetic genes were isolated. The accumulation of ASTs, calycosin, and CG increased significantly in MeJA-treated hairy roots compared with control hairy roots. Our findings will provide a valuable resource for molecular characterization of AST, calycosin, and CG biosynthetic pathways and may lead to new approaches to maximize their production and biomass productivity in the hairy roots of A. membranaceus.

  19. Maesopsin 4-O-beta-D-glucoside, a natural compound isolated from the leaves of Artocarpus tonkinensis, inhibits proliferation and up-regulates HMOX1, SRXN1 and BCAS3 in acute myeloid leukemia.

    PubMed

    Pozzesi, N; Pierangeli, S; Vacca, C; Falchi, L; Pettorossi, V; Martelli, M P; Thuy, T T; Ninh, P T; Liberati, A M; Riccardi, C; Sung, T V; Delfino, D V

    2011-06-01

    The leaves of Artocarpus tonkinensis are used in Vietnamese traditional medicine for treatment of arthritis, and the compound maesopsin 4-O-β-D-glucoside (TAT-2), isolated from them, inhibits the proliferation of activated T cells. Our goal was to test the anti-proliferative activity of TAT-2 on the T-cell leukemia, Jurkat, and on the acute myeloid leukemia, OCI-AML. TAT-2 inhibited the growth of OCI-AML (and additional acute myeloid leukemia cells) but not Jurkat cells. Growth inhibition was shown to be due to inhibition of proliferation rather than increase in cell death. Analysis of cytokine release showed that TAT-2 stimulated the release of TGF-β, yet TGF-β neutralization did not reverse the maesopsin-dependent effect. Gene expression profiling determined that maesopsin modulated 19 identifiable genes. Transcription factor CP2 was the gene most significantly modulated. Real-time PCR validated that up-regulation of sulphiredoxin 1 homolog (SRXN1), hemeoxygenase 1 (HMOX1), and breast carcinoma amplified sequence 3 (BCAS3) were consistently modulated.

  20. Antiasthmatic activity of luteolin-7-O-glucoside from Ailanthus altissima through the downregulation of T helper 2 cytokine expression and inhibition of prostaglandin E2 production in an ovalbumin-induced asthma model.

    PubMed

    Jin, Meihua; Yang, Ju Hye; Lee, Eunkyung; Lu, Yue; Kwon, Soonyoul; Son, Kun Ho; Son, Jong Keun; Chang, Hyeun Wook

    2009-09-01

    Previously, we reported that an ethanol extract of Ailanthus altissima has antiinflammatory activity in an ovalbumin (OVA)-sensitized murine asthmatic model. To determine the biological compounds from this plant, luteolin-7-O-glucoside (L7G) was isolated and its antiasthmatic activity was evaluated in an in vivo murine asthmatic model. L7G (10 to 100 mg/kg, per os (p.o.)) reduced the amount of eosinophil infiltration in bronchoalveolar lavage (BAL) fluid in a dose-dependent manner. In comparison, dexamethasone (5 mg/kg, p.o.), which was used as a positive control, also strongly inhibited the number of infiltrating eosinophils. L7G inhibited both the prostaglandin E(2) (PGE(2)) and serum immunoglobulin E level in BAL fluid in a dose-dependent manner. In addition, L7G inhibited the transcript profiles of interleukin (IL)-4, IL-5, and IL-13 mRNA expression levels in the murine asthma model, as determined using reverse transcription-polymerase chain reaction (RT-PCR). These results suggest that the antiasthmatic activity of L7G in OVA-induced lung inflammation may occur in part via the downregulation of T helper 2 cytokine transcripts as well as the inhibition of PGE(2) production. PMID:19721222

  1. Mechanisms of membrane protein insertion into liposomes during reconstitution procedures involving the use of detergents. 1. Solubilization of large unilamellar liposomes (Prepared by reverse-phase evaporation) by Triton X-100 octyl glucoside, and sodium cholate

    SciTech Connect

    Paternostre, M.T.; Roux, M.; Rigaud, J.L.

    1988-04-19

    The mechanisms governing the solubilization by Triton X-100, octyl glucoside, and sodium cholate of large unilamellar liposomes prepared by reverse-phase evaporation were investigated. The solubilization process is described by the three-stage model previously proposed for the detergents. In stage I, detergent monomers are incorporated into the phospholipid bilayers until they saturate the liposomes. At this point, i.e., stage II, mixed phospholipid-detergent micelles begin to form. By stage III, the lamellar to micellar transition is complete and all the phospholipids are present as mixed micelles. The turbidity of liposome preparations was systematically measured as a function of the amount of detergent added for a wide range of phospholipid concentrations. The results allowed a quantitative determination of the effective detergent to lipid molar ratios in the saturated liposomes. The monomer concentrations of the three detergents in the aqueous phase were also determined at the lamellar to micellar transitions. These transitions were also investigated by /sup 31/P NMR spectroscopy, and complete agreement was found with turbidity measurements. Freeze-fracture electron microscopy and permeability studies in the sublytic range of detergent concentrations indicated that during stage I of solubilization detergent partitioning between the aqueous phase and the lipid bilayer greatly affects the basic permeability of the liposomes without significantly changing the morphology of the preparations. A rough approximation of the partition coefficients was derived from the turbidity and permeability data. It is concluded that when performed systematically, turbidity measurements constitute a very convenient and powerful technique for the quantitative study of the liposome solubilization process by detergents.

  2. Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).

    PubMed

    Masuzaki, S; Shigyo, M; Yamauchi, N

    2006-02-01

    The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum-shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum-shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin formation. The multiple alien additions were selected from the crossing between allotriploid FFA (female symbol) and A. fistulosum (male symbol). The 113 plants obtained from this cross were analysed by a chromosome 5A-specific PGI isozyme marker of shallot. Thirty plants were preliminarily selected for an alien addition carrying 5A. The chromosome numbers of the 30 plants varied from 18 to 23. The other extrachromosomes in 19 plants were completely identified by using seven other chromosome markers of shallot. High-performance liquid chromatography analyses of the 19 multiple additions were conducted to identify the flavonoid compounds produced in the scaly leaves. Direct comparisons between the chromosomal constitution and the flavonoid contents of the multiple alien additions revealed that a flavonoid 3'-hydroxylase (F3'H) gene for the synthesis of quercetin from kaempferol was located on 7A and that an anonymous gene involved in the glucosidation of quercetin was on 3A or 4A. As a result of supplemental SCAR analyses by using genomic DNAs from two complete sets of A. fistulosum-shallot monosomic additions, we have assigned F3'H to 7A and flavonol synthase to 4A.

  3. Direct comparison between genomic constitution and flavonoid contents in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.).

    PubMed

    Masuzaki, S; Shigyo, M; Yamauchi, N

    2006-02-01

    The extrachromosome 5A of shallot (Allium cepa L., genomes AA) has an important role in flavonoid biosynthesis in the scaly leaf of Allium fistulosum-shallot monosomic addition lines (FF+nA). This study deals with the production and biochemical characterisation of A. fistulosum-shallot multiple alien addition lines carrying at least 5A to determine the chromosomal locations of genes for quercetin formation. The multiple alien additions were selected from the crossing between allotriploid FFA (female symbol) and A. fistulosum (male symbol). The 113 plants obtained from this cross were analysed by a chromosome 5A-specific PGI isozyme marker of shallot. Thirty plants were preliminarily selected for an alien addition carrying 5A. The chromosome numbers of the 30 plants varied from 18 to 23. The other extrachromosomes in 19 plants were completely identified by using seven other chromosome markers of shallot. High-performance liquid chromatography analyses of the 19 multiple additions were conducted to identify the flavonoid compounds produced in the scaly leaves. Direct comparisons between the chromosomal constitution and the flavonoid contents of the multiple alien additions revealed that a flavonoid 3'-hydroxylase (F3'H) gene for the synthesis of quercetin from kaempferol was located on 7A and that an anonymous gene involved in the glucosidation of quercetin was on 3A or 4A. As a result of supplemental SCAR analyses by using genomic DNAs from two complete sets of A. fistulosum-shallot monosomic additions, we have assigned F3'H to 7A and flavonol synthase to 4A. PMID:16411131

  4. Protective effects of 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside in the MPTP-induced mouse model of Parkinson's disease: Involvement of reactive oxygen species-mediated JNK, P38 and mitochondrial pathways.

    PubMed

    He, Hong; Wang, Songhai; Tian, Jiyu; Chen, Lei; Zhang, Wei; Zhao, Junjie; Tang, Haifeng; Zhang, Xiaojun; Chen, Jianzong

    2015-11-15

    Parkinson's disease (PD) is characterized by the selective death of dopaminergic neurons in the substantia nigra pars compacta. Oxidative stress-induced neuron loss is thought to play a crucial role in the pathogenesis of PD. Previous work from our group suggests that 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (TSG), an active component extracted from a traditional Chinese herb, Polygonum multiflorum thunb, can attenuate 1-methyl-4-phenyl pyridium-induced apoptosis in the neuronal cell line PC12, by inhibiting reactive oxygen species generation and modulating c-Jun N-terminal kinases (JNK) activation. Here, we investigated the protective effects of TSG against 1-methyl-4-phenyl-1,2,3,6-tetrahydropypridine (MPTP)-induced loss of tyrosine hydroxylase positive cells in mice and the underlying mechanisms. The results showed that MPTP-induced loss of tyrosine hydroxylase positive cells and reactive oxygen species generation were prevented by TSG in a dose-dependent manner. The reactive oxygen species scavenger N-acetylcysteine could also mitigate reactive oxygen species generation. Moreover, JNK and P38 were activated by MPTP, but extracellular signal-regulated protein kinases phosphorylation did not change after MPTP treatment. TSG at different doses blocked the activation of JNK and P38. The protective effect of TSG was also associated with downregulation of the bax/bcl-2 ratio, reversed the release of cytochrome c and smac, and inhibited the activation of caspase-3, -6, and -9 induced by MPTP. In conclusion, our studies demonstrated that the protective effects of TSG in the MPTP-induced mouse model of PD are involved, at least in part, in controlling reactive oxygen species-mediated JNK, P38, and mitochondrial pathways.

  5. Protective effects of 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside in the MPTP-induced mouse model of Parkinson's disease: Involvement of reactive oxygen species-mediated JNK, P38 and mitochondrial pathways.

    PubMed

    He, Hong; Wang, Songhai; Tian, Jiyu; Chen, Lei; Zhang, Wei; Zhao, Junjie; Tang, Haifeng; Zhang, Xiaojun; Chen, Jianzong

    2015-11-15

    Parkinson's disease (PD) is characterized by the selective death of dopaminergic neurons in the substantia nigra pars compacta. Oxidative stress-induced neuron loss is thought to play a crucial role in the pathogenesis of PD. Previous work from our group suggests that 2,3,5,4'-tetrahydroxystilbene-2-O-β-D-glucoside (TSG), an active component extracted from a traditional Chinese herb, Polygonum multiflorum thunb, can attenuate 1-methyl-4-phenyl pyridium-induced apoptosis in the neuronal cell line PC12, by inhibiting reactive oxygen species generation and modulating c-Jun N-terminal kinases (JNK) activation. Here, we investigated the protective effects of TSG against 1-methyl-4-phenyl-1,2,3,6-tetrahydropypridine (MPTP)-induced loss of tyrosine hydroxylase positive cells in mice and the underlying mechanisms. The results showed that MPTP-induced loss of tyrosine hydroxylase positive cells and reactive oxygen species generation were prevented by TSG in a dose-dependent manner. The reactive oxygen species scavenger N-acetylcysteine could also mitigate reactive oxygen species generation. Moreover, JNK and P38 were activated by MPTP, but extracellular signal-regulated protein kinases phosphorylation did not change after MPTP treatment. TSG at different doses blocked the activation of JNK and P38. The protective effect of TSG was also associated with downregulation of the bax/bcl-2 ratio, reversed the release of cytochrome c and smac, and inhibited the activation of caspase-3, -6, and -9 induced by MPTP. In conclusion, our studies demonstrated that the protective effects of TSG in the MPTP-induced mouse model of PD are involved, at least in part, in controlling reactive oxygen species-mediated JNK, P38, and mitochondrial pathways. PMID:26477638

  6. Determination of deoxynivalenol and deoxynivalenol-3-glucoside in wheat and barley using liquid chromatography coupled to mass spectrometry: on-line clean-up versus conventional sample preparation techniques.

    PubMed

    Nathanail, Alexis V; Sarikaya, Ebru; Jestoi, Marika; Godula, Michal; Peltonen, Kimmo

    2014-12-29

    In this study, we compared the performance of conventional sample preparation techniques used in mycotoxin analyses against automated on-line sample clean-up for the determination of deoxynivalenol (DON) and its conjugated derivative, deoxynivalenol-3-β-d-glucoside (D3G), in cereal grains. Blank wheat and barley samples were spiked with DON and D3G, extracted with a mixture of acetonitrile:water (84:16, v/v) and processed by one of the following: extract and shoot, MycoSep(®) 227 clean-up columns, MycoSep 227 with an additional acetonitrile elution step and centrifugal filtration, followed by analysis with liquid chromatography tandem mass spectrometry. Based on method performance characteristics and poor recoveries (<30%) obtained for the polar D3G with some techniques, the extract and shoot approach was chosen for the inter-laboratory method comparison study. Thus, the same spiked samples were analysed in parallel by another laboratory with an in-house validated on-line sample clean-up method, utilising TurboFlow™ chromatography coupled to high resolution mass spectrometry. Method validation was performed by determination of specificity, linearity, recovery, intra-day precision and the limits of detection and quantification. Matrix-matched linearity (R(2)>0.985) was established in the range of 100-1600 and 20-320μg/kg for DON and D3G, respectively. Average recoveries (%RSD) were acceptable with both methods for wheat and barley, ranging between 73% and 102% (3-12%) for DON and 72% and 98% (1-10%) for D3G. The benefit of using automated sample clean-up in comparison to extract and shoot is the ability to inject directly pure extracts into the mass spectrometer, offering faster analyses and improved sensitivity with minimum system maintenance.

  7. A 3D-RISM-SCF method with dual solvent boxes for a highly polarized system: application to 1,6-anhydrosugar formation reaction of phenyl α- and β-D-glucosides under basic conditions.

    PubMed

    Aono, Shinji; Hosoya, Takashi; Sakaki, Shigeyoshi

    2013-05-01

    One of the difficulties in application of the usual reference interaction site model self-consistent field (RISM-SCF) method to a highly polarized and bulky system arises from the approximate evaluation of electrostatic potential (ESP) with pure point charges. To improve this ESP evaluation, the ESP near a solute is directly calculated with a solute electronic wavefunction, that distant from a solute is approximately calculated with solute point charges, and they are connected with a switching function. To evaluate the fine solvation structure near the solute by incorporating the long-range solute-solvent Coulombic interaction with low computational cost, we introduced the dual solvent box protocol; one small box with the fine spacing is employed for the first and the second solvation shells and the other large box with the normal spacing is employed for long-range solute-solvent interaction. The levoglucosan formation from phenyl α- and β-d-glucosides under basic conditions is successfully inspected by this 3D-RISM-SCF method at the MP2 and SCS-MP2 levels, though the 1D-RISM-SCF could not be applied to this reaction due to the presence of highly polarized and bulky species. This 3D-RISM-SCF calculation reproduces the experimentally reported higher reactivity of the β-anomer. The 3D-RISM-SCF-calculated activation free energy for the β-anomer is closer to the experimental value than the PCM-calculated one. Interestingly, the solvation effect increases the difference in reactivity between these two anomers. The reason is successfully elucidated with 3D-RISM-SCF-calculated microscopic solvation structure and decomposition analysis of solute-solvent interaction.

  8. A New Lignan Glucoside from Lagochilus ilicifolius

    PubMed Central

    Jing-Shi, Qian; Cheng-Gang, Zhang; Wei, Wang; Ting, Zhang; Hong, Xu; Gui-Xin, Chou

    2015-01-01

    Background: The whole herb of Lagochilus ilicifolius has been used as a folk medicine for treating hemostatic, inflammation and ulcer in China. There were only limited reports on its chemical constituents, and no reports on its pharmacology study. Objective: To isolate compounds from the whole herb of L. ilicifolius and evaluate their cytotoxic activity. Materials and Methods: The column chromatographic techniques were used for separating the constituents of the n-butanol-soluble fraction of the 95% ethanol extract from the whole plant of L. ilicifolius. The structures of one new lignan and two known lignans were elucidated on the basis of spectroscopic analyses and comparison with literature data. The cytotoxic activities of these three lignans were evaluated using the MTT-assay against PC12 cell line derived from rat adrenal pheochromocytoma. Results: The new lignan was identified as erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol (1), and two known lignans were identified as tortoside C (2) and sisymbrifolin (3). The new lignan exhibited significant cytotoxic activity against PC12 cell line with IC50 value of 1.22 ± 0.03 μmol/L. Conclusions: A new lignan, erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol and two known lignans were isolated from the whole herbs of L. ilicifolius. The two known lignans were reported for the first time in the genus Lagochilus. Three lignans were evaluated for in vitro cytotoxic activity. The new lignan showed relatively strong cytotoxicity against PC12 cell line, while sisymbrifolin and tortoside C exibited no cytotoxicity. PMID:25709232

  9. Three new monoterpene glucosides from Sibiraea angustata.

    PubMed

    Yao, Zhengzheng; Liu, Hongdong; Xu, Xianghong; Chen, Xiaotian; Zhang, Dongming; Lai, Xuewen; Xu, Peng; Li, Bin

    2016-11-01

    Three new monoterpene glycosides, named sibiraglycoside I(1), J(2) and K(3), were isolated from an aqueous extract of the aerial portion of Sibiraea angustata. Their structures were elucidated on the basis of extensive spectroscopic data analysis (including 1D and 2D NMR and MS experiments) and compared to literature data. PMID:27348708

  10. Lepidopteran defence droplets - a composite physical and chemical weapon against potential predators

    PubMed Central

    Pentzold, Stefan; Zagrobelny, Mika; Khakimov, Bekzod; Engelsen, Søren Balling; Clausen, Henrik; Petersen, Bent Larsen; Borch, Jonas; Møller, Birger Lindberg; Bak, Søren

    2016-01-01

    Insects often release noxious substances for their defence. Larvae of Zygaena filipendulae (Lepidoptera) secrete viscous and cyanogenic glucoside-containing droplets, whose effectiveness was associated with their physical and chemical properties. The droplets glued mandibles and legs of potential predators together and immobilised them. Droplets were characterised by a matrix of an aqueous solution of glycine-rich peptides (H-WG11-NH2) with significant amounts of proteins and glucose. Among the proteins, defensive proteins such as protease inhibitors, proteases and oxidases were abundant. The neurotoxin β-cyanoalanine was also found in the droplets. Despite the presence of cyanogenic glucosides, which release toxic hydrogen cyanide after hydrolysis by a specific β-glucosidase, the only β-glucosidase identified in the droplets (ZfBGD1) was inactive against cyanogenic glucosides. Accordingly, droplets did not release hydrogen cyanide, unless they were mixed with specific β-glucosidases present in the Zygaena haemolymph. Droplets secreted onto the cuticle hardened and formed sharp crystalline-like precipitates that may act as mandible abrasives to chewing predators. Hardening followed water evaporation and formation of antiparallel β-sheets of the peptide oligomers. Consequently, after mild irritation, Zygaena larvae deter predators by viscous and hardening droplets that contain defence proteins and β-cyanoalanine. After severe injury, droplets may mix with exuding haemolymph to release hydrogen cyanide. PMID:26940001

  11. Taxiphyllin 6'-O-gallate, actinidioionoside 6'-O-gallate and myricetrin 2″-O-sulfate from the leaves of Syzygium samarangense and their biological activities.

    PubMed

    Samy, Mamdouh Nabil; Mamdouh, Nabil Samy; Sugimoto, Sachiko; Matsunami, Katsuyoshi; Otsuka, Hideaki; Kamel, Mohamed Salah

    2014-01-01

    Three new compounds were isolated from a MeOH extract of the leaves of Syzygium samarangense, one new cyanogenic glucoside, taxiphyllin 6'-O-gallate (1), one new megastigmane glucoside, actinidioionoside 6'-O-gallate (2), and one new sulfated flavonoid rhamnoside, myricetrin 2″-O-sulfate (3), together with 14 known compounds, lupeol (4), demethoxymatteucinol (5), cryptostrobin (6), betulinic acid (7), β-sitosterol glucoside (8), 2R-prunasin (9), myrciaphenone A (10), 1-feruloyl-β-D-glucopyranoside (11), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxymegastigman-7-ene (12), guaijaverin (13), myricetin 4'-methyl ether 3-O-α-L-rhamnopyranoside (14), myricetrin (15), gallic acid (16) and actinidioionoside (17). The structures of the new compounds were determined through a combination of spectroscopic, HPLC and chemical analyses.

  12. Adaptive gains through repeated gene loss: parallel evolution of cyanogenesis polymorphisms in the genus Trifolium (Fabaceae).

    PubMed

    Olsen, Kenneth M; Kooyers, Nicholas J; Small, Linda L

    2014-08-01

    Variation in cyanogenesis (hydrogen cyanide release following tissue damage) was first noted in populations of white clover more than a century ago, and subsequent decades of research have established this system as a classic example of an adaptive chemical defence polymorphism. Here, we document polymorphisms for cyanogenic components in several relatives of white clover, and we determine the molecular basis of this trans-specific adaptive variation. One hundred and thirty-nine plants, representing 13 of the 14 species within Trifolium section Trifoliastrum, plus additional species across the genus, were assayed for cyanogenic components (cyanogenic glucosides and their hydrolysing enzyme, linamarase) and for the presence of underlying cyanogenesis genes (CYP79D15 and Li, respectively). One or both cyanogenic components were detected in seven species, all within section Trifoliastrum; polymorphisms for the presence/absence (PA) of components were detected in six species. In a pattern that parallels our previous findings for white clover, all observed biochemical polymorphisms correspond to gene PA polymorphisms at CYP79D15 and Li. Relationships of DNA sequence haplotypes at the cyanogenesis loci and flanking genomic regions suggest independent evolution of gene deletions within species. This study thus provides evidence for the parallel evolution of adaptive biochemical polymorphisms through recurrent gene deletions in multiple species.

  13. A gene horizontally transferred from bacteria protects arthropods from host plant cyanide poisoning

    PubMed Central

    Wybouw, Nicky; Dermauw, Wannes; Tirry, Luc; Stevens, Christian; Grbić, Miodrag; Feyereisen, René; Van Leeuwen, Thomas

    2014-01-01

    Cyanogenic glucosides are among the most widespread defense chemicals of plants. Upon plant tissue disruption, these glucosides are hydrolyzed to a reactive hydroxynitrile that releases toxic hydrogen cyanide (HCN). Yet many mite and lepidopteran species can thrive on plants defended by cyanogenic glucosides. The nature of the enzyme known to detoxify HCN to β-cyanoalanine in arthropods has remained enigmatic. Here we identify this enzyme by transcriptome analysis and functional expression. Phylogenetic analysis showed that the gene is a member of the cysteine synthase family horizontally transferred from bacteria to phytophagous mites and Lepidoptera. The recombinant mite enzyme had both β-cyanoalanine synthase and cysteine synthase activity but enzyme kinetics showed that cyanide detoxification activity was strongly favored. Our results therefore suggest that an ancient horizontal transfer of a gene originally involved in sulfur amino acid biosynthesis in bacteria was co-opted by herbivorous arthropods to detoxify plant produced cyanide. DOI: http://dx.doi.org/10.7554/eLife.02365.001 PMID:24843024

  14. The effect of microbial starter composition on cassava chips fermentation for the production of fermented cassava flour

    NASA Astrophysics Data System (ADS)

    Kresnowati, M. T. A. P.; Listianingrum, Zaenudin, Ahmad; Trihatmoko, Kharisrama

    2015-12-01

    The processing of cassava into fermented cassava flour (fercaf) or the widely known as modified cassava flour (mocaf) presents an alternative solution to improve the competitiveness of local foods and to support national food security. However, the mass production of fercaf is being limited by several problems, among which is the availability of starter cultures. This paper presents the mapping of the effect of microbial starter compositions on the nutritional content of fercaf in order to obtain the suitable nutritional composition. Based on their enzymatic activities, the combination of Lactobacillus plantarum, Bacillus subtilis, and Aspergillus oryzae were tested during the study. In addition, commercial starter was also tested. During the fermentation, the dynamics in microbial population were measured as well as changes in cyanogenic glucoside content. The microbial starter composition was observed to affect the dynamics in microbial populationcynaogenic glucoside content of the produced fercaf. In general, steady state microbial population was reached within 12 hours of fermentation. Cyanogenic glucoside was observed to decrease along the fermentation.

  15. A gene horizontally transferred from bacteria protects arthropods from host plant cyanide poisoning.

    PubMed

    Wybouw, Nicky; Dermauw, Wannes; Tirry, Luc; Stevens, Christian; Grbić, Miodrag; Feyereisen, René; Van Leeuwen, Thomas

    2014-04-24

    Cyanogenic glucosides are among the most widespread defense chemicals of plants. Upon plant tissue disruption, these glucosides are hydrolyzed to a reactive hydroxynitrile that releases toxic hydrogen cyanide (HCN). Yet many mite and lepidopteran species can thrive on plants defended by cyanogenic glucosides. The nature of the enzyme known to detoxify HCN to β-cyanoalanine in arthropods has remained enigmatic. Here we identify this enzyme by transcriptome analysis and functional expression. Phylogenetic analysis showed that the gene is a member of the cysteine synthase family horizontally transferred from bacteria to phytophagous mites and Lepidoptera. The recombinant mite enzyme had both β-cyanoalanine synthase and cysteine synthase activity but enzyme kinetics showed that cyanide detoxification activity was strongly favored. Our results therefore suggest that an ancient horizontal transfer of a gene originally involved in sulfur amino acid biosynthesis in bacteria was co-opted by herbivorous arthropods to detoxify plant produced cyanide.DOI: http://dx.doi.org/10.7554/eLife.02365.001.

  16. Interstellar cyanogen and the temperature of the cosmic microwave background radiation

    NASA Technical Reports Server (NTRS)

    Roth, Katherine C.; Meyer, David M.; Hawkins, Isabel

    1993-01-01

    We present the results of a recently completed effort to determine the amount of CN rotational excitation in five diffuse interstellar clouds for the purpose of accurately measuring the temperature of the cosmic microwave background radiation (CMBR). In addition, we report a new detection of emission from the strongest hyperfine component of the 2.64 mm CN rotational transition (N = 1-0) in the direction toward HD 21483. We have used this result in combination with existing emission measurements toward our other stars to correct for local excitation effects within diffuse clouds which raise the measured CN rotational temperature above that of the CMBR. After making this correction, we find a weighted mean value of T(CMBR) = 2.729 (+0.023, -0.031) K. This temperature is in excellent agreement with the new COBE measurement of 2.726 +/- 0.010 K (Mather et al., 1993). Our result, which samples the CMBR far from the near-Earth environment, attests to the accuracy of the COBE measurement and reaffirms the cosmic nature of this background radiation. From the observed agreement between our CMBR temperature and the COBE result, we conclude that corrections for local CN excitation based on millimeter emission measurements provide an accurate adjustment to the measured rotational excitation.

  17. CN radical reactions with hydrogen cyanide and cyanogen - Comparison of theory and experiment

    NASA Technical Reports Server (NTRS)

    Yang, D. L.; Yu, T.; Lin, M. C.; Melius, C. F.

    1992-01-01

    The method of laser photolysis/laser-induced fluorescence is used to obtain absolute rate constants for CN radical reactions with HCN and C2N2. The rate constants were found to be temperature-dependent in the range 300-740 K and pressure independent in the range 100-600 Torr. Rice-Remsperger-Kassel-Marcus theory for both reactions employing the transition state parameters obtained by the BAC-MP4 method are made. These calculations yielded reasonable results for the CN + HCN reaction, predicting both the temperature dependence and pressure independence. No pressure effect was observed in the pressure range 100-1000 Torr at temperatures below 900 K, confirming the experimental results.

  18. Cassava cyanogens and fish mercury are high but safely consumed in the diet of native Amazonians.

    PubMed

    Dórea, José G

    2004-03-01

    The two most important staple foods (cassava and fish) in the diet of native Amazonians contain neurotoxins (linamarin and monomethyl mercury, MMHg). These same neurotoxins are public health issues in other parts of the world. Factors such as chemistry, environment, and human ecology determine the endemism of neuropathies caused by consumption of cassava (Manihot esculenta Crantz) and fish. Linamarin is a natural component of cassava tubers that can be destroyed before consumption by proper processing. Furthermore, small amounts of the toxin absorbed by people consuming cassava can be effectively metabolized if the diet contains adequate protein-containing sulfur amino acids. Naturally occurring Hg in the waters of the Amazonian rain forest is methylated to MMHg by microorganisms and bioconcentrated in the aquatic food chain. There is no effective method for MMHg removal from fish. Despite high concentrations of naturally occurring neurotoxins in cassava (linamarin) and fish (MMHg), daily consumption of these foods in large amounts over the course of a lifetime poses no health hazards for Amazonians.

  19. Resilience of cassava (Manihot esculenta Crantz) to salinity: implications for food security in low-lying regions

    PubMed Central

    Gleadow, Ros; Pegg, Amelia; Blomstedt, Cecilia K.

    2016-01-01

    Rising sea levels are threatening agricultural production in coastal regions due to inundation and contamination of groundwater. The development of more salt-tolerant crops is essential. Cassava is an important staple, particularly among poor subsistence farmers. Its tolerance to drought and elevated temperatures make it highly suitable for meeting global food demands in the face of climate change, but its ability to tolerate salt is unknown. Cassava stores nitrogen in the form of cyanogenic glucosides and can cause cyanide poisoning unless correctly processed. Previous research demonstrated that cyanide levels are higher in droughted plants, possibly as a mechanism for increasing resilience to oxidative stress. We determined the tolerance of cassava to salt at two different stages of development, and tested the hypothesis that cyanide toxicity would be higher in salt-stressed plants. Cassava was grown at a range of concentrations of sodium chloride (NaCl) at two growth stages: tuber initiation and tuber expansion. Established plants were able to tolerate 100mM NaCl but in younger plants 40mM was sufficient to retard plant growth severely. Nutrient analysis showed that plants were only able to exclude sodium at low concentrations. The foliar cyanogenic glucoside concentration in young plants increased under moderate salinity stress but was lower in plants grown at high salt. Importantly, there was no significant change in the cyanogenic glucoside concentration in the tubers. We propose that the mechanisms for salinity tolerance are age dependent, and that this can be traced to the relative cost of leaves in young and old plants. PMID:27506218

  20. Cassava root diet induces low pyruvate levels.

    PubMed

    Golay, Van K

    2010-01-01

    The high cyanogenic-glucoside carbohydrate of the cassava root (Manihot esculenta) has special properties that make it an ideal therapeutic food for lowering nicotinamide adenine dinucleotide reduced form (NADH) and inducing Sirtuin (Sirt) gene overexpression when eaten in an exclusive mono-food diet regime. The author, using himself as the sole test subject, repeatedly induced low pyruvate levels (reflective of NADH levels) after being on the diet for 1-2 weeks at a time. The possible influences of exclusive cassava dieting on redox control and Sirtuin activation will be discussed. PMID:20462383