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Digital.CSIC (162.855 recursos)

Repositorio institucional del Consejo Superior de Investigaciones Científicas. Digital.CSIC es un depósito de documentos digitales, cuyo objetivo es organizar, archivar, preservar y difundir en modo de acceso abierto la producción intelectual resultante de la actividad investigadora del CSIC.

(IQOG) Artículos post-print

Mostrando recursos 1 - 20 de 27

  1. Use of room temperature ionic liquids for the selective fractionation of bioactive ketoses from aldoses

    Carrero-Carralero, Cipriano; Ruiz-Aceituno, Laura; Ramos, Lourdes; Sanz, M. Luz; Moreno, F. Javier
    This work deals with the effective fractionation of bioactive ketoses, i.e. lactulose and tagatose, from their corresponding aldoses, lactose and galactose, in equimolar binary mixtures driven by room temperature ionic liquids, i.e. 1-ethyl-3-methylimidazolium dicyanamide ([EMIM][DCA]) and 1-butyl-3-methylimidazolium methyl sulfate ([BMIM][MeSO4]), respectively. Under assayed conditions, tagatose was found to be 6-fold more soluble on [BMIM][MeSO4] than galactose; meanwhile lactulose was 3 times more soluble than lactose on [EMIM][DCA]. As an application example in a more complex sample, a lactose isomerization mixture containing in addition lactulose and monosaccharides was enriched in this ketose by using [EMIM][DCA]. Carbohydrates were then successfully recovered from...

  2. A metabolomic study in oats (Avena sativa) highlights a drought tolerance mechanism based upon salicylate signalling pathways and the modulation of carbon, antioxidant and photo-oxidative metabolism

    Sánchez-Martín, Javier; Heald, Jim; Kingston-Smith, Alison; Winters, Ana; Rubiales, Diego; Sanz, M. Luz; Mur, Luis A. J.; Prats, Elena
    Although a wealth of information is available on the induction of one or several drought-related responses in different species, little is known of how their timing, modulation and crucially integration influence drought tolerance. Based upon metabolomic changes in oat (Avena sativa L.), we have defined key processes involved in drought tolerance. During a time course of increasing water deficit, metabolites from leaf samples were profiled using direct infusion–electrospray mass spectroscopy (DI-ESI-MS) and high-performance liquid chromatography (HPLC) ESI-MS/MS and analysed using principal component analysis (PCA) and discriminant function analysis (DFA). The involvement of metabolite pathways was confirmed through targeted assays of key...

  3. Development of HuperTacrines as non-toxic, cholinesterase inhibitors for the potential treatment of Alzheimer’s disease

    Chioua, Mourad; Pérez, Marta M.; Bautista-Aguilera, Óscar M.; Yáñez, M.; López, M. G.; Romero, A.; Cacabelos, Ramón; Bellacasa, R. P. de la; Brogi, S.; Butini, S.; Borrell, J. I.; Marco-Contelles, José
    This paper describes our preliminary results on the ADMET, synthesis, biochemical evaluation, and molecular modeling of racemic HuperTacrines (HT), new hybrids resulting from the juxtaposition of huperzine A and tacrine for the potential treatment of Alzheimer’s disease (AD). The synthesis of these HT was executed by Friedländer-type reactions of 2-amino-6-oxo-1,6-dihydropyridine-3-carbonitriles, or 7-amino-2-oxo-1,2,3,4-tetrahydro-1,6-naphthyridine- 8-carbonitriles, with cyclohexanone. In the biochemical evaluation, initial and particular attention was devoted to test their toxicity on human hepatoma cells, followed by the in vitro inhibition of human cholinesterases (hAChE, and hBuChE), and the kinetics/mechanism of the inhibition of the most potent HT; simultaneous molecular modeling on...

  4. Synthetic approaches to heterocyclic guanidines with biological activity: An update

    Zárate, Sandra G.; Santana, Andrés G.; Bastida, Agatha; Revuelta, Julia
    The guanidine functional group is an important structural motif in synthesis with a wide range of interesting properties. Guanidines are frequently found in bioactive compounds; both from natural sources or from synthetic origin, these compounds are considered fundamental entities in medicinal chemistry. The relevance of these compounds fosters the efforts to explore new methodologies for the synthesis of substances based on the guanidine core. The aim of this review is to provide a survey of the types of reactions used to prepare these classes of compounds. Given the vast number of contributions to this topic, we have focused on the...

  5. Influence of chemical structure on the solubility of low molecular weight carbohydrates in room temperature ionic liquids

    Carrero-Carralero, Cipriano; Ruiz-Aceituno, Laura; Ramos, Lourdes; Moreno, F. Javier; Sanz, M. Luz
    The use of room temperature ionic liquids (ILs) as green solvents is an emerging and innovative technology, which is quickly expanding in carbohydrate chemistry. However, information about solubility of low molecular weight carbohydrates (LMWC) in ILs is still scarce. This study provides new solubility data for several LMWC dissolved in methylimidazolium-based ILs. Different solubility values have been obtained for carbohydrates depending on their structure. In general, ketoses are more soluble than their corresponding aldoses, and trisaccharides are more soluble than mono- and disaccharides, although some exceptions have been observed depending on the tested IL. [BMIM][MeSO4] and [HMIM][Cl] acted both as...

  6. Glycosides-bearing electrospun poly(hydroxybutyrate-co-hydroxyhexanoate) substrates for the repair of injured spinal cord | Sustratos electrohilados de poli(hidroxibutirato-co-hidroxihexanoato) con glicósidos para reparación de la lesión medular

    García-Álvarez, Isabel; Doncel-Pérez, Ernesto; García-Junceda, Eduardo; Fernández-Mayoralas, Alfonso; Garrido, Leoncio
    Objective: Preparation of functionalized micro- and submicrofibers by electrospinning of polyesters with glycosides which are structural elements of proteoglycans, for application to the repair of spinal cord lesions. Material and methods: Solutions of poly(3-hydroxybutyrate-co-3-hydroxyhexanoate) with synthetic glycosides were prepared varying systematically the processing conditions. Fiber morphology assessed by scanning electron microscopy. The stability of the interaction between the glycoside and the polymer fiber was evaluated in aqueous medium, and their toxicity in cultures of neural cells. Results: The fiber morphology was altered mainly by the solution parameters. In aqueous medium, the glycoside with a sulfate group was released from fibers...

  7. Neoglycoconjugates of caseinomacropeptide and galactooligosaccharides modify adhesion of intestinal pathogens and inflammatory response(s) of intestinal (Caco-2) cells

    Laparra, José Moisés; Hernández-Hernández, Oswaldo; Moreno, F. Javier; Sanz Herranz, Yolanda
    Dietary glycoconjugates may constitute new food ingredients with the potential ability to inhibit pathogen infection by blocking or competing for bacterial adhesion sites in intestinal cells. In this study, galactooligosaccharides, obtained from transgalactosylation of lactose (GOS-La) or lactulose (GOS-Lu), were used for the glycation of caseinomacropeptide hydrolysates (hCMP). The effects of these compounds on Salmonella enterica CECT 443 and Listeria monocytogenes CECT 935 adhesion, induction of inflammatory cytokines production, and >toll-like> (TLR)-2/4 and chemokine CXCR3 receptor expression (mRNA) in intestinal epithelial (Caco-2) cells were evaluated. hCMP:GOS-La or hCMP:GOS-Lu significantly reduced pathogen adhesion. GOS-Lu and hCMP:GOS-Lu inhibited the production of IL-1β...

  8. Monomer and linkage type of galacto-oligosaccharides affect their resistance to ileal digestion and prebiotic properties in rats

    Hernández-Hernández, Oswaldo; Marín-Manzano, M. Carmen; Rubio, Luis A.; Moreno, F. Javier; Sanz, M. Luz; Clemente, Alfonso
    A detailed study was performed to compare the in vivo ileal digestibility and modulatory effects in fecal microbiota of novel galacto-oligosaccharides (GOS) derived from lactulose [GOS-Lu; degree of polymerization (DP) ≥2, 14.0% trisaccharides] and commercial GOS derived from lactose (GOS-La; DP ≥3, 35.1% trisaccharides) in growing rats (5wk old). Rats were fed either a control diet or diets containing 1% (wt:wt) of GOS-Lu or GOS-La for 14 d. Quantitative analysis of carbohydrates from dietary and ileal samples demonstrated that the trisaccharide fraction of GOS-Lu was significantly more resistant to gut digestion than that from GOS-La, as indicated by their ileal...

  9. Hydrolyzed caseinomacropeptide conjugated galactooligosaccharides support the growth and enhance the bile tolerance in lactobacillus strains

    Muthaiyan, A.; Hernández-Hernández, Oswaldo; Moreno, F. Javier; Sanz, M. Luz; Ricke, S. C.
    In this study bioactive caseinomacropeptide was conjugated with prebiotic galactooligosaccharides (hCMP:GOS) by Maillard reaction to synthesize value added prebiotic compounds to Lactobacillus strains. Growth study showed the ability of hCMP:GOS to serve as a sole carbon source for Lactobacillus strains. A significant amount of acetate and lactate was detected in cell free culture supernatant by HPLC. It demonstrated the ability of Lactobacillus strains to ferment the hCMP:GOS as a carbon source. In addition, hCMP:GOS grown Lactobacillus cells exhibited enhanced bile tolerance and retained 90% viability. Overall results of this study indicate that the hCMP conjugated GOS can be potential multipurpose...

  10. Effects of conventional and ultrasound blanching on enzyme inactivation and carbohydrate content of carrots

    Gamboa-Santos, Juliana; Montilla, Antonia; Soria, Ana C.; Villamiel, Mar
    There is a growing interest in the use of ultrasound (US) as an alternative to conventional processes. Although US has previously been applied as a pretreatment of fruits and vegetables, no investigation has been done on the usefulness of US for carrot blanching, paying special attention to its effect on enzyme inactivation and leaching losses. In the present paper, the influence of US (in bath and with probe) on peroxidase (POD) and pectinmethylesterase (PME) inactivation and on the loss of total soluble solids and carbohydrates by leaching has been evaluated. Results of this preliminary study have also been compared with...

  11. Quality parameters in convective dehydrated carrots blanched by ultrasound and conventional treatment

    Gamboa-Santos, Juliana; Soria, Ana C.; Villamiel, Mar; Montilla, Antonia
    The effect of previous ultrasound and conventional blanching treatments on drying and quality parameters (2-furoylmethyl-amino acids -as indicators of lysine and arginine participation in the Maillard reaction-, carbohydrates, total polyphenols, protein profile, rehydration ratio, microstructure changes) of convective dehydrated carrots has been assessed. The most striking feature was the influence of blanching on the subsequent 2-furoylmethyl-amino acid formation during drying, probably due to changes in the protein structure. The highest values of 2-furoylmethyl-amino acids were found in carrots conventionally blanched with water at 95 °C for 5 min. However, samples previously treated by ultrasound presented intermediate values of 2-furoylmethyl-amino acids...

  12. Quality parameters in convective dehydrated carrots blanched by ultrasound and conventional treatment

    Gamboa-Santos, Juliana; Soria, Ana C.; Villamiel, Mar; Montilla, Antonia
    The effect of previous ultrasound and conventional blanching treatments on drying and quality parameters (2-furoylmethyl-amino acids -as indicators of lysine and arginine participation in the Maillard reaction-, carbohydrates, total polyphenols, protein profile, rehydration ratio, microstructure changes) of convective dehydrated carrots has been assessed. The most striking feature was the influence of blanching on the subsequent 2-furoylmethyl-amino acid formation during drying, probably due to changes in the protein structure. The highest values of 2-furoylmethyl-amino acids were found in carrots conventionally blanched with water at 95 °C for 5 min. However, samples previously treated by ultrasound presented intermediate values of 2-furoylmethyl-amino acids...

  13. Optimisation of convective drying of carrots using selected processing and quality indicators

    Gamboa-Santos, Juliana; Soria, Ana C.; Fornari, Tiziana; Villamiel, Mar; Montilla, Antonia
    The effect of drying temperature (40-65 °C) and air rate (2-6 m s-1) on the formation of Maillard reaction indicators and vitamins content of carrots dehydrated by convection has been investigated. The range of assayed processing conditions, based on a previous central composite face design (CCD), led to moderate changes in the studied parameters, even under the most severe conditions. In addition, the drying kinetic of the process was studied taking into account the experimental quantitation of shrinkage, which allowed the determination of a first drying period with a constant rate of water evaporation per unit of exchange surface. The...

  14. In vitro bifidogenic effect of Maillard-type milk protein-galactose conjugates on the human intestinal microbiota

    Corzo-Martínez, Marta; Hernández-Hernández, Oswaldo; Villamiel, Mar; Rastall, Robert A.; Moreno, F. Javier
    This work addresses the effect of sodium caseinate (SC) and β-lactoglobulin (β-Lg) glycosylated with galactose (Gal) via the Maillard reaction on the human intestinal microbiota, using small-scale in vitro batch cultures inoculated with human faeces. The glycation process was controlled to maximise formation of the corresponding Amadori compound, tagatosyl-lysine, a derivative of tagatose. Both glycoconjugates (SC:Gal and β-Lg:Gal) induced a significant increase in bifidobacteria, whilst Lactobacillus-Enterococcus, Clostridium histolyticum, Atopobium and Bacteroides populations were unmodified. Additionally, β-Lg:Gal glycoconjugate also significantly stimulated the growth of the Clostridium coccoides-Eubacterium rectal group. SC:Gal glycoconjugate gave rise to a significant increase in acetic acid concentration....

  15. Galacto-oligosaccharides derived from lactulose exert a selective stimulation on the growth of Bifidobacterium animalis in the large intestine of growing rats

    Marín-Manzano, M. Carmen; Abecia, L.; Hernández-Hernández, Oswaldo; Sanz, M. Luz; Montilla, Antonia; Olano, Agustín; Rubio, Luis A.; Moreno, F. Javier; Clemente, Alfonso
    There is increasing interest in identifying novel dietary nondigestible carbohydrates capable of modulating the composition and/or metabolic activities of the gut microbiota. This work assessed the differential modulatory influence of novel galacto-oligosaccharides derived from lactulose (GOS-Lu) in comparison with commercial galacto-oligosaccharides derived from lactose (GOS-La) in gut microbiota of growing rats (5 weeks old). Rats were fed either a control diet or diets containing 1% (w/w) of GOS-Lu or GOS-La, and cecal and colonic contents were collected after 14 days of treatment. Compared to controls, GOS-Lu had significantly more bifidobacteria within the large intestine, showing a significant and selective increase...

  16. Design, synthesis, pharmacological evaluation, QSAR analysis, molecular modeling and ADMET of novel donepezil-indolyl hybrids as multipotent cholinesterase/monoamine oxidase inhibitors for the potential treatment of Alzheimer's disease

    Bautista-Aguilera, Óscar M.; Esteban, Gerard; Bolea, Irene; Nikolic, Katarina; Agbaba, Danica; Moraleda, Ignacio; Iriepa, Isabel; Samadi, Abdelouahid; Soriano, Elena; Unzeta, Mercedes; Marco-Contelles, José
    The design, synthesis, and pharmacological evaluation of donepezil-indolyl based amines 7-10, amides 12-16, and carboxylic acid derivatives 5 and 11, as multipotent ASS234 analogs, able to inhibit simultaneously cholinesterase (ChE) and monoamine oxidase (MAO) enzymes for the potential treatment of Alzheimer's disease (AD), is reported. Theoretical studies using 3D-Quantitative Structure-Activity Relationship (3D-QSAR) was used to define 3D-pharmacophores for inhibition of MAO A/B, AChE, and BuChE enzymes. We found that, in general, and for the same substituent, amines are more potent ChE inhibitors (see compounds 12, 13versus7 and 8) or equipotent (see compounds 14, 15versus9 and 10) than the corresponding amides,...

  17. Detection of immune complexes by matrix-assisted laser desorption/ionization mass spectrometry

    Schlosser, G.; Pocsfalvi, G.; Malorni, A.; Puerta, Angel de la; Frutos, Mercedes de; Vékey, K.
    Matrix-assisted laser desorption/ionization mass spectrometry (MALDI-MS) was used to detect an immune complex formed between β-lactoglobulin and polyclonal anti-β-lactoglobulin antibody in the gas phase. The most important experimental parameters to detect such a specific antibody-antigen complex by MALDI were the use of solutions at near-neutral pH and of sinapinic acid matrix prepared by the dried-droplet method. Under such conditions, predominantly one but also two molecules of antigen protein were complexed by the antibody. Specific formation of the antibody-antigen complex was confirmed by performing competitive reactions. Addition of antibody to a 1:1 mixture of β-lactoglobulin and one control protein resulted not...

  18. The structure of 1,1,3-trimethyl-Δ2-pyrazolinium perchlorate: An X-ray crystallographic and GIAO/DFT multinuclear NMR study

    Yap, G. P. A.; Alkorta, Ibon; Elguero, José; Jagerovic, Nadine
    The crystal and molecular structure of 1,1,3-trimethyl-Δ2- pyrazolinium perchlorate has been determined and compared with those of other pyrazolinium salts (both 1,1 and 1,2-substituted). Reported 13C and 15N chemical shifts for a series of related pyrazolines have been compared with GIAO/DFT calculations, with excellent agreement. The combination of the biological properties of pyrazolines with those of the perchlorate anion in the same molecule will be discussed.

  19. Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents

    Gómez, Ana M.; Casillas, Marta; Rodríguez, Benjamín; Valverde, Serafín; López, J. Cristobal
    Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortho-lithiation of activated arenes, to give C-1 aryl glycals in moderate yields.

  20. A synthetic route to pyranoid epoxy-exo-glycals from D-glucose

    Gómez, Ana M.; Pedregosa, Ana; Valverde, Serafín; López, J. Cristobal
    A synthetic route to a pyranose derived epoxy-exo-glycal has been developed from D-glucose. An attempted, one-pot bromination-elimination-oxirane formation, protocol that had worked well on furanoses, resulted only in the generation of 2-bromo-C-1-methyl pyranoid glycals. © ARKAT USA, Inc.

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