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Vallverdu-Queralt A.,University of Barcelona | Vallverdu-Queralt A.,CIBER ISCIII | Medina-Remon A.,University of Barcelona | Medina-Remon A.,CIBER ISCIII | And 5 more authors.
Journal of Agricultural and Food Chemistry | Year: 2011

The agronomic environments in which tomatoes are cultivated potentially affect the levels of antioxidants and other metabolites in commercial products. In this study, biochemical and metabolomic techniques were used to assess the differences between ketchups produced by organic and conventional systems. An untargeted metabolomic approach using QToF-MS was used to identify those nutrients that have the greatest impact on the overall metabolomic profile of organic ketchups as compared to conventional ones. Individual polyphenols were quantified using LC-ESI-QqQ. This multifaceted approach revealed that the agronomic environment in which tomatoes are grown induces alterations in the content of antioxidant capacity, phenolics, and other metabolites in ketchups. Organic cultivation was found to provide tomatoes and tomato-derived products with a significantly higher content of antioxidant microconstituents, whereas glutamylphenylalanine and N-malonyltryptophan were detected only in conventional ketchups. © 2011 American Chemical Society.


Valverde E.,Institute of Biomedicine IBUB | Sureda F.X.,Rovira i Virgili University | Vazquez S.,Institute of Biomedicine IBUB
Bioorganic and Medicinal Chemistry | Year: 2014

A new series of benzopolycyclic amines active as NMDA receptor antagonists were synthesized. Most of them exhibited increased activity compared with related analogues previously published. All the tested compounds were more potent than clinically approved amantadine and one of them displayed a lower IC50 value than memantine, an anti-Alzheimer's approved drug. © 2014 Elsevier Ltd. All rights reserved.


Arroniz C.,Institute of Biomedicine IBUB | Escolano C.,Institute of Biomedicine IBUB | Luque F.J.,University of Barcelona | Bosch J.,Institute of Biomedicine IBUB | Amat M.,Institute of Biomedicine IBUB
Organic and Biomolecular Chemistry | Year: 2011

Readily available chiral primary 1,2-aminoalcohols and diamines have been explored as organocatalysts for a domino Michael-aldol reaction. Their application in this organocascade process afforded cyclohexanone A with high levels of reactivity (up to 91% yield) and stereoselectivity (>97:3 d.r., up to 93% ee). Depending on the acid cocatalyst different chiral species (cyclic secondary amines vs. acyclic primary amines) might catalyse the process. In order to shed light on the catalytic activation, several experiments were carried out and a detailed possible reaction mechanism is proposed. Theoretical studies support the stereochemical outcome of the process. © The Royal Society of Chemistry 2011.


Duque M.D.,Institute of Biomedicine IBUB | Camps P.,Institute of Biomedicine IBUB | Torres E.,Institute of Biomedicine IBUB | Valverde E.,Institute of Biomedicine IBUB | And 6 more authors.
Bioorganic and Medicinal Chemistry | Year: 2010

The synthesis of several (1,2,3,5,6,7-hexahydro-1,5:3,7-dimethano-4-benzoxonin-3-yl)amines and related compounds is reported. Several of them display very similar activity to memantine as NMDA receptor antagonists. Several derivatives showed a significant level of trypanocidal activity. © 2009 Elsevier Ltd. All rights reserved.


Amat M.,Institute of Biomedicine IBUB | Arroniz C.,Institute of Biomedicine IBUB | Molins E.,CSIC - Institute of Materials Science | Escolano C.,Institute of Biomedicine IBUB | Bosch J.,Institute of Biomedicine IBUB
Organic and Biomolecular Chemistry | Year: 2011

The double cyclocondensation of symmetric pyridyl bis(oxoacids) 2b and 3b with (R)-phenylglycinol stereoselectively gave access to bis-phenylglycinol- derived oxazolopyrrolidine 9 and oxazolopiperidone 10, respectively. Application of the stereocontrolled cyclocondensation reaction to phenyl bis-γ-oxoacid 4b provided 11, which was converted to the corresponding enantiopure di(pyrrolidinyl)benzene 22. The absolute configuration of the new stereogenic centers generated in the key cyclocondenstion step was unambiguously established by X-ray crystallographic analysis. © 2011 The Royal Society of Chemistry.

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