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Análisis de Polifenoles en Alimentos y Muestras Biológicas

El análisis de compuestos bioactivos en los alimentos es un primer paso indispensable para conocer el valor funcional que estos alimentos podrán tener en el organismo humano.

Diseñamos estudios para evaluar cómo afecta el procesado tecnológico o tratamiento culinario a los compuestos bioactivos; diseñamos estudios clínicos para evaluar el efecto funcional de estos componentes en el organismo humano y estudiamos la biodisponibilidad, metabolismo y acción de la microbiota.

Los equipos con los que se han realizado los análisis son espectrómetros de masas con triple cuadrupolo (LC-MS/MS), de tiempo de vuelo (QTOF) y el LTQ-Orpitrap.

El LC-MS/MS permite la identificación de distintos metabolitos mediante Full-Scan y técnicas como Neutral Loss (NL), Precursor Ion Scan (Prec) y Product Ion Scan (PIS). Para la cuantificación se utiliza el modo de Multiple Reaction Monitoring (MRM).

Los análisis metabolómicos se están realizando con el QTOF. Esta tecnología permite la adquisición automática de los espectros de MS y MS/MS en una sola inyección cromatográfica. Los análisis con QTOF permiten obtener la masa exacta de los iones, la cual cosa es esencial para la asignación de la composición elemental y por lo tanto para la caracterización de moléculas pequeñas.

Otro equipo que se está usando recientemente es LC-LTQ-Orbitrap-MS. Esta metodología permite el análisis de MS, MS/MS y MSn para facilitar la obtención de información estructural. Debido a la especificidad de las medidas de MSn y la capacidad de eliminar las interferencias a través de la etapa inicial de selección de masas, el LTQ-Orbitrap-MS es el equipo perfecto para el análisis cualitativo; facilita la elucidación de la estructura de compuestos desconocidos.

PUBLICACIONES DEL GRUPO RELACIONADAS CON ALIMENTOS:

Tomate y derivados:

  • Vallverdú-Queralt A, Jáuregui O,  Medina-Remón A,  Andrés-Lacueva  C,  Lamuela-Raventós R.M. Improved characterization of tomato polyphenols using liquid chromatography/electrospray ionization linear ion trap quadrupole Orbitrap mass spectrometry and liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid Commun  Mass Sp. 2010; 24: 2986-2992.
  • Vallverdú-Queralt A,  Medina-Remón A,  Andres-Lacueva C, Lamuela-Raventos   R.M.  Changes in phenolic profile and antioxidant activity during production of diced tomatoes. Food Chem. 2011; 126: 1700-1707.
  • Vallverdu-Queralt A, Medina-Remon  A, Martinez-Huelamo M,  Jauregui, O,  Andres-Lacueva C, Lamuela-Raventos R.M.  Phenolic Profile and Hydrophilic Antioxidant Capacity as Chemotaxonomic Markers of Tomato Varieties. J AgrFood Chem. 2011; 59: 3994-4001.
  • Vallverdu-Queralt A, Jáuregui O, Di Lecce G, Andres-Lacueva C,  Lamuela-Raventos R.M.  Screening of the polyphenol content of tomato-based products through accurate-mass spectrometry (HPLC-ESI-QTOF). Food Chem.  2011.
  • Hussein L, Medina A, Barrionnevo A, Lammuela-Raventos RM, Andres-Lacueva C. Normal distribution of urinary polyphenol excretion among Egyptian males 7-14 years old and changes following nutritional intervention with tomato juice (Lycopersicon esculentum). Int J Food Sci Nutr. 2009;60(4):302-11.
  • Hussein L, Medina A, Barrionuevo A, Lamuela-Raventós RM, Andrés-Lacueva C. Normal distribution of urinary polyphenol excretion among male adolescents and changes associated with nutritional intervention with tomato juice (Lycopersicon esculentum). Ann Nutr Metab. 2007;51(Suppl 1):70.

Cacao:

  • Khan N, Monagas M, Llorach R, Urpí-Sardà M, Rabassa M, Estruch R, Andrés-Lacueva C. Targeted and metabolomic study of biomarkers of cocoa powder consumption: effects on inlammatory biomarkers in patients at high risk of cardiovascular disease. Agro Food Ind Hi-Tech. 2010;21(3):54-7.
  • Roura E, Andrés-Lacueva C, Estruch R, Mata-Bilbao ML, Izquierdo-Pulido M, Lamuela-Raventós RM. The effects of milk as a food matrix for polyphenols on the excretion profile of cocoa (-)-epicatechin metabolites in healthy human subjects. Br J Nutr. 2008;100(4):846-51.
  • Andres-Lacueva C, Monagas M, Khan N, Izquierdo-Pulido M, Urpi-Sarda M, Permanyer J, Lamuela-Raventós RM. Flavanol and flavonol contents of cocoa powder products: influence of the manufacturing process. J Agric Food Chem. 2008;56(9):3111-7.
  • Roura E, Andrés-Lacueva C, Estruch R, Mata-Bilbao ML, Izquierdo-Pulido M, Waterhouse AL, Lamuela-Raventós RM. Milk does not affect the bioavailability of cocoa powder flavonoid in healthy human. Ann Nutr Metab. 2007;51(6):493-8.
  • Sánchez-Rabaneda F, Jáuregui O, Casals I, Andrés-Lacueva C, Izquierdo-Pulido M, Lamuela-Raventós RM. Liquid chromatographic/electrospray ionization tandem mass spectrometric study of the phenolic composition of cocoa (Theobroma cacao). J Mass Spectrom. 2003;38(1):35-42.
  • Lamuela-Raventós RM, Andrés-Lacueva C, Permanyer J, Izquierdo-Pulido M. More antioxidants in cocoa. J Nutr. 2001;131(3):834-5.
  • Andres-Lacueva C, Lamuela-Raventós RM, Jauregui O, Casals I, Izquierdo-Pulido M, Permanyer J. An LC method for the analysis of cocoa phenolics. LC GC Europe. 2000;902-4.

Frutas cítricas:

  • Mata Bilbao ML, Andres-Lacueva C, Jáuregui O, Lamuela-Raventós RM. Determination of flavonoids in a Citrus fruit extract by LC-DAD and LC-MS. Food Chem. 2007:101(4):1742-7.
  • Medina-Remón A, Tulipani S, Rotchés-Ribalta M, Mata-Bilbao MD, Andres-Lacueva C, Lamuela-Raventos RM.A Fast Method Coupling Ultrahigh Performance Liquid Chromatography with Diode Array Detection for Flavonoid Quantification in Citrus Fruit Extracts. J Agric Food Chem. 2011:59(12):6353-6359.

Té verde:

  • Mata-Bilbao Mde L, Andrés-Lacueva C, Roura E, Jáuregui O, Torre C, Lamuela-Raventós RM. A new LC/MS/MS rapid and sensitive method for the determination of green tea catechins and their metabolites in biological samples. J Agric Food Chem. 2007;55(22):8857-63.

Vino:

  • Darias-Martin JJ, Andrés-Lacueva C, Díaz-Romero C, Lamuela-Raventós RM. Phenolic profile in varietal white wines made in the Canary Islands. Eur Food Res Tech. 2008;226(4):871-6.
  • de Andrés-de Prado R, Yuste-Rojas M, Sort X, Andrés-Lacueva C, Torres M, Lamuela-Raventós RM. Effect of soil type on wines produced from Vitis vinifera L. cv. Grenache in commercial vineyards. J Agric Food Chem. 2007;55(3):779-86.
  • Guasch-Jané MR, Andrés-Lacueva C, Jáuregui O, Lamuela-Raventós RM. First evidence of white wine in ancient Egypt from Tutankhamun's tomb. J Archaeol Sci. 2006:33(8):1075-80.
  • Guasch-Jané MR, Ibern-Gómez M, Andrés-Lacueva C, Jáuregui O, Lamuela-Raventós RM. Liquid chromatography with mass spectrometry in tandem mode applied for the identification of wine markers in residues from ancient Egyptian vessels. Anal Chem. 2004;76(6):1672-7.
  • Andres-Lacueva C, Ibern-Gómez M, Lamuela-Raventós RM, Buxaderas S, De la Torre-Boronat MC. Cinnamates and resveratrol content for sparkling wine characterization. Am J Enol Vitic. 2002;53:147-50.
  • Ibern-Gómez M, Andres-Lacueva C, Lamuela-Raventós RM, Waterhouse AL. Rapid HPLC method for phenolic compounds in red wines. Am J Enol Vitic. 2002;53:218-27.
  • Darias-Martín J, Martín-Luis B, Carrillo-López M, Lamuela-Raventós R, Díaz-Romero C, Boulton R. Effect of caffeic acid on the color of red wine. J Agric Food Chem. 2002;50(7):2062-7.
  • Ibern-Gómez M, Andrés-Lacueva C, Lamuela-Raventós RM, Lao-Luque C, Buxaderas S, de la Torre-Boronat MC. Differences in phenolic profile between oak and wood and stainless steel fermentation in white wines. Am J Enol Vitic. 2001;52(2):159-64.
  • Lamuela-Raventos RM, Huix Blanquera M, Waterhouse AL. Treatments for pinking alteration in white wines. Am J Enol Vitic. 2001;52(2):156-8.
  • Romero-Pérez AI, Lamuela-Raventós RM, Andrés-Lacueva C, de La Torre-Boronat MC. Method for the quantitative extraction of resveratrol and piceid isomers in grape berry skins. Effect of powdery mildew on the stilbene content. J Agric Food Chem. 2001;49(1):210-5.
  • Ibern-Gómez M, Andres-Lacueva C, Lamuela-Raventós RM, Buxaderas S, Singleton VL, Torre-Boronat MC. Browning of Cava (Sparking Wine) during Aging in Contact with Lees, due to the Phenolic Composition. Am J Enol Vitic. 2000;51(1):29-36.
  • Darias-Martin JJ, Rodriguez O, Diaz E, Lamuela-Raventos RM. Effect of skin contact on the antioxidant phenolics in white wine. Food Chem. 2000;71(4):483-7.
  • Mattivi F, Monetti A, Vrhovsek U, Tonon D, Andrés-Lacueva C. High-performance liquid chromatographic determination of the riboflavin concentration in white wines for predicting their resistance to light. J Chromatogr A. 2000;888(1-2):121-7.
  • Lamuela-Raventos RM, Waterhouse Al. Resveratrol and piceid in wine. Oxidants and antioxidants. 1999;299:184-90.
  • Lao CL, Lopez-Tamames E, Lamuela-Raventos RM, Buxaderas S, De La Torre-Boronat MDC. Pectic enzyme treatment effects on quality of white grape musts and wines. J Food Scie. 1997;62(6):1142.
  • Andres-Lacueva C, Lamuela-Raventós RM, Buxaderas S, Torre-Boronat MC. Influence of variety and aging on foaming properties of cava (sparkling wine) – 2. J Agric Food Chem. 1997;45(7):2520-5.
  • Andres-Lacueva C, Gallart M, López-Tamames E, Lamuela-Raventós RM. Influence of variety and aging on foaming properties of sparkling wine (cava) – 1. J Agric Food Chem. 1996;44(12):3826-9.
  • Betés-Saura C, Andrés-Lacueva C, Lamuela-Raventós RM. Phenolics in white free run juices and wines from Penedès by high performance liquid chromatography: changes during vinification. J Agric Food Chem. 1996;44(10):3040-6.
  • Romero-Pérez AI, Lamuela-Raventós RM, Buxaderas S, de la Torre-Boronat MC. Resveratrol and piceid as varietal markers of white wines. J Agric Food Chem. 1996;44(8):1975-8.
  • Romero-Pérez AI, Lamuela-Raventós RM, Waterhouse AL, de la Torre-Boronat MC. Levels of cis- and trans-resveratrol and their glucosides in white and rosé vitis vinifera wines from Spain. J Agric Food Chem. 1996;44(8):2124-8.
  • Andres-Lacueva C, López-Tamames E, Lamuela-Raventós R, Buxaderas S, de la Torre Boronat MC. Characteristics of sparkling base wines affecting foam behaviour. J Agric Food Chem. 1996;44(4):989-95.
  • De La Presa-Owens C, Lamuela-Raventos RM, Buxaderas S, De La Torre MC. Differentiation and grouping characteristics of varietal grape musts from Penedes region. Am J Enol Vit. 1995;46(3):283-91.
  • De La Presa-Owens C, Lamuela-Raventos RM, Buxaderas S, De La Torre-Boronat MC. Characterization of Macabeo, Xarello, and Parellada white wines from the Penedes region –2. Am J Enol Vit. 1995;46(4):529-41.
  • Lamuela-Raventos RM, Romero-Perez AI, Waterhouse A, De La Torre-Boronat MC. Direct HPLC analysis of cis-resveratrol and trans-resveratrol and piceid isomers in Spanish red Vitis-Vinifera wines. J Agric Food Chem. 1995;43(2):281-3.
  • Lamuela-Raventos RM, Waterhouse AL. A direct HPLC separation of wine phenolics. Am J Enol Vit. 1994;45:1-5.
  • Puigdeu M, Lamuela-Raventos RM, Buxaderas S, Torre-Boronat C. Determination of copper and iron in must: comparison of wet and dry ashing. Am J Enol Vit. 1994;45(1):25-8.
  • Waterhouse AL, Lamuela-Raventos RM. The occurrence of piceid, a stilbene glucoside, in grape berries. Phytochemistry. 1994;37(2):571-3.

 

PUBLICACIONES DEL GRUPO RELACIONADAS CON MUESTRAS BIOLÓGICAS:

Resveratrol en LDL, orina y plasma:

  • Ortuño J, Covas MI, Farre M, Pujadas M, Fitó M, Khymenets O, Andrés-Lacueva C, Roset P, Joglar J, Lamuela-Raventós RM, de la Torre R. Matrix effects on the bioavailability of resveratrol in humans. Food Chem. 2010:120(4):1123-30.
  • Zamora-Ros R, Lamuela-Raventós RM, Estruch R, Andres-Lacueva C. Resveratrol, a new biomarker of moderate wine intake? Br J Nutr. 2009;101(1):148.
  • Urpi-Sarda M, Zamora-Ros R, Lamuela-Raventos R, Cherubini A, Jauregui O, de la Torre R, Covas MI, Estruch R, Jaeger W, Andres-Lacueva C. HPLC-tandem mass spectrometric method to characterize resveratrol metabolism in humans. Clin Chem. 2007;53(2):292-9
  • Zamora-Ros R, Urpí-Sardà M, Lamuela-Raventós RM, Estruch R, Vázquez-Agell M, Serrano-Martínez M, Jaeger W, Andres-Lacueva C. Diagnostic performance of urinary resveratrol metabolites as a biomarker of moderate wine consumption. Clin Chem. 2006;52(7):1373-80.
  • Urpí-Sardà M, Jáuregui O, Lamuela-Raventós RM, Jaeger W, Miksits M, Covas MI, Andres-Lacueva C. Uptake of diet resveratrol into the human low-density lipoprotein. Identification and quantification of resveratrol metabolites by liquid chromatography coupled with tandem mass spectrometry. Anal Chem. 2005;77(10):3149-55.
  • Juan ME, Lamuela-Raventós RM, de la Torre-Boronat MC, Planas JM. Determination of trans-resveratrol in plasma by HPLC. Anal Chem. 1999;71(3):747-50.

Metabolitos de flavanoles y flavonoles del cacao:

  • Khan N, Monagas M, Llorach R, Urpí-Sardà M, Rabassa M, Estruch R, Andrés-Lacueva C. Targeted and metabolomic study of biomarkers of cocoa powder consumption: effects on inlammatory biomarkers in patients at high risk of cardiovascular disease. Agro Food Ind Hi-Tech. 2010;21(3):54-7.
  • Urpi-Sarda M, Ramiro-Puig E, Khan N, Ramos-Romero S, Llorach R, Castell M, Gonzalez-Manzano S, Santos-Buelga C, Andres-Lacueva C. Distribution of epicatechin metabolites in lymphoid tissues and testes of young rats with a cocoa-enriched diet. Br J Nutr. 2010;103(10):1393-7.
  • Urpi-Sarda M, Llorach R, Khan N, Monagas M, Rotches-Ribalta M, Lamuela-Raventos R, Estruch R, Tinahones FJ, Andres-Lacueva C. Effect of milk on the urinary excretion of microbial phenolic acids after cocoa powder consumption in humans. J Agric Food Chem. 2010;58(8):4706-11.
  • Llorach-Asunción R, Jauregui O, Urpi-Sarda M, Andres-Lacueva C. Methodological aspects for metabolome visualization and characterization. A metabolomic evaluation of the 24-hour evolution of human urine after cocoa powder consumption. J Pharm Biomed Anal. 2010;51(2):373-81.
  • Llorach R, Urpi-Sarda M, Jauregui O, Monagas M, Andres-Lacueva C. An LC-MS-based metabolomics approach for exploring urinary metabolome modifications after cocoa consumption. J Proteome Res. 2009;8(11):5060-8.
  • Urpi-Sarda M, Monagas M, Khan N, Llorach R, Lamuela-Raventós RM, Jáuregui O, Estruch R, Izquierdo-Pulido M, Andrés-Lacueva C. Targeted metabolic profiling of phenolics in urine and plasma after regular consumption of cocoa by liquid chromatography-tandem mass spectrometry. J Chromatogr A. 2009;1216(43):7258-67.
  • Monagas M, Khan N, Andres-Lacueva C, Casas R, Urpí-Sardà M, Llorach R, Lamuela-Raventós RM, Estruch R. Effect of cocoa powder on the modulation of inflammatory biomarkers in patients at high risk of cardiovascular disease. Am J Clin Nutr. 2009;90(5):1144-50.
  • Urpi-Sarda M, Monagas M, Khan N, Lamuela-Raventos RM, Santos-Buelga C, Sacanella E, Castell M, Permanyer J, Andres-Lacueva C. Epicatechin, procyanidins, and phenolic microbial metabolites after cocoa intake in humans and rats. Anal Bioanal Chem. 2009;394(6):1545-56.
  • Roura E, Andrés-Lacueva C, Estruch R, Mata-Bilbao ML, Izquierdo-Pulido M, Lamuela-Raventós RM. The effects of milk as a food matrix for polyphenols on the excretion profile of cocoa (-)-epicatechin metabolites in healthy human subjects. Br J Nutr. 2008;100(4):846-51.
  • Roura E, Andrés-Lacueva C, Estruch R, Mata-Bilbao ML, Izquierdo-Pulido M, Waterhouse AL, Lamuela-Raventós RM. Milk does not affect the bioavailability of cocoa powder flavonoid in healthy human. Ann Nutr Metab. 2007;51(6):493-8.
  • Roura E, Almajano MP, Bilbao ML, Andrés-Lacueva C, Estruch R, Lamuela-Raventós RM. Human urine: epicatechin metabolites and antioxidant activity after cocoa beverage intake. Free Radic Res. 2007;41(8):943-9.
  • Ramiro-Puig E, Urpí-Sardà M, Pérez-Cano FJ, Franch A, Castellote C, Andrés-Lacueva C, Izquierdo-Pulido M, Castell M. Cocoa-enriched diet enhances antioxidant enzyme activity and modulates lymphocyte composition in thymus from young rats. J Agric Food Chem. 2007;55(16):6431-8.
  • Roura E, Andrés-Lacueva C, Jáuregui O, Badia E, Estruch R, Izquierdo-Pulido M, Lamuela-Raventós RM. Rapid liquid chromatography tandem mass spectrometry assay to quantify plasma (-)-epicatechin metabolites after ingestion of a standard portion of cocoa beverage in humans. J Agric Food Chem. 2005;53(16):6190-4.
  • Ramiro E, Franch A, Castellote C, Andrés-Lacueva C, Izquierdo-Pulido M, Castell M. Effect of Theobroma cacao flavonoids on immune activation of a lymphoid cell line. Br J Nutr. 2005;93(6):859-66.
  • Roura E, Andrés-Lacueva C, Jáuregui O, Badia E, Estruch R, Izquierdo-Pulido M, Lamuela-Raventós RM. Rapid method for the identification of epicatechin metabolites in human plasma and urine after ingestion of cocoa beverage by LC/MS/MS. J Agric Food Chem. 2005; 53(16):6190-4.
  • Noé V, Peñuelas S, Lamuela-Raventós RM, Permanyer J, Ciudad CJ, Izquierdo-Pulido M. Epicatechin and a cocoa polyphenolic extract modulate gene expression in human CaCo-2 cells. J Nutr. 2004;134(10):2509-16.

Metabolitos de catequinas y galatos del té verde:

  • Mata-Bilbao M L, Andrés-Lacueva C, Roura E, Jáuregui O, Escribano E, Torre C, Lamuela-Raventós RM. Absorption and pharmacokinetics of green tea catechins in beagles. Br J Nutr. 2008;100(3):496-502.

Metabolitos de flavanonas de frutas cítricas:

  • Trzeciakiewicz A, Habauzit V, Mercier S, Barron D, Urpi-Sarda M, Manach C, Offord E, Horcajada MN. Molecular mechanism of hesperetin-7-O-glucuronide, the main circulating metabolite of hesperidin, involved in osteoblast differentiation. J Agric Food Chem. 2010;58(1):668-75.
  • Martínez-González MA, Lamuela-Raventos RM. The unparalleled benefits of fruit. Br J Nutr. 2009;102(7):947-8. 
  • Mata-Bilbao Mde L, Andrés-Lacueva C, Roura E, Jáuregui O, Escribano E, Torre C, Lamuela-Raventós RM. Absorption and pharmacokinetics of grapefruit flavanones in beagles. Br J Nutr. 2007;98(1):86-92.

Metabolitos de antocianos de arándanos en SNC:

  • Andres-Lacueva C, Shukitt-Hale B, Galli RL, Jauregui O, Lamuela-Raventos RM, Joseph JA. Anthocyanins in aged blueberry-fed rats are found centrally and may enhance memory. Nutr Neurosci. 2005;8(2):111-20.