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Recuperación De Compuestos Bioactivos a Partir De Subproductos Del Aceite De Oliva

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Recuperación De Compuestos Bioactivos a Partir De Subproductos Del Aceite De Oliva CONSEJO SUPERIOR DE INVESTIGACIONES CIENTÍFICAS INSTITUTO DE LA GRASA TESIS DOCTORAL RECUPERACIÓN DE COMPUESTOS BIOACTIVOS A PARTIR DE SUBPRODUCTOS DEL ACEITE DE OLIVA Memoria que presenta Dª Fátima Rubio Senent Para optar al Grado de Doctor Departamento de Nutrición y Bromatología Facultad de Farmacia, Universidad de Sevilla Sevilla, Febrero de 2011 La tesis titulada “Recuperación de compuestos bioactivos a partir de subproductos del aceite de oliva” presentada por la Licenciada en Química Dª Fátima Rubio Senent para optar al grado de Doctor, ha sido realizada bajo la co-dirección de los Doctores Juan Fernández-Bolaños Guzmán y Guillermo Rodríguez Gutiérrez, ambos Científicos del Instituto de la Grasa, siendo tutor el Doctor Francisco José Heredia Mira, Catedrático de la Facultad de Farmacia de la Universidad de Sevilla. Considerando que se han alcanzado los objetivos inicialmente previstos, y que el trabajo reúne los requisitos necesarios, autorizan su presentación V. º B.º Los directores Fdo.: Dr. Juan Fernández-Bolaños Fdo.:Guillermo Rodríguez Gutiérrez V. º B.º El tutor Fdo.: Francisco José Heredia Mira Conforme, la Directora del Departamento de Farmacología, Fdo.: Dª Ana María Cameán Fernández A mis padres Índice Índice ÍNDICE i AGRADECIMIENTOS iv 1. ABREVIATURAS. 1 2. RESUMEN. 2 3. INTRODUCCIÓN. 6 3.1. La problemática del alperujo. 6 3.2. Usos del alperujo. 10 3.2.1. Biofertilizante y/o compost. 10 3.2.2. Alimentación animal. 11 3.2.3. Energía alternativa. 12 3.2.4. Obtención de compuestos de alto valor añadido. 12 3.3. Recuperación de compuestos de interés. 14 3.3.1. Pretratamientos. 14 3.3.2 Tratamiento “steam explosion”. 15 3.3.3. Fraccionamiento de los componentes de la pared celular vegetal. 19 3.3.4. Tratamiento térmico con vapor. 20 3.4. Compuesto fenólicos. 22 3.4.1. Compuestos fenólicos en la aceituna. 22 3.4.2. Propiedades de los compuestos fenólicos. 26 3.4.3. Recuperación de compuestos fenólicos. 29 3.5. Polisacáridos y oligosacáridos. 32 3.5.1. Composición y estructura de la pared celular vegetal. 32 3.5.2. Pared celular de la aceituna. 38 3.5.3. Propiedades de los oligosacáridos de la pared celular vegetal. 40 3.5.4. Recuperación de polisacáridos y oligosacáridos. 43 4. BIBLIOGRAFÍA. 46 5. OBJETIVOS. 64 i Índice 6. RESULTADOS Y DISCUSIÓN. 66 6.1. Compuestos fenólicos y secoiridoides. 69 6.1.1. Capítulo 1: New phenolic compounds hydrothermally extracted from the olive oil by-product alperujo and their antioxidative activities. 70 6.1.2. Capítulo 2: Phenolic extract obtained from steam-treated olive oil waste: Characterization and antioxidant activity. 93 6.1.3. Capítulo 3: Influence of pH on the extraction and antioxidant activity of phenolic extracts obtained with ethyl acetate from hydrothermally treated alperujo. 112 6.1.4. Capítulo 4: Chemical characterization and properties of a polymeric phenolic fraction obtained from olive oil waste. 124 6.1.5. Capítulo 5: Inhibitory and synergistic effects of natural olive phenols on human platelet aggregation and lipid peroxidation of microsomes from vitamin E deficient rats. 143 6.1.6. Capítulo 6: Isolation and characterization of a secoiridoid derivative from two-phase olive waste (alperujo). 159 6.1.7. Capítulo 7: Isolation and identification of minor secoiridoids and phenolic components from thermally treated olive oil by-products. 182 6.1.8. Capítulo 8: A study of the precursors of the natural antioxidant phenol 3,4-dihydroxyphenylglycol in olive oil waste. 203 6.2. Polisacáridos y oligosacáridos. 218 6.2.1. Capítulo 9: Production of oligosaccharides with low molecular weights, secoiridoids and phenolic glycosides from thermally treated olive by-products. 219 6.2.2. Capítulo 10: Pectin extracted from thermally treated olive oil by-products: characterization, physico-chemical properties, in vitro bile acid and glucose binding. 245 6.2.3. Capítulo 11: Novel pectin present in new olive mill wastewater with similar emulsifiers and better biological properties than citrus pectin. 270 6.2.4. Capítulo 12: Properties of lignin, cellulose, and hemicellulose isolated from olive cake and olive stones: Binding of water, oil, bile acids and glucose. 293 ii Índice 7. CONCLUSIONES. 314 8. ANEXOS. 316 Curriculum Vitae 331 iii Agradecimientos Agradecimientos AGRADECIMIENTOS El trabajo aquí presentado ha sido posible gracias a la ayuda de diferentes personas, que de una forma u otra me han enseñado, aconsejado y conducido por el camino correcto, de forma que el resultado final es esta Tesis Doctoral. Por esta razón me gustaría dar las gracias a todas las personas que han hecho posible que este proyecto saliera hacia delante. A los Drs. D. Juan Fernández-Bolaños Guzmán y D. Guillermo Rodríguez Gutiérrez, mis directores de Tesis. Sin duda alguna los agradacemientos hacia ustedes probablemente ocuparían un volumen más extenso que esta Tesis, ya que es imposible enumerar todas las ocasiones en las que me habéis apoyado, enseñado y animado. Ha sido un placer formarme como investigadora bajo su dirección y espero a lo largo de mi vida aprovechar al máximo todos los conocimientos que me han transmitido, tanto a nivel científico como personal. Gracias por confiar y por apostar por mí. Al Dr. D. Francisco Heredia, del Departamento de Nutrición y Bromatología de la Facultad de Farmacia de Sevilla. Gracias por colaborar como tutor de este trabajo, por su completa disposición e interés. A todos los componentes del Grupo de Pared Celular. Al Dr. D. Rafael Guillén por prestarme su ayuda para familiarizarme con el manejo de distintas técnicas instrumentales, sin las cuales gran parte de este trabajo no podría haberse realizado. A los Drs., Dña. Ana Jiménez, Dña. Rocío Rodríguez, D. Antonio Gómez y Dña. Sara Jaramillo y a Olivia Cruz, por haberme prestado su ayuda siempre que lo he necesitado y por su apoyo incondicional. Muchas gracias a todos por hacer que el laboratorio sea un lugar tan agradable, en el que todo el mundo está dispuesto a echar una mano. A la Dr. Aranzazu García, por su ayuda en los estudios de actividad antimicrobiana, muchas gracias por su disposición a la hora realizar los ensayos, gracias por su tiempo, por el interés mostrado por este trabajo y por el cariño demostrado. Gracias por preocuparos por mis preocupaciones y alegraros con mis alegrías. A la Dra. D. Sara Vázquez, el Dr. D. Antonio Lama, y a Javier Tejero. No hay mejor cosa que pasártelo bien en el trabajo, y sin duda alguna eso ha sido gracias a vosotros, porque hemos trabajado mucho, pero la verdad es que también nos hemos reído y mucho. Gracias por ayudarme cuando lo he necesitado, gracias por los chistes malos, gracias por los buenos almuerzos que hemos echado y gracias por estar siempre ahí. Gracias a Sara Vázquez, por ser mí apoyo en los tres meses de estancia, por convertirse en una gran amiga y por enseñarme a ver las cosas desde otra perspectiva. A los Drs. D. Garry Duthie y Dña. Baukje de Roos del Rowett Institute of Nutrition and Health de la Universidad de Aberdeen (Escocia, Reino Unido), por haberme permitido una iv Agradecimientos estancia de tres meses bajo su dirección, gracias por su acogida, disposición, enseñanzas e interés en el trabajo realizado. Gracias a Dña. Sharon Wood por su búsqueda incansable de voluntarios para poder realizar mi trabajo. A los Drs. D. José Mª Fernández-Bolaños y Sergio Martos Delgado del Departamento de Química Orgánica de la Universidad de Sevilla, por su ayuda en la caracterización estructural de compuestos. Gracias por habernos aconsejado, ayudado y por vuestra completa disposición. A todos mis compañeros de la sede de Bellavista del Instituto de la Grasa, tanto al personal científico titular, a los becarios, al personal de mantenimiento, etc. No los enumero porque seguramente me dejaría alguien atrás, pero muchas gracias a todos, porque siempre que he necesitado algo de alguien he recibido buenas respuestas y ayuda incondicional. A la Cooperativa Oleícola El Tejar por acceder al suministro de muestras para realizar este trabajo. Al Programa Junta para la Ampliación de Estudios (JAE) del Consejo Superior de Investigaciones Científicas (CSIC) y al Fondo Social Europea por financiar la beca que ha hecho posible mi trabajo de investigación. A mis compañeros de Universidad, en especial a Rocío Martín, Sergio Martos, José Javier Plata y Luis Carlos Vicente. Porque pese a hacer algún tiempo que terminamos la carrera no hemos perdido el contacto, al contrario, seguimos estando igual o incluso más unidos que antes. Que suerte tuve al coincidir con vosotros y ahora que suerte tengo de teneros como grandes amigos. A mi familia, en especial a mis padres, por apoyarme, aconsejarme y estar siempre a mi lado, ayudándome a ser mejor persona cada día, gracias por aguantarme y por mimarme tanto y tan bien. A mi recién estrenado marido, Eu, por saber entender este complicado mundo de la investigación e interesarse por mi trabajo y por los resultados obtenidos, gracias por apoyarme en todo. Gracias. v 1. Abreviaturas 1. Abreviaturas 1. ABREVIATURAS 2,4-D Ácido 2,4-diclorofenoxiacético 2-MTHF 2-metiltetrahidrofurano 3,4-DHPEA-AC Acetato de hidroxitirosilo 3,4-DHPEA-DEA Forma dialdehídica y descarboximetilada del ácido elenólico unido a hidroxitirosol. 3,4-DHPEA-EA Aglicona de la oleuropeína ADN Ácido desoxirribonucleico ALDH2 Proteína hepática mitocondrial aldehído dehidrogenasa CSIC Consejo Superior de Investigaciones Científicas DES Solventes eutécticos profundos DHFG 3,4-dihidroxifenilglicol DP Grado de polimerización EBT Empresa de base tecnológica Gal-3 Galectina-3 Glc Glucosa HBD Donador de enlaces de hidrógeno HCl Ácido clorhídrico HDL Lipoproteínas de alta densidad HT Hidroxitirosol KOH Hidróxido de potasio LDL Lipoproteínas de baja densidad OMS Organización Mundial de la Salud p-HPEA-EA Aglicona de ligustrósido p-HPEA-EDA Forma dialdehídica y descarboximetilada del ácido elenólico unido a tirosol PMs Pectinas Modificadas ROS Especies reactivas de oxígeno SVM S.L.
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