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Estudio Con Criterios Filogenéticos Del Potencial Neuroprotector De Líquenes Parmeliáceos: Mecanismos De Acción De Sus Metabolitos Secundarios

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Estudio Con Criterios Filogenéticos Del Potencial Neuroprotector De Líquenes Parmeliáceos: Mecanismos De Acción De Sus Metabolitos Secundarios UNIVERSIDAD COMPLUTENSE DE MADRID FACULTAD DE FARMACIA Departamento de Biología Vegetal II TESIS DOCTORAL Estudio con criterios filogenéticos del potencial neuroprotector de líquenes parmeliáceos: mecanismos de acción de sus metabolitos secundarios Study witj philogenetic criteria of the neuroprotective potential of "Parmeliaceae" lichens: mechanism of action of their secondary metabolites MEMORIA PARA OPTAR AL GRADO DE DOCTOR PRESENTADA POR Carlos Fernández Moriano Directores M. Pilar Gómez-Serranillos Cuadrado Pradeep Kumar Divakar Madrid, 2018 © Carlos Fernández Moriano, 2017 UNIVERSIDAD COMPLUTENSE DE MADRID FACULTAD DE FARMACIA DEPARTAMENTOS DE FARMACOLOGÍA Y BIOLOGÍA VEGETAL II ESTUDIO CON CRITERIOS FILOGENÉTICOS DEL POTENCIAL NEUROPROTECTOR DE LÍQUENES PARMELIÁCEOS. MECANISMO DE ACCIÓN DE SUS METABOLITOS SECUNDARIOS. TESIS DOCTORAL CON MENCIÓN EUROPEA CARLOS FERNÁNDEZ MORIANO DIRIGIDA POR: DRA. M. PILAR GÓMEZ-SERRANILLOS CUADRADO DR. PRADEEP KUMAR DIVAKAR MADRID, 2017 UNIVERSIDAD COMPLUTENSE DE MADRID FACULTAD DE FARMACIA DEPARTAMENTOS DE FARMACOLOGÍA Y BIOLOGÍA VEGETAL II ESTUDIO CON CRITERIOS FILOGENÉTICOS DEL POTENCIAL NEUROPROTECTOR DE LÍQUENES PARMELIÁCEOS. MECANISMO DE ACCIÓN DE SUS METABOLITOS SECUNDARIOS. TESIS DOCTORAL CON MENCIÓN EUROPEA CARLOS FERNÁNDEZ MORIANO MADRID, 2017 UNIVERSIDAD COMPLUTENSE DE MADRID FACULTAD DE FARMACIA DEPARTAMENTOS DE FARMACOLOGÍA Y BIOLOGÍA VEGETAL II STUDY WITH PHYLOGENETIC CRITERIA OF THE NEUROPROTECTIVE POTENTIAL OF PARMELIACEAE LICHENS. MECHANISM OF ACTION OF THEIR SECONDARY METABOLITES. TESIS DOCTORAL CON MENCIÓN EUROPEA CARLOS FERNÁNDEZ MORIANO MADRID, 2017 UNIVERSIDAD COMPLUTENSE DE MADRID FACULTAD DE FARMACIA Dra. M. Pilar Gómez-Serranillos Cuadrado, Profesora Titular del Departamento de Farmacología de la Facultad de Farmacia de la Universidad Complutense de Madrid, y Dr. Pradeep Kumar Divakar, Profesor Contratado Doctor del Departamento de Biología Vegetal II de la Facultad de Farmacia de la Universidad Complutense de Madrid, CERTIFICAN: Que el presente trabajo de investigación titulado “Estudio con criterios filogenéticos del potencial neuroprotector de líquenes parmeliáceos. Mecanismo de acción de sus metabolitos secundarios” constituye la memoria de Tesis Doctoral que presenta D. Carlos Fernández Moriano para optar al grado de Doctor con Mención Europea, y que ha sido realizado en los Departamentos de Farmacología y Biología Vegetal II, ambos de la Facultad de Farmacia de la Universidad Complutense de Madrid, bajo nuestra dirección. Asimismo, concluido el trabajo experimental y bibliográfico, autorizamos su presentación y defensa en la Universidad Complutense de Madrid, para que sea juzgado por el Tribunal correspondiente. Para que conste a los efectos oportunos, firmamos el presente certificado en Madrid a 16 de enero de dos mil diecisiete. Dra. M. Pilar Gómez-Serranillos Cuadrado Dr. Pradeep Kumar Divakar Este trabajo de Tesis Doctoral ha sido realizado en los Departamentos de Farmacología y Biología Vegetal II de la Facultad de Farmacia de la Universidad Complutense de Madrid gracias a una beca pre-doctoral de Formación de Profesorado Universitario (FPU) del Ministerio de Educación, Cultura y Deporte (FPU 12/03824) concedida a Carlos Fernández Moriano. Durante el desarrollo de la Tesis Doctoral se ha realizado una estancia breve de tres meses, también financiada por el Ministerio de Educación, Cultura y Deporte e incluida en el programa formativo de Formación de Profesorado Universitario (FPU). Dicha estancia se ha realizado en el Senckenberg Biodiveristy and Climate Research Centre (Bik-F) (Frankfurt, Alemania), en el grupo de investigación de Adaptación y Clima dirigido por la Dra. Imke Schmitt. AGRADECIMIENTOS El presente trabajo ha sido realizado gracias a la financiación proporcionada por el Ministerio de Educación, Cultura y Deporte a través del programa de Formación de Profesorado Universitario. El proyecto de investigación de la Tesis Doctoral se ha desarrollado entre los grupos de investigación SYSTEMOL (del departamento de Biología Vegetal II) y Farmacología de Productos Naturales (del departamento de Farmacología), ambos de la Facultad de Farmacia de la Universidad Complutense de Madrid, y bajo la financiación del proyecto CGL2013-42498-P del Ministerio de Economía, Industria y Competitividad. Mi agradecimiento a las mencionadas instituciones. Mi más sincera gratitud a mis directores de Tesis, la Dra. M. Pilar Gómez-Serranillos Cuadrado y el Dr. Pradeep Kumar Divakar, así como a la Dra. Ana M. Crespo de las Casas, por haberme dado la oportunidad de desarrollar este trabajo bajo su sabia y profesional tutela y haberme apoyado desde el comienzo, ayudándome desde la obtención de la beca FPU hace cuatro años. Mucho han contribuido ellos a que esta tesis sea hoy presentada. Quiero hacer especial énfasis en mi agradecimiento a Pilar, por su trato cercano y cariñoso hacia mí y la ayuda y paciencia en el día a día. A lo largo de estos años he recibido, además, apoyo de muchas personas que, de una manera u otra, me han ayudado y facilitado mi trabajo y han contribuido a que este trabajo de Tesis Doctoral se haya materializado en la presente memoria. Quiero agradecer a todo el profesorado del Departamento de Farmacología, y a todos mis compañeros de módulo y departamento que en algún momento fueron doctorandos (Elena, Alba, Manal, María, Ana, etc.), con quien he compartido la rutina diaria y de quienes he aprendido muchas cosas y, sobre todo, por su ayuda para sacar adelante mi trabajo experimental. Y a Rosa, Nieves, Azucena y Jesús, por su ayuda desinteresada y su buen humor diarios. También tengo que agradecer a parte del personal del Departamento de Biología Vegetal II (Tino, David, Juan Carlos, etc.) por su buena disposición a la colaboración que ha dado lugar al presente trabajo. On the other hand, I do want to thank much Professor Imke Schmitt for giving me the opportunity to spend three fruitful and wonderful months working in her research group in the Biodiversity and Climate Research Centre (Frankfurt). I appreciate the kindness and help provided by her and all the members of the group, and I would like to give special thanks to Dr. Francesco Dal Grande for his kindness and for making my stay more comfortable and lightening up my work there. Tengo mucho que agradecer a todos mis amigos, a los de siempre y a los más recientes, por estar en los buenos momentos y en los no tan buenos, y porque sin ellos todos estos años desde que inicié los estudios de Licenciatura en Farmacia no hubieran sido lo mismo. Muchos son parte de esa familia que uno elige para disfrutar el tiempo. Pero mi mayor agradecimiento va dirigido a mi familia, porque es lo verdaderamente importante en la vida. Y porque esta tesis no sólo es fruto de mi trabajo durante los últimos cuatro años, sino que es resultado de toda la educación recibida en casa desde pequeño, y toma cuerpo gracias al continuo apoyo, comprensión y cariño recibido de ellos. Por último, GRACIAS a Laura, por tu apoyo y por compartir la vida conmigo. Gracias por todo en general y por nada en particular. Las palabras sobran, y debes sentirte partícipe de este trabajo. A mis abuelos ÍNDICE DE FIGURAS Y TABLAS FIGURAS Figura 1. Sección transversal de un talo liquénico tipo. Figura 2. Distribución geográfica de los líquenes parmeliáceos. Figura 3. Especímenes representativos de las especies Cetrelia braunsiana, Cetraria islandica, Evernia prunastri, Parmotrema saccatilobum, Usnea ghattensis y Vulpicida canadensis. Figura 4. Clasificación filogenética de la familia Parmeliaceae y distribución de las especies objeto de estudio en los distintos clados. Figura 5. Estructuras químicas de ejemplos de metabolitos secundarios de líquenes según grupos de estructuras. Figura 6. Clasificación de los metabolitos liquénicos según rutas biosintéticas. Figura 7. Dibujo esquemático que representa las principales unidades funcionales del SNC. Figura 8. Estructura de la BHE. Figura 9. Desequilibrio entre especies pro-oxidantes y antioxidantes que conduce al EO. Figura 10. Las actividades de las enzimas antioxidantes se encuentran interconectadas por las ERO intermedias. Figura 11. Bioquímica del estrés oxidativo. Adaptada de Halliwell, 2007. Figura 12. Estructura del factor Nrf2 con sus distintos dominios, y esquema representativo de la activación del sistema de señalización celular Keap-1/Nrf2/ARE. Figura 13. Microfotografías representativas de la morfología de las líneas celulares utilizadas. Figura 14 Fotografía del cromatógrafo de HPLC Agilent 1260 Infinity usado para el análisis fitoquímico de los extractos de líquenes parmeliáceos. Figura 15. Esquema explicativo del procedimiento para el ensayo de MTT. Figura 16. Ejemplo de una placa del ensayo DPPH. Figura 17. Fundamento del empleo de la DCFH-DA para la medida de la generación intracelular de ERO. Figura 18. Cromatograma representativo de una muestra de MDA patrón (5 μM). Figura 19. Ejemplo de curva patrón de trolox y su regresión lineal de área bajo la curva. Figura 20. Resultados de viabilidad celular de la línea SH-SY5Y bajo los tratamientos (24 h) con los seis extractos metanólicos. Figura 21. Resultados de viabilidad celular de la línea U373-MG bajo los tratamientos (24 h) con los seis extractos metanólicos. Figura 22. Resultados del ensayo de actividad LDH bajo los distintos tratamientos (24 h) con los extractos metanólicos. Modelo celular SH-SY5Y. Figura 23. Resultados del ensayo de actividad LDH bajo los distintos tratamientos (24 h) con los extractos metanólicos. Modelo
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