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Estudio De La Composición Alcaloídica De Narcissus Broussonetii Y De Tres Especies Brasileñas Del Género Hippeastrum (Amaryllidaceae)

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Estudio De La Composición Alcaloídica De Narcissus Broussonetii Y De Tres Especies Brasileñas Del Género Hippeastrum (Amaryllidaceae) Estudio de la composición alcaloídica de Narcissus broussonetii y de tres especies brasileñas del género Hippeastrum (Amaryllidaceae) Jean Paulo de Andrade ADVERTIMENT. La consulta d’aquesta tesi queda condicionada a l’acceptació de les següents condicions d'ús: La difusió d’aquesta tesi per mitjà del servei TDX (www.tdx.cat) i a través del Dipòsit Digital de la UB (diposit.ub.edu) ha estat autoritzada pels titulars dels drets de propietat intel·lectual únicament per a usos privats emmarcats en activitats d’investigació i docència. No s’autoritza la seva reproducció amb finalitats de lucre ni la seva difusió i posada a disposició des d’un lloc aliè al servei TDX ni al Dipòsit Digital de la UB. No s’autoritza la presentació del seu contingut en una finestra o marc aliè a TDX o al Dipòsit Digital de la UB (framing). Aquesta reserva de drets afecta tant al resum de presentació de la tesi com als seus continguts. En la utilització o cita de parts de la tesi és obligat indicar el nom de la persona autora. ADVERTENCIA. La consulta de esta tesis queda condicionada a la aceptación de las siguientes condiciones de uso: La difusión de esta tesis por medio del servicio TDR (www.tdx.cat) y a través del Repositorio Digital de la UB (diposit.ub.edu) ha sido autorizada por los titulares de los derechos de propiedad intelectual únicamente para usos privados enmarcados en actividades de investigación y docencia. No se autoriza su reproducción con finalidades de lucro ni su difusión y puesta a disposición desde un sitio ajeno al servicio TDR o al Repositorio Digital de la UB. No se autoriza la presentación de su contenido en una ventana o marco ajeno a TDR o al Repositorio Digital de la UB (framing). Esta reserva de derechos afecta tanto al resumen de presentación de la tesis como a sus contenidos. En la utilización o cita de partes de la tesis es obligado indicar el nombre de la persona autora. WARNING. On having consulted this thesis you’re accepting the following use conditions: Spreading this thesis by the TDX (www.tdx.cat) service and by the UB Digital Repository (diposit.ub.edu) has been authorized by the titular of the intellectual property rights only for private uses placed in investigation and teaching activities. Reproduction with lucrative aims is not authorized nor its spreading and availability from a site foreign to the TDX service or to the UB Digital Repository. Introducing its content in a window or frame foreign to the TDX service or to the UB Digital Repository is not authorized (framing). Those rights affect to the presentation summary of the thesis as well as to its contents. In the using or citation of parts of the thesis it’s obliged to indicate the name of the author. UNIVERSITAT DE BARCELONA FACULTAT DE FARMÀCIA DEPARTAMENT DE PRODCUTES NATURALS, BIOLOGIA VEGETAL I EDAFOLOGIA ESTUDIO DE LA COMPOSICIÓN ALCALOÍDICA DE NARCISSUS BROUSSONETII Y DE TRES ESPECIES BRASILEÑAS DEL GÉNERO HIPPEASTRUM (AMARYLLIDACEAE) JEAN PAULO DE ANDRADE 2014 UNIVERSITAT DE BARCELONA FACULTAT DE FARMÀCIA DEPARTAMENT DE PRODCUTES NATURALS, BIOLOGIA VEGETAL I EDAFOLOGIA PROGRAMA DE DOCTORAT: RECERCA, DESENVOLUPAMENT I CONTROL DE MEDICAMENTS ESTUDIO DE LA COMPOSICIÓN ALCALOÍDICA DE NARCISSUS BROUSSONETII Y DE TRES ESPECIES BRASILEÑAS DEL GÉNERO HIPPEASTRUM (AMARYLLIDACEAE) Memòria presentada per Jean Paulo de Andrade per optar al títol de doctor per la Universitat de Barcelona Director: Dr. Jaume Bastida Armengol Director: Dr. José Angelo S. Zuanazzi Doctorando: Jean Paulo de Andrade JEAN PAULO DE ANDRADE 2014 AGRADECIMIENTOS La experiencia de haber vivido estos casi 5 años en Barcelona ha sido única, tanto a nivel profesional como personal. En primer lugar, agradezco profundamente a mi Director de Tesis, Dr. Jaume Bastida, por haberme aceptado bajo su tutoría y por los conocimientos adquiridos en el ámbito de la fitoquímica y del RMN, así como en el campo de la investigación en general. Extiendo este agradecimiento a los doctores Carles Codina y Francesc Viladomat que, conjuntamente con Jaume, conducen de manera ejemplar este grupo caracterizado por una amplia trayectoria científica y dedicada labor docente, tan manifestada por todos aquellos que han tenido la oportunidad de conocerles. La actitud siempre cercana e interesada en el bien estar de cada uno de sus estudiantes y colaboradores también les diferencia. En este sentido, les agradezco profundamente todos estos años ahí vividos. Agradezco a la Agencia Española de Cooperación para el Desarrollo (AECID) por haberme concedido beca de 4 años para la realización de ésta Tesis Doctoral. Hago llegar un especial agradecimiento a Sra. Teresa María de Manuel Ochoa. Por otra parte, quiero expresar mi agradecimiento a aquellos que han, probablemente, compartido más tiempo conmigo tanto a nivel laboral como personal. Laura, Ying, Natalia y Strahil, muchas gracias por todo lo que he aprendido de ustedes, de vuestros trabajos, de vuestros ejemplos y, por supuesto, por su amistad. Natalia y Strahil, muchas gracias por lo que aprendí de ustedes respecto a la técnica de GC-MS. A Natalia, sobretodo, gracias por la siempre dispuesta ayuda con el castellano. Extiendo además mis agradecimientos a las personas quienes he tenido el gusto de coincidir en alguna temporada en el laboratorio. Michella, Edison, Stefania, Buket, Alina, Beatrice, Matteo, Nikoletta y Carmelina, gracias por la huella que habéis dejado y por las amistades que perduran. De la misma forma, quiero agradecer a los compañeros de otros laboratorios por las comidas, charlas, partidos, cumpleaños, viajes, en fin… Oscar, Susana, Miriam, Joan, Marta, Ana Gallego, Ana Belén, Dani, Dulce, Jann, Kosta, Diego, Liliana, Miren, Lucie, Xavi, Alejandra y un especial agradecimiento a Rafa, Karla y Marta Strzelec. De la misma manera, extiendo el agradecimiento a los amigos de otros Departamentos como Esperanca, Mathias, Paloma, Andrea y, sobretodo, Brezana. Muchas gracias por su amistad. A todos aquellos quiénes hemos compartido piso: Marc, Lourdes, Mireia y Pepito, gracias por su amistad y por el constante intercambio cultural que hemos disfrutado, sobretodo al enseñarme la cultura catalana. En la misma línea, vuelvo a agradecer al Mathias en conjunto con Paulete y Martini. Gracias por nuestro compañerismo y las tantas anécdotas que hemos vivido. Un abrazo muy cálido a todos mis compañeros del “Consulado del Gremio de Barcelona”, especialmente a Marta y Gi, por el haberme acogido en sus casas cuando fue necesario. Agradezco también a Carmina, Cisco, Benjamin por todo lo que compartimos juntos. Quisiera expresar un fuerte agradecimiento al personal del CCiT-UB, por su grandiosa colaboración en la realización de los experimentos que hicieron posible esta Tesis. Principalmente a la Dra. Asunción Marín (GC-MS, Facultad de Farmacia), a la Dra. Ana Linares (RMN, Facultad de Farmacia), al Dr. Miguel Feliz y a la Dra. Ma. Antonia Molins (RMN, PCB), al Dr. Alberto Adeva y a la Dra. Olga Jáuregui (HPLC-MS, PCB) y a la Dra. Mercè Font-Bardia (Rayos-X, SCT). Desde mi laboratorio de origen, hago llegar un abrazo de agradecimiento al Dr. Jose Angelo S. Zuanazzi, por todos estos años de investigación. Extiendo la gratitud a todos del laboratorio de Farmacognosia (UFRGS), especialmente a Raquel, Rafaela, Eduardo, Marina, Leticia, Roger y Miriam, quiénes hemos estado más tiempo trabajando juntos. Agradezco también al cuadro docente de la Universidad de Costa Rica (UCR), CIPRONA (UCR) y de la Universidad Nacional de Costa Rica (UNA) por haber hecho posible mi estancia allá, colaborando en distintos proyectos de investigación a parte de la experiencia docente. Un agradecimiento especial al Franklin Binns, Jonathan Parra, Juan Araya, Nien Tzu Weng, Roy Pérez y, sobretodo, Don Luis Poveda. Expreso mi profundo agradecimiento a mi familia por siempre haberme apoyado en la realización de mis sueños, por el amor sin límites y por los valores que me hacen fuerte al caminar por la vida. No hay palabras para describirlo. Simplemente gracias. En los momentos de mayor dificultad, siempre he tenido la oportunidad de contar con la ayuda incondicional especialmente de dos personas. Xavier Zarza y Marcelino Wagner, al igual que para mi familia, no tengo palabras para describirlo: simplemente les digo ¡GRACIAS! A todos ustedes que han sido partícipes de que hoy esté aquí… ¡MUCHAS GRACIAS! Listado de Abreviaciones AChE Enzima acetilcolinesterasa AD Enfermedad de Alzheimer ADN Ácido Desoxirribonucleico ARN Ácido Ribonucleico BSTFA N,O-bis-(trimetilsilil)trifluoroacetamida Calcd calculado CD Dicroísmo Circular CD3OD Metanol deuterado CDCl3 Cloroformo deuterado CHCl3 Cloroformo COSY Correlation spectroscopy (1H-1H) EI Ionización por impacto de electrones EIMS Espectrometría de masas por impacto electrónico EtOAc Acetato de etilo EtOH Etanol GC Cromatografía de gases GC-MS Cromatografía de gases acoplada a espectrometría de masas HMBC Heteronuclear Multiple Bond Correlation (1H-13C) HPLC Cromatografía líquida de alta resolución HPLC-ESI-MS Cromatografía líquida de alta resolución – Electrospray – Espectrometría de masas HPLC-ESI-MS/MS Cromatografía líquida de alta resolución – Electrospray – Espectrometría de masas en tándem HR-ESI-MS Espectrometría de Masa – Electrospray – Alta Resolución HRMS Espectrometría de Masa de Alta Resolución HR-QTOF-MS Espectrometría de Masa – Analisador Cuadrupolo – Analisador de Tiempo de Vuelo – Alta Resolución HSQC Heteronuclear Single Quantum Correlation (1H-13C) IC50 Concentración Inhibitoria de 50% IR Infrarrojo IUPAC Unión Internacional de Química Pura
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