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Lamiaceae Extracts and Compounds for Topical Application Through Nano Delivery Systems

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Lamiaceae Extracts and Compounds for Topical Application Through Nano Delivery Systems Doctoral Program in Health Sciences D420 Lamiaceae extracts and compounds for topical application through nano delivery systems Doctoral thesis presented by: Filipe Jorge da Silva Pereira Alcalá de Henares, 2017 II DEPARTAMENTO DE CIENCIAS ESCOLA DE CIÊNCIAS E TECNOLOGIAS DA BIOMEDICAS SAÚDE En virtud del acuerdo de colaboración con la Universidade Lusófona de Humanidades e Tecnologías Programa de doctorado D420 - ciencias de la salud Extractos de Lamiaceae y compuestos para aplicación tópica através de un sistema nano de liberación Tesis doctoral presentada por: Filipe Jorge da Silva Pereira Directores: Prof. Dra. Patrícia Rijo Prof. Dra. Catarina Reis Prof. Dra. Ana M. Díaz Lanza Alcalá de Henares, 2017 DPTO. CIENCIAS BIOMÉDICAS Unidad Docente de Farmacología Facultad de Medicina Universidad de Alcalá Ctra. Barcelona, Km. 33,600 28871 Alcalá de Henares (Madrid) Telf.: 91 885 45 49 - Fax: 91 885 45 91 e-mail: [email protected] PROF. D. PEDRO DE LA VILLA POLO, COORDENADOR DEL PROGRAMA DE DOCTORADO EN CIENCIAS DE LA SALUD, CERTIFICA: Que el trabajo titulado: “Lamiaceae extracts and compounds for topical application through nano delivery systems” ha sido realizado por D. Filipe Jorge da Silva Pereira, bajo la dirección de las Dras. Ana María Díaz- Lanza, Profesora Titular de Farmacología del Dpto. de Ciencias Biomédicas, de la Universidad de Alcalá, Patrícia Dias de Mendonça Rijo Profesora Auxiliar y Profesora de Química Farmacéutica de la Escola de Ciências e Tecnologias da Saúde de la Universidade Lusófona de Humanidades e UNIVERSIDAD DE ALCALÁ, PATRIMONIO DE LA HUMANIDAD Tecnologias de Lisboa y Ana Catarina Beco Pinto Reis Profesora Asistente y Profesora de Tecnología Farmacéutica en la Faculdade de Farmácia de la Universidade de Lisboa, respectivamente y cumple todos los requisititos para su defensa pública como Tesis Doctoral. Alcalá de Henares, 28 de julio de dos mil diecisiete. II DPTO. CIENCIAS BIOMÉDICAS Unidad Docente de Farmacología Facultad de Medicina Universidad de Alcalá Ctra. Barcelona, Km. 33,600 28871 Alcalá de Henares (Madrid) Telf.: 91 885 45 49 - Fax: 91 885 45 91 e-mail: [email protected] PATRÍCIA DIAS DE MENDONÇA RIJO, PROFESORA AUXILIAR Y PROFESORA DE QUÍMICA FARMACÊUTICA DA UNIVERSIDADE LUSOFONA DE HUMANIDADES E TECNOLOGIAS, ANA MARÍA DÍAZ-LANZA, PROFESORA TITULAR DE UNIVERSIDAD DEL ÁREA DE FARMACOLOGÍA DEL DEPARTAMENTO DE CIENCIAS BIOMÉDICAS DE LA FACULTAD DE FARMACIA DE LA UNIVERSIDAD DE ALCALÁ Y ANA CATARINA BECO PINTO REIS, PROFESORA AUXILIAR Y PROFESORA DE TECNOLOGIA FARMACÉUTICA NA FACULDADE DE FARMÁCIA DE LA UNIVERSIDADE DE LISBOA. CERTIFICAN: Que la memoria para optar al Grado de Doctor, elaborada por Filipe Jorge da Silva Pereira, cuyo título es: "Lamiaceae extracts and compounds for topical application through nano delivery systems” ha sido realizada bajo su dirección y que reúne todos los requisitos necesarios para su juicio y calificación. UNIVERSIDAD DE ALCALÁ, PATRIMONIO DE LA HUMANIDAD Y para que así conste, firman el presente certificado en Alcalá de Henares a 24 de julio de dos mil diecisiete. Patrícia Rijo Catarina Pinto Reis Ana Mª Díaz-Lanza Aos meus pais e avó II Acknowledgements Those were excellent years of learning, with good and less good moments but that are part of my growth. I would like to leave a few words of appreciation to people who have been present on this journey. Firstly, I would like to express my gratitude to my advisors Prof. Dr. Patrícia Rijo and Prof. Dr. Catarina Reis for all the support during PhD research. Without their support and efford, this work would never have been possible. I am also grateful to all CBios group, laboratory assistants and students of ULHT that I had pleasure to meet. I would also like to express my gratitude to Dr. Ana Mª Díaz-Lanza for its availability during all processes of the thesis. I would like to thank the support of my laboratory colleagues, Diogo Matias, Catarina Silva and Luis Roque. There were days of good humor and friendship that made this a much more pleasant journey. Also to Catarina Garcia and Ana Mota who I worked with, it was great to worked with you. A very special gratitude goes out to research groups outside ULHT, with which I had the pleasure to work: Prof. Pedro Faísca and Prof. Carlos Afonso group from FFUL (specially to Carlos Monteiro and Monica Estevão), Prof. Lia Ascenção and Prof. Rodrigo Almeida group from FCUL (specially to Filipa, Catarina Antunes and Ana Carreira) and Prof. Rita Sobral from FCT-UNL. A special mention to people of Gomensoro PZ, particularly to Luis Proença for availability of time and my colleague and friend Daniela Roque for your support. I am grateful to my friends, that they are more than family, who have supported me along the way: João, Fernando, Carla, Telma and Janete. Also, I am grateful to my family members who supported me and encouraged all this time. A special thanks to my companion Filipa Carneiro who attended me in this life course. Their understanding and support were essential during the last years. To my pillars, my best friends, my parents, who always strove to give me the best education and the best of affections. I know the road to you has never been easy but it seems to have made up for it. I know that I can count on your support and you can always count on me. For my grandmother, thank you for your support and for being who you are. I really love you all. Thanks for all your support! Lamiaceae extracts and compounds for topical application through nano delivery systems Filipe Jorge da Silva Pereira Index 1 Figure index ........................................................................................................... VII 2 Table index ............................................................................................................. XI 3 Abstract ................................................................................................................. XIII 4 Resumen ................................................................................................................ XV 5 Abbreviations and acronyms list ........................................................................ XVII 1 Chapter 1 .................................................................................................................. 1 1.1 Introduction ........................................................................................................ 3 1.2 Royleanones, rearranged royleanones and royleanones-related diterpenes of natural origin ................................................................................................................ 3 1.3 Royleanone and royleanone-related abietanes ................................................... 4 1.4 Rearranged royleanones ................................................................................... 19 1.4.1 Seco-abietanes .......................................................................................... 19 1.4.2 Abeo-abietanes ......................................................................................... 21 1.4.3 Other abietane quinones ........................................................................... 22 1.5 Total synthesis ................................................................................................. 34 1.5.1 Royleanones and derivatives .................................................................... 34 1.6 Biological activity ............................................................................................ 43 1.7 Conclusions ...................................................................................................... 45 1.8 Hypothesis and objectives ............................................................................... 47 2 Chapter 2 ................................................................................................................ 49 2.1 Introduction ...................................................................................................... 51 2.2 Material and methods ....................................................................................... 52 2.2.1 Plant Material ........................................................................................... 52 2.2.2 Chemicals ................................................................................................. 52 2.2.3 Extraction Methods .................................................................................. 53 III Doctoral thesis in Health Science Universidade Lusófona and Universidad de Alcalá 2.2.4 Extraction quantification of AHR by HPLC-DAD .................................. 53 2.2.5 Preparation and Characterization of the 7α-Acetoxy-6β- hidroxyroyleanone Sample Used in the Structural and Thermal Studies ............... 54 2.2.6 Single Crystal X-ray Diffraction. ............................................................. 54 2.2.7 Differential Scanning Calorimetry (DSC) ................................................ 55 2.3 Results and Discussion .................................................................................... 56 2.3.1 Extraction optimization of 7α-acetoxy-6β-hydroxyroyleanone (AHR) by HPLC-DAD ............................................................................................................ 56 2.3.2 Single Crystal X-ray Diffraction (SCXRD) ............................................. 57 2.3.3 Differential Scanning Calorimetry (DSC) ................................................ 61 2.4 Conclusions .....................................................................................................
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