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Determinación Del Potencial Del Hongo Liquenizado Bunodophoron Melanocarpum Como Fuente De Compuestos Duales Con Actividad Foto-Protectora Y Antioxidante

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Determinación Del Potencial Del Hongo Liquenizado Bunodophoron Melanocarpum Como Fuente De Compuestos Duales Con Actividad Foto-Protectora Y Antioxidante Determinación del potencial del hongo liquenizado Bunodophoron melanocarpum como fuente de compuestos duales con actividad foto-protectora y antioxidante Juan José Argüello Galindo Universidad Nacional de Colombia Facultad de Ciencias, Departamento de Farmacia Bogotá D.C, Colombia 2019 Determinación del potencial del hongo liquenizado Bunodophoron melanocarpum como fuente de compuestos duales con actividad foto-protectora y antioxidante Juan José Argüello Galindo Tesis presentada como requisito parcial para optar al título de: Magíster en Ciencias Farmacéuticas Directora: Ph.D. Norma Angélica Valencia Islas Profesora Asociada, Departamento de Farmacia Universidad Nacional de Colombia Co-director: Ph.D. José Leopoldo Rojas Araque Profesor Asociado, Departamento de Química Universidad Nacional de Colombia Línea de Investigación: Obtención de sustancias bioactivas a partir de fuentes naturales Grupo de Investigación en Química Medicinal (GRIQUIMED) Grupo de Investigación en Estudios Biológicos y Fisicoquímicos de Líquenes Colombianos Universidad Nacional de Colombia Facultad de Ciencias, Departamento de Farmacia Bogotá D.C, Colombia 2019 Me acreditan ser uno de los trabajadores más duros, y quizás lo soy, si el pensamiento es equivalente a la labor, ya que he dedicado a ello casi todas mis horas despierto. Pero si el trabajo es interpretado como la ejecución definida en un tiempo específico, según reglas rígidas, entonces podría ser que soy el peor de los holgazanes. Nikola Tesla VII Resumen La radiación ultravioleta (UV) posee fuerte vínculo con el cáncer de piel debido a sus efectos ionizantes y a la producción de estrés oxidativo que genera efectos negativos sobre las macromoléculas de este órgano. Por ello, para su prevención se hace uso de sustancias con actividad antioxidante y foto-protectora. Pese al uso de estos agentes, el aumento en la incidencia de este cáncer, lo ha convertido en un problema de salud pública a nivel nacional y mundial, enfatizando en la necesidad de contar con agentes antioxidantes y foto-protectores más eficaces para su prevención. Entre las fuentes naturales que pueden ser exploradas para obtener estas sustancias, los líquenes son organismos idóneos que poseen la capacidad de adaptarse a ambientes extremos de radiación UV gracias a que biosintetizan compuestos con dichas propiedades que les permiten protegerse ante tales condiciones. El presente trabajo se centró en la obtención de compuestos antioxidantes y/o foto-protectores a partir del hongo liquenizado Bunodophoron melanocarpum colectado en el páramo de Sumapaz, Colombia, ecosistema de alta montaña. Este estudio condujo al aislamiento y caracterización de los compuestos: esferoforina (1); ácido evernínico (2); ácido esferoforol carboxílico (3) y friedelina (4). La esferoforina y el ácido esferoforol carboxílico resultaron ser agentes duales con propiedades antioxidantes, cuyo mecanismo involucra la captación de radicales libres, la reducción de iones férricos y la inhibición de la peroxidación de lípidos; y con propiedades foto-protectoras, particularmente contra la radiación UVB. Todos los compuestos presentaron características de lipofilicidad y energía libre de Gibbs de transferencia adecuadas para actuar en la piel. De las sustancias objeto de estudio, (1) y (3) constituyen compuestos prometedores para el desarrollo de formulaciones destinadas a la prevención de patologías asociadas con la sobreexposición a la radiación solar, entre ellos el cáncer de piel. Palabras clave: Liquen - Bunodophoron melanocarpum – Antioxidante - Foto- protector - Estrés oxidativo. VIII Determinación del potencial del hongo liquenizado B melanocarpum como fuente de compuestos duales con actividad foto-protectora y antioxidante Abstract Ultraviolet radiation (UV) has a strong link with skin cancer owing to its ionizing effects and the produccion of oxidative stress, generating negative effects on macromolecules. Therefore, for its prevention, substances with antioxidant and photo-protective activity are used. Despite the use of photo-protective agents, the increase in the incidence of skin cancer has made it a public health problem nationally and globally, emphasizing the need of more effective antioxidant and photo-protective agents for its prevention. Among the natural sources that can be explored to obtain these substances, lichens are suitable organisms with the ability to adapt to external UV radiation environments. By biosynthesizing compounds with multiple properties, they can survive to a wide variety of conditions. The present work focused on obtaining antioxidant and/or photo-protective compounds from the lichenized fungus Bunodophoron melanocarpum collected at the high mountain ecosystem of the Sumapaz moorland, Colombia. This study led to the isolation and characterization of the compounds: sphaerophorin (1); everninic acid (2); sphaerophorol carboxylic acid (3) and friedelin (4). Sphaerophorin and esferoforol sphaerophorol carboxylic acid turned out to be dual agents with antioxidant properties, whose mechanism involves capture of free radicals, reduction of ferric ions and inhibition of lipid peroxidation; and photo-protective properties, particularly against UVB radiation. All the compounds had characteristics of lipophilicity and Gibbs free energy of transfer suitable to act on the skin. Of the substances under study, (1) and (3) are promising compounds for the development of formulations aimed to prevent pathologies associated with overexposure to solar radiation, including skin cancer. Keywords: Lichen - Bunodophoron melanocarpum - Antioxidant - Photo-protector - Oxidative stress. IX Contenido Pág. Resumen VII Lista de Figuras ............................................................................................................. XII Lista de Tablas .............................................................................................................. 15 Lista de Símbolos y abreviaturas ................................................................................. 17 Planteamiento del problema y justificación ................................................................ 20 1. Marco conceptual y estado del arte ........................................................... 25 1.1 Especies reactivas, oxidantes y estrés oxidativo ............................................ 25 1.1.1 Exposición a la radiación solar como factor principal de estrés oxidativo a nivel dérmico .................................................................................................. 28 1.2 Cáncer de piel ............................................................................................... 33 1.3 Antioxidantes y su papel en la piel ................................................................. 36 1.4 Fotoprotectores.............................................................................................. 39 1.5 Hongos Líquenizados .................................................................................... 46 1.5.1 Usos tradicionales de los hongos liquénizados ................................... 47 1.5.2 Metabolitos secundarios de hongos liquénizados ................................ 50 1.5.3 Actividad biológica de metabolitos secundarios de los hongos liquénizados ...................................................................................................... 52 1.5.3.1 Actividad antioxidante y fotoprotectora de extractos y sustancias liquénicas .......................................................................................................... 53 1.5.4 Antecedentes de la especie Bunodophoron melanocarpum ................ 64 1.5.4.1 Taxonomía .......................................................................................... 64 1.5.4.2 Hábitat y distribución ........................................................................... 65 1.5.4.3 Constituyentes químicos ..................................................................... 65 1.5.4.4 Usos tradicionales ............................................................................... 67 1.5.4.5 Actividad biológica .............................................................................. 67 2. Hipótesis ...................................................................................................... 68 3. Objetivos ...................................................................................................... 69 3.1 Objetivo general............................................................................................. 69 3.2 Objetivos específicos ..................................................................................... 69 4. Materiales y métodos .................................................................................. 70 4.1 Lugar de realización ...................................................................................... 70 4.2 Colecta e identificación taxonómica del material liquénico ............................. 70 X Determinación del potencial del hongo liquenizado B melanocarpum como fuente de compuestos duales con actividad foto-protectora y antioxidante 4.3 Estudio químico ..............................................................................................72 4.3.1 Procedimientos experimentales generales ...........................................72 4.3.2 Operaciones previas a la preparación del extracto ..............................74 4.3.3 Extracción de Bunodophoron melanocarpum ......................................74 4.3.4 Fraccionamiento primario del extracto de
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