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Piperaceae) Y Determinación De Actividad Insecticida Sobre Spodoptera Frugiperda (Lepidóptera)

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Piperaceae) Y Determinación De Actividad Insecticida Sobre Spodoptera Frugiperda (Lepidóptera) Estudio fitoquímico de dos especies del género Piper (Piper subtomentosum, Piper septuplinervium) (Piperaceae) y determinación de actividad insecticida sobre Spodoptera frugiperda (Lepidóptera) Mónica Constanza Ávila Murillo Universidad Nacional de Colombia Facultad de Ciencias, Departamento de Química Bogotá, Colombia 2014 Estudio fitoquímico de dos especies del género Piper (Piper subtomentosum, Piper septuplinervium) (Piperaceae) y determinación de actividad insecticida sobre Spodoptera frugiperda (Lepidóptera) Mónica Constanza Ávila Murillo Tesis o trabajo de investigación presentada(o) como requisito parcial para optar al título de: Doctor en Ciencias Química Director (a): Doctor, MSc, Químico. Luis Enrique Cuca Suarez Línea de Investigación: Química de Productos Naturales Grupo de Investigación: Estudio Químico y de Actividad biológica de Rutáceas y Miristicáceas Colombianas Universidad Nacional de Colombia Facultad de Ciencias, Departamento de Química Bogotá, Colombia 2014 Resumen El presente trabajo combina estudios fitoquímicos y de actividad insecticida sobre una plaga polífaga, con el fín de contribuir a la búsqueda de productos naturales potencialmente útiles en el sector agrícola. El trabajo comprende aislamiento bioguiado y caracterización de metabolitos secundarios presentes en las inflorescencias de P. subtomentosum y la parte aérea de P. septuplinervium, caracterización química de 3 aceites esenciales de las mismas especies, modificaciones estructurales de algunos de los flavonoides naturales obtenidos, síntesis de chalconas y evaluación de la actividad insecticida sobre S. frugiperda de los extractos, aceites esenciales, compuestos aislados, y los compuestos obtenidos por síntesis y semisíntesis. El estudio fitoquímico bioguiado desarrollado en las dos especies vegetales condujo al aislamiento y caracterización de 9 metabolitos secundarios, de los cuales el ácido protocatéquico C8 (17,16 ppm) y el flavonol galangina C2 (13,63 ppm) fueron los metabolitos más activos contra la larvas de S. frugiperda. Debido al reconocido papel de los flavonoides en la relaciones planta-insecto, y a que fueron los metabolitos aislados en mayor cantidad en este trabajo, se evaluó la actividad antialimentaria de una serie de compuestos de tipo flavonoide: flavonoides aislados de diferentes especies vegetales, flavonoides modificados estructuralmente (dos de ellos sin previos reportes en la literatura), y flavonoides obtenidos por síntesis (dos de ellos sin previos reportes en la literatura) estableciendo relaciones estructura-actividad. El estudio de los aceites esenciales de las especies vegetales estudiadas, mostró que el contenido de monoterpenos de los aceites de inflorescencias de P. subtomentosum (44%) y parte aérea de P. septuplinervium (77%) es el responsable de la toxicidad fumigante que presentan dichos aceites esenciales (13,2 µL/L de aire y 9,41 µL/L de aire respectivamente). Se determinó que los monoterpenos canfeno, α y β-pineno, y limoneno, son algunos de los metabolitos responsables de la actividad fumigante, siendo el canfeno el que posee la mayor actividad con CL50 < 0,57 µg/L de aire. Palabras Clave: Piper septuplinervium, Piper subtomentosum, Piperaceae, Spodoptera frugiperda, flavonoides, terpenos. Abstract The present research combines phytochemical studies and insecticidal activity on polyphagous pest, with the aim of contributing to the search of potentially useful natural products in the agricultural sector. The work consists of isolation and characterization of the secondary metabolites present in the inflorescences of Piper subtomentosum and the aerial part of Piper septuplinervium, chemical characterization of three essential oils of the same species, structural modifications of some natural flavonoids, chalcone synthesis and insecticidal activity evaluation on S. frugiperda of the extracts, essential oils, isolated compounds, and the compounds obtained by synthesis and semisynthesis. The bioassay-guided phytochemical study of the two species leads to the isolation and characterization of 9 secondary metabolites, of which protocatechuic acid C8 (17.16 ppm) and flavonol galangina C2 (13.63 ppm) were the most active metabolites against S. frugiperda. Due to the recognized role of flavonoids in plant-insect relationships and for being the metabolites isolated in greater amounts in this work, the antifeedant activity of flavonoids type compounds was evaluated establishing structure-activity relationships. The compounds evaluated were: flavonoids isolated from different plant species, structurally modified flavonoids (two of them with no previous reports in the literature), and flavonoids obtained by synthesis (two of them with no previous reports in the literature). The study of essential oils showed that the content of monoterpenes in inflorescences of P. subtomentosum (44%) and aerial part of P. septuplinervium (77%) oils is responsible for the fumigant toxicity of essential oils (13,2 µL/L of air and 9,41 µL/L of air respectively). the monoterpenes camphene, α and β-pinene and limonene, are some of the metabolites responsible for the fumigant activity. Camphene was the more active metabolite with LC50<0.57 µg/L of air. Keywords: Piper septuplinervium, Piper subtomentosum, Piperaceae, Spodoptera frugiperda, flavonoids, terpenes. Contenido INTRODUCCIÓN .................................................................................................. 1 1. COMPOSICIÓN QUÍMICA Y DETERMINACIÓN DE ACTIVIDAD INSECTICIDA DE LOS ACEITES ESENCIALES DE Piper subtomentosum Y Piper septuplinervium (PIPERACEAE). ............................................................. 9 1.1. Generalidades ..................................................................................................................... 9 1.1.1 Insecticidas a partir de aceites esenciales de plantas .................................................... 10 1.1.2 Aceites esenciales obtenidos de especies de la familia Piperaceae. ............................. 11 1.1.3 Insecticidas comerciales a base de aceites esenciales. ................................................. 15 1.2 Materiales y Métodos ....................................................................................................... 16 1.2.1. Análisis Químico de los aceites esenciales ...................................................................... 16 1.2.2 Determinación de actividad insecticida de aceites esenciales. ......................................... 17 1.3 Resultados y discusión ................................................................................................... 20 1.3.1. Composición química de los aceites esenciales ................................................... 20 1.3.2. Determinación de actividad insecticida de los aceites esenciales ...................... 24 1.4 Conclusiones .................................................................................................................... 40 1.5 Bibliografía ........................................................................................................................ 41 2. ESTUDIO FITOQUÍMICO BIOGUIADO DE LOS EXTRACTOS ETANÓLICOS DE INFLORESCENCIAS DE Piper subtomentosum Y PARTE AÉREA DE Piper septuplinervium. .................................................................. 57 2.1 Generalidades ................................................................................................................... 57 2.1.1 Sustancias aisladas de plantas como insecticidas ......................................................... 58 2.1.2 Metabolitos fijos aislados de la familia Piperaceae. ........................................................ 63 2.2 Materiales y Métodos ....................................................................................................... 79 2.2.1 General ........................................................................................................................... 79 2.2.2 Material Vegetal .............................................................................................................. 80 2.2.3 Material Biológico ........................................................................................................... 80 2.2.4 Determinación de actividad insecticida ........................................................................... 80 2.2.5 Estudio fitoquímico bioguiado de la parte aérea de P. septuplinervium ........................ 81 2.2.6 Estudio fitoquímico bioguiado de las inflorescencias de P. subtomentosum .................. 82 2.2.7 Determinación del efecto de los extractos etanólicos de parte aérea de P. septuplinervium e inflorescencias de P. subtomentosum sobre el ciclo de vida de S. frugiperda…………………………………………………………………………………………………83 2.3 Resultados y discusión ................................................................................................... 85 2.3.1 Estudio fitoquímico bioguiado de la parte aérea de P. septuplinervium y las inflorescencias de P. subtomentosum. ....................................................................................... 85 2.3.2 Efecto de los extractos etanólicos de parte aérea de P. septuplinervium y las inflorescencias de P. subtomentosum sobre el ciclo de vida de S. frugiperda ......................... 108 2.4 Conclusiones .................................................................................................................. 114 2.5. Bibliografía .....................................................................................................................
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