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Programa De Ciencias Y Tecnología Analítica. Estilben Universidad de Concepción Dirección de Postgrado Facultad de Farmacia -Programa de Ciencias y Tecnología Analítica. Estilbenoides y proantocianidinas en sarmientos de vides: Caracterización, incidencia de las condiciones de guarda post-poda, actividad antioxidante y antiproliferativa en células cancerosas. Tesis para optar al grado de Doctor en Ciencias y Tecnología Analítica. Vania Stephanie Sáez Pulgar CONCEPCIÓN-CHILE 2018 Profesor Guía: Dr. Dietrich von Baer von Lochow Profesor Co-Guía: Dra. Claudia Mardones Peña Dpto. de Análisis Instrumental, Facultad de Farmacia. Universidad de Concepción ii Tabla de contenidos. Índice de figuras..................................................................................................................vii Índice de tablas.....................................................................................................................xi Resumen..............................................................................................................................xiii Capítulo 1: Introducción. ..................................................................................................... 1 1.1. Industria vitivinícola en Chile. ..................................................................................... 2 1.2. Alternativas de manejo de residuos de la industria vitivinícola. ................................. 3 1.3. (Poli)fenoles bioactivos en Vitis vinífera. .................................................................... 6 1.3.1. Flavonoides: .......................................................................................................... 6 1.3.2. Proantocianidinas: ................................................................................................. 7 1.4. No flavonoides: .......................................................................................................... 10 1.4.1. Ácidos fenólicos: ................................................................................................. 10 1.4.2. Estilbenoides: ...................................................................................................... 11 1.5. Sarmientos como fuente de compuestos bioactivos................................................... 17 1.5.1. Flavonoides en sarmientos: ................................................................................. 17 1.5.2 Concentración de compuestos no flavonoides en sarmientos: ............................. 19 1.5.3. Factores que influyen en la concentración de estilbenoides en sarmientos de Vitis vinifera .......................................................................................................................... 23 1.6. Aislamiento de estilbenoides en órganos de la vid .................................................... 25 1.7. Test de reducción de tetrazolio (MTT) para la medición in vitro de viabilidad celular…………….. .......................................................................................................... 29 1.8. Análisis de estilbenoides y procianidinas por HPLC. ................................................ 31 1.8.1. Cromatografia bidimensional .............................................................................. 35 2. Hipótesis y Objetivos ...................................................................................................... 39 2.1. Hipótesis: .................................................................................................................. 39 2.2. Objetivo General: .................................................................................................... 39 2.3. Objetivos específicos: ............................................................................................... 40 3. Estrategia analítica para el análisis de estilbenoides y procianidinas en sarmientos........ 41 3.1. Aislamiento de estilbenoides desde sarmientos ......................................................... 41 3.2. Caracterización y elucidación estructural de oligoestilbenoides ............................... 42 3.3. Ensayos de actividad antiproliferante de estilbenoides en células cancerosas .......... 42 iii 3.4. Determinación cuantitativa de estilbenoides y proantocianidinas en sarmientos: incidencia de condiciones el proceso de guarda post-poda .............................................. 42 3.5. Perfil de estilbenoides y procianidinas en sarmientos mediante LC x LC ................ 43 4. Referencias: ...................................................................................................................... 44 Capítulo 2: Oligostilbenoids in Pinot Noir Grape Cane Extract: Isolation, Characterization, Antioxidant Capacity and in vitro Anti-proliferative Effect on Cancer Cells ........................................................................................................................ 65 Abstract.................................................................................................................................66 1. Introduction ................................................................................................................... 68 2. Material and methods .................................................................................................... 71 2.1 Solvents and reagents .................................................................................................. 71 2.2 Grape cane extract ...................................................................................................... 72 2.3 Purification of extract by centrifugal partition chromatography ................................ 72 2.4 Identity assignment by HPLC-DAD-QToF and quantification by HPLC-DAD-FL .. 73 2.5 Isolation of oligostilbenoids by semi-preparative HPLC-UV .................................... 74 2.6 Structural determination of isolated oligostilbenoids by NMR spectroscopy ............ 74 2.7 Antioxidant capacity of isolated oligostilbenoids ....................................................... 75 2.8 Antiproliferative assay in human cell lines ................................................................. 75 3. Results and Discussion .................................................................................................. 76 3.1 Purification of grape cane extract by CPC .................................................................. 76 3.2 Purificación of the major and minor oligostilbenoids by semi-preparative HPLC- UV.....................................................................................................................................83 3.3 Antioxidant capacity of stilbenoids ............................................................................ 90 3.4 Antiproliferative assay in human cell lines ................................................................. 94 4. Conclusions ...................................................................................................................... 97 Acknowledgments ................................................................................................................ 97 References: ........................................................................................................................... 98 Supplementary material: ..................................................................................................... 105 iv Capítulo 3: sección 1, C18 core-shell column with in-series absorbance and fluorescence detection for simultaneous monitoring of changes in stilbenoid and proanthocyanidin concentrations during grape cane storage ...................................... 123 Abstract ............................................................................................................................... 124 1. Introduction .................................................................................................................... 126 2. Materials and methods .................................................................................................... 129 2.1 Chemicals used .................................................................................................... 129 2.2 Plant material used ............................................................................................... 130 2.3 Extraction method used............................................................................................. 130 2.4 Identification of analytes using HPLC-DAD-FL-ESI-MS/MS ................................ 131 2.5 HPLC-DAD-FL conditions for quantitative determination of analytes ................... 132 2.6 Calculations ......................................................................................................... 132 3. Results and discussion .................................................................................................... 133 3.1 Identification of analytes using HPLC-DAD-FL-ESI-MS/MS ................................ 133 3.2 Chromatographic separation ..................................................................................... 137 3.3 Quantification of proanthocyanidins and stilbenoids in grape canes ....................... 139 3.4. Effect of relative humidity during post-pruning storage on stilbenoid concentrations..................................................................................................................142 3. 5. Changes in proanthocyanidin levels in canes during post-pruning storage ............ 146 4. Conclusions ...................................................................................................................
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