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Seminari Recerca Ff 201905 GALANTAMINA (Gal) Y ENF. ALZHEIMER (EA) OH H LA BIODIVERSITAT COM A FONT DE O MeO RECURSOS NATURALS PER NMe UNA EXPLOTACIÓ SOSTENIBLE Galantamina . Reminyl® Razadyne® (USA) Dr. JAUME BASTIDA Grup de Productes Naturals Facultat de Farmàcia. UB [email protected] Leucojum aestivum Narcissus cv Carlton Hippeastrum papilio OTROS ALCALOIDES DE LAS AMARYLLIDACEA OTROS ALCALOIDES DE LAS AMARYLLIDACEA OH Patente: US2016024074 (A1) Montanina OR1 Narciclasina y Pancratistatina OMe Fracción de alcaloides de los H O O OH bulbos de Rhodophiala bifida OR2 Antitumorales. Fase clínica. NH O Inhiben selectivamente: O N H OH O Tratamiento/prevención de: • crecimiento sarcoma M5076 sal de piridinio de O + 3,4-O-fosfato cíclico NH • artritis reumatoide . de narciclasina R ,R = P • proliferación de leucemia 1 2 O narciclasina R1=R2=H linfocítica P388 • colitis ulcerosa OH Inducen apoptosis específica en • sepsis HO OR1 cáncer de mama. • osteoporosis H O • infecciones inflamatorias OR2 H NH • artritis psoriásica O Inventores: OH O Gnieslaw de Oliveira, P.; Pereira Ramos • artritis crónica juvenil Pedrazza, G.; Farinon, M; Ricardo • otras enf. inflamatorias no sal sódica de O Problemas de solubilidad de la Machado, X.; Zuanazzi, J.A.S.; Spies, F. 3,4-O-fosfato cíclico P de pancratistatina R1,R2= + específicas de articulaciones O Na base UFRGS y HCPA (RS, Brasil) pancratistatina R1=R2=H 3 DESARROLLO SOSTENIBLE , CAMBIO CLIMÁTICO Y ECOSISTEMAS UNIVERSIDADES IMPLICADAS ESPAÑA Diversidad Biológica para el Desarrollo Sostenible Universidad de Barcelona MÉXICO Unv Nacional VENEZUELA Autónoma de México Objetivos Específicos Universidad de los Andes COLOMBIA Universidad de Antioquia BRASIL • bioprospección de Amaryllidaceae Universidad del Cauca UF do Espírito Santo UF do Rio Grande do Sul • evaluar los recursos ECUADOR Universidad Tecnológica Indoamérica BOLIVIA • identificar nuevos compuestos Esc. Superior Politécnica Chimborazo Unv Mayor de San Andrés • identificar nuevas fuentes Gal PERÚ PARAGUAY Unv Nacional de Trujillo Unv Nacional de Asunción • bases para aprovechamiento sostenible Unv Nacional de Moquegua • obtención de Gal a nivel de planta piloto CHILE ARGENTINA Universidad de Talca Universidad Nacional de San Juan > 125 investigadores de diferentes áreas 5 6 LA FAMILIA AMARYLLIDACEAE AMARYLLIDACEAE DE IBEROAMERICA ANTIGUA familia Amaryllidaceae familia Amaryllidaceae subfam. Amaryllidoideae familia Agapanthaceae subfam. Agapanthoideae a b c d familia Alliaceae subfam. Allioideae APG 2009 NUEVA . e f g h i Amaryllidaceae Agapanthaceae Alliaceae j k l m [a] Eucharis amazonica, [b] Rhodophiala moelleri, [c] Rhodophiala andicola, [d] Hymenocallis littoralis, Chase, Reveal, Fay (2009) Botanical Journal of the Linnean Society 161 : 132-6 7 [e] Sprekelia formosissima, [f] Ismene amancaes, [g] Worsleya procera, [h] Zephyranthes grandiflora, 8 [i] Phaedranassa dubia, [j] Hippeastrum calyptratum, [k] Hp. striatum, [l] Hp. argentinum, [m] Hp. psittacinum 1. BIOPROSPECCIÓN: MUESTREO 1. BIOPROSPECCIÓN: ANÁLISIS GENÉTICO 1. Cumplimiento de los requisitos legales: Convenio sobre la Phaedranassa viridiflora Baker Biodiversidad (1993) y Protocolo de Nagoya (2010) 2. Prospección de la Biodiversidad. Recolección 300 g PF 3. Colección de material de Herbario centralizado en la UTI Ecuador (Quito, Ecuador), integrado en el Missouri Botanical . Garden (http://tropicos.org/ ) . 4. Banco de germoplasma . Micropropagación bulbos Prof. Alan Meerow Oleas, Meerow, Ortega (2016) Genetic structure of the threatened Phaedranassa 9 schizantha (Amaryllidaceae) Botanical Journal of the Linnean Society 1-11 2. ESTUDIO PRELIMINAR: LOS ALCALOIDES 2. ESTUDIO PRELIMINAR: ALCALOIDES PRINCIPALES 12 11 OH 3 2 4 OH HO 4 2 HO 1 MeN 3 3 4a 5' 10 10b H - Lycorina, Lycoris radiata 2 4 10 H 10b HO 4' 6' β 9 10a MeO 9 10a 1 2 HO 1 3 5 1 O 11 4a 6 H H H - Aislamiento: Gerrad, 1877 NH α N 12 O 3' 1' O 8 6a 8 HO β MeO 6a 6 10 10b H 4 2' ' 7 6 7 9 10a O - Caracterización estructural: O 11 norbelladinanorbelladine lycorinalycorine homolycorinahomolycorine 4a OH Nagakawa et al., 1956 : 2 2 2 3 3 . H 1 OH 1 OMe 1 OH 12 11 11 3 N 10 10 OH 10 H 4 - Numeración: 8 6a O 9 10a 4a 4 O 9 10a 4a 4 O 9 10a O 10b 10b 10b OH 7 6 H 12 H 12 4a Ghosal, Saini & Razdan, 1985 N N NH O 8 6a O 8 6a O 8 6a 6 7 6 7 6 7 crininacrinine haemanthaminahaemanthamine OH O narciclasinanarciclasine OMe Bastida, Lavilla, Viladomat (2006) Chemical and biological aspects of Narcissus 1 OMe 3 alkaloids. In The Alkaloids 63 : 87-179 10 11 11a 2 2 2 4 3 OH O 9 10a OH 1 Bastida, Berkov, Torras, Pigni, de Andrade, Martínez, Codina, Viladomat (2011) H 4a 1 4a 3 O 10 NMe 12 10 10b 9 10a 4 MeO 9 10a Chemical and biological aspects of Amaryllidaceae alkaloids. In Recent Advances O 11 4 10b 12 O 8 6a H N 4a in Pharmaceutical Sciences, 65-100 OH 7 6 11 12 O Berkov, Osorio, Viladomat, Bastida (2019) Chemodiversity, Chemotaxonomy and O 8 6a montaninamontanine 8 6a NMe 7 6 7 6 Chemoecology of Amaryllidaceae alkaloids. In The Alkaloids 83 : 000 12 tazettinatazettine galanthaminegalantamina 2. ESTUDIO PRELIMINAR DE LAS MUESTRAS 2. ESTUDIO PRELIMINAR: GC-MS 1. Extracción de 300 g PF estudios preliminares: caracterizar compuestos a [0.001%] de PF 2. Escasa manipulación 3. Instrumental/técnicas avanzadas . Programa de Temperatura: Derivatización: 100-180 °C a 15 °C/min, 180-300 °C a 5°C/min, 5 mg extracto + Piridina (50 µL) mantener 10 min a 300 °C 90 min a 40 °C con BSTFA (50 µL) T Inyector: 250 °C // Flujo (He): 0.8 mL/min Evaporar a sequedad N2 [1mg/mL] // Inyección: 1 µL // Split 1:20 Redisolver en 250 µL de MeOH - Los valores del Indice de Kovats (RI) de los compuestos se mide con mezcla patrón de alcanos saturados (C9-C36) 13 Torras, Berkov, Jáuregui, Caujapé, Viladomat, Codina, Bastida (2010) Phytochem. Anal. 21 , 80-8 Detección de Galantamina Quimiotipos de Leucojum aestivum en Bulgaria Ly -chemotype near Black Sea Hly -chemotype found along Danube, separated from South by Balkans . Gal -chemotype in the South El contenido medio de Gal varia de 0.003 a 0.08% (PS) en el Norte, hasta un 0.42% en las poblaciones del Sur. Algunos individuos alcanzan el 0.65% en Gal Berkov, Georgieva, Kondakova, Viladomat, Bastida, Atanassov, Codina (2013) Biochemical 15 Systematics and Ecology 46 : 152-61 16 3. CARACTERIZACIÓN PARCIAL: LC-SPE-NMR 3. CARACTERIZACIÓN PARCIAL: LC-SPE-NMR F1 , m/z 350 C18 H23 NO 6 OMe HO OH H MeO H N . MeO O narcissidine N-oxide (CD 3OD) t (min) %B 0 5 3 5 48 22 51 100 56 100 57 5 60 5 18 4. DOCKING DIANAS EA: ACE, BCE, GSK-3βββ 5. MICROPROPAGACIÓN in vitro ACE Torpedo californica GSK-3βββ SER200 Preparación Esterilización ASP200 del bulbo superficial LYS85 GLU199 Seccionado . del bulbo TYR130 GLY117 ASP264 Obtención de O Formación de Introducción al O nuevos brotes cultivo in vitro twin-scales OH OAc H H oscuridad, 23±1°C placa basal O O MeO MeO Sellés, Bergoñón, Viladomat, Bastida, Codina (1999). Plant Cell Tissue and Organ NMe NH Culture 49 : 129-36 Galantamina Acetilleucovernina Sellés, Viladomat, Bastida, Codina (1999). Plant Cell Reports 18 : 646-51 20 5. MICROPROPAGACIÓN in vitro 5. MICROPROPAGACIÓN in vitro : Leucojum aestivum Murashige & Skoog Operaciones + Sacarosa 3% previas + Agar 0.8% BAP-NAA (5:1 mg/L) oscuridad, 23±1°C Brotes t-s Transferencia a medio Bulbo inicial líquido, Sacarosa 6% sin agar ni hormonas . BAP 2 mg/mL + NAA 0.15 mg/mL 4-6 semanas Repicaje 15 días Baby foods Inoculación a medios 30 mL, 110 rpm de Engrosamiento y Fotoperiodo 16/8h Enraizamiento T 23±1°C MS + Sacarosa 6% + Agar 0.8% arena /turba (1:1) + NAA (0.1 mg/L) Trasplante 3 meses después o Carbón activo al suelo 21 22 5. MICROPROPAGACIÓN in vitro : Hippeastrum papilio 5. MICROPROPAGACIÓN in vitro ❶ ❷ ❸ . ❹ ❺ ❻ aclimatación ❶ Twin scaling on MS + 2 mg/L BAP and 0,1 mg/L NAA, ❷ Bulb formation 30 days after scaling, ❸ Bulb formation 50 days after scaling, ❹ Bulb growing in temporary immersion, ❺ Bulbs ready for planting, ❻ Acclimated bulbs Colque, Viladomat, Bastida, Codina (2002). Journal of Horticultual Science & Biotech. 23 77 : 739-43 6. COMPLETAR CARACTERIZACIÓN ESTRUCTURAL 7. ENSAYOS DE LAS ACTIVIDADES in vitro E in vivo HMBC MS, HRMS ααα pf, [ ]D, UV, IR Docking RMN 1D: H1/C13 /DEPT RMN 2D: COSY, HMQC LC-SPE-NMR Micropropagación NOESY, HMBC del material vegetal Elucidación estructural Rayos X, CD MS, RMN (1D/2D), IR, GC-MS HRMS, UV, CD, X-rays . NOESY Muestra Extracto LC-DAD Compuesto Puro Ensayos Biológicos Estudios in vitro/in vivo Antiprotozoarios Apoptosis enfermedades neurodegenerativas Rayos X 26 7. ESTUDIO ACTIVIDADES in vitro : INHIBICIÓN ACE/BCE 7. ESTUDIO ACTIVIDADES in vitro : INHIBICIÓN GSK3 βββ FRACCIÓN DE ALCALOIDES / + SUSTRATO + ALCALOIDE ATP exceso GSK3 βββ P . SUSTRATO + + ADP 2) Detección actividad Kinasa ATP remanente a. conversión ADP ATP 1) ADP Glo ® Luciferina O HO S N O + Agotar ATP nuevo ATP N S + 1/2 O2 b. Luciferasa / Mg +2 HO S N O AMP + N S + PPi + CO2 Oxiluciferina Ellman, Courtney, Andres jr, Featherstone (1961) Biochemical Pharmacol. 7: 88-90 López, Bastida, Viladomat, Codina (2002) Life Sciences 71 : 2521-2529 27 Baki, Bielik, Molnár, Szendrei, Keresü (2007) Assay and Drug DevelopmentTechnology 5: 75-83 7. ESTUDIO ACTIVIDADES in vitro : NEUROPROTECCIÓN CARACTERIZACIÓN MORFOLÓGICA NEURONAS Núcleos Dendritas Superposición - Cultivos primarios Hoescht MAP 2 Merge embriones rata Medio Wistar E18 Neuronas corteza cerebral - Ensayo de Citotoxicidad FA LDH FA (μg/mL) . DIV 0 6 7 8 0,75 6,00 Glu 125µM 1,50 12,00 - Ensayo de Neuroprotección (toxicidad por Glu) Núcleos condensados de conexiones Pérdida 3,00 24,00 FA Glu LDH Pretratamiento DIV 0 6 7 8 LDH: Lactato Deshidrogenasa Z.
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