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Búsqueda de sustancias bioactivas a partir de dos especies de la flora colombiana: alcaloides de "Phaedranassa dubia" (Amaryllidaceae) y biflavonoides de "Garcinia madruno" (Clusiaceae).

Authors: Osorio Durango, Edison Javier;

Búsqueda de sustancias bioactivas a partir de dos especies de la flora colombiana: alcaloides de "Phaedranassa dubia" (Amaryllidaceae) y biflavonoides de "Garcinia madruno" (Clusiaceae).

Abstract

El objetivo del presente trabajo ha sido la búsqueda de sustancias bioactivas en dos especies de la flora colombiana. Se pretendió aislar y caracterizar los metabolitos secundarios sintetizados por Phaedranassa dubia (Amaryllidaceae) y Garcinia madruno (Clusiaceae), además de estudiar la actividad antiprotozoaria in vitro y de evaluar la actividad antioxidante de los metabolitos aislados. El trabajo fitoquímico realizado con Phaedranassa dubia ha permitido el aislamiento de un nuevo alcaloide de tipo Amaryllidaceae, fedranamina, cuya estructura se ha establecido por análisis espectroscópicos (UV, EM, RMN y CD). Otros alcaloides identificados en esta especie han sido: pseudolicorina, sanguinina, galantamina, epinorgalantamina, hemantamina, ungeremina y zefbetaina. De otro lado, se ha reportado por primera vez el producto natural 7'-O-(6'-acetil)-glucósido de morelloflavona, al cual se ha dado el nombre trivial de madrunoudeasido, un nuevo biflavonoide aislado del extracto metanólico de las partes aéreas de Garcinia madruno (Clusiaceae). Es la primera vez que se reporta un biflavonoide acetil-glucósido, aislado del género Garcinia. Igualmente se reportan los biflavonoides amentoflavona, morelloflavona, volkensiflavona, fukugisido y spicatasido, a partir de la misma especie vegetal. La evaluación in vitro frente a cuatro diferentes parasitos antiprotozoarios se realizó utilizando los diferentes compuestos. Los alcaloides ungeremina, pseudolicorina y hemantamina presentaron buena actividad en el ensayo in vitro frente a Trypanosoma brucei rhodesiense, T. cruzi y Plasmodium falciparum con valores de IC50 menores de 1 µg/mL. Se ha estudiado, igualmente, la actividad antioxidante de los biflavonoides aislados de G. madruno, por medio de los métodos del 2,2'-difenil-1-picrilhidracil (DPPH·) y de la inhibición de la peroxidación de lipoproteínas de baja densidad (LDL). En general, los compuestos con enlace inter-flavonoide C3→C8' presentan una potente actividad captadora de radicales DPPH·. Los biflavonoides que presentan esta característica en combinación con una sustitución 3',4'-dihidroxi (catecol) en el anillo E, un doble enlace entre C-2' y C-3' y una función carbonilo en la posición C-4', son los captadores de radicales más activos. En relación a los inhibidores de la peroxidación de LDL, los mejores inhibidores son los compuestos con enlace inter-flavonoide C3→C8': morelloflavona y volkensiflavona. la fracción biflavonoide (FB) aislada de G. madruno, compuesta principalmente por morelloflavona, volkensiflavona y amentoflavona. Los datos sugieren que FB podría ser un excelente candidato para ser utilizado como antioxidante. Es probable que se produzcan procesos de sinergismo en la FB, toda vez que presenta una actividad captadora de radicales y una inhibición de la peroxidación de LDL superior, en algunos casos, a los compuestos más activos.

The bulbs of Phaedranassa dubia (Amaryllidaceae) were found to contain the novel compound phaedranamine, together with seven known alkaloids. The structure and stereochemistry of the alkaloids were determined by physical and spectroscopic methods. An in vitro screening against four different parasitic protozoa was carried out using the isolated compounds. The alkaloids ungeremine, pseudolycorine and haemanthamine showed good activity in in vitro assays against Trypanosoma brucei rhodesiense, T. cruzi and Plasmodium falciparum with IC50 values in the range of 1 µg/mL or lower. On the other hand, six biflavonoids were isolated from Garcinia madruno (Clusiaceae) and then 7"-O-(6""-acetyl)-glucoside of morelloflavone (5) has proven to be a new compound. The antioxidant activity of the biflavonoids against low-density lipoproteins peroxidation was studied by means of TBARS assay. The antioxidant potential of a biflavonoid fraction (BF) was also evaluated and correlated with its biflavonoid content. Lipid peroxidation was significantly reduced in the presence of the BF, morelloflavone being mainly responsible for this effect.

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Flavonoids, Botanical chemistry, Amaril·lidàcies, Amaryllidaceae, Ciències de la Salut, Antioxidants, Guttiferae, Substàncies bioactives, Bioflavonoïdes, Gutíferes, Fitoquímica, 615, Flavonoides

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popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
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This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
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