Constituents from Tithonia diversifolia. Stereochemical Revision of 2α-Hydroxytirotundin
Keywords:
Tagitinins, 2-hydroxytirotundin Compositae, tithonia diversifolia, sesquiterpene lactones, furanheliangolides, stereochemical revisionAbstract
Abstract. A chemical study of the aerial parts of Tithonia diversifolia led to the isolation and stereostructural characterization of tagitinins A (1), C (2) and F (3), and a mixture of sterols. Tagitinin A (1) underwent spontaneous dehydration to 4 during the course of its 1H NMR measurement in CDCl3. The stereochemical analysis of 2á-hydroxytirotundin (5), an isomer of 1 previously reported by Kinghorn et al, led to the correction of its 3S,10S configuration to the 3S,10R stereochemistry. In addition, bioactivity evaluation of isolates showed them to exhibit moderate anti-inflammatory and cytotoxic activity.
Resumen. Un estudio químico de las partes aéreas de Tithonia diversifolia permitió el aislamiento y la caracterización estructural de las tagitininas A (1), C (2) y F (3), y una mezcla de esteroles. La tagitinina A (1) experimentó una deshidratación para formar 4 durante la adquisición de la 1H RMN en CDCl3. El análisis estereoquímico de 2á- hidroxitirotundina (5), un isómero de 1 previamente informado por Kinghorn et al, condujo a la corrección de su configuración 3S,10S por la estereoquímica 3S,10R. Adicionalmente, la bioevaluación de los compuestos aislados mostró que estos poseen actividades antiinflamatoria y citotóxica moderadas.
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