Componentes de umbelíferas. XVII. Cumarinas sencillas del Seseli tortuosum L.B.S. Eur.

Abstract

De la parte aérea del Seseli tortuosum L.B.S. Eur. se han obtenido las siguientes cumarinas sencillas: Herniarina (I), auraptenol (II), 7-hidroxi-8-(2'-hidroxi-3'-metil-3'-butenil)-cumarina (III), hidrato de meranzina (IV), 7-metoxi-8-(2'hidroxi-3'etoxi-3'-metil-butil)-cumarina (III), hidrato de meranzina (IV), 7-metoxi-8-(2'-hidroxi-3'-etoxi-3'-metil-butil)-cumarina (V), 7-metoxi-8-2'oxo-3'-metil-butil)-cumarina (XII), 7-metoxi-8-(2'formil-2'-metil-propil)-cumarina (XIII), 7-metoxi-8(2' 3'-dihidroxi-3'-metil-butil)-cumarina (XIV), 5,7-dimetoxi-8-((2'-hidroxi-3'-metil-3'-butenil)-cumarina (XVIII), 5-metoxi-7-hidroxi-8-(2'-hidroxi-3'-metil-3'-butenil)-cumarina (XIX), 5,7-dimetoxi-8-(2'-oxo-3'-metil-butil)-cumarina (XX) y 5,7-dimetoxi-8-(2'hidroxi-3'-etoxi-3'-metil-butil)-cumarina (XXII). Estos productos han sido estudiados por sus propiedades físicas y químicas, describiéndose por primera vez los componentes III, IV, XIV y XXII. Los XIII y XX, también fueron obtenidos por primera vez de esta planta. Asimismo se sugiere que la isoprenilación de cumarinas en el género Seseli puede tener lugar directamente por el pirofosfato de &&-isopentenilo, como vía alternativa a las del pirofosfato de 3,3-dimetilalilo, para la que se expone un posible camino.

From the aerial part of Seseli tortuosum LBS Eur, the following simple coumarins have been isolated: herniarin (I), auraptenol (II), 7-hydroxy-8-(2'-hydroxy-3'-methyl-3'-butenyl)-coumarin (III), meranzine hydrate (IV), 7-methoxy-8-(2'-hydroxy-3'-ethoxy-3'-methyl-butyl)-coumarin (V), 7-methoxy-8-(2'-oxo-3'-methyl-butyl)-coumarin (XII), 7-methoxy-8-(2'-formyl-2'-methyl-propyl)-coumarin (XIII), 7-methoxy-8-(2',3'-dihydroxy-3'-methyl-butyl)-coumarin (XIV), 5, 7-dimethoxy-8-(2'-hydroxy-3'-methyl-3'-butenyl)-coumarin (XVIII), 5-methoxy-7-hydroxy-8-(2'-hydroxy-3'-methyl-3'-butenyl), coumarin (XIX), 5, 7-dimethoxy-8-(2'-oxo-3'-methyl-butyl)-coumarin (XX) and 5, 7-dimethoxy-8-(2'-hydroxy-3'-ethoxy-3'methyl-butyl)-coumarin (XXII). The physical and chemical properties of these products were studied; constituents III, XIV, XIX and XXII were found in this plant for the first time, as were the XII and XX. It is possible that the isoprenylization of coummarins from the genus Seseli may take place directly by the &&-isopentenyl pyrophosphate as well as by the 3,3-dimethyl) = allyl pyrophospate for which a route has been hypothesized.