RESUMEN
A phenylpropanoid 1, a slovenolide 2, and two germacranes bearing a methylthiopropenoate moiety, 3 and 4, along with twenty known metabolites have been isolated from the roots of Thapsia villosa var. villosa L. The structures of two known phenylpropanoids 5 and 6 have been corrected. Compounds 7 and 8 showed activity as potential inhibitors of the sarco- and endoplasmic Ca(2+)-dependent ATPases (SERCA) pump. Compounds 9, 10 and 11 increased significantly the cytoplasmic free calcium concentration ([Ca(2+)](c)) in human platelets in a concentration-dependent manner.
Asunto(s)
Plaquetas/metabolismo , ATPasas Transportadoras de Calcio/antagonistas & inhibidores , Calcio/sangre , Inhibidores Enzimáticos/farmacología , Extractos Vegetales/farmacología , Thapsia/química , Relación Dosis-Respuesta a Droga , Inhibidores Enzimáticos/aislamiento & purificación , Compuestos Heterocíclicos con 3 Anillos/aislamiento & purificación , Compuestos Heterocíclicos con 3 Anillos/farmacología , Humanos , Lactonas/aislamiento & purificación , Lactonas/farmacología , Estructura Molecular , Extractos Vegetales/química , Raíces de Plantas , Propanoles/química , Propanoles/aislamiento & purificación , Sesquiterpenos/química , Sesquiterpenos/aislamiento & purificación , Sesquiterpenos/farmacología , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/aislamiento & purificación , Sesquiterpenos de Germacrano/farmacología , Sesquiterpenos de Guayano/aislamiento & purificación , Sesquiterpenos de Guayano/farmacología , Compuestos de Sulfhidrilo/aislamiento & purificación , AzufreRESUMEN
Four meroterpenoids (3a, 3b, 4 and 5), a prenylated pyran-2-one (2) along with the known compounds 7-O-geranylscopoletin (1), and thapsitranstagin (6) have been isolated from the roots of Thapsia transtagana. The presence of 1 and 2 supports the biogenetic hypothesis that transtaganolides, a group of bioactive metabolites, are meroterpenoids which come from an O-prenylated coumarin via successive pericyclic reactions.
Asunto(s)
Productos Biológicos/biosíntesis , Piranos/aislamiento & purificación , Terpenos/aislamiento & purificación , Thapsia/química , Espectroscopía de Resonancia Magnética , Piranos/metabolismo , Espectrometría de Masa por Ionización de Electrospray , Terpenos/metabolismoRESUMEN
Nine new eudesmanolides (1-9), two new guaianolides (12 and 13), and a new germacrane (10), along with a previously reported guaianolide (11), have been isolated from the roots of Thapsia nitida var. meridionalis. Thapsia nitida var. nitida also afforded compound 13 along with a new guaianolide (14). The structure of 13 was confirmed by X-ray crystallographic analysis. Compounds 1, 2, and 11-14 have been tested as potential inhibitors of the sarco- and endoplasmic Ca2+-dependent ATPases (SERCA) pump. None of them showed significant activities.
Asunto(s)
Plantas Medicinales/química , ATPasas Transportadoras de Calcio del Retículo Sarcoplásmico/antagonistas & inhibidores , Sesquiterpenos/aislamiento & purificación , Thapsia/química , Cristalografía por Rayos X , Conformación Molecular , Estructura Molecular , Raíces de Plantas/química , Sesquiterpenos/química , Sesquiterpenos/farmacología , EspañaRESUMEN
Five phenylpropanoids have been isolated from the roots of Thapsia transtagana. Their structures have been elucidated by spectroscopic means.
Asunto(s)
Apiaceae/química , Propanoles/química , Propanoles/aislamiento & purificación , Estructura Molecular , Marruecos , Raíces de Plantas/químicaRESUMEN
Four novel and unusual C-19 compounds from Thapsia transtagana, named transtaganolides A-D, have been isolated. Their structures were established by physical methods, including X-ray analysis of transtaganolides A and B. This is the first time that a 7-methoxy-4,5-dihydro-3H-oxepin-2-one ring has been found in a natural product. [structure: see text]