RESUMEN
Chemical investigation of Santolina insularis afforded 11 germacrane sesquiterpenes (1-11), four of which (2, 3, 10, and 11) are new. The stereostructures of these compounds have been established by a combination of spectroscopic techniques (mainly NMR), chemical transformations, and application of the modified Mosher method. Compounds 8 and 10 showed a potent and selective cytotoxic activity against the human colon carcinoma cell line.
Asunto(s)
Antineoplásicos Fitogénicos/aislamiento & purificación , Asteraceae/química , Plantas Medicinales/química , Sesquiterpenos de Germacrano/aislamiento & purificación , Antineoplásicos Fitogénicos/química , Antineoplásicos Fitogénicos/farmacología , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Italia , Estructura Molecular , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos de Germacrano/química , Sesquiterpenos de Germacrano/farmacología , EstereoisomerismoRESUMEN
The eudesmane sesquiterpenoids 1-3 and the trans-chrysanthemyl monoterpenoid 4 have been isolated from the aerial parts of Santolina insularis, a bush endemic to Sardinia. The absolute stereostructures of these novel compounds and of two known but incompletely characterized chrysanthemanes (5, 6) were established by spectroscopic techniques and by application of the modified Mosher method. The presence of the p-menthane aldehyde eucamalol (7) gives credit to the widespread use of S. insularis to fend off mosquitoes.
Asunto(s)
Asteraceae/química , Monoterpenos/aislamiento & purificación , Plantas Medicinales/química , Sesquiterpenos de Eudesmano/aislamiento & purificación , Animales , Culicidae/efectos de los fármacos , Eucalyptus/química , Italia , Estructura Molecular , Monoterpenos/química , Resonancia Magnética Nuclear Biomolecular , Sesquiterpenos de Eudesmano/química , Terpenos/química , Terpenos/farmacologíaRESUMEN
Cascarilla is a commercially available and cheap source of polyfunctionalized diterpenoids belonging to the clerodane structural type. In addition to the bitter triol cascarillin, 10 additional new diterpenoids (eluterins A-J) have been isolated and characterized by spectroscopic means. Structural diversity within cascarilla clerodanes involves mainly the linkage between the carbocyclic and the heterocyclic moieties and the functionalization of C-3, C-4, and C-6 of the decalin core. Cascarillin was shown to be a mixture of interconverting gamma-lactols and not a gamma-hydroxyaldehyde as previously reported.