RESUMO
Biyouyanagiol (1), an acylphloroglucinol-related compound having a unique cyclopenta-1,3-dione moiety, was isolated from a Japanese traditional medicinal plant, Hypericum chinense, together with three new spiro-lactone-related derivatives, biyouyanagin B (2), 5,6-dihydrohyperolactone D (3), and 4-hydroxyhyperolactone D (4). Their structures were established on the basis of spectroscopic evidence. In a cytotoxicity assay against human cancer cell lines including multidrug-resistant (MDR) cancer cell lines, several compounds demonstrated enhanced cytotoxicity against MDR KB cells in the presence of colchicine.
Assuntos
Hypericum/química , Lactonas/isolamento & purificação , Plantas Medicinais/química , Sesquiterpenos/isolamento & purificação , Compostos de Espiro/isolamento & purificação , Antineoplásicos Fitogênicos/química , Antineoplásicos Fitogênicos/farmacologia , Colchicina/farmacologia , Resistência a Múltiplos Medicamentos/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Japão , Células KB , Lactonas/química , Lactonas/farmacologia , Estrutura Molecular , Folhas de Planta/química , Sesquiterpenos/química , Sesquiterpenos/farmacologia , Compostos de Espiro/química , Compostos de Espiro/farmacologiaRESUMO
Phloroglucinol derivatives tomoeones A-H (1-8) and three known compounds were isolated from leaves of Hypericum ascyron. Their structures were established based on spectroscopic analyses. They are all acylphloroglucinol derivatives possessing a spiro skeleton with geminal isoprenyl groups and a monoterpene moiety, and they are stereoisomers to each other at C-4 and C-13. They appear to be a class of phloroglucinol derivatives. Cytotoxicities of the isolated phloroglucinol derivatives against human tumor cell lines, including multidrug-resistant (MDR) cancer cell lines, were evaluated. Tomoeone F (6) demonstrated significant cytotoxicity against KB cells with an IC50 value of 6.2 microM. Compound 6 was also cytotoxic against MDR cancer cell lines (KB-C2 and K562/Adr), which was more potent than doxorubicin.
