New steroidal alkaloids from the roots of Buxus sempervirens

Phytochemical studies on the ethanolic extract of the roots of Buxus sempervirens L. of Turkish origin have resulted in the isolation of four new steroidal alkaloids, (+)-16 alpha-hydroxy-N-a-benzoylbuxadine [(20S)-16 alpha-hydroxy-3 beta-(benzoylamino)-20- (dimethylamino)-9,10-seco-buxa-9(11),1(10)-diene] (1), (+)-semperviraminone [3 beta-(dimethylamino)-20-oxo-9,10-seco-buxa-9(11),1-(10),16(17)-triene] (2), (+)-N-a-demethylsemperviraminone [3 beta-(methylamino)-20-oxo-9,10-seco-buxa-9(11),1(10),16(17)-triene] (3), and (+)-buxaminol-C [(20S)-16 alpha-hydroxy-3 beta-(methylamino)-20-(dimethylamino)-9,10-seco-buxa-9(11) ,10(19)-diene] (4). Four known steroidal alkamines, (-)-(E)-cyclobuxaphylamine [(20E)-16-oxo-3 beta-(methylamino)-9 beta,10 beta-cyclobuxa-7(8),17(20)-diene] (5), (-)-(Z)-cyclobuxaphylamine [(20Z)-16-oxo-3 beta-(methylamino)-9 beta,10 beta-cyclobuxa-7(8),17(20)-diene] (6), (+)-cyclomicrobuxeine [3 beta-(dimethylamino)-20-oxo-9 beta,10 beta-cyclobuxa-4(30),16(17)- diene] (7), and (+)-papilamine [(20S)-3 beta,20-bis(methylamino)-9,10-seco-buxa-9(11),10(19)-diene] (8), were also isolated for the first time from this species. Their structures were elucidated on the basis of extensive spectroscopic studies.