Novel bioactive steroidal alkaloids from Pachysandra procumbens

(+)-(20S)-20-(Dimethylamino)-3 alpha-(methylbenzoylamino)-11-methylene-5 al pha-pregnane (1), a steroidal alkaloid with a new substitution pattern, was isolated from the entire plant of Pachysandra procumbens. together with fo ur other new steroidal alkaloids, (+)-(2OS)-3-(benzoylamino)-20-(dimethylam ino)-5 alpha-pregn-2en-4 beta-ol (2), (+)-(20S)-20-(dimethylamino)-16 alpha -hydroxy-3 beta-(3'alpha-isopropyl)-lactam-5 alpha-pregn-4-one (3), (+)-(20 S)-20-(dimethylamino)-3 alpha-(methylbenzoylaminoa)-5 alpha-pregn-12 beta-g amma l acetate (4), and (+)-(20S)-20(dimethylamino)-3 alpha-(methylsenecioy lamino)-5 alpha pregn-12 beta-ol (5), as well as two known compounds, (+)-p achysamine H (6) and(+)-pachysandrine B (7). The structures of the new comp ounds were determined by spectroscopic methods. Compounds 1-7 were evaluate d for their potential cancer chemopreventive properties using an in vitro e strone sulfatase assay. (C) 2000 Elsevier Science Ltd. All rights reserved.