Novel bioactive steroidal alkaloids from Pachysandra procumbens

(+)-(20S)-20-(Dimethylamino)-3 alpha-(methylbenzoylamino)-11-methylene-5 alpha-pregnane (1), a steroidal alkaloid with a new substitution pattern, was isolated from the entire plant of Pachysandra procumbens. together with four other new steroidal alkaloids, (+)-(2OS)-3-(benzoylamino)-20-(dimethylamino)-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), (+)-(20S)-20-(dimethylamino)-3 alpha-(methylbenzoylaminoa)-5 alpha-pregn-12 beta-gamma l acetate (4), and (+)-(20S)-20(dimethylamino)-3 alpha-(methylsenecioylamino)-5 alpha pregn-12 beta-ol (5), as well as two known compounds, (+)-pachysamine H (6) and(+)-pachysandrine B (7). The structures of the new compounds were determined by spectroscopic methods. Compounds 1-7 were evaluated for their potential cancer chemopreventive properties using an in vitro estrone sulfatase assay. (C) 2000 Elsevier Science Ltd. All rights reserved.