Isosteroidal Alkaloids From Fritillaria Shuchengsis And Synthesis Of Wanpeinine A Derivatives

Fritillaria shuchengensis S. C. Chen et S. F. Yin, a well-known medicinal plant that can be found in Shucheng, Anhui province, has been used as an antitussive agent.A novel isosteroidal alkaloid, shuchengine (1) along with five known bases ebeinine (2), verticinoneβ-N-oxide (3), wanpeinine A (4), edpetiline (5) and zhebeininoside (6) were isolated from Fritillaria shuchengensis. The structures were determined with the help of spectroscopic studies.The acylation and alkylation of wanpeinine A has given 3β,6a-diacetylwanpeinine A (7),3β,6α-dipropionylwanpeinine A (8),3β,6α-dichloracetylwanpeinine A (9) 3β,6α-dibenzoylwanpeinine A (10),3β-methoxyacylwanpeinine A (11),3β, 6α-dimethoxymethylwanpeinine A (12),3β,6α-dimethylsulfonylwanpeinine A (13),3β,6α-diethylwanpeinine A (14)和N,3β,6α,20β-tetramethylwanpeinine A (15). All of the compounds were new compounds except 7.