东北红豆杉针叶中两个双重排紫杉烷内酯化合物的结构鉴定

Structural identification of two bisabeotaxane lactones from needles of Taxus cuspidata

目的研究东北红豆杉Taxuscuspidata针叶中的化学成分。方法采用硅胶柱色谱及制备薄层色谱法分离、纯化化学成分,用一维和二维核磁共振技术鉴定化合物结构。结果从东北红豆杉针叶的甲醇提取物中分离出两个罕见的双重排紫杉烷内酯类化合物wallifoliol()和tasumatrolH()。结论此两种化合物为首次从东北红豆杉中分离得到,在氘代氯仿溶液中化合物在室温下可以转化成5α-乙酰基-2α-苯甲酰氧基-4α,7β,9α,13α,20-五羟基-11(15→1),11(10→9)双重排紫杉烷-11-烯-10,15-内酯()。

Objective To study chemical constituents from the needles of Taxus cuspidata. Methods Chemical constituents were isolated by column chromatography and preparative TLC. The structures were identified on the basis of 1D- and 2DNMR spectral analyses. Results Two rare bisabeotaxane lactones were isolated from the methanol extract of T. cuspidata needles. The structures were established as 4β- acetoxy-2α-benzoyloxy-7β 9α, 13α-trihydroxy-5, 20-epoxy-ll（15→1）, 11 （10→9）bisabeotaxa-11-- 10, 15-1actone （wallifoliol） （ Ⅰ ） and 5α-acetoxy-2α-benzoyloxy-4α, 7β, 9α, 13α, 20-pentahydroxy-ll （15→1）, 11 （10→9） bisabeotaxa-11-en-10, 15-lactone （wallifoliol） （ Ⅰ ） and 5α-acetoxy-2α-benzoyloxy-4α, 7β, 9α, 13α, 20-pentahydroxy-11 （15→1）, 11 （10→9） bisabeotaxa-11-en-10, 15-lactone （tasumatrol H） （ Ⅲ ）. Conclusion Both of them are isolated from this plant for the first time. Compound Ⅰ can be converted into 20-acetoxy-2α-benzoy- loxy-4α, 5α, 7β, 9α, 13α-pentahydroxy-11（15→1）, 11（10→9）bisabeotaxa-11-en-10, 15-lactone （Ⅱ）in CDCl3 solution, but it is stable in acetone-d6 solution at ambient temperature.