[关键词]
[摘要]
目的研究生长在加拿大的东北红豆杉Taxus cuspidata的化学成分。方法采用硅胶柱色谱、制备薄层色谱和HPLC制备色谱法分离、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。结果从生长在加拿大的东北红豆杉的针叶中分离得到了10个紫杉烷二萜类化合物,分别鉴定为2α,9α-二乙酰氧基-5α-桂皮酰氧基-10β-羟基-紫杉烷-4(20),11-二烯-13-酮(10-去乙酰基紫杉宁,Ⅰ)、2α,10β-二乙酰氧基-5α-桂皮酰氧基-9α-羟基-紫杉烷-4(20),11-二烯-13-酮(9-去乙酰基紫杉宁,Ⅱ)、2α,9α,10β-三乙酰氧基-5α-桂皮酰氧基-13α-羟基-紫杉烷-4(20),11-二烯(13-二氢紫杉宁,13-去乙酰基紫杉宁E,紫杉佐匹定,Ⅲ)、2α,9α,10β-三乙酰氧基-5α-桂皮酰氧基-13α-羟基-13,16-环氧-紫杉烷-4(20),11-二烯(taxezopidine J,Ⅳ)、2α,7β,9α,10β,13-五乙酰氧基-5α-桂皮酰氧基-11α-羟基-紫杉烷-4(20),12-二烯(紫杉平,taxuspine D,Ⅴ)、2α,7α,9α,10β-四乙酰氧基-5α-桂皮酰氧基-11β-羟基-12,16-环氧-紫杉烷-4(20)-烯-13-酮(紫杉吉酚,taxagifine,Ⅵ)、2α,7β,9α,10β,19-五乙酰氧基-5α,11α-二羟基-12,16-环氧-紫杉烷-4(20)-烯-13-酮(19-去苯甲酰基-19-乙酰基紫杉宁M,Ⅶ)、2α,5β,13α-三乙酰氧基-1β,7β,9α,10β-四羟基-4,20-环氧-紫杉烷-11-烯(7β,9α,10β-三去乙酰基-1β-羟基-巴卡亭Ⅰ,南方红豆杉醇,taxumairol C,Ⅷ)、4α,10β,13α-三乙酰氧基-2α-苯甲酰氧基-1β,7β,9α-三羟基-5,20-环氧-紫杉烷-11-烯(9-二氢-13-乙酰基-巴卡亭Ⅲ,Ⅸ)、4α,13α-二乙酰氧基-2α-苯甲酰氧基-7β,9α,10β,15-四羟基-5,20-环氧-11(15→1)重排紫杉烷-11-烯(7,9,10-三去乙酰基重排巴卡亭Ⅵ,Ⅹ)。结论化合物Ⅷ、Ⅹ为首次从东北红豆杉中分离得到。化合物Ⅲ为首次从东北红豆杉针叶中分离得到。
[Key word]
[Abstract]
Objective To study the chemical constituents in Taxus cuspidata from Canada.Methods Chemical constituents were isolated by column chromatography,preparative TLC,and preparative HPLC.The structures were identified on the basis of 1D-and 2D-NMR spectral analyses.Results Ten taxane diterpenoids were isolated from the needls of T.cuspidata grown in Canada.They were identified as:2 α,9 α-diacetoxy-5 α-cinnamoyloxy-10 β-hydroxyl-taxa-4(20),11-diene-13-one(10-deacetyltaxinine)(Ⅰ);2 α,10 β-biacetoxy-5 α-cinnamoyloxy-9α-hydroxyl-taxa-4(20),11-diene-13-one(9-deacetyltaxinine)(Ⅱ);2 α,9 α,10 β-triacetoxy-5 α-cinnamoyloxy-13 α-hydroxyl-taxa-4(20),11-diene(Ⅲ);2 α,9 α,10 β-triacetoxy-5 α-cinnamoyloxy-13 α-hydroxyl-13,16-epoxy-taxa-4(20),11-diene(taxezopidine J)(Ⅳ);2 α,7 β,9 α,10 β,13-pentaacetoxy-5 α-cinnamoyloxy-11 α-hydroxyl-taxa-4(20),12-diene(taxuspine D)(Ⅴ);2 α,7 α,9 α,10 β-tetraacetoxy-5 α-cinnamoyloxy-11 β-hydroxyl-12,16-epoxy-taxa-4(20)-ene-13-one(taxagifin)(Ⅵ);2 α,7 β,9 α,10 β,19-pentaacetoxy-5 α,11 α-dihydroxyl-12,16-epoxy-taxa-4(20)-ene-13-one(19-debenzoyl-19-acetyl-taxinine M)(Ⅶ);2 α,5 β,13 α-triacetoxy-1 β,7 β,9 α,10 β-tetrahydroxy-4,20-epoxy-taxa-11(12)-ene(taxumairol C)(Ⅷ);4 α,10 β,13 α-triacetoxy-2 α-benzoyloxy-1 β,7 β,9 α-trihydroxyl-5,20-epoxy-taxa-11-ene(9-dihydro-13-acetyl-baccatin Ⅲ)(Ⅸ);4 α,13 α-diacetoxy-2 α-benzoyloxy-7 β,9 α,10 β,15-tetrahydroxyl-5,20-epoxy-11(15→1)-abeo-taxa-11-ene(7,9,10-tri-deacetyl-abeo-baccatin Ⅵ)(Ⅹ).Conclusion Compounds Ⅷ and Ⅹ are obtained from T.cuspidata for the first time.Compound Ⅲ is obtained from the needls of T.cuspidata for the first time.
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[基金项目]
科技部863科研基金资助项目(2003AA2Z3527);河北省自然科学基金资助项目(08B032);河北省引进留学人员基金课题