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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。
Objective To study the chemical composition of Taxus cuspidata, a species of Taxus cuspidata grown in Canada. Methods Chemical constituents were isolated and purified by silica gel column chromatography, preparative thin layer chromatography and HPLC preparative chromatography. Compound structures were identified by one-dimensional and two-dimensional nuclear magnetic resonance techniques. Results Ten taxane diterpenoids were isolated from the needles of Taxus cuspidata grown in Canada and identified as 2α,9α-diacetoxy-5α-cinnamoyloxy-10β-hydroxy-violet. Pentane-4(20),11-dien-13-one (10-deacetyltaxane, I), 2α,10β-diacetoxy-5α-cinnamoyloxy-9α-hydroxy-violet Xantane-4(20),11-dien-13-one (9-deacetyltaxane, II), 2α,9α,10β-triacetoxy-5α-cinnamoyloxy-13α-hydroxy - Taxane-4 (20), 11-diene (13-dihydrotaxane, 13-deacetyltaxane-E, zabididine, III), 2α, 9α, 10β-triacetyl Oxy-5α-cinnamoyloxy-13α-hydroxy-13,16-epoxy-taxane-4(20),11-diene (taxezopidine J,IV), 2α,7β,9α,10β,13 - pentaacetoxy-5α-cinnamoyloxy-11α-hydroxy-taxane-4(20),12-diene (taxanepine D,V), 2α,7α,9α,10β-tetraacetyl Oxy-5α-cinnamoyloxy-11β-hydroxy-12,16-epoxy-taxane-4(20)-en-13-one (taxamine, VI), 2α, 7β, 9α,10β,19-pentaacetoxy-5α,11α-dihydroxy-12,16-epoxy-taxane-4(20)-ene-13-one (19-to Formyl-19-Acetyl-Taxonine M,VII),2α,5β,13α-Triacetoxy-1β,7β,9α,10β-Tetrahydroxy-4,20-epoxy-taxane-11- Alkenes (7β, 9α, 10β-trideacetyl-1β-hydroxy-baccatin I, southern taxol, taxumairol C, VIII), 4α, 10β, 13α-triacetoxy-2α-benzoyloxy -1β,7β,9α-trihydroxy-5,20-epoxy-taxane-11-ene (9-dihydro-13-acetyl-baccatine III, IX), 4α, 13α-diacetyl Oxy-2α-benzoyloxy-7β,9α,10β,15-tetrahydroxy-5,20-epoxy-11(15→1) rearrangement taxane-11-ene (7,9,10 - Trideacetylation rearranges bakatin VI, X). Conclusion Compounds VIII and X are isolated from Taxus cuspidata for the first time. Compound III was isolated from the needles of Taxus cuspidata for the first time.