钩吻的化学成分研究
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摘要
目的研究马钱科胡蔓藤属植物钩吻Gelsemium elegans的化学成分。方法采用硅胶、Sephadex LH-20、HPLC等色谱方法进行分离纯化,通过理化性质及核磁共振谱学数据对分得的化合物进行结构鉴定。结果从钩吻的95%乙醇提取物中分离得到15个化合物,分别鉴定为钩吻素子(1)、钩吻素甲(2)、钩吻绿碱(3)、钩吻素己(4)、花椒毒素(5)、香柑内酯(6)、异茴芹内酯(7)、欧前胡素(8)、蛇床子素(9)、对羟基苯甲酸(10)、香草酸(11)、β-谷甾醇(12)、β-胡萝卜苷(13)、钩吻内酰胺(14)、16-表伏康树卡平碱(15)。结论化合物5～9为首次从该种植物中分离得到。
Objective The chemical constituents were isolated and identified in order to find the bioactive natural products from Gelsemium elegans. Methods Silica gel, sephadex LH-20 and HPLC column chromatographic techniques were used for separation and purification of the compounds and extensive spectral analysis spectrum were employed for structural elucidation. Results Fifteen compounds were separated from G. elegans, identified by physicochemical properties, spectral analysis and other means. They are koumine(1), gelsemine(2), gelsevirine(3), gelsemicine(4), xanthotoxin(5), bergapten(6), isopimpinellin(7), imperatorin(8), osthol(9), p-hydroxybenzoic acid(10), vanilla acid(11), β-sitosterol(12), β-daucosterol(13), gelsemamide(14), and 16-epivoacarpine(15). Conclusion Compounds 5—9 are first isolated from the plants in genus Gelsemium Juss.
Objective The chemical constituents were isolated and identified in order to find the bioactive natural products from Gelsemium elegans. Methods Silica gel, sephadex LH-20 and HPLC column chromatographic techniques were used for separation and purification of the compounds and extensive spectral analysis spectrum were employed for structural elucidation. Results Fifteen compounds were separated from G. elegans, identified by physicochemical properties, spectral analysis and other means. They are koumine(1), gelsemine(2), gelsevirine(3), gelsemicine(4), xanthotoxin(5), bergapten(6), isopimpinellin(7), imperatorin(8), osthol(9), p-hydroxybenzoic acid(10), vanilla acid(11), β-sitosterol(12), β-daucosterol(13), gelsemamide(14), and 16-epivoacarpine(15). Conclusion Compounds 5—9 are first isolated from the plants in genus Gelsemium Juss.
引文
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[14]Zhou P,Takaishi Y,Duan H Q,et al.Coumarins and bicoumarin from Ferula sumbul:Anti-HIV activity and inhibition of cytokine release[J].Phytochemistry,2000,53(6):689-697.
[15]牛雪梅,黎胜红,纳智.疏花毛萼香茶菜的化学成分研究[J].中草药,2003,34(4):300-303.
[16]高慧媛,隋安丽,陈艺虹,等.中药黄独的化学成分[J].沈阳药科大学学报,2003,20(3):178-180.
[17]Lin L Z,Cordell G A,Ni C Z,et al.Gelsemamide and11-methoxygelemamide,two novel secoimdole alkaloids from Gelsemium elegans[J].Tetrahedron Lett,1989,30(10):1177-1180.
[18]Kogure N,Nishiya C,Kitajima M,et al.Six new indole alkaloids from Gelsemium sempervirens Ait.f.[J].Tetrahedron Lett,2005,46(35):5857-5862.
[2]张华,吴水生,王英豪.钩吻化学成分及临床应用研究进展[J].医药前沿,2015,5(19):9-11.
[3]Sakai S.Chemical studies of indole alkaloids[J].Yakugaku Zasshi,1995,115(5):351-369.
[4]Kogure N,Ishii N,Kobayashi H,et al.New iridoids from Gelsemium species[J].Chem Pharm Bull,2008,56(6):870-872.
[5]张彬锋,侴桂新,王峥涛.钩吻非生物碱类化学成分研究[J].中国中药杂志,2009,34(18):2334-37.
[6]Francois K H,Angele C.Structure of koumine,an alkaloid from Gelsemium elegans Benth[J].Tetrahedron Lett,1981,22(8):733-734.
[7]Schun Y,Geoffrey A C.Studies on the NMR spectroscopic properties of gelsemine-revisions and refinements[J].J Nat Prod,1985,48(6):969-971.
[8]Wenkert E,Chang C J,Cochran D W,el al.Carbon-13nuclear magnetic resonance spectroscopy of naturally occurring substances.VIII.Structure of gelsevirine[J].Experientia,1972,28(4):377-379.
[9]Sakai S,Takayama H,Yokota M.Studies on the indole alkaloids from Gelsemium elegans:Structural elucidation,proposal of biogenetic route,and biomimetic synthesis of koumine and humantenine skeletons[J].天然有機化合物討論会講演要旨集,1987(29):224-231.
[10]张才煜,张本刚,李秀伟.独活化学成分的研究[J].解放军药学学报,2007,23(4):241-245.
[11]赵爱红,杨秀伟.兴安白芷脂溶性部位中新的天然产物[J].中草药,2014,45(13):1820-28.
[12]Benahmed M,Akkal S,Elomri A,et al.Secondary constituents from Carum montanum[J].Chem Nat Compds,2008,44(4):510-511.
[13]赵博,杨鑫宝,杨秀伟.防风化学成分的研究[J].中国中药杂志,2010,35(12):1569-72.
[14]Zhou P,Takaishi Y,Duan H Q,et al.Coumarins and bicoumarin from Ferula sumbul:Anti-HIV activity and inhibition of cytokine release[J].Phytochemistry,2000,53(6):689-697.
[15]牛雪梅,黎胜红,纳智.疏花毛萼香茶菜的化学成分研究[J].中草药,2003,34(4):300-303.
[16]高慧媛,隋安丽,陈艺虹,等.中药黄独的化学成分[J].沈阳药科大学学报,2003,20(3):178-180.
[17]Lin L Z,Cordell G A,Ni C Z,et al.Gelsemamide and11-methoxygelemamide,two novel secoimdole alkaloids from Gelsemium elegans[J].Tetrahedron Lett,1989,30(10):1177-1180.
[18]Kogure N,Nishiya C,Kitajima M,et al.Six new indole alkaloids from Gelsemium sempervirens Ait.f.[J].Tetrahedron Lett,2005,46(35):5857-5862.