蒺藜茎叶的化学成分研究
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摘要
目的:研究蒺藜Tribulus terrestris L.茎叶的化学成分。方法:采用大孔树脂、MCI树脂、RP-C18键合硅胶柱色谱、Sephadex LH-20凝胶柱色谱、反相制备高效液相色谱等技术对蒺藜提取物进行分离纯化,并根据理化性质和波谱手段进行结构鉴定。结果:从蒺藜茎叶30%大孔树脂洗脱物中分离得到12个化合物,鉴定出10个化合物,分别为乙酰丁香酮-4’-O-β-D-吡喃葡萄糖苷(1),异嗪皮啶-7-O-β-D-吡喃葡萄糖苷(2),异鼠李素-3-O-β-D-葡萄糖基-7-O-β-D-吡喃葡萄糖苷(3),槲皮素-3-O-β-D-龙胆双糖苷(4),异荭草苷(5),山奈酚-3-O-β-D-龙胆双糖基-7-O-β-D-吡喃葡萄糖苷(6),异鼠李素-3-O-β-D-龙胆双糖基-7-O-β-D-吡喃葡萄糖苷(7),Terrestrinone A2(8),邻苯二甲酸二丁酯(9)和邻苯二甲酸二辛酯(10)。结论:化合物1和5为首次在该属中分离得到。
Objective: To investigate the chemical constituents in the stems and leaves of Tribulus terrestris. Methods: The compounds were isolated and purified by a combination of various column chromatographies techniques including macroporous resin, MCI resin, reversed-phase C18 silica gel, Sephadex LH-20 columns, and reversed-phase HPLC. The structures were identified by means of chemical evidences and spectral analyses including MS, 1H-NMR, and 13C-NMR. Results: Twelve compounds were isolated and 10 were identified as 3', 3'-dimethoxy-4'-hydroxyacetophenone-4'-O-β-D-glucopyranoside(1), isofraxidin-7-O-β-D-glucopyranoside(2), isorhamnetin-3-O-β-D-glucosyl-7-O-β-D-glucoside(3), quercetin-3-O-β-Dgentiobioside(4), isoorientin(5), kaempfero l-3-O-β-D-gentiobioside-7-O-D–glucoside(6), isorhamnetin-3-O-β-D-gentiobioside-7-O-D-glucoside(7), Terrestrinone A2(8), dibutyl phthalate(9), dioctyl phthalate(10). Conclusion: Compounds 1 and 5 are isolated from the plants of Tribulus for the first time.
Objective: To investigate the chemical constituents in the stems and leaves of Tribulus terrestris. Methods: The compounds were isolated and purified by a combination of various column chromatographies techniques including macroporous resin, MCI resin, reversed-phase C18 silica gel, Sephadex LH-20 columns, and reversed-phase HPLC. The structures were identified by means of chemical evidences and spectral analyses including MS, 1H-NMR, and 13C-NMR. Results: Twelve compounds were isolated and 10 were identified as 3', 3'-dimethoxy-4'-hydroxyacetophenone-4'-O-β-D-glucopyranoside(1), isofraxidin-7-O-β-D-glucopyranoside(2), isorhamnetin-3-O-β-D-glucosyl-7-O-β-D-glucoside(3), quercetin-3-O-β-Dgentiobioside(4), isoorientin(5), kaempfero l-3-O-β-D-gentiobioside-7-O-D–glucoside(6), isorhamnetin-3-O-β-D-gentiobioside-7-O-D-glucoside(7), Terrestrinone A2(8), dibutyl phthalate(9), dioctyl phthalate(10). Conclusion: Compounds 1 and 5 are isolated from the plants of Tribulus for the first time.
引文
[1]国家药典委员会.中华人民共和国药典(一部).北京:中国医药科技出版社,2010
[2]国家中医药管理局《中华本草》编委会.中华本草(第四册第十二卷).上海:上海科学技术出版社,1999:745
[3]桂海水.蒺藜茎叶化学成分及含量测定研究.北京:北京中医药大学,2013
[4]Itoh T,Ninomiya M,Nozawa Y,et al.Chalcone glycosides isolated from aerial parts of Brassica rapa L.′hidabeni′suppress antigenstimulated degranulation in rat basophilic leukemia RBL-2H3cells.Bioorg Med Chem,2010,18(19):7052-7057
[5]袁珂,朱建鑫,斯金平,等.草珊瑚正丁醇部位化学成分及抑菌活性研究.中国中药杂志,2008,33(15):1843-1846
[6]Saleh N A M,Ahmed A A,Abdalla M F.Flavonoid glycosides of Tribulus pentandrus and T.Terrestris.Phytochemistry,1982,21(8):1995-2000
[7]曲宁宁,杨松松.蒺藜黄酮类化学成分的分离和鉴定.辽宁中医药大学学报,2007,9(3):182-183
[8]Noori Mitra,Dehshiri Mohammad-Mehdi,Zolfaghari Mohammad Reza.Tribulus Terrestris L.(Zygophyllaceae)Flavonoid Compounds.International Journal of Modern Botany,2012,2(3):35-39
[9]王艳.刺蒺藜药理作用及化学成分的研究概况.北京中医学院学报,1989,12(6):30-32
[10]Seong Su Hong,Yun-Hyeok Choi,Wonsik Jeong,et al.Two new furostanol glycosides from the fruits of Tribulus terrestris.Tetrahedron Letters,2013,54(30):3967-3970
[11]杨光忠,何思文.藤黄化学成分的研究.中南民族大学学报(自然科学版),2013,32(2):63-65
[2]国家中医药管理局《中华本草》编委会.中华本草(第四册第十二卷).上海:上海科学技术出版社,1999:745
[3]桂海水.蒺藜茎叶化学成分及含量测定研究.北京:北京中医药大学,2013
[4]Itoh T,Ninomiya M,Nozawa Y,et al.Chalcone glycosides isolated from aerial parts of Brassica rapa L.′hidabeni′suppress antigenstimulated degranulation in rat basophilic leukemia RBL-2H3cells.Bioorg Med Chem,2010,18(19):7052-7057
[5]袁珂,朱建鑫,斯金平,等.草珊瑚正丁醇部位化学成分及抑菌活性研究.中国中药杂志,2008,33(15):1843-1846
[6]Saleh N A M,Ahmed A A,Abdalla M F.Flavonoid glycosides of Tribulus pentandrus and T.Terrestris.Phytochemistry,1982,21(8):1995-2000
[7]曲宁宁,杨松松.蒺藜黄酮类化学成分的分离和鉴定.辽宁中医药大学学报,2007,9(3):182-183
[8]Noori Mitra,Dehshiri Mohammad-Mehdi,Zolfaghari Mohammad Reza.Tribulus Terrestris L.(Zygophyllaceae)Flavonoid Compounds.International Journal of Modern Botany,2012,2(3):35-39
[9]王艳.刺蒺藜药理作用及化学成分的研究概况.北京中医学院学报,1989,12(6):30-32
[10]Seong Su Hong,Yun-Hyeok Choi,Wonsik Jeong,et al.Two new furostanol glycosides from the fruits of Tribulus terrestris.Tetrahedron Letters,2013,54(30):3967-3970
[11]杨光忠,何思文.藤黄化学成分的研究.中南民族大学学报(自然科学版),2013,32(2):63-65