孔雀草茎、叶化学成分的分离鉴定
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摘要
目的:孔雀草Tagetes patula是菊科Asteraceae植物,近代研究发现花中含有大量叶黄素具有抗氧化活性,根中得到的噻吩类衍生物具有抗菌活性,根部甲醇提取物中分得的柠檬酸、苹果酸具有降压活性,该文旨在研究其茎、叶化学成分,揭示其治疗疾病的物质基础。方法:采用95%乙醇,减压回收溶剂得浓缩物,将浓缩物溶于水中,用乙酸乙酯萃取。取乙酸乙酯萃取物,用硅胶柱、开放ODS柱及制备HPLC等色谱技术进行分离纯化,根据化合物的理化性质,1H-NMR,13C-NMR等光谱数据进行结构鉴定。结果:从乙酸乙酯萃取部分中分离得到8个化合物,经光谱分析确定其结构分别为丁香脂素-4'-O-β-D-葡萄糖苷(1),2-甲氧基-4-(2-丙烯基)苯基-β-D-葡萄糖苷(2),邻苯二甲酸二丁酯(3),万寿菊素(4),β-胡萝卜苷(5),β-谷甾醇(6),4-烯丙基-2,6-二甲氧基苯基葡萄糖苷(7),1-β-D-吡喃葡萄糖苷-2,6-二甲氧基-4-丙烯基苯酚(8)。结论:化合物1,2,3,7,8为首次从孔雀草中分离得到,同时也是首次从万寿菊属植物中分离得到。该研究为综合开发及寻找天然植物性抗炎、抗氧化活性成分提供一定的化学依据和基础。
Objective: Tagetes patula is compositae plants of the genus of Asteraceae. The modern researches showed that its flowers contained a large amount of lutein with antioxidant activity. The thiophene derivatives in the roots exhibited antimicrobial activity. The citric acid and malic acid obtained from the methanol extract of root showed hypotensive activity. The aim of this study was to investigate the chemical constituents of stems and leaves of T. patula for the first time,and to reveal the material basis for the treatment of diseases.Method: The herbs of T. patula were extracted with 95% ethanol. Then the extract was combined and evaporated in vacuum to residue,which was suspended in water and successively partitioned with ethyl acetate. Part of the ethyl acetate extract was isolated and purified by various column chromatographs such as silica gel,ODS column and preparative HPLC. Then the structures of isolated and purified compounds were determined by physicalchemical property and spectral analysis such as13 C-NMR and1 H-NMR. Result: Six compounds were identified as syringaresinol-4'-O-β-D-monoglucoside(1), 2-methoxy-4-(2-propenyl) phenyl-β-D-glucoside(2), dibutyl phthalate(3),patuletin(4),β-daucostero(5),β-glutamyl sterol(6),4-allyl-2,6-dimethoxy phenyl glucoside(7),and 1-β-D-glucopyranosyl-2,6-dimethoxy-4-propenylphenol(8). Conclusion: Compounds 1,2,3,7 and8 were isolated from the genus of Tagetes for the first time,providing certain chemical basis and foundation for the comprehensive development and the search for anti-inflammatory and antioxidant active substances in natural plants.
Objective: Tagetes patula is compositae plants of the genus of Asteraceae. The modern researches showed that its flowers contained a large amount of lutein with antioxidant activity. The thiophene derivatives in the roots exhibited antimicrobial activity. The citric acid and malic acid obtained from the methanol extract of root showed hypotensive activity. The aim of this study was to investigate the chemical constituents of stems and leaves of T. patula for the first time,and to reveal the material basis for the treatment of diseases.Method: The herbs of T. patula were extracted with 95% ethanol. Then the extract was combined and evaporated in vacuum to residue,which was suspended in water and successively partitioned with ethyl acetate. Part of the ethyl acetate extract was isolated and purified by various column chromatographs such as silica gel,ODS column and preparative HPLC. Then the structures of isolated and purified compounds were determined by physicalchemical property and spectral analysis such as13 C-NMR and1 H-NMR. Result: Six compounds were identified as syringaresinol-4'-O-β-D-monoglucoside(1), 2-methoxy-4-(2-propenyl) phenyl-β-D-glucoside(2), dibutyl phthalate(3),patuletin(4),β-daucostero(5),β-glutamyl sterol(6),4-allyl-2,6-dimethoxy phenyl glucoside(7),and 1-β-D-glucopyranosyl-2,6-dimethoxy-4-propenylphenol(8). Conclusion: Compounds 1,2,3,7 and8 were isolated from the genus of Tagetes for the first time,providing certain chemical basis and foundation for the comprehensive development and the search for anti-inflammatory and antioxidant active substances in natural plants.
引文
[1]《全国中草药汇编》编写组.全国中草药汇编.第2卷[M].3版.北京:人民卫生出版社,2014:299.
[2]中国科学院《中国植物志》编辑委员会.中国植物志.第75卷[M].北京:科学出版社,1979:422.
[3]贺士元,邢其华,尹祖堂,等.北京植物志(下)[M].1992年修订版.北京:北京出版社,1993:1504.
[4]Padma V,Suman K,Satyawati S.Tagetes:A multipurpose plant[J].Bioresour Technol,1997,62(1/2):29-35.
[5]Ivancheva S,Zdravkova M.Flavonoids in Tagetes patula[J].Fitoterapia,1993,64(6):555.
[6]Bhardwaj D K,Bisht M S,Uain S C,et al.Quercetagetin5-methyl ether from the petals of Tagetes patula[J].Phytochemistry,1980,19(4):713-714.
[7]Politi F,Watanabe V,Sorrechia R,et al.Evaluation of Tagetes patula L.(Asteraceae)against filamentous and entomopathogenic fungi[J].Planta Med,2012,78(11):112.
[8]Politi F A,Fernandes G M,Rodrigues E R,et al.Antifungal,antiradical and cytotoxic activities of extractives obtained from Tagetes patula L.(Asteraceae),a potential acaricide plant species[J].Microb Pathog,2016,95(6):15-20.
[9]Bano H,Ahmed S W,Azhar I,et al.Chemical constituents of Tagetes patula L.[J].Pak J Pharm Sci,2006,15(2):1-12.
[10]Menelaou M A,Vargas D,Fischer N H,et al.Biosynthetic studies of bithiophenes in hairy root cultures of Tagetes patula using 13C-labeled acetates[J].Spectrosc Lett,1991,24(3):353-370.
[11]Bano H,Ahmed S W,Azhar I,et al.Chemical constituents of Tagetes patula L.[J].Pak J Pharm Sci,2002,15(2):1-12.
[12]Yasukawa K,Kasahara Y.Effects of flavonoids from french marigold(florets of Tagetes patula L.)on acute inflammation model[J].Int J Inflamm,2013,2013:309-493.
[13]Saleem R,Ahmad M,Naz A,et al.Hypotensive and toxicological study of citric acid and other constituents from Tagetes patula roots[J].Arch Pharm Res,2004,27(10):1037-1042.
[14]Romagnoli C,Mares D,Fasulo M P,et al.Antifungal effects ofα-terthienyl from Tagetes patula on five dermatophytes[J].Phytother Res,2010,8(6):332-336.
[15]Kasahara Y,Yasukawa K,Kitanaka S,et al.Effect of methanol extract from flower petals of Tagetes patula L.on acute and chronic inflammation model[J].Phytother Res Ptr,2002,16(3):217-222.
[16]Bhattacharyya S,Datta S,Mallick B,et al.Lutein content and in vitro antioxidant activity of different cultivars of Indian marigold flower(Tagetes patula L.)extracts[J].J Agri Food Chem,2010,58(14):8259-8264.
[17]吴剑峰,陈四保,陈士林,等.香港远志化学成分研究[J].药学学报,2007,42(7):757-761.
[18]Schwab W,Scheller G,Schreier P.Glycosidically bound aroma components from sour cherry[J].Phytochemistry,1990,29(2):607-612.
[19]潘争红,吴云飞,宁德生,等.毛果巴豆根的化学成分研究[J].广西植物,2014,34(2):148-150,255.
[20]邓双炳,菅晓勇,任启生,等.旋覆花化学成分研究(英文)[J].中国现代应用药学,2011,28(4):330-334.
[21]管惠娟,张雪,屠凤娟,等.铁皮石斛化学成分的研究[J].中草药,2009,40(12):1873-1876.
[22]van Kiem P,van Minn C,Dat N T,et al.Two new phenylpropanoid glycosides from the stem bark of Acanthopanax trifoliatus[J].Arch Pharm Res,2004,26(12):1014-1017.
[2]中国科学院《中国植物志》编辑委员会.中国植物志.第75卷[M].北京:科学出版社,1979:422.
[3]贺士元,邢其华,尹祖堂,等.北京植物志(下)[M].1992年修订版.北京:北京出版社,1993:1504.
[4]Padma V,Suman K,Satyawati S.Tagetes:A multipurpose plant[J].Bioresour Technol,1997,62(1/2):29-35.
[5]Ivancheva S,Zdravkova M.Flavonoids in Tagetes patula[J].Fitoterapia,1993,64(6):555.
[6]Bhardwaj D K,Bisht M S,Uain S C,et al.Quercetagetin5-methyl ether from the petals of Tagetes patula[J].Phytochemistry,1980,19(4):713-714.
[7]Politi F,Watanabe V,Sorrechia R,et al.Evaluation of Tagetes patula L.(Asteraceae)against filamentous and entomopathogenic fungi[J].Planta Med,2012,78(11):112.
[8]Politi F A,Fernandes G M,Rodrigues E R,et al.Antifungal,antiradical and cytotoxic activities of extractives obtained from Tagetes patula L.(Asteraceae),a potential acaricide plant species[J].Microb Pathog,2016,95(6):15-20.
[9]Bano H,Ahmed S W,Azhar I,et al.Chemical constituents of Tagetes patula L.[J].Pak J Pharm Sci,2006,15(2):1-12.
[10]Menelaou M A,Vargas D,Fischer N H,et al.Biosynthetic studies of bithiophenes in hairy root cultures of Tagetes patula using 13C-labeled acetates[J].Spectrosc Lett,1991,24(3):353-370.
[11]Bano H,Ahmed S W,Azhar I,et al.Chemical constituents of Tagetes patula L.[J].Pak J Pharm Sci,2002,15(2):1-12.
[12]Yasukawa K,Kasahara Y.Effects of flavonoids from french marigold(florets of Tagetes patula L.)on acute inflammation model[J].Int J Inflamm,2013,2013:309-493.
[13]Saleem R,Ahmad M,Naz A,et al.Hypotensive and toxicological study of citric acid and other constituents from Tagetes patula roots[J].Arch Pharm Res,2004,27(10):1037-1042.
[14]Romagnoli C,Mares D,Fasulo M P,et al.Antifungal effects ofα-terthienyl from Tagetes patula on five dermatophytes[J].Phytother Res,2010,8(6):332-336.
[15]Kasahara Y,Yasukawa K,Kitanaka S,et al.Effect of methanol extract from flower petals of Tagetes patula L.on acute and chronic inflammation model[J].Phytother Res Ptr,2002,16(3):217-222.
[16]Bhattacharyya S,Datta S,Mallick B,et al.Lutein content and in vitro antioxidant activity of different cultivars of Indian marigold flower(Tagetes patula L.)extracts[J].J Agri Food Chem,2010,58(14):8259-8264.
[17]吴剑峰,陈四保,陈士林,等.香港远志化学成分研究[J].药学学报,2007,42(7):757-761.
[18]Schwab W,Scheller G,Schreier P.Glycosidically bound aroma components from sour cherry[J].Phytochemistry,1990,29(2):607-612.
[19]潘争红,吴云飞,宁德生,等.毛果巴豆根的化学成分研究[J].广西植物,2014,34(2):148-150,255.
[20]邓双炳,菅晓勇,任启生,等.旋覆花化学成分研究(英文)[J].中国现代应用药学,2011,28(4):330-334.
[21]管惠娟,张雪,屠凤娟,等.铁皮石斛化学成分的研究[J].中草药,2009,40(12):1873-1876.
[22]van Kiem P,van Minn C,Dat N T,et al.Two new phenylpropanoid glycosides from the stem bark of Acanthopanax trifoliatus[J].Arch Pharm Res,2004,26(12):1014-1017.
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