傣药奶子藤根的生物碱类成分研究
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摘要
目的:研究傣药奶子藤根的化学成分。方法:采用甲醇对奶子藤根的粗粉进行浸渍和回流提取,利用硅胶、反相硅胶、制备薄层色谱、半制备高效液色谱等多种柱色谱法对奶子藤根中的生物碱类成分进行分离纯化,通过NMR和ESI-MS等波谱技术以及与文献报道数据比对,鉴定化合物结构。结果:从奶子藤根中分离得到9个化合物,分别鉴定为:狗牙花碱(1)、非洲伏康树碱(2)、 7-羟基吲哚海尼山辣椒碱(3)、6-酮基伊菠加因(4)、14,15-环氧-氮-甲基白坚木胺(5)、14,15-二羟基-氮-甲基白坚木胺(6)、伊波叶黄素(7)、喜树次碱(8)、lirofolines A(9)。结论:以上化合物均为首次从奶子藤属植物中分离得到。
Objective:To study alkaloids from the root of Bousigonia mekongensis.Methods:The coarse powder of the root from Bousigonia mekongensis was impregnated and reflux extracted by methanol.The alkaloids were isolated and purified by using various chromatographic techniques,including silica gel,ODS,pre-TLC and HPLC.Their structures were elucidated by NMR and ESI-MS spectroscopy and compared with the reported data.Results:Nine alkaloids were isolated and identified as coronaridine(1),voacristine(2),heyneanine hydroxyindolenine(3),6-oxoibogaine(4),N-methylvoaphylline(5),voafinidine aspidosamine(6),iboluteine(7),venoterpine(8),lirofolines A(9),respectively.Conclusion:All compounds are isolated from the Bousigonia genus for the first time.
Objective:To study alkaloids from the root of Bousigonia mekongensis.Methods:The coarse powder of the root from Bousigonia mekongensis was impregnated and reflux extracted by methanol.The alkaloids were isolated and purified by using various chromatographic techniques,including silica gel,ODS,pre-TLC and HPLC.Their structures were elucidated by NMR and ESI-MS spectroscopy and compared with the reported data.Results:Nine alkaloids were isolated and identified as coronaridine(1),voacristine(2),heyneanine hydroxyindolenine(3),6-oxoibogaine(4),N-methylvoaphylline(5),voafinidine aspidosamine(6),iboluteine(7),venoterpine(8),lirofolines A(9),respectively.Conclusion:All compounds are isolated from the Bousigonia genus for the first time.
引文
[1] 蒋英,李秉滔.中国植物志[M].第63卷.北京:科学出版社,1977:32.
[2] 曾君,曾湘荣.傣药雅解沙把(百解胶囊)的研究概况[J].中国民族民间医药,2009,18(21):23-24.
[3] 李世源,杨春涛,曾晓丽,等.奶子藤茎的化学成分研究[J].云南民族大学学报(自然科学版),2014,23(4):235-238.
[4] Fu YH,Li SL,Li SF,et al.Cytotoxic eburnamine-aspidospermine type bisindole alkaloids from Bousigonia mekongensis[J].Fitoterapia,2014,98:45-52.
[5] Fu YH,He HP,Di YT,et al.Mekongenines A and B,two new alkaloids from Bousigonia mekongensis[J].Tetrahedron Letters,2012,53:3642-3646.
[6] 刘波,刘书剑,李玉擒,等.狗牙花生物碱成分分析[J].中国实验方剂学杂志,2017,23(17):76-80.
[7] Okuyama E,Gao L,Yamazaki M.Analgesic components from bornean medicinal plants,Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir.[J].Chemical & Pharmaceutical Bulletin,1992,40(8):2075-2079.
[8] 陈红梅,邓赟,宋川霞,等.伏康树中单萜吲哚类生物碱及其NMR波谱特征[J].中国实验方剂学杂志,2015,21(7):216-222.
[9] Pereira PS,Franca SF,Oliveira PVA,et al.Chemical constituents from Tabernaemontana catharinensis root bark:A brief NMR review of indole alkaloids and in vitro cytotoxicity[J].Quimica Nova,2008,31(1):20-24.
[10] Sharma P,Cordell GA.Heyneanine hydroxyindolenine,a new indole alkaloid from Ervatamia coronaria var.plena[J].Journal of Natural Products,1988,51(3):528-531.
[11] Lim KH,Raja VJ,Bradshaw TD,et al.Ibogan,tacaman,and cytotoxic bisindole alkaloids from Tabernaemontana.Cononusine,an iboga alkaloid with unusual incorporation of a pyrrolidone moiety[J].Journal of Natural Products,2015,78(5):1129-1138.
[12] Kam TK,Anuradha S,Loh KY.Voafinidine and Voalenine,novel indoles of the aspidosperma-type from Tabernaemontana[J].Natural Product Letters,1996,8(1):49-53.
[13] Kam TS,Pang HS,Lim TM.Biologically active indole and bisindole alkaloids from Tabernaemontana divaricate[J].Cheminform,2003,1(8):1292-1297.
[14] Wenkert E,Gottlieb HE.The C(2)Stereochemistry of Iboluteine[J].Heterocycles,1977,7(2):753.
[15] Ravao T,Richard B,Zeches M,et al.The configuration of venoterpine[J].Tetrahedron Letters,1985,26(7):837-838.
[16] Low YY,Lim KH,Choo YM,et al.Structure,biological activity,and a biomimetic partial synthesis of the lirofolines,novel pentacylic indole alkaloids from Tabernaemontana[J].Tetrahedron Letters.2010,51(2):269-272.
[2] 曾君,曾湘荣.傣药雅解沙把(百解胶囊)的研究概况[J].中国民族民间医药,2009,18(21):23-24.
[3] 李世源,杨春涛,曾晓丽,等.奶子藤茎的化学成分研究[J].云南民族大学学报(自然科学版),2014,23(4):235-238.
[4] Fu YH,Li SL,Li SF,et al.Cytotoxic eburnamine-aspidospermine type bisindole alkaloids from Bousigonia mekongensis[J].Fitoterapia,2014,98:45-52.
[5] Fu YH,He HP,Di YT,et al.Mekongenines A and B,two new alkaloids from Bousigonia mekongensis[J].Tetrahedron Letters,2012,53:3642-3646.
[6] 刘波,刘书剑,李玉擒,等.狗牙花生物碱成分分析[J].中国实验方剂学杂志,2017,23(17):76-80.
[7] Okuyama E,Gao L,Yamazaki M.Analgesic components from bornean medicinal plants,Tabernaemontana pauciflora Blume and Tabernaemontana pandacaqui Poir.[J].Chemical & Pharmaceutical Bulletin,1992,40(8):2075-2079.
[8] 陈红梅,邓赟,宋川霞,等.伏康树中单萜吲哚类生物碱及其NMR波谱特征[J].中国实验方剂学杂志,2015,21(7):216-222.
[9] Pereira PS,Franca SF,Oliveira PVA,et al.Chemical constituents from Tabernaemontana catharinensis root bark:A brief NMR review of indole alkaloids and in vitro cytotoxicity[J].Quimica Nova,2008,31(1):20-24.
[10] Sharma P,Cordell GA.Heyneanine hydroxyindolenine,a new indole alkaloid from Ervatamia coronaria var.plena[J].Journal of Natural Products,1988,51(3):528-531.
[11] Lim KH,Raja VJ,Bradshaw TD,et al.Ibogan,tacaman,and cytotoxic bisindole alkaloids from Tabernaemontana.Cononusine,an iboga alkaloid with unusual incorporation of a pyrrolidone moiety[J].Journal of Natural Products,2015,78(5):1129-1138.
[12] Kam TK,Anuradha S,Loh KY.Voafinidine and Voalenine,novel indoles of the aspidosperma-type from Tabernaemontana[J].Natural Product Letters,1996,8(1):49-53.
[13] Kam TS,Pang HS,Lim TM.Biologically active indole and bisindole alkaloids from Tabernaemontana divaricate[J].Cheminform,2003,1(8):1292-1297.
[14] Wenkert E,Gottlieb HE.The C(2)Stereochemistry of Iboluteine[J].Heterocycles,1977,7(2):753.
[15] Ravao T,Richard B,Zeches M,et al.The configuration of venoterpine[J].Tetrahedron Letters,1985,26(7):837-838.
[16] Low YY,Lim KH,Choo YM,et al.Structure,biological activity,and a biomimetic partial synthesis of the lirofolines,novel pentacylic indole alkaloids from Tabernaemontana[J].Tetrahedron Letters.2010,51(2):269-272.