矮紫堇中1个新的异喹啉生物碱分离与鉴定
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摘要
藏族特色药材矮紫堇为罂粟科植物尼泊尔黄堇Corydalis hendersonii的干燥全草,具有清热止痛、降压等功效。作为系统阐明矮紫堇防治缺血性心脏病药效物质的内容之一,本研究通过反相硅胶柱(ODS),羟丙基葡聚糖凝胶LH-20(Sephadex LH-20)及半制备HPLC等色谱方法从其乙醇提取物中分离得到1个新的异喹啉生物碱,其结构经MS,NMR等波谱方法鉴定,定名为矮紫堇碱G(hendersine G,1)。矮紫堇碱G可视为四氢小檗碱与琥珀酸的缩合产物,为新的结构骨架,但因为获得量少且结构复杂,目前没有确定其立体构型。本研究丰富了矮紫堇的药效物质研究内容,也为该药材中新颖结构分子的进一步挖掘提供了一定启示。
As part of systematic research of Corydalis hendersonii,a typical traditional Tibetan herbal medicine with clearing heat,relieving pain,and lowering blood pressure effects,a novel isoquinoline alkaloid,named hendersine G was isolated from the ethanol extract of the whole plant by various chromatographic techniques,including silica gel column,reverse phase column( ODS),Sephadex LH-20,and semi-preparative HPLC. Its structure was elucidated by MS,NMR and other spectroscopic data analysis. Hendersine G can be regarded as a condensation product of a tetrahydroberberine and a succinic acid,however,its absolute configuration has not been determined due to its structural complexity and less obtained amount. This present study provides an inspiration for further exploration of novel molecules from C. hendersonii.
As part of systematic research of Corydalis hendersonii,a typical traditional Tibetan herbal medicine with clearing heat,relieving pain,and lowering blood pressure effects,a novel isoquinoline alkaloid,named hendersine G was isolated from the ethanol extract of the whole plant by various chromatographic techniques,including silica gel column,reverse phase column( ODS),Sephadex LH-20,and semi-preparative HPLC. Its structure was elucidated by MS,NMR and other spectroscopic data analysis. Hendersine G can be regarded as a condensation product of a tetrahydroberberine and a succinic acid,however,its absolute configuration has not been determined due to its structural complexity and less obtained amount. This present study provides an inspiration for further exploration of novel molecules from C. hendersonii.
引文
[1]中国科学院《中国植物志》编辑委员会.中国植物志.第32卷[M].北京:科学出版社,1999:362.
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[7]尹旭,张倩,张和新歌,等.藏族药矮紫堇的化学成分研究[J].中国中药杂志,2018,43(9):1758-1763.
[8]魏春华,程虹毓,高燕萍,等.藏药矮紫堇解热镇痛抗炎作用的研究[J].中国新药杂志,2017,26(3):337-342.
[9]BAI R,YIN X,FENG X,et al.Corydalis hendersonii Hemsl.protects against myocardial injury by attenuating inflammation and fibrosis via NF-κB and JAK2-STAT3signaling pathways[J].J Ethnopharmacol,2017,207:174-183.
[10]YIN X,BAI R F,GUO Q,et al.Hendersine A,a novel isoquinoline alkaloid from Corydalis hendersonii[J].Tetrahedron Lett,2016,57(43):4858-4862.
[11]YIN X,ZHAO F,FENG X,et al.Four new spirobenzylisoquinoline N-oxide alkaloids from the whole plant of Corydalis hendersomii[J].Fitoterapia,2018,128:31-35.
[12]GUO Q,YANG H,LIU X,et al.New zwitterionic monoterpene indole alkaloids from Uncaria rhynchophylla[J].Fitoterapia,2018,127:47-55.
[13]YUAN D,MA B,WU C,et al.Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia[J].J Nat Prod,2008,71(7):1271-1274.
[14]LI B,ZHOU M,ZHANG G.Four new alkaloids from Hypecoum leptocarpum Hook.f.et Thoms[J].Indian J Chem B,2001,40B(12):1215-1218.
[15]ZHOU J Y,TONG X J,LIAN W Y,et al.Chemical study on the alkaloids of Corydalis hsuchowensis[J].Planta Med,1991,57(2):156-158.
[16]CHANG J,CHU Z B,SONG J,et al.Two novel isoquinoline alkaloids from the seedling of Corydalis decumbens[J].Tetrahedron Lett,2014,56(1):225-228.
[2]帝玛尔·丹增彭措.晶珠本草(藏文)[M].北京:民族出版社,1986:374.
[3]国家中医药管理局《中华本草》编委会.中华本草·藏药卷[M].上海:上海科学技术出版社,2002:344-345.
[4]高燕萍,吴强,梁健,等.矮紫堇生物碱成分[J].中国实验方剂学杂志,2016,22(17):67-70.
[5]高燕萍,吴强,梁健,等.藏族药矮紫堇化学成分分离鉴定[J].中国实验方剂学杂志,2016,22(18):60-63.
[6]舒花,马学燕,李鑫,等.矮紫堇总生物碱的含量测定及其抗炎活性研究[J].西北药学杂志,2015,30(5):602-604.
[7]尹旭,张倩,张和新歌,等.藏族药矮紫堇的化学成分研究[J].中国中药杂志,2018,43(9):1758-1763.
[8]魏春华,程虹毓,高燕萍,等.藏药矮紫堇解热镇痛抗炎作用的研究[J].中国新药杂志,2017,26(3):337-342.
[9]BAI R,YIN X,FENG X,et al.Corydalis hendersonii Hemsl.protects against myocardial injury by attenuating inflammation and fibrosis via NF-κB and JAK2-STAT3signaling pathways[J].J Ethnopharmacol,2017,207:174-183.
[10]YIN X,BAI R F,GUO Q,et al.Hendersine A,a novel isoquinoline alkaloid from Corydalis hendersonii[J].Tetrahedron Lett,2016,57(43):4858-4862.
[11]YIN X,ZHAO F,FENG X,et al.Four new spirobenzylisoquinoline N-oxide alkaloids from the whole plant of Corydalis hendersomii[J].Fitoterapia,2018,128:31-35.
[12]GUO Q,YANG H,LIU X,et al.New zwitterionic monoterpene indole alkaloids from Uncaria rhynchophylla[J].Fitoterapia,2018,127:47-55.
[13]YUAN D,MA B,WU C,et al.Alkaloids from the leaves of Uncaria rhynchophylla and their inhibitory activity on NO production in lipopolysaccharide-activated microglia[J].J Nat Prod,2008,71(7):1271-1274.
[14]LI B,ZHOU M,ZHANG G.Four new alkaloids from Hypecoum leptocarpum Hook.f.et Thoms[J].Indian J Chem B,2001,40B(12):1215-1218.
[15]ZHOU J Y,TONG X J,LIAN W Y,et al.Chemical study on the alkaloids of Corydalis hsuchowensis[J].Planta Med,1991,57(2):156-158.
[16]CHANG J,CHU Z B,SONG J,et al.Two novel isoquinoline alkaloids from the seedling of Corydalis decumbens[J].Tetrahedron Lett,2014,56(1):225-228.