艾叶中差向异构体physanicantriol和14-epi-physanicantriol的分离制备
|
摘要
目的建立中药艾叶中一对半日花烷型二萜类差向异构体physanicantriol(1)和14-epi-physanicantriol(2)的分离制备方法。方法艾叶95%乙醇提取物的二氯甲烷萃取物经Diaion HP-20大孔吸附树脂、硅胶和Sephadex LH-20柱色谱分离,并用半制备HPLC纯化得到差向异构体1和2的混合物。最后通过硅胶H柱色谱分离得到差向异构体1和2单体化合物,色谱条件:固定相为硅胶H,洗脱剂为正己烷-二氯甲烷-异丙醇(1∶1∶0.15,V/V/V)。化合物1和2的结构通过MS和NMR并结合文献确定。结果和结论两个二萜类化合物为首次从菊科植物中分离得到。该法分离效果好、简便快速,可用于差向异构体1和2的分离制备。
Objective To establish a method for the preparative separation and isolation of the epimeric labdenetriols,physanicantriol(1)and 14-epi-physanicantriol(2),from the leaves of Artemisia argyi. Methods The CH_2Cl_2 fraction of 95% Et OH extract from the leaves of A. argyi was separated by Diaion HP-20,silica gel and Sephadex LH-20 column chromatography and purified by semi-preparative HPLC to obtain an epimeric mixture of 1 and 2. Then,the epimeric mixture was separated by silica gel H column chromatography with eluting by n-hexane-CH_2Cl_2-isopropyl alcohol(1∶1∶0.15,V/V/V)to obtain compounds 1 and 2. The structures of 1 and 2 were identified by comparing MS and NMR data with those reported in the literature. Results and Conclusion Two diterpenoids were isolated for the first time from the family Compositae. This method is effective,convenient and rapid,and is suitable for the separation and preparation of the epimers 1 and 2.
Objective To establish a method for the preparative separation and isolation of the epimeric labdenetriols,physanicantriol(1)and 14-epi-physanicantriol(2),from the leaves of Artemisia argyi. Methods The CH_2Cl_2 fraction of 95% Et OH extract from the leaves of A. argyi was separated by Diaion HP-20,silica gel and Sephadex LH-20 column chromatography and purified by semi-preparative HPLC to obtain an epimeric mixture of 1 and 2. Then,the epimeric mixture was separated by silica gel H column chromatography with eluting by n-hexane-CH_2Cl_2-isopropyl alcohol(1∶1∶0.15,V/V/V)to obtain compounds 1 and 2. The structures of 1 and 2 were identified by comparing MS and NMR data with those reported in the literature. Results and Conclusion Two diterpenoids were isolated for the first time from the family Compositae. This method is effective,convenient and rapid,and is suitable for the separation and preparation of the epimers 1 and 2.
引文
[1]国家药典委员会.中华人民共和国药典(一部)[M].北京:中国医药科技出版社,2015:89
[2]李真真,吕洁丽,张来宾,等.艾叶的化学成分及药理作用研究进展[J].国际药学研究杂志,2016,43(6):1059-1066.
[3]周峰,秦路平,连佳芳,等.艾叶的化学成分、生物活性和植物资源[J].药学实践杂志,2000,18(2):96-98,103.
[4]Wang S,Sun J,Zeng KW,et al.Sesquiterpenes from Artemisia argyi:absolute configurations and biological activities[J].Eur J Org Chem,2014,2014(5):973-983.
[5]Zhang LB,Lv JL,Chen HL,et al.Chemical constituents from Artemisia argyi and their chemotaxonomic significance[J].Biochem Syst Ecol,2013,50(10):455-458.
[6]Lv JL,Li ZZ,Zhang LB.Two new flavonoids from Artemisia argyi with their anticoagulation activities[J].Nat Prod Res,2018,32(6):632-639.
[7]Wang S,Jiang Y,Zeng KW,et al.Anti-neuroinflammatory constituents from Artemisia argyi[J].J Chin Pharm Sci,2013,22(4):377-380.
[8]Maldonado E,Pérez-Castorena AL,Romero Y,et al.Absolute configuration of labdane diterpenoids from Physalis nicandroides[J].J Nat Prod,2015,78(2):202-207.
[2]李真真,吕洁丽,张来宾,等.艾叶的化学成分及药理作用研究进展[J].国际药学研究杂志,2016,43(6):1059-1066.
[3]周峰,秦路平,连佳芳,等.艾叶的化学成分、生物活性和植物资源[J].药学实践杂志,2000,18(2):96-98,103.
[4]Wang S,Sun J,Zeng KW,et al.Sesquiterpenes from Artemisia argyi:absolute configurations and biological activities[J].Eur J Org Chem,2014,2014(5):973-983.
[5]Zhang LB,Lv JL,Chen HL,et al.Chemical constituents from Artemisia argyi and their chemotaxonomic significance[J].Biochem Syst Ecol,2013,50(10):455-458.
[6]Lv JL,Li ZZ,Zhang LB.Two new flavonoids from Artemisia argyi with their anticoagulation activities[J].Nat Prod Res,2018,32(6):632-639.
[7]Wang S,Jiang Y,Zeng KW,et al.Anti-neuroinflammatory constituents from Artemisia argyi[J].J Chin Pharm Sci,2013,22(4):377-380.
[8]Maldonado E,Pérez-Castorena AL,Romero Y,et al.Absolute configuration of labdane diterpenoids from Physalis nicandroides[J].J Nat Prod,2015,78(2):202-207.