目的 研究雷山石杉的化学成分。方法 使用制备薄层、硅胶柱色谱、Sephadex LH-20及半制备高效液相色谱法等手段进行分离、纯化,结合文献资料、理化性质、1H-NMR及13C-NMR数据进行结构鉴定。结果 分离得到10个化合物,分别鉴定为(15R)-12,16-epoxy-11,14-dihydroxy-8,11,13-abietatrien-7-one(Ⅰ),21-epi-serratenediol-3,21-acetate(Ⅱ),serratene-diol-3-acetate(Ⅲ),21-epi-serratenediol-3-acetate(Ⅳ),21α-hydroxy-serrat-14-en-3β-ol(Ⅴ),21β-hydroxy-serrat-14-en-3β-ol(Ⅵ),石杉碱甲( huperzine A,Ⅶ),蔗糖(Ⅷ),β-谷甾醇(Ⅸ),胡萝卜苷(Ⅹ)。结论 化合物Ⅰ~Ⅹ均首次从该植物中分离到。
Abstract
OBJECTIVE To study the chemical constituents in the whole plant of Huperzia leishangensis. METHODS Compounds were isolated and purified by Prep-TLC,silica gel chromatography,Sephadex LH-20 and preparative high performance liquid chromatography,and their structures were identified on the basis of comprehensive analysis of their physical and chemical properties,NMR data and literatures. RESULTS Ten compounds were isolated and elucidated as(15R)-12,16-epoxy-11,14-dihydroxy-8,11,13-abietatrien-7-one(Ⅰ),21-epi-serratenediol-3,21-acetate(Ⅱ),serratenediol-3-acetate(Ⅲ),21-epi-serratenediol-3-acetate(Ⅳ), 21α-hydroxy-serrat-14-en-3β-ol(Ⅴ),21β-hydroxy-serrat-14-en-3β-ol(Ⅵ),huperzine A(Ⅶ),sucrose(Ⅷ),β-sitosterol(Ⅸ) and β-daucosterol(Ⅹ). CONCLUSION Compound Ⅰ-Ⅹ were for the first time isolated from H. leishangensis.
关键词
雷山石杉 /
化学成分 /
(15R)-12 /
16-epoxy-11 /
14-dihydroxy-8 /
11 /
13-abietatrien-7-one /
21-epi-serratenediol-3 /
21-acetate /
serratene-diol-3-acetate
{{custom_keyword}} /
Key words
Huperzia leishangensis /
chemical constituents /
(15R)-12,16-epoxy-11,14-dihydroxy-8,11,13-abietatrien-7-one /
21-epi-serratenediol-3,21-acetate /
serratene-diol-3-acetate
{{custom_keyword}} /
中图分类号:
R284
{{custom_clc.code}}
({{custom_clc.text}})
{{custom_sec.title}}
{{custom_sec.title}}
{{custom_sec.content}}
参考文献
[1] WANG P S,WANG Y Y. Ferns Flora of Guizhou (贵州蕨类植物志). Guiyang:Guizhou Science and Technology Press,2001:367.[2] PAN L T,ZHAO J H,SUN Q W. Medicinal Ferns of Guizhou(贵州药用蕨类植物). Guiyang:Guizhou Science and Technology Press,2012:30.[3] LIU J S,ZHU Y L,YU C M,et al. The structures of huperzine A and B,two new alkaloids exhibiting marked anticholinesterase activity. Can J Chem,1986,64:837-839.[4] YUAN J Q,ZHOU X L,WANG S,et al. Advances in studies on chemical constituents of Huperzia serrata and their pharmacological effects. Chin Tradit Herb Drug(中草药),2012,43(2):399-407.[5] YU H,LI W M,JIAN J Y,et al. Advances in studies on the pharmacokinetics of treatment of Alzheimer′s drug . Chin Pharm J (中国药学杂志),2007,42(15):1121-1125.[6] SHI Q H,FU J F,GE D,et al. Huperzine A relieves acute hypobaric-induced oxidative stress injury in rat brain . Chin Pharm J (中国药学杂志),2012,47(17):1378-1380.[7] WANG ,PAN S L. Content of huperzine A in 23 species from Chinese herbal medicine Qiancengta. Chin Pharm J(中国药学杂志),2009,44(16):1212-1214.[8] XIE Y C,ZHANG Q M,JIN S H,et al. Quantitative determination of huperzine A tablets by a new HPLC method of substitute for reference substance . Chin Pharm J(中国药学杂志),2008,43(3):217-221.[9] WANG C,LI Q J,ZOU J,et al. Content of huperzine A from Chinese Miao minzu medicine Huperzia leishangensis by HPLC . Chin J Ethnomed Ethnopharm(中国民族医药杂志),2008,5(5):54-55.[10] YANG Y B,YANG X Q,XU Y Q,et al. Two diterpenoids from herbs of Huperzia serrata. China J Chin Mater Med(中国中药杂志),2009,34(8):987-989.[11] WEN J F. Chemical investigations on Huperzia serrata(Thunb)Trev and Tripterginum wifordii Hook. F . Nanning:Guangxi University,2009.[12] PEI G,ZHOU P H,HE G X,et al. Studies on liposoluble constituents of Huperzia crispate Ching . Nat Prod Res Devel(天然产物研究与开发),2004,16(3):213-214. [13] LI J,HAN Y Y,LIU J S. Studies on triterpenoids of Huperzia serrata Thunb. . Acta Pharm Sin(药学学报),1988,23(7):549-552.[14] LOU C,CHEN Z,ZHANG W F,et al. Chemical constituents of Huperzia serrata. Chin Trad Herb Drug(中草药),2011,42(12):2407-2409.[15] ZHOU B N,ZHU D Y,HUANG M F,et al. NMR Assignments of huperzine A,serratinine and lucidioline. Phytochemistry,1993,34(5):1425-1428.[16] YANG L,ZHAO Y Y,TU Y Y. Chemical constituents from Matteuccia struthiopteris. China J Chin Mater Med(中国中药杂志),2003,28(3):278-279.
{{custom_fnGroup.title_cn}}
脚注
{{custom_fn.content}}
基金
贵州省科技计划项目(黔科合GY字3038号)
{{custom_fund}}