美花圆叶筋骨草的化学成分研究
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摘要
目的研究美花圆叶筋骨草Ajuga ovalifolia var.calantha的化学成分。方法采用硅胶柱色谱、Sephadex LH-20凝胶柱色谱、ODS柱色谱和半制备型高效液相色谱等方法分离纯化,通过波谱学手段进行结构鉴定。结果从美花圆叶筋骨草全草95%乙醇提取物中分离得到了13个化合物,分别鉴定为(16S)-12,16-epoxy-11,14-dihydroxy-17(15→16)-abeo-abieta-8,11,13-trien-7-one(1)、痢止蒿乙素(2)、ajudecumin A(3)、14,15-dihydroajugapitin(4)、杯苋甾酮(5)、β-谷甾醇(6)金合欢素(7)、芹菜素(8)、木犀草素(9)、东莨菪亭(10)、异东莨菪亭(11)、4-羟基-3-甲氧基苯甲醛(12)、乙酰香子兰酮(13)。结论化合物1、10~13为首次从该属植物中分离得到,化合物2~5、7均为首次从该植物中分离得到;并对化合物1进行了单晶X射线衍射实验,首次得到化合物1的单晶X射线衍射晶体结构数据。
Objective To investigate the chemical constituents of Ajuga ovalifolia var. calantha. Methods The 95% ethanol extract from the whole herb of A. ovalifolia var. calantha was separated and purified by column chromatography over silica gel, Sephadex LH-20, ODS, and RP-HPLC. Their chemical structures were identified on the basis of physicochemical characteristics and spectral analyses. Results Thirteen compounds were isolated and identified as(16S)-12,16-epoxy-11,14-dihydroxy-17(15→16)-abeo-abieta-8,11,13-trien-7-one(1), ajuforrestin B(2), ajudecumin A(3), 14,15-dihydroajugapitin(4), cyasterone(5), β-sitosterol(6), acacetin(7), apigenin(8), luteolin(9), scopoletin(10), isoscopoletin(11), 4-hydroxy-3-methoxy-benzaldehyde(12), and acetovanillon(13). Conclusion Compounds 1 and 10—13 are reported from the genus Ajuga Linn., and compounds 2—5 and 7 are isolated from this plant for the first time. Single crystal X-ray diffraction experiment is carried out for compound 1, and the crystal structure data of single crystal X-ray diffraction of compound 1 is obtained for the first time.
Objective To investigate the chemical constituents of Ajuga ovalifolia var. calantha. Methods The 95% ethanol extract from the whole herb of A. ovalifolia var. calantha was separated and purified by column chromatography over silica gel, Sephadex LH-20, ODS, and RP-HPLC. Their chemical structures were identified on the basis of physicochemical characteristics and spectral analyses. Results Thirteen compounds were isolated and identified as(16S)-12,16-epoxy-11,14-dihydroxy-17(15→16)-abeo-abieta-8,11,13-trien-7-one(1), ajuforrestin B(2), ajudecumin A(3), 14,15-dihydroajugapitin(4), cyasterone(5), β-sitosterol(6), acacetin(7), apigenin(8), luteolin(9), scopoletin(10), isoscopoletin(11), 4-hydroxy-3-methoxy-benzaldehyde(12), and acetovanillon(13). Conclusion Compounds 1 and 10—13 are reported from the genus Ajuga Linn., and compounds 2—5 and 7 are isolated from this plant for the first time. Single crystal X-ray diffraction experiment is carried out for compound 1, and the crystal structure data of single crystal X-ray diffraction of compound 1 is obtained for the first time.
引文
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[15]蔡祯艳,易刚强,李云耀,等.筋骨草属植物中新克罗烷型二萜类成分的核磁共振谱图特征[J].中南药学,2014,12(11):1108-1112.
[2]周荣汉,段金廒.植物化学分类学[M].上海:上海科学技术出版社,2005.
[3]杨永昌.藏药志[M].西宁:青海人民出版社,1991.
[4]Lima K S B,Guedes M L S,Silveira E R.Abietane diterpenes from Hyptis crassifolia Mart.ex Benth.(Lamiaceae)[J].J Braz Chem Soc,2015,26(1):32-39.
[5]王爱国,吕扬,冯孝章.痢止蒿化学成分的研究[J].药学学报,1994,29(12):899-904.
[6]Wang B,Wang X N,Shen T,et al.Rearranged abietane diterpenoid hydroquinones from aerial parts of Ajugadecumbens Thunb[J].Phytochem Lett,2012,5(2):271-275.
[7]Camps F,Coll J,Dargallo O,et al.Neo-clerodane diterpenoids from Ajuga pseudoiva[J].Phytochemistry,1984,23(2):387-389.
[8]陈幸,黎万寿,梁溢,等.川牛膝化学成分的鉴定[J].中草药,2004,35(9):978-979.
[9]Xu D,Huang Z,Cen Y J,et al.Antifeedant activities of secondary metabolites from Ajuga nipponensis against adult of striped flea beetles,Phyllotreta striolata[J].JPest Sci,2009,82(2):195-202.
[10]孙占平,桂丽萍,郭远强,等.金疮小草化学成分的分离与鉴定[J].沈阳药科大学学报,2012,29(10):758-764.
[11]Fu M Q,Xiao G S,Wu J J,et al.Chemical constituents from Pericarpium Citri Reticulatae[J].Chin Herb Med,2017,9(1):86-91.
[12]Ito J,Chang F R,Wang H K,et al.Anti-AIDS agents.48.1 Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis[J].J Nat Prod,2001,64(10):1278-1281.
[13]潘晓辉,李硕,李瑜.驼绒藜化学成分研究[J].天然产物研究与开发,2005,17(3):290-293.
[14]Ni B R,Dong X X,Fu J,et al.Phytochemical and biological properties of Ajuga decumbens(Labiatae):A Review[J].Tropical J Pharm Res,2015,14(8):1525-1536.
[15]蔡祯艳,易刚强,李云耀,等.筋骨草属植物中新克罗烷型二萜类成分的核磁共振谱图特征[J].中南药学,2014,12(11):1108-1112.