白钩藤的化学成分研究
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摘要
目的研究白钩藤Uncaria sessilifructus带钩茎枝的化学成分。方法采用硅胶、MCI、Sephadex LH-20等柱色谱方法分离纯化,根据理化性质及波谱数据鉴定化合物结构。结果从白钩藤干燥带钩茎枝95%乙醇提取物中分离得到了14个非生物碱类化合物:木栓酮(1)、桦木醇(2)、钝鸡蛋花素(3)、豆甾-4-烯-3-酮(4)、β-谷甾醇(5)、β-胡萝卜苷(6)、24-烯-环阿尔廷酮(7)、角鲨烯(8)、维生素E(9)、α-tocopherolquinone(10)、(-)-alloaromadendrene(11)、丁香色酮(12)、东莨菪内酯(13)、bis(2-ethylhexyl)phthalate(14);3个吲哚生物碱类化合物:大叶帽柱木碱(15)、异大叶帽柱木碱(16)、isomitraphylline N-oxide(17)。结论化合物1、4、8、11、13为首次从钩藤属植物中分离得到,所有化合物均为首次从白钩藤中分离得到。
Objective To study the chemical constituents from the stems with hooks of Uncaria sessilifructus.Methods The chemical constituents were isolated and purified by chromatography on silica gel,MCI,Sephadex LH-20 columns,etc.The structures of compounds were elucidated by spectral analyses.Results Fourteen non-alkaloids compounds were isolated from the 95% ethanol extract from the stems with hooks of U.sessilifructus,and the structures were identified as friedelin(1),betulin(2),obtusalin(3),stigmast-4-en-3-one(4),β-sitosterol(5),β-daucosterol(6),24-en-cycloartenone(7),squalene(8),vitamin E(9),α-tocopherolquinone(10),(-)-alloaromadendrene(11),eugenin(12),scopoletin(13),and bis(2-ethylhexyl) phthalate(14); Three alkaloids were identified as mitraphylline(15),isomitraphylline(16),and isomitraphylline N-oxide(17).Conclusion compounds 1,4,8,11,and 13 are obtained from the plants of genus Uncaria Schreber nom.cons.for the first time,and all the above compounds are obtained from the stems with hooks of U.sessilifructus for the first time.
Objective To study the chemical constituents from the stems with hooks of Uncaria sessilifructus.Methods The chemical constituents were isolated and purified by chromatography on silica gel,MCI,Sephadex LH-20 columns,etc.The structures of compounds were elucidated by spectral analyses.Results Fourteen non-alkaloids compounds were isolated from the 95% ethanol extract from the stems with hooks of U.sessilifructus,and the structures were identified as friedelin(1),betulin(2),obtusalin(3),stigmast-4-en-3-one(4),β-sitosterol(5),β-daucosterol(6),24-en-cycloartenone(7),squalene(8),vitamin E(9),α-tocopherolquinone(10),(-)-alloaromadendrene(11),eugenin(12),scopoletin(13),and bis(2-ethylhexyl) phthalate(14); Three alkaloids were identified as mitraphylline(15),isomitraphylline(16),and isomitraphylline N-oxide(17).Conclusion compounds 1,4,8,11,and 13 are obtained from the plants of genus Uncaria Schreber nom.cons.for the first time,and all the above compounds are obtained from the stems with hooks of U.sessilifructus for the first time.
引文
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[3]中国药典[S].一部.2010.
[4]云南省食品药品监督管理局.云南省中药材标准[M].昆明:云南出版集团公司云南科技出版社,2007.
[5]Long C L,Li R.Ethnobotanical studies on medicinal plants used by the Red-headed Yao People in Jinping,Yunnan Province,China[J].J Ethnopharmacol,2004,90(2/3):389-395.
[6]Heitzman M E,Neto C C,Winiarz E,et al.Ethnobotany,phytochemistry and pharmacology of Uncaria(Rubiaceae)[J].Phytochemistry,2005,66(1):5-29.
[7]Wang D M,Huang L F.Composition of volatile oil from the leaves of Uncaria sessilifructus Roxb.[J].J App Pharm Sci,2012,2:50-53.
[8]Zhang M J,Liu B,Liao S G,et al.Uncarilic acid and secouncarilic acid,two new triterpenoids from Uucaria sessilifructus[J].Molecules,2013,18(8):9727-9734.
[9]陈艳琰,段金廒,唐于平,等.芫花化学成分研究[J].中草药,2013,44(4):397-402.
[10]张嫩玲,胡江苗,刘玉清,等.毛叶合欢的化学成分[J].中草药,2010,41(7):1075-1078.
[11]Siddiqui S,Hafeez F,Begum S,et al.Kaneric acid,a new triterpene from the leaves of Nerium-oleander[J].J Nat Prod,1986,49(6):1086-1090.
[12]傅建,梁光义,张建新,等.茸毛木蓝化学成分研究[J].现代药物与临床,2013,28(3):265-268.
[13]Su K,Gong M,Zhou J,et al.Study on chemical composition of Nauclea officinalis leaves[J].Inter J Chem,2009,1(2):77-81.
[14]He H P,Cai Y Z,Sun M,et al.Extraction and purification of squalene from Amaranthus grain[J].J Agric Food Chem,2002,50(2):368-372.
[15]Matsuo M,Urano S.13C NMR Spectra of tocopherols and2,2-dimethylchromanols[J].Tetrahedron,1976,32(2):229-231.
[16]Rasool N,Khan A Q,Ahmad V U,et al.A benzoquinone and a coumestan from Psoralea plicata[J].Phytochemistry,1991,30(8):2800-2803.
[17]Faure R,Ramanoelina A R P,Rakotonirainy O,et al.Two-dimensional nuclear magnetic resonance of sesquiterpenes.4-Application to complete assignment of1H and13C NMR spectra of some aromadendrane derivatives[J].Magn Reson Chem,1991,29(9):969-971.
[18]Tsui W Y,Brown G D.Chromones and chromanones from Baeckea frutescens[J].Phytochemistry,1996,43(4):871-876.
[19]Adfa M,Yoshimura T,Komura K,et al.Antitermite activities of coumarin derivatives and scopoletin from Protium javanicum Burm.f.[J].J Chem Ecol,2010,36(7):720-726.
[20]Li J T,Yin B L,Liu Y,et al.Mono-aromatic constituents of Dendrobium longicornu[J].Chem Nat Compd,2009,45(2):234-236.
[21]Seki H,Takayama H,Aimi N,et al.A nuclear-magneticreso nance study on the 11 stereoisomers of heteroyohimbine-type oxindole alkaloids[J].Chem Pharm Bull,1993,41(12):2077-2086.
[22]Kitajima M,Nakayama T,Kogure N,et al.New heteroyohimbine-type oxindole alkaloid from the leaves of Thai Mitragyna hirsuta[J].J Nat Med,2007,61(2):192-195.