毛麝香的化学成分研究(Ⅱ)
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摘要
采用硅胶、凝胶、半制备液相等分离技术,对毛麝香Adenosma glutinosum(L.)Druce乙醇提取物的乙酸乙酯、石油醚以及正丁醇部位进行化学成分研究,从中分离得到了12个化合物。根据核磁共振、质谱等谱图数据和文献对照等研究方法,鉴定化合物结构分别为:30-醛基-白桦脂酸(1),1,3,5-三甲氧基苯(2),3,5-二甲氧基苯乙酮(3),β-谷甾醇(4),豆甾醇(5),大黄素甲醚(6),芝麻素(7),早熟素Ⅱ(8),棕榈酸(9),正二十六醇(10),D-阿洛醇(11),芹菜素-7-O-β-D-葡萄糖醛酸丁酯(12)。所有化合物均为首次从毛麝香属中分离得到。
In order to investigate the chemical constituents from Adenosma glutinosum comprehensively,the chemical ingredients of the ethyl acetate,petroleum and n-butanol fraction of the extracts were isolated. Then,twelve compounds were obtained by various chromatographic techniques. Their structures were determined by spectroscopic analysis and literature comparison method,they were: 30-oxo-betulinic acid(1),1,3,5-trimethoxybenzene(2),3,5-dimethoxyacetophenone(3),β-sitosterol(4),stigmasterol(5),physcion(6),sesamin(7),precocene Ⅱ(8),palmitic acid(9),hexacosyl alcohol(10),D-allitol(11),apigenin-7-O-β-D-glucuronide butyl ester(12),respectively. All compounds were isolated from this plant for the first time.
In order to investigate the chemical constituents from Adenosma glutinosum comprehensively,the chemical ingredients of the ethyl acetate,petroleum and n-butanol fraction of the extracts were isolated. Then,twelve compounds were obtained by various chromatographic techniques. Their structures were determined by spectroscopic analysis and literature comparison method,they were: 30-oxo-betulinic acid(1),1,3,5-trimethoxybenzene(2),3,5-dimethoxyacetophenone(3),β-sitosterol(4),stigmasterol(5),physcion(6),sesamin(7),precocene Ⅱ(8),palmitic acid(9),hexacosyl alcohol(10),D-allitol(11),apigenin-7-O-β-D-glucuronide butyl ester(12),respectively. All compounds were isolated from this plant for the first time.
引文
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[11]谭冰心,彭光天,于思,等.毛麝香的化学成分研究[J].中草药,2017,48(10):2024-2027.TAN B X,PENG G T,YU S,et al.The chemical constituents from the Herb of Adenosma glutinosum(L.)Druce[J].Chinese Traditional and Herbal Drugs,2017,48(10):2024-2027.
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[16]王岩,周莉玲,李锐,等.显齿蛇葡萄化学成分的研究[J].中药材,2002,25(4):254-256.WANG Y,ZHOU L L,LI R,et al.Studies on the chemical constituents from Ampelopsis grossedentata[J].Journal of Chinese Medicinal Materials,2002,25(4):254-256.
[17]毛春芳,施忠,罗琳,等.HPLC法同时测定大黄中芦荟大黄素等11种成分的量[J].中草药,2014,45(16):2400-2403.MAO C F,SHI Z,LUO L,et al.Simultaneous determination of 11 constituents in Rhei Radix et Rhizoma by HPLC[J].Chinese Traditional and Herbal Drugs,2014,45(16):2400-2403.
[18]李显珍,李春远,吴伦秀,等.苦槛蓝叶化学成分研究[J].中草药,2011,42(11):2204-2207.LI X Z,LI C Y,WU L X,et al.Chemical constituents from leaves of Myoporum bontioides[J].Chinese Traditional and Herbal Drugs,2011,42(11):2204-2207.
[19]郭占京,黄宏妙,卢汝梅,等.桂产藿香蓟的挥发油化学成分分析[J].广西中医药,2009,32(3):55-56.GUO Z J,HUANG H M,LU R M,et al.Analysis of the Chemical composition of the Essential Oil in Ageratum conyzoides.L.from Guangxi[J].Guangxi Journal of Traditional Chinese Medicine,2009,32(3):55-56.
[20]梁爽,陈海生,王厚鹏,等.二杈狗牙花化学成分的研究(Ⅱ)[J].第二军医大学学报,2007,28(4):425-426.LIANG S,CHEN H S,WANG H P,et al.Study on chemical constituents of Tabernaemontana divaricata(Ⅱ)[J].Academic Journal of Second Military Medical University,2007,28(4):425-426.
[21]刘志平,崔健国,刘红星,等.蒲葵叶化学成分研究[J].广西植物,2007,27(1):140-142.LIU Z P,CUI J G,LIU H X,et al.Chemical constituents from leaves of Livistona chinensis[J].Guihaia,2007,27(1):140-142.
[22]高锦明,董泽军,刘吉开.蓝黄红菇的化学成分[J].云南植物研究,2000,22(1):85-89.GAO J M,DONG Z J,LIU J K.The constituents of the Basidiomycetes Russula cyanoxantha[J].Acta Botanica Yunnanica,2000,22(1):85-89.
[23]李波,林中文,赵映梅,等.多舌飞蓬化学成分的研究[J].中草药,1999,30(8):561-563.LI B,LIN Z W,ZHAO Y M,et al.Studies on the chemical constituents of Erigeron multiradiatus[J].Chinese Traditional and Herbal Drugs,1999,30(8):561-563.
[2]张琴,张明明,邵帅,等.大头陈药理作用和毒性作用的初步研究[J].时珍国医国药,2011,22(5):1293-1294.ZHANG Q,ZHANG M M,SHAO S,et al.Preliminary study on pharmacological action and toxicity of Adenosma indianum[J].Lishizhen Medicine and Materia Medica Research,2011,22(5):1293-1294.
[3]钟卫红,莫惠芳,罗英伟.复方毛麝香洗剂治疗皮肤病疗效观察[J].新中医,1999,31(11):39-39.ZHONG W H,MO H F,LUO Y W.The therapeutic effect of compound prescription of Adenosma glutinosum(L.)Druce on skin disease[J].Journal of New Chinese Medicine,1999,31(11):39-39.
[4]汪存存,卫罡,李润美.毛麝香挥发油成分的GC-MS分析[J].中国中医药信息杂志,2008,15(2):36-37.WANG C C,WEI G,LI R M.GC-MS analysis of volatile oil in Adenosma glutinosum(L.)Druce[J].Chinese Journal of Information on TCM,2008,15(2):36-37.
[5]国家中医药管理局《中华本草》编委会.中华本草[M].上海:上海科学技术出版社,1999.China’s State Administration of Traditional Chinese Medicine of the Chinese Herbal Medicine Editorial Board.Chinese materia medica[M].Shanghai:Shanghai Scientific&Technical Publishers,1999.
[6]杨东娟,詹怀先,石磊.毛麝香叶挥发油化学成分研究[J].西北林学院学报,2013,28(2):164-167.YANG D J,ZHAN H X,SHI L.Chemical constituents of volatile oil from the leaves of Adenosma glutinosum[J].Journal of Northwest Forestry University,2013,28(2):164-167.
[7]VIGUSHIN D M,POON G K,BODDY A,et al.Phase I and pharmacokinetic study of D-limonene in patients with advanced cancer[J].Cancer Chemother Pharmacol,1989,42(2):111-117.
[8]RIPPLE G H,GOULD M N,STEWART J A,et al.Phase I clinical trial of perillyl alcohol administered daily[J].Clin Cancer Res,1998,4(5):1159-1164.
[9]江纪武,肖庆祥.植物药有效成分手册[M].北京:中国轻工业出版社,1989:427-428.WANG J W,XIAO Q X.Botanicals active ingredient manual[M].Beijing:China Light Industry Press,1989:427-428.
[10]RAPHAELI T J,KUTTAN G.Effect of naturally occurring monoberpenes carvone,limnene and perillic acid in the inhibition of experimental lung metastasic induced by B16F-10 melanorna cells[J].J Exp Clin Cancer Res,2003,22(3):419-424.
[11]谭冰心,彭光天,于思,等.毛麝香的化学成分研究[J].中草药,2017,48(10):2024-2027.TAN B X,PENG G T,YU S,et al.The chemical constituents from the Herb of Adenosma glutinosum(L.)Druce[J].Chinese Traditional and Herbal Drugs,2017,48(10):2024-2027.
[12]FRANCISCO A M,ANA M S,JUAN C G G,et al.Bioactive polar triterpenoids from Mellilotus messanensis[J].Phytochemistry,1998,49(3):709-717.
[13]黄鹰,常睿洁,金惠子,等.观光木酚性成分研究[J].天然产物研究与开发,2012,24(2):176-178.HUANG Y,CHANG R J,JIN H Z,et al.Phenolic Constituents from Tsoongiodendron odorum Chun[J].Nat Prod Res Dev,2012,24(2):176-178.
[14]饶丽丽,张敉,李鹏,等.西藏牛皮消的化学成分研究[J].昆明理工大学学报(自然科学版),2014,39(5):82-87.RAO L L,ZHANG M,LI P,et al.Study on the chemical constituents of Cynanchum saccatum[J].Journal of Kunming University of Science and Technology(Natural Science Edition),2014,39(5):82-87.
[15]郑聪聪,苏艳芳,陈磊,等.白花碎米荠的化学成分研究[J].中草药,2013,44(19):2657-2660.ZHENG C C,SU Y F,CHEN L,et al.Chemical constituents from Cardamine leucantha[J].Chinese Traditional and Herbal Drugs,2013,44(19):2657-2660.
[16]王岩,周莉玲,李锐,等.显齿蛇葡萄化学成分的研究[J].中药材,2002,25(4):254-256.WANG Y,ZHOU L L,LI R,et al.Studies on the chemical constituents from Ampelopsis grossedentata[J].Journal of Chinese Medicinal Materials,2002,25(4):254-256.
[17]毛春芳,施忠,罗琳,等.HPLC法同时测定大黄中芦荟大黄素等11种成分的量[J].中草药,2014,45(16):2400-2403.MAO C F,SHI Z,LUO L,et al.Simultaneous determination of 11 constituents in Rhei Radix et Rhizoma by HPLC[J].Chinese Traditional and Herbal Drugs,2014,45(16):2400-2403.
[18]李显珍,李春远,吴伦秀,等.苦槛蓝叶化学成分研究[J].中草药,2011,42(11):2204-2207.LI X Z,LI C Y,WU L X,et al.Chemical constituents from leaves of Myoporum bontioides[J].Chinese Traditional and Herbal Drugs,2011,42(11):2204-2207.
[19]郭占京,黄宏妙,卢汝梅,等.桂产藿香蓟的挥发油化学成分分析[J].广西中医药,2009,32(3):55-56.GUO Z J,HUANG H M,LU R M,et al.Analysis of the Chemical composition of the Essential Oil in Ageratum conyzoides.L.from Guangxi[J].Guangxi Journal of Traditional Chinese Medicine,2009,32(3):55-56.
[20]梁爽,陈海生,王厚鹏,等.二杈狗牙花化学成分的研究(Ⅱ)[J].第二军医大学学报,2007,28(4):425-426.LIANG S,CHEN H S,WANG H P,et al.Study on chemical constituents of Tabernaemontana divaricata(Ⅱ)[J].Academic Journal of Second Military Medical University,2007,28(4):425-426.
[21]刘志平,崔健国,刘红星,等.蒲葵叶化学成分研究[J].广西植物,2007,27(1):140-142.LIU Z P,CUI J G,LIU H X,et al.Chemical constituents from leaves of Livistona chinensis[J].Guihaia,2007,27(1):140-142.
[22]高锦明,董泽军,刘吉开.蓝黄红菇的化学成分[J].云南植物研究,2000,22(1):85-89.GAO J M,DONG Z J,LIU J K.The constituents of the Basidiomycetes Russula cyanoxantha[J].Acta Botanica Yunnanica,2000,22(1):85-89.
[23]李波,林中文,赵映梅,等.多舌飞蓬化学成分的研究[J].中草药,1999,30(8):561-563.LI B,LIN Z W,ZHAO Y M,et al.Studies on the chemical constituents of Erigeron multiradiatus[J].Chinese Traditional and Herbal Drugs,1999,30(8):561-563.