王亚男;林生;陈明华;江冰娅;郭庆兰;朱承根;王素娟;杨永春;石建功;
WANG Ya′nan,LIN Sheng,CHEN Minghua,JIANG Bingya,GUO Qinglan, ZHU Chenggen,WANG Sujuan,YANG Yongchun,SHI Jiangong(State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China)

• 1:天然药物活性物质与功能国家重点实验室中国医学科学院北京协和医学院药物研究所

摘要(Abstract)：

通过大孔吸附树脂、MCI树脂、正相硅胶、Sephadex LH-20、制备薄层色谱和反相HPLC等多种色谱分离方法相结合,从天麻水提物中分离得到23个化合物;借助多种波谱学分析方法鉴定他们的结构为:4-羟基-3-(4-羟基苄基)苄基甲醚(1),4-(甲氧甲基)苯基-1-O-β-D-吡喃葡萄糖苷(2),4-羟基-3-(4-羟基苄基)苯甲醛(3),4-(4-羟基苄基)-2-甲氧基苯酚(4),4,4'-亚甲基双(2-甲氧基苯酚)(5),L-苯基乳酸(6),3-甲氧基-4-羟基苄基乙醚(7),对羟基苯甲醇(8),对羟基苄基甲醚(9),对羟基苄基乙醚(10),对羟基苯甲醛(11),对羟基苯甲酸(12),对甲氧基苯甲酸(13),天麻素(14),4-(乙氧甲基)苯基-1-O-β-D-吡喃葡萄糖苷(15),对醛基苯基-1-O-β-D-吡喃葡萄糖苷(16),对甲苯基-1-O-β-D-吡喃葡萄糖苷(17),甲基-O-β-D-吡喃葡萄糖苷(18),5-羟甲基糠醛(19),派立辛(20),派立辛B(21),派立辛C(22)和薯蓣皂苷元(23)。其中化合物1和2为新化合物,化合物3～7,18和23为首次从该属植物中分离得到,并首次报道化合物4的碳谱数据。
Two new compounds(1 and 2),together with twenty-one known compounds(3-23),were isolated by a combination of various chromatographic techniques including column chromatography over macroporous resin,MCI gel,silica gel,and Sephadex LH-20 and reversed-phase HPLC.Their structures were identified by spectroscopic data analysis as 4-hydroxy-3-(4-hydroxybenzyl)benzyl methyl ether(1),4-(methoxymethyl) phenyl-1-O-β-D-glucopyranoside(2),hibicutaiwanin(3),4-(4-hydroxybenzyl)-2-methoxyphenol(4),4,4′-methylenebis(2-methoxyphenol)(5),L-phenyllactic acid(6),4-hydroxy-3-methoxybenzyl ethol ether(7),p-hydroxylbenzyl alcohol(8),p-hydroxylbenzyl methyl ether(9),p-hydroxylbenzyl ethyl ether(10),p-hydroxybenzaldehyde(11),p-hydroxybenzoic acid(12),p-hydroxybenzoic acid(13),gastrodin(14),4-(ethoxymethyl) phenyl-1-O-β-D-glucopyranoside(15),4-(β-D-glucopyranosyloxy)benzaldehyde(16),p-methylphenyl-1-O-β-D-glucopyranoside(17),methyl-O-β-D-glucopyranoside(18),5-hydroxymethl-furan aldehyde(19),parishin(20),parishin B(21),parishin C(22),and diosgenin(23).The 13C-NMR data of compound 4 was first reported.

关键词(KeyWords)： 天麻;水提物;化学成分;4-羟基-3-(4-羟基苄基)苄基甲醚;4-(甲氧甲基)苯基-1-O-β-D-吡喃葡萄糖苷
Gastrodia elata;aqueous extract;chemical constituents;4-hydroxy-3-(4-hydroxybenzyl)benzyl methyl ether;4-(methoxymethyl) phenyl-1-O-β-D-glucopyranoside

Abstract:

Keywords:

基金项目(Foundation): 国家自然科学基金项目(30825044,20932007);; 国家“重大新药创制”科技重大专项(2011ZX09307-002-01)

作者(Author): 王亚男;林生;陈明华;江冰娅;郭庆兰;朱承根;王素娟;杨永春;石建功;
WANG Ya′nan,LIN Sheng,CHEN Minghua,JIANG Bingya,GUO Qinglan, ZHU Chenggen,WANG Sujuan,YANG Yongchun,SHI Jiangong(State Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China)

Email:

DOI:

参考文献(References)：

• [1]国家中医药管理局中华本草编委会.中华本草.第8卷[M].上海:上海科学技术出版社,1999:716.
• [2]刘星堦,杨毅.中药天麻成分的研究Ⅰ.香荚兰醇的提取与鉴定[J].上海第一医学院学报,1958(S1):67.
• [3]Yu S S,Zhao J,Zheng W P,et al.Neuroprotective effect of4-hydroxybenzyl alcohol against transient focal cerebral ischemiavia anti-apoptosis in rats[J].Brain Res,2010,1308:167.
• [4]Huang N K,Chern Y,Fang J M,et al.Neuroprotective principlesfrom Gastrodia elata[J].J Nat Prod,2007,70(4):571.
• [5]Zeng X,Zhang S,Zhang L,et al.A study of the neuroprotectiveeffect of the phenolic glucoside gastrodin during cerebral ischemi-a in vivo and in vitro[J].Planta Med,2006,72(15):1359.
• [6]Kim S T,Kim J D,Lyu Y S,et al.Neuroprotective effect of someplant extracts in cultured CT105-induced PC12 cells[J].BiolPharm Bull,2006,29(10):2021.
• [7]杨菁,白秀珍,孙黎光,等.天麻水煎剂对醋氨酚引起肝损伤的保护作用及机制研究[J].数理医药学杂志,2003,16(5):453.
• [8]王志平,付蕾,刘蕾,等.天麻素对CCl4诱导小鼠肝损伤的保护作用[J].武警医学院学报,2008,17(9):762.
• [9]Wu P L,Wu T S,He C X,et al.Constituents from the stems ofHibiscus taiwanensis[J].Chem Pharm Bull,2005,53(1):56.
• [10]Ye Q,Huang Y,Rusowicz A,Palaniswamy,et al.Understandingand controlling the formation of an impurity during the develop-ment of muraglitazar,a PPAR dual agonist[J].Org Process ResDev,2009,14(1):238.
• [11]Schwarz B,Hofmann T.Identification of novel orosensory activemolecules in cured vanilla beans(Vanilla planifolia)[J].J Ag-ric Food Chem,2009,57(9):3729.
• [12]Shevchenko S M,Yakobsons Yu K,Gindin V A,et al.Conforma-tional analysis of 10-benzylanthrones[J].J Org Chem USSR:English Translation,1986,22(1):158.
• [13]Santis G D,Zhu Z L,Greenberg W A,et al.An enzyme libraryapproach to biocatalysis:development of nitrilases for enantiose-lective production of carboxylic acid derivatives[J].J Am ChemSoc,2002,124(31):9024.
• [14]Sutoh K,Kobata K,Watanabe T.Stability of capsinoid in varioussolvents[J].J Agric Food Chem,2001,49(8):4026.
• [15]周俊,杨雁宾,杨崇仁.天麻的化学研究I.天麻化学成分的分离和鉴定[J].化学学报,1979,37(3):183.
• [16]黄占波.天麻活性成分及大川芎粉针剂的研究[D].沈阳:沈阳药科大学,2006.
• [17]Taguchi H,Yosioka I,Yamasaki K,et al.Studies on the constitu-ents of Gastrodia elata Blume[J].Chem Pharm Bull,1981,29(1):55.
• [18]王莉,肖红斌,梁鑫淼.天麻化学成分研究(Ⅰ)[J].中草药,2003(7):584.
• [19]唐霆,左来福,纳智,等.总序葱臭木茎干的化学成分研究[J].中国中药杂志,2012,37(9):1237.
• [20]赵鑫,朱瑞良,姜标,等.胡颓子有效部位化学成分研究[J].中国中药杂志,2006,31(6):472.
• [21]Huang Z B,Wu Z,Chen F K,et al.The protective effects of phe-nolic constituents from Gastrodia elata on the cytotoxicity inducedby KCl and glutamate[J].Arch Pharm Res,2006,29(11):963.
• [22]黄占波,宋冬梅,陈发奎.天麻化学成分的研究(Ⅰ)[J].中国药物化学杂志,2005,15(4):227.
• [23]Agrawal P K.NMR spectroscopy in the structural elucidation ofoligosaccharides and glycosides[J].Phytochemistry 1992,31(10):3307.
• [24]Pyo M K,Jin J L,Koo Y K,et al.Phenolic and furan type com-pounds isolated from Gastrodia elata and their anti-platelet effects[J].Arch Pharm Res,2004,27(4):381.
• [25]Lin J H,Liu Y C,Hua J P,et al.Parishins B and C from rhizo-mes of Gastrodia elata[J].Phytochemistry,1996,42(2):549.
• [26]Tobari A,Teshima M,Koyanagi J,et al.Spirostanols obtained bycyclization of pseudosaponin derivatives and comparison of anti-platelet agglutination activities of spirostanol glycosides[J].EurJ Med Chem,2000,35(5):511.
• [27]赵志勇.长药隔重楼化学成分的研究[D].天津:天津大学,2010.
• [28]Hayashi J,Sekine T,Deguchi S,et al.Phenolic compounds fromGastrodia rhizome and relaxant effects of related compounds onisolated smooth muscle preparation[J].Phytochemistry,2002,59(5):513.
• [29]Yang X D,Zhu J,Yang R,et al.Phenolic constituents from therhizomes of Gastrodia elata[J].Nat Prod Res,2007,21(2):180.
• [30]Han A R,Shin H J,Jeon H R,et al.Two new phenolic com-pounds from the rhizomes of Gastrodia elata Blume[J].HelvChim Acta,2011,94(7):1310.
• [31]郝小燕,谭宁华,周俊.黔产天麻的化学成分[J].云南植物研究,2000,22(1):81.