宽苞糙苏根化学成分研究
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摘要
目的研究宽苞糙苏根的化学成分。方法用硅胶柱色谱、凝胶柱色谱、以及制备高效液相色谱等多种色谱分离手段进行分离纯化,用有机波谱手段鉴定分离得到的化合物结构。结果从宽苞糙苏根的体积分数95%乙醇提取物中分离得到17个化合物,分别鉴定为lamalbid(1),螃蟹甲苷Ⅰ(2),螃蟹甲苷Ⅱ(3),山栀苷甲酯(4),6-乙酰山栀苷甲酯(5),8-乙酰山栀苷甲酯(6),sesamoside(7),5,9-epi-7,8-didehydropenstemoside(8),毛蕊花糖苷(9),异毛蕊花糖苷(10),连翘酯苷B (11),alyssonoside (12),松果菊苷(13),(17S)-2α,3α,18β,23,24-pentahydroxy-19(18→17)-abeo-28-norolean-12-en-21-one (14),(17S)-19(18→17)-abeo-12-en-28-norolean-2α,3α,18β,19,23,24-hexaol (15),木栓酮(16)和大豆苷(17)。结论所有化合物均为首次从宽苞糙苏中分离得到的化合物,其中化合物1,8,16～17为首次从糙苏属中分离得到的化合物。
OBJECTIVE To study the chemical constituents from the rhizome of Phlomis umbrosa. METHODS Chemical constituents were isolated by repeated column chromatographies( Toyopearl HW-40 C and preparative HPLC). The structures were elucidated on the basis of spectral data analysis. RESULTS Seventeen compounds were isolated from the 95% ethanol aqueous extract of P. umbrosa and the structures were identified as lamalbid( 1),phloyoside Ⅰ( 2),phloyoside Ⅱ( 3),6-O-acetylshanzhiside methyl ester( 4),shanzhiside methyl ester( 5),8-acetylshanzhiside methyl ester( 6),sesamoside( 7),5,9-epi-7,8-didehydropenstemoside( 8),verbascoside( 9),isoverbascoside( 10),forsythoside B( 11),alyssonoside( 12),echinacoside( 13),( 17 S)-2α,3α,18β,23,24-pentahydroxy-19( 18→17)-abeo-28-norolean-12-en-21-one( 14),( 17 S)-19( 18→17)-abeo-12-en-28-norolean-2α,3α,18β,19,23,24-hexaol( 15),friedelin( 16),and daidzein( 17). CONCLUSION All compounds are isolated from this plant for the first time,compounds 1,8,16-17 are isolated from genus Phlomis for the first time.
OBJECTIVE To study the chemical constituents from the rhizome of Phlomis umbrosa. METHODS Chemical constituents were isolated by repeated column chromatographies( Toyopearl HW-40 C and preparative HPLC). The structures were elucidated on the basis of spectral data analysis. RESULTS Seventeen compounds were isolated from the 95% ethanol aqueous extract of P. umbrosa and the structures were identified as lamalbid( 1),phloyoside Ⅰ( 2),phloyoside Ⅱ( 3),6-O-acetylshanzhiside methyl ester( 4),shanzhiside methyl ester( 5),8-acetylshanzhiside methyl ester( 6),sesamoside( 7),5,9-epi-7,8-didehydropenstemoside( 8),verbascoside( 9),isoverbascoside( 10),forsythoside B( 11),alyssonoside( 12),echinacoside( 13),( 17 S)-2α,3α,18β,23,24-pentahydroxy-19( 18→17)-abeo-28-norolean-12-en-21-one( 14),( 17 S)-19( 18→17)-abeo-12-en-28-norolean-2α,3α,18β,19,23,24-hexaol( 15),friedelin( 16),and daidzein( 17). CONCLUSION All compounds are isolated from this plant for the first time,compounds 1,8,16-17 are isolated from genus Phlomis for the first time.
引文
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[29]LIU P,DENG R X,YIN W P,et al.A new nortriterpenoid from Phlomis umbrosa[J].Chem Nat Compd,2010,46(4):566-568.
[30]DENG R X,DUAN W L,LIU P,et al.Secondary metabolites from the roots of Phlomis umbrosa[J].J Asia Nat Prod Res,2011,13(3):230-237.
[31]YANG S Q.Study on extraction,separation and biosynthesis of terpenoids from Lamium barbatum[D].Xi‘an:Northwest University,2010.
[32]YU Z X,WANG G L,BIANBA C R,et al.Studies on chemical constituents of phlomis medicinalis dielsi[J].Chin J Chin Mater Med(中国中药杂志),2006,31(8):656-658.
[33]DELAZAR A,BYRES M,GIBBONS S,et al.Iridoid glycosides from Eremostachys glabra[J].J Nat Prod,2004,67(9):1584-1587.
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[35]LIU P,YANG Y L,DENG R X,et al.Studies on chemical constituents of glycosides from Syringa Pubenscens[J].Chin J Exp Tradit Med Form(中国实验方剂学杂志),2011,17(19):127-131.
[36]LIU J,XIE T,WEI X L,et al.Chemical studies on Rabdosia rubescens[J].Chin J Nat Med(中国天然药物),2004,2(5):23-26.
[37]WANG T,LIU Y,LI X,et al.Isoflavones from green vegetable soya beans and their antimicrobial and antioxidant activities[J].J Sci Food Agr,2017,98(5):2043-2047.
[2]LI M X,SHANG X F,JIA Z P,et al.Phytochemical and biological studies of plants from the genus phlomis[J].Chem Biodivers,2010,7(2):283-301.
[3]Institute of Botany,the Chinese Academy of Sciences.China's Higher Plant Map(Volume 3)[中国高等植物图鉴(第三册)][M].Beijing:Science Press,1980:650.
[4]Nanjing University of Chinese Medicine.Dictionary of Traditional Chinese Medicine(Volume 2)[中药大辞典(下册)][M].Shanghai:Shanghai Science Press,2006:3759.
[5]WANG D R,CHEN W J,QIAN Z,et al.Common antirheumatic plant medicines used by Tujia people in Western Hubei[J].Chin J Chin Mater Med(中国中药杂志),1993,18(10):581-584.
[6]DENG R X,LI J B,LIU P,et al.Advance on the chemical and pharmacological studies on Plants of phlomis genus[J].Strait Pharm J(海峡药学),2009,21(1):3-5.
[7]LEE S J.Korean Folk Medicine[M].Seoul:Publishing Center of Seoul National University,1966:119.
[8]SHIN T Y,KIM S H,KIM D K,et al.Phlomis umbrosa root inhibits mast cell-dependent allergic reactions and inflammatory cytokine secretion[J].Phytother Res,2008,22(2):153-158.
[9]LEE J K,LEE D G,KWAK B Y,et al.Effect of combined extract of Hansogdan(Phlomis umbrosa)and Dalgaebi(Commelinacommunis)as a milk additive for enhancing the growth of physical height in vivo[J].Food Sci Biotechnol,2012,21(3):875-879.
[10]LEE D H,KIM Y S,SONG J B,et al.Effects of Phlomis umbrosa root on longitudinal bone growth rate in adolescent female rats[J].Molecules,2016,21(4):461.
[11]SHANG X F,WANG J H,LI M X,et al.Antinociceptive and anti-inflammatory activities of Phlomis umbrosa Turczextract[J].Fitoterapia,2011,82(4):716-721.
[12]YI J H,XIAO Z Y.Chemical constituents and taxonomic significance of plants of the genera crassulaceae and lamiophlomis[J].Chin Tradit Herb Drugs(中草药),1992,23(7):382-384.
[13]BUT P P H,KIMURA T,SUNG C K,et al.International Collation of Traditional Folk Medicine[M].New Jersey:World Scientific Publishing,1997:137.
[14]TIAN G H,LIU C F,LAI P H,et al.Study on volatile components and biology activities of the essential oil from leaf of Phlomis umbrosa[J].Sci Tech Food Ind(食品工业科技),2008,29(5):106-109.
[15]TIAN G H,LIU C F,WEI C,et al.Study on the polysaccharideobtained from medicinal herb Phlomis umbrosa[J].Food Sci Tech(食品科技),2009,34(6):206-209.
[16]CHU S S,LIU Q Z,JIANG G H,et al.Chemical composition and insecticidal activity of the essential oil derived from Phlomis umbrosa against two grain storage insects[J].J Essent Oil Bear Pl,2013,16(1):51-58.
[17]GUO S J,GAO L M,CHENG D L.Iridoids from Phlomis umbrosa[J].Pharmazie,2001,56(2):178-180.
[18]ZHAO J,YANG X W.Study on the chemical constituents of Phlomis umbrosa[J].Chin Tradit Herb Drugs(中草药),1999,(2):90-93.
[19]LIU S W,FU H Z,LIN W H.Study on the chemical constituents of Phlomis umbrosa[J].Chin Tradit Herb Drugs(中草药),1999,30(3):161-163.
[20]YANG Y L,GUO S J,SUN K,et al.The hydrophilic chemical constituents of Phlomis umbrosa[J].J Lanzhou Univ(Nat Sci)(兰州大学学报自科科学版),2004,40(2):67-71.
[21]DING M M,YAN F L,TAN J,et al.Two new dammarane-type glycosides from Phlomis umbrosa[J].Nat Prod Res,2014,28(1):18-23.
[22]LIU P,YAO Z,LI H Q,et al.Four new nortriterpenoids from Phlomis umbrosa[J].Hel Chimi Acta,2007,90(3):601-606.
[23]LIU P,TAKAISHI Y,DUAN H Q.Two new phenylethanoid glycosides from the roots of Phlomis umbrosa[J].Chin Chem Lett,2007,18(2):155-157.
[24]LIU P,TENG J,ZHANG Y W,et al.Chemical constituents from rhizome of Phlomis umbrosa[J].Acta Pharm Sin(药学学报),2007,42(4):401-404.
[25]LIU P,YAO Z,ZHANG W,et al.Novel nortriterpenes from Phlomis umbrosa[J].Chem Pharm Bull,2008,56(7):951-955.
[26]LIU P,LI L Y,NIU R Q,et al.Two novel nortriterpenes from the roots of Phlomis umbrosa[J].Chin Chem Lett,2008,19(10):1228-1230.
[27]LIU P,DENG R X,DUAN H Q,et al.Phenylethanoid glycosides from the roots of Phlomis umbrosa[J].J Asia Nat Prod Res,2009,11(1):69-74.
[28]LIU P,DENG R X,DUAN H Q,et al.Chemical constituents from roots of Phlomis umbrosa[J].Chin J Chin Mater Med(中国中药杂志),2009,34(7):867-870.
[29]LIU P,DENG R X,YIN W P,et al.A new nortriterpenoid from Phlomis umbrosa[J].Chem Nat Compd,2010,46(4):566-568.
[30]DENG R X,DUAN W L,LIU P,et al.Secondary metabolites from the roots of Phlomis umbrosa[J].J Asia Nat Prod Res,2011,13(3):230-237.
[31]YANG S Q.Study on extraction,separation and biosynthesis of terpenoids from Lamium barbatum[D].Xi‘an:Northwest University,2010.
[32]YU Z X,WANG G L,BIANBA C R,et al.Studies on chemical constituents of phlomis medicinalis dielsi[J].Chin J Chin Mater Med(中国中药杂志),2006,31(8):656-658.
[33]DELAZAR A,BYRES M,GIBBONS S,et al.Iridoid glycosides from Eremostachys glabra[J].J Nat Prod,2004,67(9):1584-1587.
[34]IHSAN C,HOSNY M,KHALIFA T,et al.Phenylpropanoid glycosides from Marrubium alysson[J].Phytochemistry,1992,31(10):3624-3626.
[35]LIU P,YANG Y L,DENG R X,et al.Studies on chemical constituents of glycosides from Syringa Pubenscens[J].Chin J Exp Tradit Med Form(中国实验方剂学杂志),2011,17(19):127-131.
[36]LIU J,XIE T,WEI X L,et al.Chemical studies on Rabdosia rubescens[J].Chin J Nat Med(中国天然药物),2004,2(5):23-26.
[37]WANG T,LIU Y,LI X,et al.Isoflavones from green vegetable soya beans and their antimicrobial and antioxidant activities[J].J Sci Food Agr,2017,98(5):2043-2047.