胡峻;张权;齐梦蝶;康利平;南铁贵;杨健;袁媛;詹志来;刘勇;黄璐琦;
HU Jun;ZHANG Quan;QI Meng-die;KANG Li-ping;NAN Tie-gui;YANG Jian;YUAN Yuan;ZHAN Zhi-lai;LIU Yong;HUANG Lu-qi;Beijing University of Chinese Medicine;China Academy of Chinese Medical Sciences,National Resource Center for Chinese Materia Medica,State Key Laboratory Breeding Base of Dao-di Herbs;

• 1:北京中医药大学
• 2:中国中医科学院中药资源中心道地药材国家重点实验室培育基地

摘要(Abstract)：

应用超高效液相色谱-四极杆飞行时间串联质谱联用技术(UPLC-Q-TOF-MS)对川西吊石苣苔的化学成分进行定性研究。采用Waters ACQUITY UPLC-BEH-C18S色谱柱(2.1 mm×100 mm,1.7μm),以0.1%甲酸水-乙腈为流动相梯度洗脱,检测波长210~400 nm,ESI负离子模式进行检测,根据精确分析量及碎片信息,结合数据库匹配进行结构鉴定。结果从川西吊石苣苔中共鉴定出57个成分,其中42个苯乙醇苷类成分,5个苯甲醇苷类成分,6个黄酮类成分,4个其他类型化合物,其中有43个化合物为苦苣苔科中首次发现,并初步推测了1个新苯甲醇苷类化合物。该研究首次对川西吊石苣苔化学成分进行整体研究,为该植物的深入研究奠定基础。
The Ultra-high Performance Liquid Chromatography Quadrupole Time-of-flight Mass Spectrometry( UPLC-Q-TOFMS) was applied to analyze the chemical components in Lysinotus wilsonii. A Waters ACQUITY UPLC-BEH-C18 S column( 2. 1mm × 100 mm,1. 7 μm) was used with a gradient elution of acetonitrile-water containing 0. 1 % formic acid. The mass spectrometry equipped with ionization source was used and the data was collected in negative ion mode. Results showed that 57 components were identified as 42 phenylethanoid glycosides,5 benzyl alcohol glycosides,6 flavonoids and 4 other components. Among them,43 compounds were firstly identified in Gensneriaceae and one benzyl alcohol glycoside may be a new compound. We have quite completely identified the components in L. wilsonii for the first time,which may lay the foundation for further study and utilization of the medicinal plant.

关键词(KeyWords)： 液质联用;川西吊石苣苔;化学成分
UPLC-Q-TOF-MS;Lysinotus wilsonii;chemical constituents

Abstract:

Keywords:

基金项目(Foundation): 中医药行业科研专项(201407003)

作者(Author): 胡峻;张权;齐梦蝶;康利平;南铁贵;杨健;袁媛;詹志来;刘勇;黄璐琦;
HU Jun;ZHANG Quan;QI Meng-die;KANG Li-ping;NAN Tie-gui;YANG Jian;YUAN Yuan;ZHAN Zhi-lai;LIU Yong;HUANG Lu-qi;Beijing University of Chinese Medicine;China Academy of Chinese Medical Sciences,National Resource Center for Chinese Materia Medica,State Key Laboratory Breeding Base of Dao-di Herbs;

Email:

DOI:

参考文献(References)：

• [1]中国药材公司.中国中药资源志要[M].北京:科学出版社,1994:1177.
• [2]Liu Y,Wagner H,Bauer R.Nevadensinglycosides from Lysionotus pauciflorus[J].Phytochemistry,1996,42(4):1203.
• [3]Liu Y,Wagner H,Bauer R.Phenylpropanoids and flavonoid glycosides from Lysionotus pauciflorus[J].Phytochemistry,1998,48(2):339.
• [4]Liu P,Deng R X,Duan H Q,et al.Phenylethanoid glycosides from the roots of Phlomis umbrosa[J].J Asian Nat Prod Res,2009,11(1):69.
• [5]Juliao,Lisieux de S,Piccinelli,et al.Phenylethanoid glycosides from Lantana fucata with in vitro anti-inflammatory activity[J].J Nat Prod,2009,72(8):1424.
• [6]Liu Y,Seligmann O,Wagner H,et al.Paucifloside,a new phenylpropanoid glycoside from Lysionotus pauciflorus[J].Nat Prod Lett,1995,7(1):23.
• [7]Zubair,Muhammad,Nybom H,et al.Detection of genetic and phytochemical differences between and within populations of Plantago major L.(plantain)[J].Sci Hortic-Amsterdam,2012,136:9.
• [8]Porter,Elaine A K,Geoffrey C V,et al.Phenylethanoid glycosides in tepals of Magnolia salicifolia and their occurrence in flowers of Magnoliaceae[J].Phytochemistry,2015,117:185.
• [9]Li C T,Liu Y Q,Abdulla,et al.Determination of phenylethanoid glycosides in Lagotis brevituba Maxim.by high-performance liquid chromatography-electrospray ionization tandem mass spectrometry[J].Anal Lett,2014,47(11):1862.
• [10]Wan J F,Yuan J Q,Mei Z N,et al.Phenolic glycosides from Boschniakia himalaica[J].Chin Chem Lett,2012,23(5):579.
• [11]Jaiswal R,Kuhnert N.Identification and characterization of the phenolic glycosides of Lagenaria siceraria Stand.(Bottle Gourd)fruit by liquid chromatography-tandem mass spectrometry[J].J Agr Food Chem,2014,62(6):1261.
• [12]Zhao J,Guo J,Zhang Y,et al.Chemical constituents from the roots and stems of Stauntonia brachyanthera Hand-Mazz and their bioactivities[J].J Func Foods,2015,14:374.
• [13]Yang J H,Kondratyuk T P,Jermihov K C,et al.Bioactive compounds from the fern Lepisorus contortus[J].J Nat Prod,2011,74(2):129.
• [14]Mathuram V,Patra A,Kundu A B.A phenyl propanoid glycoside from Nyctanthes arbortristis[J].J Ind Chem Soci,1997,74(8):653.
• [15]Phakeovilay,Chiobouaphong D,Wannaporn S,et al.Phenylethanoid and flavone glycosides from Ruellia tuberosa L.[J].J Nat Med,2013,67(1):228.
• [16]Xia Y G,Yang B Y,Liang J K,et al.Caffeoyl phenylethanoid glycosides from unripe fruits of Forsythia suspensa[J].Chem Nat Comp,2015,51(4):656.
• [17]Cai H,Xie Z Y,Liu G H,et al.Isolation,identification and activities of natural antioxidants from Callicarpa kwangtungensis Chun[J].PLo S ONE,2014,9(3):e930001.
• [18]Zubair M,Nybom H A,Maria R,et al.Detection of genetic and phytochemical differences between and within populations of Plantago major L.(plantain)[J].Sci Horti(Amsterdam),2012,136:9.
• [19]Zhou Z L,Zhang H L.Phenolic and iridoid glycosides from the rhizomes of Cyperus rotundus L[J].Med Chem Res,2013,22(10):4830.
• [20]Jensen,Soren R A,Dirk C O,et al.Veronica:iridoids and cornoside as chemosystematic markers[J].Biochem Syst Ecol,2005,33(10):1031.
• [21]Barros J,Marconi R M,Renata R S,et al.Anti-inflammatory and antioxidant activities of Lantana radula Swartz and its phenylethanoid glycosides[J].J Med Plants Res,2014,8(47):1354.
• [22]Stanoeva J P,Stefova M,Stefkov G K,et al.Chemotaxonomic contribution to the Sideritis species dilemma on the Balkans[J].Biochem Syst Ecol,2015,61:477.
• [23]Nazemiyeh H,Shoeb M,Movahhedin N,et al.Phenolic compounds and their glycosides from Stachys schtschegleevii(Lamiaceae)[J].Biochemical Syst Ecol,2006,34(9):721.
• [24]Zhang J Y,Li C,Che Y Y,et al.LTQ-Orbitrap-based strategy for traditional Chinese medicine targeted class discovery,identification and herbomics research:a case study on phenylethanoid glycosides in three different species of Herba Cistanches[J].RSC Advances,2015,5(98):80816.
• [25]Sinaphet B,Noiarsa P,Rujirawat S,et al.Dolichandroside,a new phenolic triglycoside from Dolichandrone serrulata(DC.)Seem[J].J Nat Med,2006,60(3):251.
• [26]Taskova R M,Kokubun T,Ryan K G,et al.Phenylethanoid and iridoid glycosides in the New Zealand snow hebes(Veronica,Plantaginaceae)[J].Chem Pharm Bull,2010,58(5):703.
• [27]Suo M R,Ohta T,Takano F,et al.Bioactive phenylpropanoid glycosides from Tabebuia avellanedae[J].Molecules,2013,18:7336.
• [28]郗峰,邓君,王彦涵.藏药短管兔耳草中1个新苯乙醇苷类化合物[J].中国中药杂志,2009,34(16):2054.
• [29]Huang Q,Qiao X B,Xu X J.Potential synergism and inhibitors to multiple target enzymes of Xuefu Zhuyu Decoction in cardiac disease therapeutics:a computational approach[J].Bioorg Med Chem Lett,2007,17(6):1779.
• [30]Jabeen,B,Riaz,N,Saleem,M,et al.Isolation of natural compounds from Phlomis stewartii showingα-glucosidase inhibitory activity[J].Phytochemistry,2013,96:443.
• [31]Sahpaz S,Hennebelle T,Bailleul F.Marruboside,a new phenylethanoid glycoside from Marrubium vulgare L.[J].Nat Prod Lett,2002,16(3):195.
• [32]Taskova R M,Kokubun T,Ryan K G,et al.Phenylethanoid and iridoid glycosides in the New Zealand snow hebes(Veronica,Plantaginaceae)[J].Chem Pharm Bull,2010,58(5):703.
• [33]Kirmizibekmez H,Piacente S,Pizza C,et al.Iridoid and phenylethanoid glycosides from Phlomis nissolii and P.capitata[J].Chem Sci,2004,59(5):609.
• [34]Morikawa T,Pan Y,Ninomiya K,et al.Acylated phenylethanoid oligoglycosides with hepatoprotective activity from the desert plant Cistanche tubulosa[J].Bioor Med Chem,2010,18(5):1882.
• [35]Saracoglu I,Harput U S,Inoue M,et al.New phenylethanoid glycosides from Veronica pectinata var.glandulosa and their free radical scavenging activities[J].Chem Pharm Bull,2002,50(5):665.
• [36]Zhou F Y,She J,Wang Y G.Synthesis of a benzyl-protected analog of arenarioside,a trisaccharide phenylpropanoid glycoside[J].Carbohydr Res,2006,341(15):2469.
• [37]Lei L,Jiang Y,Liu X M,et al.New glycosides from Cistanche salsa[J].Helv Chim Acta,2007,90(1):79.
• [38]Xu F M M,Hisashi H,Hiroki S,et al.Structures of new flavonoids and benzofuran-type stilbene and degranulation inhibitors of rat basophilic leukemia cells from the Brazilian herbal medicine Cissus sicyoides[J].Chem Pharm Bull,2009,57(10):1089.
• [39]Yadava R.N,Satnami D.K.Chemical constituents from Cassia occidentalis Linn[J].Indian J Chem B Org Chem Med Chem,2011,50B(8):1112.
• [40]Bagrii A K,Kurmaz B V,Litvinenko V I.New bioside of quercetin[J].Khim Prir Soedin,1966,2(2):85.
• [41]张忠立,左月明,徐璐,等.三白草黄酮类化学成分的研究[J].中草药,2011,42(8):1490.
• [42]Ma C Y,Hu L M,Fu Q Y,et al.Separation of four flavonoids from Rhodiola rosea by online combination of sample preparation and countercurrent chromatography[J].J Chromatogra A,2013,1306:12.
• [43]Liu M M,Zhou L,He P L,et al.Discovery of flavonoid derivatives as anti-HCV agents via pharmacophore search combining molecular docking strategy[J].Euro J Med Chem,2012,52:33.
• [44]Adhikari B,Devkota H P,Joshi K R,et al.Two new diacetylene glycosides:bhutkesoside A and B from the roots of Ligusticopsis wallichiana[J].Nat Prod Res,2015,doi:10.1080/14786419.2015.1118635.
• [45]Tanikawa T,Fridman M,Zhu W J,et al.Using biological performance similarity to inform disaccharide library design[J].J Am Chem Soc,2009,131(14):5075.
• [46]Hu X P,Shao M M,Song X,et al.Anti-influenza virus effects of crude phenylethanoid glycosides isolated from Ligustrum purpurascens via inducing endogenous interferon-γ[J].J Ethnopharmacol,2015,179:128.
• [47]Morikawa T,Ninomiya K,Kuramoto H,et al.Phenylethanoid and phenylpropanoid glycosides with melanogenesis inhibitory activity from the flowers of Narcissus tazetta var.chinensis[J].J Nat Med,2016,70(1):89.
• [48]Gao Y,Zong C J,Liu F,et al.Evaluation of the intestinal transport of a phenylethanoid glycoside-rich extract from Cistanche deserticola across the Caco-2 cell monolayer model[J].PLo S ONE,2015,10(2):e01164901.
• [49]Wang Y J,Zhou S M,Xu G,et al.Interferenceof phenylethanoid glycosides from Cistanche tubulosa with the MTT assay[J].Molecules,2015,20(5):8060.
• [50]Encalada M A,Rehecho S,Ansorena Di,et al.Antiproliferative effect of phenylethanoid glycosides from Verbena officinalis L.on colon cancer cell lines[J].LWT-Food Sci Technol,2015,63(2):1016.