《中国药典》收载的钩藤基原植物吲哚生物碱研究进展
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摘要
茜草科Rubiaceae钩藤属Uncaria植物全世界有34种,我国11种、1变型,《中国药典》收载钩藤U. rhynchophylla、大叶钩藤U. macrophylla、毛钩藤U. hirsuta、华钩藤U. sinensis和无柄果钩藤U. sessilifructus作为中药钩藤的基原植物。钩藤属植物特征性成分为吲哚生物碱,此外还含有三萜、木脂素、黄酮等。为了进一步明确中药钩藤的活性物质基础以及不同部位化学成分差异,该文对以上5种钩藤基原植物中的吲哚生物碱研究进展进行综述。
Uncaria genus( Rubiaceae) contains 34 species all over the world,of which 11 species and one variant are present in China. Five species,namely U. rhynchophylla,U. macrophylla,U. hirsuta,U. sinensis and U. sessilifructus,are documented in Chinese Pharmacopoeia as the raw materials of Uncariae Ramulus Cum Uncis. Indole alkaloids are the characteristic constituents of Uncaria plants,in addition to triterpenes,lignans and flavones. This paper reviews the progress of indole alkaloids and their distribution within the five Uncaria species documented in Chinese Pharmacopoeia for better understanding the active constituents of Uncariae Ramulus Cum Uncis.
Uncaria genus( Rubiaceae) contains 34 species all over the world,of which 11 species and one variant are present in China. Five species,namely U. rhynchophylla,U. macrophylla,U. hirsuta,U. sinensis and U. sessilifructus,are documented in Chinese Pharmacopoeia as the raw materials of Uncariae Ramulus Cum Uncis. Indole alkaloids are the characteristic constituents of Uncaria plants,in addition to triterpenes,lignans and flavones. This paper reviews the progress of indole alkaloids and their distribution within the five Uncaria species documented in Chinese Pharmacopoeia for better understanding the active constituents of Uncariae Ramulus Cum Uncis.
引文
[1]刘贵,冯孝章.中药钩藤及其同属植物的研究概况[J].中国药学杂志,1991,26(10):583.
[2]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,1999:483.
[3]广西壮族自治区革命委员会卫生局.广西本草选编[M].南宁:广西人民出版社,1974:886.
[4]余再柏,秦松云.国产钩藤类中药资源调查研究[J].中国中药杂志,1999,24(4):198.
[5]王宛.我国钩藤药材资源现状调查[J].中国药师,2008,11(11):1368.
[6] Ndagijimana A,Wang X,Pan G,et al. A review on indole alka-loids isolated from Uncaria rhynchophylla and their pharmacologi-cal studies[J]. Fitoterapia,2013,86:35.
[7] Zhang Q,Zhao J J,Xu J,et al. Medicinal uses,phytochemistryand pharmacology of the genus Uncaria[J]. J Ethnopharmacol,2015,173:48.
[8] Laus G. Advances in chemistry and bioactivity of the genus Uncar-ia[J]. Phytother Res,2004,18(4):259.
[9] Jung J W,Ahn N Y,Oh H R,et al. Anxiolytic effects of theaqueous extract of Uncaria rhynchophylla[J]. J Ethnopharmacol,2006,108(2):193.
[10]王江恺,刘建利.钩藤属植物中吲哚生物碱的研究进展[J].天然产物研究与开发,2011,23(4):776.
[11]中国药典.一部[S]. 2015:257.
[12] Murakami Y,Zhao Q,Harada K,et al. Choto-san,a Kampo for-mula,improves chronic cerebral hypoperfusion-induced spatiallearning deficit via stimulation of muscarinic M-1 receptor[J].Pharmacol Biochem Behav,2005,81(3):616.
[13] Ishida Y,Ebihara K,Tabuchi M,et al. Yokukansan,a tradition-al Japanese medicine,enhances the L-DOPA-induced rotationalresponse in 6-hydroxydopamine-lesioned rats:possible inhibitionof COMT[J]. Biol Pharm Bull,2016,39(1):104.
[14] Zhao Y H,Liu Y D,Guan Y,et al. Effect of Yinian Jiangya Yinon primary hypertension in early stage-A clinical observations on40 patients[J]. J Tradit Chin Med,2010,30(3):171.
[15] Tateno M,Ukai W,Ono T,et al. Neuroprotective effects of Yi-Gan San against beta amyloid-induced cytotoxicity on rat corticalneurons[J]. Prog Neuropsychopharmacol Biol Psychiatry,2008,32(7):1704.
[16] Gai Y N,Chen H,Wu C Y,et al. Analysis of the traditionalmedicine Yi Gan San by the fragmentation patterns of cadambineindole alkaloids using HPLC coupled with high-resolution MS[J]. J Sep Sci,2013,36(23):3723.
[17]中国科学院中国植物志编辑委员会.中国植物志[M].北京:科学出版社,1999,71(1):247.
[18] Zhang J G,Geng C A,Huang X Y,et al. Chemical and biologi-cal comparison of different sections of Uncaria rhynchophylla(Gou-Teng)[J]. Eur J Mass Spectrom(Chichester),2017,23(1):11.
[19] Zhang J G,Huang X Y,Ma Y B,et al. Dereplication-guided i-solation of a new indole alkaloid triglycoside from the hooks of Un-caria rhynchophylla by LC with ion trap time-of-flight MS[J].J Sep Sci,2018,41(7):1532.
[20] Wei X,Jiang L P,Guo Y,et al. Indole alkaloids inhibiting neu-ral stem cell from Uncaria rhynchophylla[J]. Nat Prod Bio-prospect,2017,7(5):413.
[21]刘芳鑫.两种药用植物节节草和大叶钩藤的化学成分研究[D].昆明:云南中医学院,2017.
[22] Wang K,Zhou X Y,Wang Y Y,et al. Macrophyllionium andmacrophyllines A and B,oxindole alkaloids from Uncaria macro-phylla[J]. J Nat Prod,2011,74(1):12.
[23] Aimi N,Yamanaka E,Shinma N,et al. Studies on plants contai-ning indole alkaloids.Ⅵ. minor bases of Uncaria rhynchophyllaMiq[J]. Chem Pharm Bull,1977,25(8):2067.
[24] Ma B,Wu C F,Yang J Y,et al. Three new alkaloids from theleaves of Uncaria rhynchophylla[J]. Helv Chim Acta,2009,92(8):1575.
[25] Kong F,Ma Q,Huang S,et al. Tetracyclic indole alkaloids withantinematode activity from Uncaria rhynchophylla[J]. Nat ProdRes,2017,31(12):1403.
[26]布赫,王立乾,唐振球,等. UPLC-ESI-Q-TOF-MS~E快速鉴定钩藤中吲哚类生物碱[J].化学工程师,2018,32(4):20.
[27] Yang Z D,Duan D Z,Du J,et al. Geissoschizine methyl ether,acorynanthean-type indole alkaloid from Uncaria rhynchophylla as apotential acetylcholinesterase inhibitor[J]. Nat Prod Res,2012,26(1):22.
[28] Guo Q,Yang H,Liu X,et al. New zwitterionic monoterpene in-dole alkaloids from Uncaria rhynchophylla[J]. Fitoterapia,2018,127:47.
[29]温欣.钩藤化学成分、提取工艺及药理活性研究[D].济南:山东中医药大学,2009.
[30] Xie S,Shi Y,Wang Y,et al. Systematic identification and quan-tification of tetracyclic monoterpenoid oxindole alkaloids in Uncar-ia rhynchophylla and their fragmentations in Q-TOF-MS spectra[J]. J Pharm Biomed Anal,2013,81-82(7):56.
[31]史玉俊.华钩藤中的羟吲哚生物碱[J].中草药,1994(12):653.
[32] Zhang Q,Chen L,Hu L J,et al. Two new ortho benzoquinonesfrom Uncaria rhynchophylla[J]. Chin J Nat Med,2016,14(3):232.
[33] Yuan D,Ma B,Wu C F,et al. Alkaloids from the leaves of Un-caria rhynchophylla and their inhibitory activity on NO productionin lipopolysaccharide-activated microglia[J]. J Nat Prod,2008,71(7):1271.
[34]孙广利.华钩藤和大叶钩藤的化学成分和生物活性研究[D].北京:北京协和医学院,2012.
[35] Yang W Z,Zhang Y B,Pan H Q,et al. Supercritical fluid chro-matography for separation and preparation of tautomeric 7-epimer-ic spiro oxindole alkaloids from Uncaria macrophylla[J]. J PharmBiomed Anal,2016,134:352.
[36]郑嘉宁,王定勇.大叶钩藤生物碱类化学成分研究[J].中医药导报,2009,15(1):80.
[37] Pan H Q,Yang W Z,Zhang Y B,et al. An integrated strategyfor the systematic characterization and discovery of new indole al-kaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbi-trap-MS[J]. Anal Bioanal Chem,2015,407(20):6057.
[38] Pan H Q,Yang W Z,Zhao D,et al. New monoterpenoid oxin-dole alkaloid derivatives from the stems of Uncaria hirsuta Havil.and their cytotoxicity and tandem mass spectrometric fragmenta-tion[J]. Fitoterapia,2016,116:85.
[39]刘红梅,蒋忠.华钩藤中新的氧化吲哚生物碱甙[J].药学学报,1993(11):849.
[40]辛文波,顾平,侴桂新,等.毛钩藤叶生物碱成分的研究[J].中国中药杂志,2008,33(17):2124.
[41] Chang C W,Yeh Y Y,Chang L C,et al. Rapid determination ofoxindole alkaloids in Cat's claw by HPLC using ionic liquid-basedmicrowave-assisted extraction and silica monolithic column[J].Biomed Chromatogr,2016,doi:org/10. 1002/bmc.3925.
[42] Zhang Q,Lin C,Duan W,et al. Preparative separation of sixrhynchophylla alkaloids from Uncaria macrophylla wall by pH-zone refining counter-current chromatography[J]. Molecules,2013,18(12):15490.
[43] Hemingway S R,Phillipson J D. Proceedings:alkaloids from S.American species of Uncaria(Rubiaceae)[J]. J Pharm Pharma-col,1974,26:13.
[44]黄瑞松,张鹏,覃冬杰,等.大叶钩藤植物不同部位中钩藤碱分析[J].中成药,2012,34(4):710.
[45] Liu H M,Feng X Z. Oxindole alkaloids from Uncaria sinensis[J].Phytochemistry,1993,33(3):707.
[46] Phillipson J D,Hemingway S R,Ridsdale C E. Alkaloids of Un-caria. V. Their occurrence and chemotaxonomy[J]. Lloydia,1978,41(6):503.
[47]张茂娟,刘冰,安彦峰,等.白钩藤的化学成分研究[J].中草药,2014,45(2):175.
[48] Ahmad R,Salim F. Chapter 12-oxindole alkaloids of Uncaria(Rubiaceae,subfamily Cinchonoideae):a review on its struc-ture,properties,and bioactivities[J]. Stud Nat Prod Chem,2015,45:485.
[49] Phillipson J D,Hemingway S R. Alkaloids of Uncaria attenuata,U. orientalis and U. Canescens[J]. Phytochemistry,1975,14(8):1855.
[50] Tantivatana P,Ponglux D,Wongseripipatana S,et al. Alkaloidsof Uncaria,7. alkaloids of U. attenuata(U. salaccensis)from N.E. Thailand[J]. Planta Med,1980,40(11):299.
[51]肖海文.复方布洛芬片有关物质及钩藤化学成分制备研究[D].广州:广东药学院,2014.
[52]焦扬,王模强,华丹,等.中药钩藤化学成分研究[J].天津医科大学学报,2013,19(2):107.
[53] Aimi N,Shito T,Fukushima K,et al. Studies on plants contai-ning indole alkaloids.Ⅷindole alkaloid glycosides and other con-stituents of the leaves of Uncaria rhynchophylla MIQ[J]. ChemPharm Bull,2008,30(11):4046.
[54]辛文波,侴桂新,王峥涛.钩藤生物碱类成分研究[J].中草药,2009,40(2):204.
[55] Kam T S,Lee K H,Goh S H. Alkaloid distribution in MalaysianUncaria[J]. Phytochemistry,1992,31(6):2031.
[56] Hong S S,Han X H,Park S Y,et al. Monoamine oxidase inhibi-tor from Uncaria rhynchophylla[J]. Nat Prod Sci,2005,11(3):145.
[57] Endo K,Oshima Y,Kikuchi H,et al. Hypotensive principles ofUncaria hooks[J]. Planta Med,1983,49(11):188.
[58] Qu J,Gong T,Ma B,et al. Comparative study of fourteen alka-loids from Uncaria rhynchophylla hooks and leaves using HPLC-diode array detection-atmospheric pressure chemical ionization/MS method[J]. Chem Pharm Bull,2012,60(1):23.
[59] Xin W B,Chou G X,Wang Z T. Two new alkaloids from theleaves of Uncaria hirsuta Haviland[J]. Chin Chem Lett,2008,19(8):931.
[60] Xin W B,Chou G X,Wang Z T. Bis(monoterpenoid)indole al-kaloid glucosides from Uncaria hirsuta[J]. Phytochem Lett,2011,4(3):380.
[61] Ponglux D,Wongseripipatana S,Aimi N,et al. Structure andsynthesis of two new types of oxindole alkaloids found from Uncar-ia salaccensis[J]. Chem Pharm Bull,1990,38(2):573.
[62] Phillipson J D,Hemingway S R,Bisset N G,et al. Angustineand related alkaloids from species of Mitragyna,Nauclea,Uncar-ia,and Strychnos[J]. Phytochemistry,1974,13(6):973.
[63]段少卿.钩藤化学成分及抗氧化活性研究[D].南宁:广西师范大学,2010.
[64] Jia J F,Zhang Y,Huang X J,et al. New monoterpenoid alkaloidsfrom the aerial parts of Uncaria hirsuta[J]. Nat Prod Res,2014,28(13):971.
[65] Geng C A,Huang X Y,Ma Y B,et al.(±)-Uncarilins A andB,dimeric isoechinulin-type alkaloids from Uncaria rhynchophyl-la[J]. J Nat Prod,2017,80(4):959.
[66] Shi J S,Yu J X,Chen X P,et al. Pharmacological actions of Un-caria alkaloids,rhynchophylline and isorhynchophylline[J]. ActaPharmacol Sin,2003,24(2):97.
[67] Zhou J Y,Zhou S W. Isorhynchophylline:a plant alkaloid withtherapeutic potential for cardiovascular and central nervous systemdiseases[J]. Fitoterapia,2012,83(4):617.
[68]周吉银,周世文,贺燕.异钩藤碱药理作用的最新研究进展[J].中成药,2013,35(3):596.
[69]李俊葵,刘伟,彭菊,等.钩藤碱对甲基苯丙胺依赖小鼠位置偏爱和海马谷氨酸受体1表达的影响[J].中国实验方剂学杂志,2014,20(18):128.
[70]汪江涛,丁伯平.钩藤碱和异钩藤碱药理作用研究进展[J].中国医药导刊,2012,14(7):1224.
[71] Chou C H,Gong C L,Chao C C,et al. Rhynchophylline fromUncaria rhynchophylla functionally turns delayed rectifiers intoA-type K+channels[J]. J Nat Prod,2009,72(5):830.
[72] Zhou J,Zhou S. Antihypertensive and neuroprotective activities ofrhynchophylline:the role of rhynchophylline in neurotransmissionand ion channel activity[J]. J Ethnopharmacol,2010,132(1):15.
[73]孙安盛,吴芹,刘国雄.异钩藤碱合用双肼苯哒嗪对清醒动物的降压效应及血流动力学的影响[J].中国中西医结合杂志,1996(s1):45.
[74] Zhang W B,Chen C X,Sim S M,et al. In vitro vasodilatormechanisms of the indole alkaloids rhynchophylline and isorhyn-chophylline,isolated from the hook of Uncaria rhynchophylla(Miquel)[J]. Naunyn Schmiedebergs Arch Pharmacol,2004,369(2):232.
[75] Xian Y F,Fan D,Ip S P,et al. Antidepressant-like effect ofisorhynchophylline in mice[J]. Neurochem Res,2016,42(2):678.
[76] Pengsuparp T,Indra B,Nakagawasai O,et al. Pharmacologicalstudies of geissoschizine methyl ether, isolated from Uncariasinensis Oliv.,in the central nervous system[J]. Eur J Pharma-col,2001,425(3):211.
[77] Nishi A,Yamaguchi Y,Sekiguchi K,et al. Geissoschizine meth-yl ether,an alkaloid in Uncaria hook,is a potent serotonin1A re-ceptor agonist and candidate for amelioration of aggressiveness andsociality by Yokukansan[J]. Neuroscience,2012,207:124.
[2]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,1999:483.
[3]广西壮族自治区革命委员会卫生局.广西本草选编[M].南宁:广西人民出版社,1974:886.
[4]余再柏,秦松云.国产钩藤类中药资源调查研究[J].中国中药杂志,1999,24(4):198.
[5]王宛.我国钩藤药材资源现状调查[J].中国药师,2008,11(11):1368.
[6] Ndagijimana A,Wang X,Pan G,et al. A review on indole alka-loids isolated from Uncaria rhynchophylla and their pharmacologi-cal studies[J]. Fitoterapia,2013,86:35.
[7] Zhang Q,Zhao J J,Xu J,et al. Medicinal uses,phytochemistryand pharmacology of the genus Uncaria[J]. J Ethnopharmacol,2015,173:48.
[8] Laus G. Advances in chemistry and bioactivity of the genus Uncar-ia[J]. Phytother Res,2004,18(4):259.
[9] Jung J W,Ahn N Y,Oh H R,et al. Anxiolytic effects of theaqueous extract of Uncaria rhynchophylla[J]. J Ethnopharmacol,2006,108(2):193.
[10]王江恺,刘建利.钩藤属植物中吲哚生物碱的研究进展[J].天然产物研究与开发,2011,23(4):776.
[11]中国药典.一部[S]. 2015:257.
[12] Murakami Y,Zhao Q,Harada K,et al. Choto-san,a Kampo for-mula,improves chronic cerebral hypoperfusion-induced spatiallearning deficit via stimulation of muscarinic M-1 receptor[J].Pharmacol Biochem Behav,2005,81(3):616.
[13] Ishida Y,Ebihara K,Tabuchi M,et al. Yokukansan,a tradition-al Japanese medicine,enhances the L-DOPA-induced rotationalresponse in 6-hydroxydopamine-lesioned rats:possible inhibitionof COMT[J]. Biol Pharm Bull,2016,39(1):104.
[14] Zhao Y H,Liu Y D,Guan Y,et al. Effect of Yinian Jiangya Yinon primary hypertension in early stage-A clinical observations on40 patients[J]. J Tradit Chin Med,2010,30(3):171.
[15] Tateno M,Ukai W,Ono T,et al. Neuroprotective effects of Yi-Gan San against beta amyloid-induced cytotoxicity on rat corticalneurons[J]. Prog Neuropsychopharmacol Biol Psychiatry,2008,32(7):1704.
[16] Gai Y N,Chen H,Wu C Y,et al. Analysis of the traditionalmedicine Yi Gan San by the fragmentation patterns of cadambineindole alkaloids using HPLC coupled with high-resolution MS[J]. J Sep Sci,2013,36(23):3723.
[17]中国科学院中国植物志编辑委员会.中国植物志[M].北京:科学出版社,1999,71(1):247.
[18] Zhang J G,Geng C A,Huang X Y,et al. Chemical and biologi-cal comparison of different sections of Uncaria rhynchophylla(Gou-Teng)[J]. Eur J Mass Spectrom(Chichester),2017,23(1):11.
[19] Zhang J G,Huang X Y,Ma Y B,et al. Dereplication-guided i-solation of a new indole alkaloid triglycoside from the hooks of Un-caria rhynchophylla by LC with ion trap time-of-flight MS[J].J Sep Sci,2018,41(7):1532.
[20] Wei X,Jiang L P,Guo Y,et al. Indole alkaloids inhibiting neu-ral stem cell from Uncaria rhynchophylla[J]. Nat Prod Bio-prospect,2017,7(5):413.
[21]刘芳鑫.两种药用植物节节草和大叶钩藤的化学成分研究[D].昆明:云南中医学院,2017.
[22] Wang K,Zhou X Y,Wang Y Y,et al. Macrophyllionium andmacrophyllines A and B,oxindole alkaloids from Uncaria macro-phylla[J]. J Nat Prod,2011,74(1):12.
[23] Aimi N,Yamanaka E,Shinma N,et al. Studies on plants contai-ning indole alkaloids.Ⅵ. minor bases of Uncaria rhynchophyllaMiq[J]. Chem Pharm Bull,1977,25(8):2067.
[24] Ma B,Wu C F,Yang J Y,et al. Three new alkaloids from theleaves of Uncaria rhynchophylla[J]. Helv Chim Acta,2009,92(8):1575.
[25] Kong F,Ma Q,Huang S,et al. Tetracyclic indole alkaloids withantinematode activity from Uncaria rhynchophylla[J]. Nat ProdRes,2017,31(12):1403.
[26]布赫,王立乾,唐振球,等. UPLC-ESI-Q-TOF-MS~E快速鉴定钩藤中吲哚类生物碱[J].化学工程师,2018,32(4):20.
[27] Yang Z D,Duan D Z,Du J,et al. Geissoschizine methyl ether,acorynanthean-type indole alkaloid from Uncaria rhynchophylla as apotential acetylcholinesterase inhibitor[J]. Nat Prod Res,2012,26(1):22.
[28] Guo Q,Yang H,Liu X,et al. New zwitterionic monoterpene in-dole alkaloids from Uncaria rhynchophylla[J]. Fitoterapia,2018,127:47.
[29]温欣.钩藤化学成分、提取工艺及药理活性研究[D].济南:山东中医药大学,2009.
[30] Xie S,Shi Y,Wang Y,et al. Systematic identification and quan-tification of tetracyclic monoterpenoid oxindole alkaloids in Uncar-ia rhynchophylla and their fragmentations in Q-TOF-MS spectra[J]. J Pharm Biomed Anal,2013,81-82(7):56.
[31]史玉俊.华钩藤中的羟吲哚生物碱[J].中草药,1994(12):653.
[32] Zhang Q,Chen L,Hu L J,et al. Two new ortho benzoquinonesfrom Uncaria rhynchophylla[J]. Chin J Nat Med,2016,14(3):232.
[33] Yuan D,Ma B,Wu C F,et al. Alkaloids from the leaves of Un-caria rhynchophylla and their inhibitory activity on NO productionin lipopolysaccharide-activated microglia[J]. J Nat Prod,2008,71(7):1271.
[34]孙广利.华钩藤和大叶钩藤的化学成分和生物活性研究[D].北京:北京协和医学院,2012.
[35] Yang W Z,Zhang Y B,Pan H Q,et al. Supercritical fluid chro-matography for separation and preparation of tautomeric 7-epimer-ic spiro oxindole alkaloids from Uncaria macrophylla[J]. J PharmBiomed Anal,2016,134:352.
[36]郑嘉宁,王定勇.大叶钩藤生物碱类化学成分研究[J].中医药导报,2009,15(1):80.
[37] Pan H Q,Yang W Z,Zhang Y B,et al. An integrated strategyfor the systematic characterization and discovery of new indole al-kaloids from Uncaria rhynchophylla by UHPLC/DAD/LTQ-Orbi-trap-MS[J]. Anal Bioanal Chem,2015,407(20):6057.
[38] Pan H Q,Yang W Z,Zhao D,et al. New monoterpenoid oxin-dole alkaloid derivatives from the stems of Uncaria hirsuta Havil.and their cytotoxicity and tandem mass spectrometric fragmenta-tion[J]. Fitoterapia,2016,116:85.
[39]刘红梅,蒋忠.华钩藤中新的氧化吲哚生物碱甙[J].药学学报,1993(11):849.
[40]辛文波,顾平,侴桂新,等.毛钩藤叶生物碱成分的研究[J].中国中药杂志,2008,33(17):2124.
[41] Chang C W,Yeh Y Y,Chang L C,et al. Rapid determination ofoxindole alkaloids in Cat's claw by HPLC using ionic liquid-basedmicrowave-assisted extraction and silica monolithic column[J].Biomed Chromatogr,2016,doi:org/10. 1002/bmc.3925.
[42] Zhang Q,Lin C,Duan W,et al. Preparative separation of sixrhynchophylla alkaloids from Uncaria macrophylla wall by pH-zone refining counter-current chromatography[J]. Molecules,2013,18(12):15490.
[43] Hemingway S R,Phillipson J D. Proceedings:alkaloids from S.American species of Uncaria(Rubiaceae)[J]. J Pharm Pharma-col,1974,26:13.
[44]黄瑞松,张鹏,覃冬杰,等.大叶钩藤植物不同部位中钩藤碱分析[J].中成药,2012,34(4):710.
[45] Liu H M,Feng X Z. Oxindole alkaloids from Uncaria sinensis[J].Phytochemistry,1993,33(3):707.
[46] Phillipson J D,Hemingway S R,Ridsdale C E. Alkaloids of Un-caria. V. Their occurrence and chemotaxonomy[J]. Lloydia,1978,41(6):503.
[47]张茂娟,刘冰,安彦峰,等.白钩藤的化学成分研究[J].中草药,2014,45(2):175.
[48] Ahmad R,Salim F. Chapter 12-oxindole alkaloids of Uncaria(Rubiaceae,subfamily Cinchonoideae):a review on its struc-ture,properties,and bioactivities[J]. Stud Nat Prod Chem,2015,45:485.
[49] Phillipson J D,Hemingway S R. Alkaloids of Uncaria attenuata,U. orientalis and U. Canescens[J]. Phytochemistry,1975,14(8):1855.
[50] Tantivatana P,Ponglux D,Wongseripipatana S,et al. Alkaloidsof Uncaria,7. alkaloids of U. attenuata(U. salaccensis)from N.E. Thailand[J]. Planta Med,1980,40(11):299.
[51]肖海文.复方布洛芬片有关物质及钩藤化学成分制备研究[D].广州:广东药学院,2014.
[52]焦扬,王模强,华丹,等.中药钩藤化学成分研究[J].天津医科大学学报,2013,19(2):107.
[53] Aimi N,Shito T,Fukushima K,et al. Studies on plants contai-ning indole alkaloids.Ⅷindole alkaloid glycosides and other con-stituents of the leaves of Uncaria rhynchophylla MIQ[J]. ChemPharm Bull,2008,30(11):4046.
[54]辛文波,侴桂新,王峥涛.钩藤生物碱类成分研究[J].中草药,2009,40(2):204.
[55] Kam T S,Lee K H,Goh S H. Alkaloid distribution in MalaysianUncaria[J]. Phytochemistry,1992,31(6):2031.
[56] Hong S S,Han X H,Park S Y,et al. Monoamine oxidase inhibi-tor from Uncaria rhynchophylla[J]. Nat Prod Sci,2005,11(3):145.
[57] Endo K,Oshima Y,Kikuchi H,et al. Hypotensive principles ofUncaria hooks[J]. Planta Med,1983,49(11):188.
[58] Qu J,Gong T,Ma B,et al. Comparative study of fourteen alka-loids from Uncaria rhynchophylla hooks and leaves using HPLC-diode array detection-atmospheric pressure chemical ionization/MS method[J]. Chem Pharm Bull,2012,60(1):23.
[59] Xin W B,Chou G X,Wang Z T. Two new alkaloids from theleaves of Uncaria hirsuta Haviland[J]. Chin Chem Lett,2008,19(8):931.
[60] Xin W B,Chou G X,Wang Z T. Bis(monoterpenoid)indole al-kaloid glucosides from Uncaria hirsuta[J]. Phytochem Lett,2011,4(3):380.
[61] Ponglux D,Wongseripipatana S,Aimi N,et al. Structure andsynthesis of two new types of oxindole alkaloids found from Uncar-ia salaccensis[J]. Chem Pharm Bull,1990,38(2):573.
[62] Phillipson J D,Hemingway S R,Bisset N G,et al. Angustineand related alkaloids from species of Mitragyna,Nauclea,Uncar-ia,and Strychnos[J]. Phytochemistry,1974,13(6):973.
[63]段少卿.钩藤化学成分及抗氧化活性研究[D].南宁:广西师范大学,2010.
[64] Jia J F,Zhang Y,Huang X J,et al. New monoterpenoid alkaloidsfrom the aerial parts of Uncaria hirsuta[J]. Nat Prod Res,2014,28(13):971.
[65] Geng C A,Huang X Y,Ma Y B,et al.(±)-Uncarilins A andB,dimeric isoechinulin-type alkaloids from Uncaria rhynchophyl-la[J]. J Nat Prod,2017,80(4):959.
[66] Shi J S,Yu J X,Chen X P,et al. Pharmacological actions of Un-caria alkaloids,rhynchophylline and isorhynchophylline[J]. ActaPharmacol Sin,2003,24(2):97.
[67] Zhou J Y,Zhou S W. Isorhynchophylline:a plant alkaloid withtherapeutic potential for cardiovascular and central nervous systemdiseases[J]. Fitoterapia,2012,83(4):617.
[68]周吉银,周世文,贺燕.异钩藤碱药理作用的最新研究进展[J].中成药,2013,35(3):596.
[69]李俊葵,刘伟,彭菊,等.钩藤碱对甲基苯丙胺依赖小鼠位置偏爱和海马谷氨酸受体1表达的影响[J].中国实验方剂学杂志,2014,20(18):128.
[70]汪江涛,丁伯平.钩藤碱和异钩藤碱药理作用研究进展[J].中国医药导刊,2012,14(7):1224.
[71] Chou C H,Gong C L,Chao C C,et al. Rhynchophylline fromUncaria rhynchophylla functionally turns delayed rectifiers intoA-type K+channels[J]. J Nat Prod,2009,72(5):830.
[72] Zhou J,Zhou S. Antihypertensive and neuroprotective activities ofrhynchophylline:the role of rhynchophylline in neurotransmissionand ion channel activity[J]. J Ethnopharmacol,2010,132(1):15.
[73]孙安盛,吴芹,刘国雄.异钩藤碱合用双肼苯哒嗪对清醒动物的降压效应及血流动力学的影响[J].中国中西医结合杂志,1996(s1):45.
[74] Zhang W B,Chen C X,Sim S M,et al. In vitro vasodilatormechanisms of the indole alkaloids rhynchophylline and isorhyn-chophylline,isolated from the hook of Uncaria rhynchophylla(Miquel)[J]. Naunyn Schmiedebergs Arch Pharmacol,2004,369(2):232.
[75] Xian Y F,Fan D,Ip S P,et al. Antidepressant-like effect ofisorhynchophylline in mice[J]. Neurochem Res,2016,42(2):678.
[76] Pengsuparp T,Indra B,Nakagawasai O,et al. Pharmacologicalstudies of geissoschizine methyl ether, isolated from Uncariasinensis Oliv.,in the central nervous system[J]. Eur J Pharma-col,2001,425(3):211.
[77] Nishi A,Yamaguchi Y,Sekiguchi K,et al. Geissoschizine meth-yl ether,an alkaloid in Uncaria hook,is a potent serotonin1A re-ceptor agonist and candidate for amelioration of aggressiveness andsociality by Yokukansan[J]. Neuroscience,2012,207:124.