β-环糊精及其衍生物对异槲皮苷的包合作用研究
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摘要
第一章:本章简要综述了环糊精包合技术的研究进展,着重阐述了环糊精及其衍生物在药物方面的应用研究,并概述了异槲皮苷的基本化学性质和药理作用。
第二章:采用共沉淀法制备了异槲皮苷的β-环糊精固体包合物,并用紫外光谱、红外光谱和核磁共振法表征了包合物。利用紫外-可见分光光度法建立了包合物中异槲皮苷的含量测定方法,低、中、高三种浓度的异槲皮苷溶液的日内和日间精密度分别为1.66%、1.42%、0.28%和1.99%、1.34%、1.26%,回收率分别为102.60±0.19%、102.61±0.59%、103.19±0.61%。在此基础上,对异槲皮苷在β-环糊精中的相溶解度进行研究,发现异槲皮苷与β-环糊精形成了1:1型包合物。溶解度研究显示异槲皮苷被制备成固体包合物后,其溶解度提高了822倍。溶出度研究发现异槲皮苷被β-环糊精包合后其溶出度得到显著增强,在30min内,溶出度由原来的41.48%提高至89.80%。
第三章:采用共沉淀法、超声法和研磨法制备了异槲皮苷的β-环糊精固体包合物,以包封率、载药率以及溶解度为主要参考指标,优选出共沉淀法做为IQ-β-CD包合物制备的最佳方法。并利用正交试验设计优选出包合物制备的最佳条件为主客体分子比2:1,搅拌时间6 h,搅拌温度55℃。
第四章:采用搅拌法对异槲皮苷的羟丙基-β-环糊精固体包合物进行制备,利用紫外光谱、红外光谱和核磁共振法表征了包合物。采用紫外-可见分光光度法建立了包合物中异槲皮苷的含量测定方法,日内和日间精密度均小于2%,回收率分别为100.73±0.82%、101.84±1.12%、103.11±0.93%。通过相溶解度的研究,发现异槲皮苷与羟丙基-β-环糊精之间形成A_L型的1:1型包合物。溶解度研究发现异槲皮苷被制备成固体包合物后,其溶解度提高了15.66倍,与此同时,异槲皮苷的溶出度研究显示其溶出度由原来的30min内累积溶出41.48%提高至15min内累积溶出98.96%。
第五章:以收率、包封率、载药率和溶解度为考察指标,通过对搅拌法、超声法和研磨法三种包合物制备方法的评价,优选出包合物制备的最佳方法,并利用正交试验设计优化出包合物制备的最佳条件为主客体分子比3:1,搅拌时间6h,搅拌温度55℃。
Chapter 1:The recent development of cyclodextrins inclusion technique has been reviewed and especially focused on the application of cyclodextrins and their derivatives in pharmaceutical industry.The chemical and biological properties of isoquercitrin(IQ) were summarized.
Chapter 2:The inclusion complex of IQ withβ-cyclodextrin(β-CD) was prepared and characterized by UV-vis absorption spectroscopy(UV),Fourier transformation-infrared(FTIR) spectroscopy and ~1H Nuclear magnetic resonance(~1H-NMR) spectroscopy.An exact and precise method for UV-vis absorption spectroscopy determination of IQ was developed.The precision experiments within-day and between-day were 1.66%,1.42%,0.28%and 1.99%,1.34%,1.26%,respectively.Results of recovery experiment were 102.60±0.19%,102.61±0.59%and 103.19±0.61%,respectively.The phase solubility diagram of IQ withβ-CD was classified as A_L-type,which suggested IQ was inserted into theβ-CD cavity to form a 1:1 inclusion complex.Further,it is found that the water solubility and dissolution rate of IQ were significantly increased by forming an inclusion complex withβ-CD. The aqueous solubility of IQ-β-CD was 8.22 times higher than that of IQ.The dissolution rate of IQ-β-CD complex was 89.80%within 30 min,while the dissolution rate of IQ was 41.48%which was evidently enhanced by the complex of IQ withβ-CD.
Chapter 3:The solid inclusion complex of IQ withβ-CD was prepared by using coprecipitation,ultrasonic and kneading method,respectively.The recovery,inclusion rate,load drug and solubility of IQ were adopted as index to optimize the best method for inclusion preparation.The orthogonal experiment design was applied to optimize the preparation process of inclusion complex.The optimum entrapment conditions were as follows:the reaction time was 6 h,the molar ratio of IQ intoβ-CD was 1:2,the reaction temperature was 55℃.
Chapter 4:The inclusion complex of IQ with hydroxypropy-β-cyclodextrin (HP-β-CD) was prepared and characterized by UV,Fourier FTIR and ~1H-NMR.An exact and precise method for UV-vis absorption spectroscopy determination of IQ was developed.The precision experiments within-day and between-day were not more than 2%,respectively.Results of recovery experiment were 100.73±0.82%,101.84±1.12%and 103.11±0.93%, respectively.The phase solubility diagram of IQ with HP-β-CD was classified as A_L-type,which suggested IQ was inserted into the HP-β-CD cavity to form a 1:1 inclusion complex.Further,it is found that the water solubility and dissolution rate of IQ were significantly increased by forming an inclusion complex with HP-β-CD.The solubility of IQ-HP-β-CD was 15.66 times higher than that of IQ.The dissolution rate of IQ-HP-β-CD complex was 98.96%within 15 min,while the dissolution rate of IQ was 41.48%within 30 min which was evidently enhanced by the complex of IQ with HP-β-CD.
Chapter 5:The solid inclusion complex of IQ with HP-β-CD was prepared by using stirring,ultrasonic and kneading method,respectively.The recovery, inclusion rate,load drug and solubility of IQ were adopted as index to optimize the best method for inclusion preparation.The orthogonal experiment design was applied to optimize the preparation process of inclusion complex.The optimum entrapment conditions were as follows:the reaction time was 6h,the molar ratio of IQ into HP-β-CD was 1:3,the reaction temperature was 55℃.
第二章:采用共沉淀法制备了异槲皮苷的β-环糊精固体包合物,并用紫外光谱、红外光谱和核磁共振法表征了包合物。利用紫外-可见分光光度法建立了包合物中异槲皮苷的含量测定方法,低、中、高三种浓度的异槲皮苷溶液的日内和日间精密度分别为1.66%、1.42%、0.28%和1.99%、1.34%、1.26%,回收率分别为102.60±0.19%、102.61±0.59%、103.19±0.61%。在此基础上,对异槲皮苷在β-环糊精中的相溶解度进行研究,发现异槲皮苷与β-环糊精形成了1:1型包合物。溶解度研究显示异槲皮苷被制备成固体包合物后,其溶解度提高了822倍。溶出度研究发现异槲皮苷被β-环糊精包合后其溶出度得到显著增强,在30min内,溶出度由原来的41.48%提高至89.80%。
第三章:采用共沉淀法、超声法和研磨法制备了异槲皮苷的β-环糊精固体包合物,以包封率、载药率以及溶解度为主要参考指标,优选出共沉淀法做为IQ-β-CD包合物制备的最佳方法。并利用正交试验设计优选出包合物制备的最佳条件为主客体分子比2:1,搅拌时间6 h,搅拌温度55℃。
第四章:采用搅拌法对异槲皮苷的羟丙基-β-环糊精固体包合物进行制备,利用紫外光谱、红外光谱和核磁共振法表征了包合物。采用紫外-可见分光光度法建立了包合物中异槲皮苷的含量测定方法,日内和日间精密度均小于2%,回收率分别为100.73±0.82%、101.84±1.12%、103.11±0.93%。通过相溶解度的研究,发现异槲皮苷与羟丙基-β-环糊精之间形成A_L型的1:1型包合物。溶解度研究发现异槲皮苷被制备成固体包合物后,其溶解度提高了15.66倍,与此同时,异槲皮苷的溶出度研究显示其溶出度由原来的30min内累积溶出41.48%提高至15min内累积溶出98.96%。
第五章:以收率、包封率、载药率和溶解度为考察指标,通过对搅拌法、超声法和研磨法三种包合物制备方法的评价,优选出包合物制备的最佳方法,并利用正交试验设计优化出包合物制备的最佳条件为主客体分子比3:1,搅拌时间6h,搅拌温度55℃。
Chapter 1:The recent development of cyclodextrins inclusion technique has been reviewed and especially focused on the application of cyclodextrins and their derivatives in pharmaceutical industry.The chemical and biological properties of isoquercitrin(IQ) were summarized.
Chapter 2:The inclusion complex of IQ withβ-cyclodextrin(β-CD) was prepared and characterized by UV-vis absorption spectroscopy(UV),Fourier transformation-infrared(FTIR) spectroscopy and ~1H Nuclear magnetic resonance(~1H-NMR) spectroscopy.An exact and precise method for UV-vis absorption spectroscopy determination of IQ was developed.The precision experiments within-day and between-day were 1.66%,1.42%,0.28%and 1.99%,1.34%,1.26%,respectively.Results of recovery experiment were 102.60±0.19%,102.61±0.59%and 103.19±0.61%,respectively.The phase solubility diagram of IQ withβ-CD was classified as A_L-type,which suggested IQ was inserted into theβ-CD cavity to form a 1:1 inclusion complex.Further,it is found that the water solubility and dissolution rate of IQ were significantly increased by forming an inclusion complex withβ-CD. The aqueous solubility of IQ-β-CD was 8.22 times higher than that of IQ.The dissolution rate of IQ-β-CD complex was 89.80%within 30 min,while the dissolution rate of IQ was 41.48%which was evidently enhanced by the complex of IQ withβ-CD.
Chapter 3:The solid inclusion complex of IQ withβ-CD was prepared by using coprecipitation,ultrasonic and kneading method,respectively.The recovery,inclusion rate,load drug and solubility of IQ were adopted as index to optimize the best method for inclusion preparation.The orthogonal experiment design was applied to optimize the preparation process of inclusion complex.The optimum entrapment conditions were as follows:the reaction time was 6 h,the molar ratio of IQ intoβ-CD was 1:2,the reaction temperature was 55℃.
Chapter 4:The inclusion complex of IQ with hydroxypropy-β-cyclodextrin (HP-β-CD) was prepared and characterized by UV,Fourier FTIR and ~1H-NMR.An exact and precise method for UV-vis absorption spectroscopy determination of IQ was developed.The precision experiments within-day and between-day were not more than 2%,respectively.Results of recovery experiment were 100.73±0.82%,101.84±1.12%and 103.11±0.93%, respectively.The phase solubility diagram of IQ with HP-β-CD was classified as A_L-type,which suggested IQ was inserted into the HP-β-CD cavity to form a 1:1 inclusion complex.Further,it is found that the water solubility and dissolution rate of IQ were significantly increased by forming an inclusion complex with HP-β-CD.The solubility of IQ-HP-β-CD was 15.66 times higher than that of IQ.The dissolution rate of IQ-HP-β-CD complex was 98.96%within 15 min,while the dissolution rate of IQ was 41.48%within 30 min which was evidently enhanced by the complex of IQ with HP-β-CD.
Chapter 5:The solid inclusion complex of IQ with HP-β-CD was prepared by using stirring,ultrasonic and kneading method,respectively.The recovery, inclusion rate,load drug and solubility of IQ were adopted as index to optimize the best method for inclusion preparation.The orthogonal experiment design was applied to optimize the preparation process of inclusion complex.The optimum entrapment conditions were as follows:the reaction time was 6h,the molar ratio of IQ into HP-β-CD was 1:3,the reaction temperature was 55℃.
引文
[1]SZEJTLI J.Minutes Int Sym Cyclodextrins 6th[Z].Paris Stante,1992.521.
[2]SZEJTLI J.Proc Int Symp Cyclodextrins 4th[Z].Kluwer Dordrecht,1988.347.
[3]PERI D,WYANDT C M,CLEARY R W,HIKAL A H,JONES A B.Inclusion complexes of tolnaftate with β-cyclodextrin and hydroxy-β-cyclodextrin[J].Drug.Dev.Ind Pharm.1994,20(8):1401-1410.
[4]SZENTE L,GAL-FUZY M,SZEJTLI J.Proceeding of 1~(st) International Symposium on Cyclodextrins[J].Budapest,1981.
[5]MAHEDERO M C,MUNOZ DE LA PENA A,BAUTISTA A,and AARON J J.An Investigation of Inclusion Complexes of Cyclodextrins with Phenylurea Herbicides by Photochemically-Induced Fluorescence.Analytical Applications[J].J.Incl.Phenom.Macro.Chem.2002,42(1/2):61-70.
[6]DUCHENE D.ED.Cyclodextrins and their Industrial Uses[M].Editions de Sante,Paris,1987.
[7]SZEJTLI J.Translated by Nogradi M and Horvath K.Cyclodextrins and their inclusion complexes[M].Ed Akademi Kiado,Budapest,1982.
[8]Bender M L,KomiyAmA M.Cyclodextrin Chemistry[M].Springer-Verlag Berlin,1978.
[9]SZEJTLI J,OSA T.Comprehensive SuprAmoleculAr Chemistry[M].Pergamon,1996.
[10]刘育,尤长城,张衡益.超分子化学-合成受体的分子识别与组装[M].天津:南开大学出版社,2001
[11]FROMMING K H,SZEJTLI J.Cyclodextrins in PharmAcy.Kluwer Academic[M]:Dordrecht,The Netherlands,1994.
[12]宋乐新,孟庆金,游效曾.环糊精和环糊精包合物[J].无机化学学报,1997,13(4):368-374.
[13]CONNORS K A.The Stability of Cyclodextrin Complexes in Solution[J].Chem.Rev.1997,97:1325-1357.
[14]JOZESEF S.Cyclodextrin:Introduction[J].Chem.Rev.1998,98(5):1731-1742.
[15]FERANCOVA A,LABUDA J.Cyclodextrins as electrode modifiers.Fresenius[J].J.Anal.Chem.2001,370:1-10.
[16]LAWRENCE D S,JIANG T,LEVETT M.Self-Assembling Supramolecular Complexes[J].Chem.Rev.1995,95:2229-2260.
[17]姚力,姚静,于洪生.环糊精在药物制剂方面的新应用[J].药学进展,2003,27(5):279-283.
[18]KANETO U,FUMITOSHI H,TETSUMI L.Cyclodextrin Drug Carder Systems[J].Chem.Rev.1998,98(5):2045-2076.
[19]谷福根,高水泉,崔福德.磺丁基醚-β-环糊精及其在药剂学中的应用[J].中国新药杂志,2004,13(1):15-19.
[20]王亚娜,孙俊梅,余丽丽.环糊精及衍生物/药物包合常数的测定方法及其应用[J].药学进展,2004,28(1):23-28.
[21]黎洪珊,王培玉.β-环糊精的研究进展及在药剂学上的应用[J].Chin.Pharm.1999,34(4):220-223.
[22]HIRAYAMA F,LEKAMA K.Cyclodextrin-based controlled drug release system[J].Adv.Drug Deliv.Rev.1999,36(3):125-141.
[23]白云娥,漆小梅.β-环糊精在中药方面的应用[J].中国医院药学杂志,2000,20(4):237-238.
[24]谢伯泰,杨国武,谢薇梅.羟丙基-β-环糊精特性及其在医药领域中的应用与安全 性[J].国外医药-合成药、生化药、制剂分册,2002,23(5):302-306.
[25]郭圣荣,高惠君.环糊精及其提高药物溶解度和稳定性的研究进展[J].中国医药工业杂志,1998,29(6):281-286.
[26]刘友平,秦春梅,鄂丹.β-环糊精包合物在中药领域的应用进展[J].中草药2003,34(7):4-7.
[27]姚力,姚静,于洪生.环糊精在药物制剂方面的新应用[J].药学进展,2003,27(5):279-283.
[28]谷福根,高水泉,崔福德.磺丁基醚-β-环糊精及其在药剂学中的应用[J].中国新药杂志,2004,13(1):15-19.
[29]COHEN J,LACH L.Interaction of pharmaceuticals with schardinger dextrins Ⅰ.Interaction with hydroxybenzoic acids and p-hydroxybenzoates[J].J Pharm Sci,1963,52(2):132-136.
[30]CRAMER F,SAENGER W,SPATZ H-Ch.Inclusion compounds.Ⅺ Ⅹ.The formation of inclusion compounds of α-cyclodextrin in acqueous solutions.Thermodynamics and kinetics[J].J Am Chem Soc,1967,89(1):14-20.
[31]李津明.现代制药技术[M].北京:中国医药科技出版社,2005.
[32]张勇,黄贤智.荧光光谱法研究α-溴代萘与β-环糊精2:2重叠包络物的形成[J].化学学报,1997,55:69-75.
[33]江云宝,黄贤智,陈国珍.荧光光谱和吸收光谱研究醇与β-环糊精的相互作用[J].化学物理学报,1991,7(3):289-293.
[34]朱晓峰,许旭,林炳承.β-环糊精和十二烷基硫酸钠包合作用的微量热法研究[J].高等学校化学学报,1998,19(9):1504-1506.
[35]刘淑琴,刘志敏,潘景浩.环糊精及其包合物的电化学研究及应用[J].电化学,1996,2(4):430-434.
[36]王烈群,景舒,张宏宇.包合物的研制及溶出速率测定[J].中国中药杂志,1994,25(12):540-543.
[37]ZHONG LU,BO CHENG,YELI HU,YOUHONG ZHANG,GUOLIN ZOU.Complexation of resveratrol with cyclodextrins:Solubility and antioxidant activity[J].Food Chemistry,2009,113:17-20.
[38]双少敏.相溶解法测定β-环糊精-芦丁包合物的形成常数[J].分析化学,1998,26(5):564-567.
[39]李向军,连军.相溶解度法研究芦荟大黄素和环糊精及其衍生物的包结作用[J].分析科学学报,1999,15(5):368-371.
[40]李向军,连军,张勇.β-环糊精衍生物对大黄酚的增溶效应[J].应用化学,1999,16(3):112-113.
[41]李向军,连军,双少敏.大黄素甲醚-β-环糊精超分子体系包结行为研究[J].化不应用与研究,1999,11(3):298-301.
[42]董川,李俊芬,双少敏,杨频,环糊精包结物的形成及光谱表征[J].光谱实验室,2000,17(3):247-256.
[43]THANH HUONG HOANG THI,NATHALIE AZAROUAL,MARIE-PIERRE FLAMENT.Characterization and in vitro evaluation of the formoterol/cyclodextrin complex for pulmonary administration by nebulization[J].European Journal of Pharmaceutics and Biopharmaceutics,2009,72:214-218.
[44]缪振春.核磁共振技术在药物与环糊精包合物的结构分析中的应用[J].药物分析杂志,1985,5(5):316-319.
[45]WOOD D J,HRUSKA F E,SAENGER W H.NMR study of the inclusion of aromatic moleculesin α-cyclodextrin[J].J.Amer.Chem.Soc.1977,99(6):1735-1740.
[46]RAEAT S,JAIN SK.Solubility enhancement of celecoxib using β-cyclodextrin inclusion complexes[J].Eur J Pharm Biopharm,2004,57:263-267.
[47]ALI H AL-MARZOUQ,HANAN M ELWY,IHSAN SHEHADI,ABDU ADEM.Physicochemical properties of antifungal drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques[J].Journal of Pharmaceutical and Biomedical Analysis,2009,49:227-233.
[48]ZERROUK N,GINES DORADO JM,ARNAUD P,UND CHEMTOB,C.Physical characteristics of inclusion compounds of 5-ASA in a and β-cyclodextrins[J].Int J Pharm,1998,171:19-29.
[49]YI LU,XINGWANG ZHANG,JIE LAI,ZONGNING YIN,WEIWU.Physical characterization of meloxicam-β-cyclodextrin inclusion complex pellets prepared by a fluid-bed coating method[J].Particuology,2009,7:1-8.
[50]ZAIBUNNISA ABDUL HAIYEE,NORASHIKIN SAIM,MAMOT SAID,ROSLI MD,ILLIAS,WAN AIDA WAN MUSTAPHA,OSMAN HASSAN.Characterization of cyclodextrin complexes with turmeric oleoresin[J].Food Chemistry,2009,114:459-465.
[51]CAMILA FRANCO,LIEGE SCHWINGEL,IVANA LULA,RUBEN D SINISTERRA,LETlCIA SCHERER KOESTER,VALQUIRIA LINCK BASSANI.Studies on coumestrol/β-cyclodextrin association:Inclusion complex characterization[J].International Journal of Pharmaceutics,2009,369:5-11.
[52]江云宝,黄贤智,陈国珍.荧光光谱和吸收光谱研究醇与β-环糊精的相互作用[J].化学物理学报,1991,7(3):289-293.
[53]PAWEl GORNAS,GRA_ZYNA NEUNERT,KRZYSZTOF BACYNSKI,KRZYSZTOF POLEWSKI.Beta-cyclodextrin complexes with chlorogenic and caffeic acids from coffe brew:spectroscopic,thermodynamic and molecular modelling study.Food Chemistry,2009,114:190-196.
[54]袁云程.Cotton效应[J].化学通报,1983,(3):52-57.
[55]郭瑞云,常俊标,林素凤.β-环糊精包结几种萘衍生物的圆二色性的研究[J].光谱学与光普分析,1996,16(2):38-41.
[56]LU R,WNAG H,TONG L.Spectroscopic studies on inclusion complexes of MAQO and MPQO with cyclodextrins[J].Mat Sci Eng C-Bio S,1999,10:7-11.
[57]CRISMA M,FORNASIER R,MARCUZZI F.The crystal structure of the 1:1 inclusion complex of β-cyclodextrin with squaric acid[J].Carbohydr Res,2001,333:145-151.
[58]AREE T,CHAICHIT N.Crystal structure of β-cyclodextrin-dimethylsufoxide inclusion complex[J].Carbohydr Res,2002,337:2487-2494.
[59]NOZAWA Y,NAWA H,SADZUKA Y,et al.Mechanical complex formation of tolbutamide with β-cyclodextrin by solid phase roll mixing[J].Pharm Acta Helv,1997,72:37-42.
[60]JOZSEF S.Cyclodextrin Complexed Generic Drugs are Generally not Bio-equivalent with the Reference Products:Therefore the Increase in Number of Marketed Drug/Cyclodextrin Formulations is so Slow[J].J.Incl.Phenom.Macro.Chem.2005,52:1-11.
[61]吴佩颖,徐莲英,陶建生.难溶性药物增溶方法研究进展[J].中成药,2005,27(9):9-12.
[62]何静,王章阳,刘松青.格列齐特-羟丙基-β-环糊精包合物的制备[J].第三军医大学学报,2004,26(11):984-986.
[63]BRUNO A,REZENDE,STEYNER F,CORTES,FREDERICO B,DE SOUSA,IVANA S,LULA,MARTINE SCHMITT,RUBEN D,SINISTERRA,VIRGINIA S, LEMOS.Complexation with β-cyclodextrin confers oral activity on the flavonoid dioclein[J].International Journal of P harmaceutics,2009,367:133-139.
[64]NAGASE Y,HIRATA M,WADA K,et al.Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether β-cyclodextrin[J].Int.J.Pharm.2001,229:163-172.
[65]卢毅,张彤,陶建生,林敏.京尼平-β-环糊精包合物制备工艺研究[J].中国药学杂志,2008,43(20),1568-1573.
[66]朱海涛,陈吉炎,黄良永,王章元,涂自良.奥硝唑-β-环糊精包合物的制备及其质量控制[J].中国药房,2005,16(17),1305-1306.
[67]LUO YC,YUAN XW.Study on inclusion complex of oil from Rhizoma Angelicae Sinensis with β-cyclodextrin[J].J.Chin.Med Mat.1999,22(7):357-358.
[68]王靖,张铁军,王文燕.羟丙基-β-环糊精对降香挥发油包合作用的研究[J].中草药,2006,37(5):700-703.
[69]张幸生.薄荷油β-环糊精包合物的制备工艺研究[J].时珍国医国药,2005,16(12):1270-1271.
[70]JARHO P,JARVINEN K,URTTI A,STELLA V J,JARVINEN T.Modified β-cyclodextrin(SBE-β-CD) with viscous vehicle improves the ocular delivery and tolerability of pilocarpine prodrug in rabbits[J].J.Pharrn.Pharmacol.1996,48(3):263-269.
[71]陆彬主编.药物新剂型与新技术[M].北京:人民卫生出版社,1998,34-36.
[72]王克军,李化军,赵毅民.相转移催化合成陆地棉苷和金丝桃苷[J].解放军药学学报,2005,21(2):85-87.
[73]周杰,胡永洲.陆地棉苷与金丝桃苷的合成研究[J].浙江大学学报(医学版),2002,31(6):410-413.
[74]杭丽君,唐演轩.中药红花的化学成份研究[J].现代应用药学,1995,12(2):19-20.
[75]王先荣,王红萍,杜安全.异槲皮甙的半合成[J].中国药物化学杂志,1993,3(3):195-196.
[76]IRMGARD M,DETLF W.Flavonoid glycosides from arnicamontana and arnica ahamissonis[J].Plant Medica,1987,53(5):434-437.
[77]李勇军,骆宏丰,王永林,盛宛云,胡昌奇.头花蓼黄酮类化学成分的研究[J].中国药学杂志,2000,35(5):300-302.
[78]MORIWAKI M.Enzymatically Modified Isoquercitrin[J].Soft Drinks International 2006,Feb:21-23.
[79]SOSA S,PACE R,BORNANCIN A,MORAZZONI P,RIVA A,TUBARO A,DELLA-LOGGIA R.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L[J].Journal of Pharmacy and Pharmacology,2007,59:703-709.
[80]VITOR RF,MOTA FILIPE H,TEIXEIRA G,BORGES C,RODRIGUES AI,TEIXEIRA A,PAULO A.Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury[J].Journal of Ethnopharmacology,200493(2/3):363-370.
[81]国家医药管理局中草药情报中心站编.植物有效成分手册[M].北京:人民卫生出版社,1986.
[82]Li Y J,LUO H F,WANG Y L,et al.Studies on the chemical constituents of flavonoids from polygonum capitatum[J].Chinese Pharmaceutical Journal,2000,35(5):300-302.
[83]IRMGARD M,DETLF W.Flavonoid glycosides from arnica Montana and arnica aham issonis[J].Plant Medica,1987,53(5):434-437.
[84]AMARAL A C F,KUSTER R M,CONCALVES J C S,CONCALVES J C S.Antiviral investigation on the flavonoids of Chamaesyle thymifolia[J].Fitoterapia,1999,70(3):293-295.
[85]PAULKE A,NOLDNER M,SCHUBERT-ZSILAVECZ M,WURGLICS M.St.John's wort flavonoids and their metabolites show antidepressant activity and accumulate in brain after multiple oral doses[J].Pharmazie,Die,2008,63(4):296-302.
[86]VERONIKA BUTTERWECK,SANSEI NISHIBE,TSUTOMU SASAKI,MASARU UCHIDA.Antidepressant Effects of Apocynum venetum Leaves in a Forced Swimming Test[J].Biological & pharmaceutical bulletin,2001,24(7):848-851.
[87]BUTTERWECK V,JURGENLIEMK G,NAHRSTEDT A,WINTERHOFF H.Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test[J].Planta Medica,2000,66(1),3-6.
[88]ROGERIO AP,KANASHIRO A,FONTANARI C,DA-SILVA EV,LUCISANO-VALIM YM,SOARES EG,FACCIOLI LH.Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma[J].Inflammation research,2007,56(10):402-408.
[89] FEMNANDEZ J, REYES R, PONCE H, OROPEZA M, VANCALSTEREN MR,JANKOWSKI C, CAMPOS MG Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways [J]. European Journal of Pharmacology, 2005,522(1/3): 108-115.
[90] MORIKAWA K, NONAKA M, NARAHARA M, TORII T, KAWAGUCHI K,YOSHIKAWA T, KAMAZAWA Y, MORIKAWA S. Inhibitory effect of quercetin on carrageenan-induced inflammation in rats [J]. Life sciences, 2003, 74 (6), 709-721.
[91] CLAIRE DUFOUR, MICHELE LOONIS. Flavonoids and their oxidation products protect efficiently albumin-bound linoleic acid in a model of plasma oxidation. Biochimica et Biophysica Acta [J]. General Subjects, 2007,1770(6): 958-965.
[92] KIM MIYEON, KIM YOUNGCHAN, CHUNG SHINKYO. Identification and in vitro biological activities of flavonols in garlic leaf and shoot: inhibition of soybean lipoxygenase and hyaluronidase activities and scavenging of free radicals [J]. Journal of the Science of Food and Agriculture, 2005, 85(4): 633-640.
[93] LEE MH, LIN RD, SHEN LY, YANG LL, YEN KY, HOU WC. Monoamine oxidase B and free radical scavenging activities of natural flavonoids in Melastoma candidum D.Don [J]. Journal of Agricultural and Food Chemistry, 2001, 49(11): 5551-5555.
[94] PAPAIOANNOU P, LAZARI D, KARIOTI A, SOULELES C, HEILMANN J,HADJIPAVLOU-LITINA D, SKALTSA H. Phenolic compounds with antioxidant activity from Anthemis tinctoria L. (Asteraceae). Zeitschrift fur Naturforschung. C, A [J]. Journal of Biosciences, 2007, 62(5-6): 326-330.
[95] SHAN FANG, GUIXING Ren, JUNSHENG BIAN, HONGMEI LI, YUNLONG LI,JUNJUN HU, RUFA LIN. Study on the Antioxidant Ability and Safety of Products from Transformation of Flavones of Buckwheat [J]. Advances in buckwheat research, 2007:539-544.
[96] JOUBERT E, WINTERTON P, BRITZ TJ, FERREIRA D. Superoxide anion and alpha,alpha-diphenyl-beta-picrylhydrazyl radical scavenging capacity of rooibos (Aspalathus linearis) aqueous extract, crude phenolic fractions, tannin and flavonoids [J]. Food research international, 2004,37(2): 33-138.
[97] ZHANG ZS, CHANG Q, ZHU M, HUANG Y, HO WKK, CHEN ZY.Characterization of antioxidants present in hawthorn fruits [J]. The Journal of nutritional biochemistry,2001,3(12):144-152.
[98]PAULO A,MARTINS S,BRANCO P,DIAS T,BORGES C,RODRIGUES AI,COSTA MD,TEIXEIRA A,MOTA-FILIPE H.The opposing effects of the flavonoids isoquercitrin and sissotrin,isolated from Pterospartum tridentatum,on oral glucose tolerance in rats[J].Phytotherapy Research,2008,22(4):539-543.
[99]KIM HY,MOON BH,LEE HJ,ChOI DH.Flavonol glycosides from the leaves of Eucommia ulmoides O.with glycation inhibitory activity[J].Journal of Ethnopharmacology,2004,93(2/3):227-230.
[100]SNIJMAN PW,SWANEVELDER S,JOUBERT E,GREEN IR,GELDERBLOM WC.The antimutagenic activity of the major flavonoids of rooibos(Aspalathus linearis):some dose-response effects on mutagen activation-flavonoid interactions[J].Mutation Research,2007,631(2):111-123.
[101]KROGH R,KROTH R,BERTI C,MADEIRA AO,SOUZA MM,CECHINEL FILHO-V,DELLE,MONACHE-F,YUNES RA.Isolation and identification of compounds with antinociceptive action from Ipomoea pes-caprae(L.) R.Br.[J].Pharmazie,Die 1999,54(6):464-466.
[1]SOSA S,PACE R,BORNANCIN A,MORAZZONI P,RIVA A,TUBARO A,DELLA-LOGGIA R.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L[J].Journal of Pharmacy and Pharmacology,2007,59,703-709.
[2]VITOR RF,MOTA FILIPE H,TEIXEIRA G,BORGES C,RODRIGUES AI,TEIXEIRA A,PAULO A.Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury[J].Journal of Ethnopharmacology,200493(2/3):363-370.
[3]国家医药管理局中草药情报中心站编.植物有效成分手册[M].北京:人民卫生出版社,1986.
[4]Li Y J,LUO H F,WANG Y L,et al.Studies on the chemical constituents of flavonoids from polygonum capitatum[J].Chinese Pharmaceutical Journal,2000,35(5):300-302.
[5]KROGH R,KROTH R,BERTI C,MADEIRA AO,SOUZA MM,CECHINEL FILHO-V,DELLE,MONACHE-F,YUNES RA.Isolation and identification of compounds with antinocicepfive action from Ipomoea pes-caprae(L.) R.Br.[J].Pharmazie,Die 1999,54(6):464-466.
[6]SNIJMAN PW,SWANEVELDER S,JOUBERT E,GREEN IR,GELDERBLOM WC.The antimutagenic activity of the major flavonoids of rooibos(Aspalathus linearis):some dose-response effects on mutagen activation-flavonoid interactions[J].Mutation Research,2007,631(2):111-123.
[7]L QIAN,Y GUAN,H XIAO.Preparation and characterization of inclusion complexes of a cationic β-cyclodextrin polymer with butylparaben or triclosan[J].International Journal of Pharmaceutics,2008,357:244-251.
[8]LI-PING RUAN,BO-YANG YU,GUANG-MIAO FU,DAN-NI ZHU.Improving the solubility of ampelopsin by solid dispersions and inclusion complexes[J].Journal of Pharmaceutical and Biomedical Analysis,2005,38:457-464.
[9]LU Z,CHEN GB,HU YL,ZHANG YH,ZOU GL.Complexation of resveratrol with cyclodextrins:Solubility and antioxidant activity[J].Food Chemistry,2009,113:17-20.
[10]宋俊峰,王福民,何平.抗癌药物马蔺子素的β-环糊精包络物研究[J].药学学报,2002,37(12):963-966.
[11]R.FICARRA,S.TOMMASINI,D.RANERI,M.L.CALABRO,M.R.DIBELLA,C.RUSTICHELLI,M.C.GAMBERINI,P.FICARRA.Study of flavonoids/β-cyclodextrins inclusion complexes by NMR,FT-IR,DSC,X-ray investigation[J].Journal of Pharmaceutical and Biomedical Analysis,2002,29:1005-1014.
[12]SILVANA TOMMASINI,DANIELA RANERI,RITA FICARRA,MARIA LUISA CALABRO,ROSANNA STANCANELLI,PAOLA FICARRA.Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin[J].Journal of Pharmaceutical and Biomedical Analysis,2004,35:379-387.
[13]OMAIRA,BHANUDASK,YOGESHP,SAMEERL.Effect of β-cyclodextrin and hydroxypropyl-β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of cefdinir[J].J Pharm Biomed Anal,2008,47:535-540.
[14]T HIGUCHI,K A CONNORS.Phase solubility techniques[J].Adv.Anal.Chem.Instrum.1965,4:117-212.
[15]国家药典委员会,中国药典2005二部[S].北京:化学工业出版社,2000.
[1]MAMORU FUKUDA,DAVE A MILLER,NICHOLAS A PEPPAS,JAMES W MCGINITY.International Influence of sulfobutyl ether β-cyclodextrin(Captisol(?)) on the dissolution properties of a poorly soluble drug from extrudates prepared by hot-melt extrusion[J].Journal of Pharmaceutics,2008,350:188-196.
[2]LI-PING RUAN,BO-YANG YU,GUANG-MIAO FU,DAN-NI ZHU.Improving the solubility of ampelopsin by solid dispersions and inclusion complexes[J].Journal of Pharmaceutical and Biomedical Analysis,2005,38:457-464.
[3]M L CALABRO,S TOMMASINI,P DONATO,D RANERI,R STANCANELLI,P FICARRA,R FICARRA,C COSTA,S CATANIA,C RUSTICHELLI,G GAMBERINI.Effects of α-and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones[J].Journal of Pharmaceutical and Biomedical Analysis,2004,35:365-377.
[4]邵伟,王金山,王春香,米广太,王大庆.槲皮素-β-环糊精包合物的研究[J].高等学校化学学报,1998,19(7):1101-1103.
[5]CAROLINA JULLIAN,LORENA MOYANO,CLAUDIA YANEZ,CLAUDIO OLEA-AZAR.Complexation of quercetin with three kinds of cyclodextrins:An antioxidant study[J].Spectrochimica Acta Part A.2007,67:230-234.
[6]ML CALABRO,S TOMMASINI,P DONATO,R STANCANELLI,D RANERI,S CATANIA,C COSTA,V VILLARI,P FICARRA,R FICARRA.The rutin/β-cyclodextrin interactions in fully aqueous solution:spectroscopic studies and biological assays[J].Journal of Pharmaceutical and Biomedical Analysis,2005,36:1019-1027.
[7]DING HAIYUN,CHAO JIANBIN,ZHANG GUOMEI,SHUANG SHAOMIN,PAN JINHAO.Preparation and spectral investigation on inclusion complex of β-cyclodextrin with rutin[J].Spectrochimica Acta Part A,2003,59:3421-3429.
[8]张国权.应用概率统计[M].北京:科学出版社,2004.
[1]HATSUMI AKI,TOKIHIRO NIIYA,YUKIKO IWASE,MAGOBEI YAMAMOTO.Multimodal inclusion complexes between barbiturates and 2-hydroxypropyl-β-cyclodextrin in aqueous solution:Isothermal titration microcalorimetry,13C NMR spectrometry,and molecular dynamics simulation[J].Journal of Pharmaceutical Sciences,2001,98(8):1186-1197.
[2]WDAEA,WELLERPJ.Handbook of Phannaceutieal ExciPienis[M].Washington:American Phmaraceutical Association,1994.
[3]王亚南,王洪权,窦媛媛.羟丙基-β-环糊精在药剂学中的应用与研究[J].食品与药品,2007,9(04),47-50.
[4]陶涛.羟丙基倍他环糊精的特性及其药剂学应用[J].中国医药工业杂志,2002,33(6):304-306.
[5]SOSA S,PACE R,BORNANCIN A,MORAZZONI P,RIVA A,TUBARO A,DELLA-LOGGIA R.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L[J].Journal of Pharmacy and Pharmacology,2007,59,703-709.
[6]VITOR RF,MOTA FILIPE H,TEIXEIRA G;BORGES C,RODRIGUES AI,TEIXEIRA A,PAULO A.Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury[J].Journal of Ethnopharmacology,200493(2/3):363-370.
[7]国家医药管理局中草药情报中心站编.植物有效成分手册[M].北京:人民卫生出版社,1986.
[8]Li Y J,LUO H F,WANG Y L,et al.Studies on the chemical constituents of flavonoids from polygonum capitatum[J].Chinese Pharmaceutical Journal,2000,35(5):300-302.
[9]KROGH R,KROTH R,BERTI C,MADEIRA AO,SOUZA MM,CECHINEL FILHO-V,DELLE,MONACHE-F,YUNES RA.Isolation and identification of compounds with antinociceptive action from Ipomoea pes-caprae(L.) R.Br.[J].Pharmazie,Die 1999,54(6):464-466.
[10]SNIJMAN PW,SWANEVELDER S,JOUBERT E,GREEN IR,GELDERBLOM WC.The antimutagenic activity of the major flavonoids of rooibos(Aspalathus linearis):some dose-response effects on mutagen activation-flavonoid interactions[J].Mutation Research,2007,631(2):111-123.
[11]T HIGUCHI,K A CONNORS.Phase solubility techniques[J].Adv.Anal.Chem.Instrum.1965,4:117-212.
[12]国家药典委员会,中国药典2005二部[S].北京:化学工业出版社,2000.
[1]何仲贵.环糊精包合物技术[M].北京:人民卫生出版社,2008.
[2]卢毅,张彤,陶建生,林敏.京尼平-β-环糊精包合物制备工艺研究[J].中国药学杂志,2008,43(20):1568-1573.
[3]张学农,阎雪莹,唐丽华,龚金红,张强.马蔺子素-羟丙基-β-环糊精包合物的制备、鉴定及包合作用[J],药学学报,2005,40(4):369-372.
[4]宋俊峰,何平,王福民.抗癌药物马蔺子素的β-环糊精包络物研究[J].药学学报,2002,37(12):963-966.
[5]邵伟,谢清春,王春香,米广太,王大庆.槲皮素-羟丙基-β-环糊精包合物的研究[J].中药材 2002,25(2):121-123.
[6]邵伟,许伟,李爱国,席延伟,王春香.槲皮素与羟丙基-β-环糊精包合物的药物动力学研究[J].中药材,2005,28(1):47-50.
[2]SZEJTLI J.Proc Int Symp Cyclodextrins 4th[Z].Kluwer Dordrecht,1988.347.
[3]PERI D,WYANDT C M,CLEARY R W,HIKAL A H,JONES A B.Inclusion complexes of tolnaftate with β-cyclodextrin and hydroxy-β-cyclodextrin[J].Drug.Dev.Ind Pharm.1994,20(8):1401-1410.
[4]SZENTE L,GAL-FUZY M,SZEJTLI J.Proceeding of 1~(st) International Symposium on Cyclodextrins[J].Budapest,1981.
[5]MAHEDERO M C,MUNOZ DE LA PENA A,BAUTISTA A,and AARON J J.An Investigation of Inclusion Complexes of Cyclodextrins with Phenylurea Herbicides by Photochemically-Induced Fluorescence.Analytical Applications[J].J.Incl.Phenom.Macro.Chem.2002,42(1/2):61-70.
[6]DUCHENE D.ED.Cyclodextrins and their Industrial Uses[M].Editions de Sante,Paris,1987.
[7]SZEJTLI J.Translated by Nogradi M and Horvath K.Cyclodextrins and their inclusion complexes[M].Ed Akademi Kiado,Budapest,1982.
[8]Bender M L,KomiyAmA M.Cyclodextrin Chemistry[M].Springer-Verlag Berlin,1978.
[9]SZEJTLI J,OSA T.Comprehensive SuprAmoleculAr Chemistry[M].Pergamon,1996.
[10]刘育,尤长城,张衡益.超分子化学-合成受体的分子识别与组装[M].天津:南开大学出版社,2001
[11]FROMMING K H,SZEJTLI J.Cyclodextrins in PharmAcy.Kluwer Academic[M]:Dordrecht,The Netherlands,1994.
[12]宋乐新,孟庆金,游效曾.环糊精和环糊精包合物[J].无机化学学报,1997,13(4):368-374.
[13]CONNORS K A.The Stability of Cyclodextrin Complexes in Solution[J].Chem.Rev.1997,97:1325-1357.
[14]JOZESEF S.Cyclodextrin:Introduction[J].Chem.Rev.1998,98(5):1731-1742.
[15]FERANCOVA A,LABUDA J.Cyclodextrins as electrode modifiers.Fresenius[J].J.Anal.Chem.2001,370:1-10.
[16]LAWRENCE D S,JIANG T,LEVETT M.Self-Assembling Supramolecular Complexes[J].Chem.Rev.1995,95:2229-2260.
[17]姚力,姚静,于洪生.环糊精在药物制剂方面的新应用[J].药学进展,2003,27(5):279-283.
[18]KANETO U,FUMITOSHI H,TETSUMI L.Cyclodextrin Drug Carder Systems[J].Chem.Rev.1998,98(5):2045-2076.
[19]谷福根,高水泉,崔福德.磺丁基醚-β-环糊精及其在药剂学中的应用[J].中国新药杂志,2004,13(1):15-19.
[20]王亚娜,孙俊梅,余丽丽.环糊精及衍生物/药物包合常数的测定方法及其应用[J].药学进展,2004,28(1):23-28.
[21]黎洪珊,王培玉.β-环糊精的研究进展及在药剂学上的应用[J].Chin.Pharm.1999,34(4):220-223.
[22]HIRAYAMA F,LEKAMA K.Cyclodextrin-based controlled drug release system[J].Adv.Drug Deliv.Rev.1999,36(3):125-141.
[23]白云娥,漆小梅.β-环糊精在中药方面的应用[J].中国医院药学杂志,2000,20(4):237-238.
[24]谢伯泰,杨国武,谢薇梅.羟丙基-β-环糊精特性及其在医药领域中的应用与安全 性[J].国外医药-合成药、生化药、制剂分册,2002,23(5):302-306.
[25]郭圣荣,高惠君.环糊精及其提高药物溶解度和稳定性的研究进展[J].中国医药工业杂志,1998,29(6):281-286.
[26]刘友平,秦春梅,鄂丹.β-环糊精包合物在中药领域的应用进展[J].中草药2003,34(7):4-7.
[27]姚力,姚静,于洪生.环糊精在药物制剂方面的新应用[J].药学进展,2003,27(5):279-283.
[28]谷福根,高水泉,崔福德.磺丁基醚-β-环糊精及其在药剂学中的应用[J].中国新药杂志,2004,13(1):15-19.
[29]COHEN J,LACH L.Interaction of pharmaceuticals with schardinger dextrins Ⅰ.Interaction with hydroxybenzoic acids and p-hydroxybenzoates[J].J Pharm Sci,1963,52(2):132-136.
[30]CRAMER F,SAENGER W,SPATZ H-Ch.Inclusion compounds.Ⅺ Ⅹ.The formation of inclusion compounds of α-cyclodextrin in acqueous solutions.Thermodynamics and kinetics[J].J Am Chem Soc,1967,89(1):14-20.
[31]李津明.现代制药技术[M].北京:中国医药科技出版社,2005.
[32]张勇,黄贤智.荧光光谱法研究α-溴代萘与β-环糊精2:2重叠包络物的形成[J].化学学报,1997,55:69-75.
[33]江云宝,黄贤智,陈国珍.荧光光谱和吸收光谱研究醇与β-环糊精的相互作用[J].化学物理学报,1991,7(3):289-293.
[34]朱晓峰,许旭,林炳承.β-环糊精和十二烷基硫酸钠包合作用的微量热法研究[J].高等学校化学学报,1998,19(9):1504-1506.
[35]刘淑琴,刘志敏,潘景浩.环糊精及其包合物的电化学研究及应用[J].电化学,1996,2(4):430-434.
[36]王烈群,景舒,张宏宇.包合物的研制及溶出速率测定[J].中国中药杂志,1994,25(12):540-543.
[37]ZHONG LU,BO CHENG,YELI HU,YOUHONG ZHANG,GUOLIN ZOU.Complexation of resveratrol with cyclodextrins:Solubility and antioxidant activity[J].Food Chemistry,2009,113:17-20.
[38]双少敏.相溶解法测定β-环糊精-芦丁包合物的形成常数[J].分析化学,1998,26(5):564-567.
[39]李向军,连军.相溶解度法研究芦荟大黄素和环糊精及其衍生物的包结作用[J].分析科学学报,1999,15(5):368-371.
[40]李向军,连军,张勇.β-环糊精衍生物对大黄酚的增溶效应[J].应用化学,1999,16(3):112-113.
[41]李向军,连军,双少敏.大黄素甲醚-β-环糊精超分子体系包结行为研究[J].化不应用与研究,1999,11(3):298-301.
[42]董川,李俊芬,双少敏,杨频,环糊精包结物的形成及光谱表征[J].光谱实验室,2000,17(3):247-256.
[43]THANH HUONG HOANG THI,NATHALIE AZAROUAL,MARIE-PIERRE FLAMENT.Characterization and in vitro evaluation of the formoterol/cyclodextrin complex for pulmonary administration by nebulization[J].European Journal of Pharmaceutics and Biopharmaceutics,2009,72:214-218.
[44]缪振春.核磁共振技术在药物与环糊精包合物的结构分析中的应用[J].药物分析杂志,1985,5(5):316-319.
[45]WOOD D J,HRUSKA F E,SAENGER W H.NMR study of the inclusion of aromatic moleculesin α-cyclodextrin[J].J.Amer.Chem.Soc.1977,99(6):1735-1740.
[46]RAEAT S,JAIN SK.Solubility enhancement of celecoxib using β-cyclodextrin inclusion complexes[J].Eur J Pharm Biopharm,2004,57:263-267.
[47]ALI H AL-MARZOUQ,HANAN M ELWY,IHSAN SHEHADI,ABDU ADEM.Physicochemical properties of antifungal drug-cyclodextrin complexes prepared by supercritical carbon dioxide and by conventional techniques[J].Journal of Pharmaceutical and Biomedical Analysis,2009,49:227-233.
[48]ZERROUK N,GINES DORADO JM,ARNAUD P,UND CHEMTOB,C.Physical characteristics of inclusion compounds of 5-ASA in a and β-cyclodextrins[J].Int J Pharm,1998,171:19-29.
[49]YI LU,XINGWANG ZHANG,JIE LAI,ZONGNING YIN,WEIWU.Physical characterization of meloxicam-β-cyclodextrin inclusion complex pellets prepared by a fluid-bed coating method[J].Particuology,2009,7:1-8.
[50]ZAIBUNNISA ABDUL HAIYEE,NORASHIKIN SAIM,MAMOT SAID,ROSLI MD,ILLIAS,WAN AIDA WAN MUSTAPHA,OSMAN HASSAN.Characterization of cyclodextrin complexes with turmeric oleoresin[J].Food Chemistry,2009,114:459-465.
[51]CAMILA FRANCO,LIEGE SCHWINGEL,IVANA LULA,RUBEN D SINISTERRA,LETlCIA SCHERER KOESTER,VALQUIRIA LINCK BASSANI.Studies on coumestrol/β-cyclodextrin association:Inclusion complex characterization[J].International Journal of Pharmaceutics,2009,369:5-11.
[52]江云宝,黄贤智,陈国珍.荧光光谱和吸收光谱研究醇与β-环糊精的相互作用[J].化学物理学报,1991,7(3):289-293.
[53]PAWEl GORNAS,GRA_ZYNA NEUNERT,KRZYSZTOF BACYNSKI,KRZYSZTOF POLEWSKI.Beta-cyclodextrin complexes with chlorogenic and caffeic acids from coffe brew:spectroscopic,thermodynamic and molecular modelling study.Food Chemistry,2009,114:190-196.
[54]袁云程.Cotton效应[J].化学通报,1983,(3):52-57.
[55]郭瑞云,常俊标,林素凤.β-环糊精包结几种萘衍生物的圆二色性的研究[J].光谱学与光普分析,1996,16(2):38-41.
[56]LU R,WNAG H,TONG L.Spectroscopic studies on inclusion complexes of MAQO and MPQO with cyclodextrins[J].Mat Sci Eng C-Bio S,1999,10:7-11.
[57]CRISMA M,FORNASIER R,MARCUZZI F.The crystal structure of the 1:1 inclusion complex of β-cyclodextrin with squaric acid[J].Carbohydr Res,2001,333:145-151.
[58]AREE T,CHAICHIT N.Crystal structure of β-cyclodextrin-dimethylsufoxide inclusion complex[J].Carbohydr Res,2002,337:2487-2494.
[59]NOZAWA Y,NAWA H,SADZUKA Y,et al.Mechanical complex formation of tolbutamide with β-cyclodextrin by solid phase roll mixing[J].Pharm Acta Helv,1997,72:37-42.
[60]JOZSEF S.Cyclodextrin Complexed Generic Drugs are Generally not Bio-equivalent with the Reference Products:Therefore the Increase in Number of Marketed Drug/Cyclodextrin Formulations is so Slow[J].J.Incl.Phenom.Macro.Chem.2005,52:1-11.
[61]吴佩颖,徐莲英,陶建生.难溶性药物增溶方法研究进展[J].中成药,2005,27(9):9-12.
[62]何静,王章阳,刘松青.格列齐特-羟丙基-β-环糊精包合物的制备[J].第三军医大学学报,2004,26(11):984-986.
[63]BRUNO A,REZENDE,STEYNER F,CORTES,FREDERICO B,DE SOUSA,IVANA S,LULA,MARTINE SCHMITT,RUBEN D,SINISTERRA,VIRGINIA S, LEMOS.Complexation with β-cyclodextrin confers oral activity on the flavonoid dioclein[J].International Journal of P harmaceutics,2009,367:133-139.
[64]NAGASE Y,HIRATA M,WADA K,et al.Improvement of some pharmaceutical properties of DY-9760e by sulfobutyl ether β-cyclodextrin[J].Int.J.Pharm.2001,229:163-172.
[65]卢毅,张彤,陶建生,林敏.京尼平-β-环糊精包合物制备工艺研究[J].中国药学杂志,2008,43(20),1568-1573.
[66]朱海涛,陈吉炎,黄良永,王章元,涂自良.奥硝唑-β-环糊精包合物的制备及其质量控制[J].中国药房,2005,16(17),1305-1306.
[67]LUO YC,YUAN XW.Study on inclusion complex of oil from Rhizoma Angelicae Sinensis with β-cyclodextrin[J].J.Chin.Med Mat.1999,22(7):357-358.
[68]王靖,张铁军,王文燕.羟丙基-β-环糊精对降香挥发油包合作用的研究[J].中草药,2006,37(5):700-703.
[69]张幸生.薄荷油β-环糊精包合物的制备工艺研究[J].时珍国医国药,2005,16(12):1270-1271.
[70]JARHO P,JARVINEN K,URTTI A,STELLA V J,JARVINEN T.Modified β-cyclodextrin(SBE-β-CD) with viscous vehicle improves the ocular delivery and tolerability of pilocarpine prodrug in rabbits[J].J.Pharrn.Pharmacol.1996,48(3):263-269.
[71]陆彬主编.药物新剂型与新技术[M].北京:人民卫生出版社,1998,34-36.
[72]王克军,李化军,赵毅民.相转移催化合成陆地棉苷和金丝桃苷[J].解放军药学学报,2005,21(2):85-87.
[73]周杰,胡永洲.陆地棉苷与金丝桃苷的合成研究[J].浙江大学学报(医学版),2002,31(6):410-413.
[74]杭丽君,唐演轩.中药红花的化学成份研究[J].现代应用药学,1995,12(2):19-20.
[75]王先荣,王红萍,杜安全.异槲皮甙的半合成[J].中国药物化学杂志,1993,3(3):195-196.
[76]IRMGARD M,DETLF W.Flavonoid glycosides from arnicamontana and arnica ahamissonis[J].Plant Medica,1987,53(5):434-437.
[77]李勇军,骆宏丰,王永林,盛宛云,胡昌奇.头花蓼黄酮类化学成分的研究[J].中国药学杂志,2000,35(5):300-302.
[78]MORIWAKI M.Enzymatically Modified Isoquercitrin[J].Soft Drinks International 2006,Feb:21-23.
[79]SOSA S,PACE R,BORNANCIN A,MORAZZONI P,RIVA A,TUBARO A,DELLA-LOGGIA R.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L[J].Journal of Pharmacy and Pharmacology,2007,59:703-709.
[80]VITOR RF,MOTA FILIPE H,TEIXEIRA G,BORGES C,RODRIGUES AI,TEIXEIRA A,PAULO A.Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury[J].Journal of Ethnopharmacology,200493(2/3):363-370.
[81]国家医药管理局中草药情报中心站编.植物有效成分手册[M].北京:人民卫生出版社,1986.
[82]Li Y J,LUO H F,WANG Y L,et al.Studies on the chemical constituents of flavonoids from polygonum capitatum[J].Chinese Pharmaceutical Journal,2000,35(5):300-302.
[83]IRMGARD M,DETLF W.Flavonoid glycosides from arnica Montana and arnica aham issonis[J].Plant Medica,1987,53(5):434-437.
[84]AMARAL A C F,KUSTER R M,CONCALVES J C S,CONCALVES J C S.Antiviral investigation on the flavonoids of Chamaesyle thymifolia[J].Fitoterapia,1999,70(3):293-295.
[85]PAULKE A,NOLDNER M,SCHUBERT-ZSILAVECZ M,WURGLICS M.St.John's wort flavonoids and their metabolites show antidepressant activity and accumulate in brain after multiple oral doses[J].Pharmazie,Die,2008,63(4):296-302.
[86]VERONIKA BUTTERWECK,SANSEI NISHIBE,TSUTOMU SASAKI,MASARU UCHIDA.Antidepressant Effects of Apocynum venetum Leaves in a Forced Swimming Test[J].Biological & pharmaceutical bulletin,2001,24(7):848-851.
[87]BUTTERWECK V,JURGENLIEMK G,NAHRSTEDT A,WINTERHOFF H.Flavonoids from Hypericum perforatum show antidepressant activity in the forced swimming test[J].Planta Medica,2000,66(1),3-6.
[88]ROGERIO AP,KANASHIRO A,FONTANARI C,DA-SILVA EV,LUCISANO-VALIM YM,SOARES EG,FACCIOLI LH.Anti-inflammatory activity of quercetin and isoquercitrin in experimental murine allergic asthma[J].Inflammation research,2007,56(10):402-408.
[89] FEMNANDEZ J, REYES R, PONCE H, OROPEZA M, VANCALSTEREN MR,JANKOWSKI C, CAMPOS MG Isoquercitrin from Argemone platyceras inhibits carbachol and leukotriene D4-induced contraction in guinea-pig airways [J]. European Journal of Pharmacology, 2005,522(1/3): 108-115.
[90] MORIKAWA K, NONAKA M, NARAHARA M, TORII T, KAWAGUCHI K,YOSHIKAWA T, KAMAZAWA Y, MORIKAWA S. Inhibitory effect of quercetin on carrageenan-induced inflammation in rats [J]. Life sciences, 2003, 74 (6), 709-721.
[91] CLAIRE DUFOUR, MICHELE LOONIS. Flavonoids and their oxidation products protect efficiently albumin-bound linoleic acid in a model of plasma oxidation. Biochimica et Biophysica Acta [J]. General Subjects, 2007,1770(6): 958-965.
[92] KIM MIYEON, KIM YOUNGCHAN, CHUNG SHINKYO. Identification and in vitro biological activities of flavonols in garlic leaf and shoot: inhibition of soybean lipoxygenase and hyaluronidase activities and scavenging of free radicals [J]. Journal of the Science of Food and Agriculture, 2005, 85(4): 633-640.
[93] LEE MH, LIN RD, SHEN LY, YANG LL, YEN KY, HOU WC. Monoamine oxidase B and free radical scavenging activities of natural flavonoids in Melastoma candidum D.Don [J]. Journal of Agricultural and Food Chemistry, 2001, 49(11): 5551-5555.
[94] PAPAIOANNOU P, LAZARI D, KARIOTI A, SOULELES C, HEILMANN J,HADJIPAVLOU-LITINA D, SKALTSA H. Phenolic compounds with antioxidant activity from Anthemis tinctoria L. (Asteraceae). Zeitschrift fur Naturforschung. C, A [J]. Journal of Biosciences, 2007, 62(5-6): 326-330.
[95] SHAN FANG, GUIXING Ren, JUNSHENG BIAN, HONGMEI LI, YUNLONG LI,JUNJUN HU, RUFA LIN. Study on the Antioxidant Ability and Safety of Products from Transformation of Flavones of Buckwheat [J]. Advances in buckwheat research, 2007:539-544.
[96] JOUBERT E, WINTERTON P, BRITZ TJ, FERREIRA D. Superoxide anion and alpha,alpha-diphenyl-beta-picrylhydrazyl radical scavenging capacity of rooibos (Aspalathus linearis) aqueous extract, crude phenolic fractions, tannin and flavonoids [J]. Food research international, 2004,37(2): 33-138.
[97] ZHANG ZS, CHANG Q, ZHU M, HUANG Y, HO WKK, CHEN ZY.Characterization of antioxidants present in hawthorn fruits [J]. The Journal of nutritional biochemistry,2001,3(12):144-152.
[98]PAULO A,MARTINS S,BRANCO P,DIAS T,BORGES C,RODRIGUES AI,COSTA MD,TEIXEIRA A,MOTA-FILIPE H.The opposing effects of the flavonoids isoquercitrin and sissotrin,isolated from Pterospartum tridentatum,on oral glucose tolerance in rats[J].Phytotherapy Research,2008,22(4):539-543.
[99]KIM HY,MOON BH,LEE HJ,ChOI DH.Flavonol glycosides from the leaves of Eucommia ulmoides O.with glycation inhibitory activity[J].Journal of Ethnopharmacology,2004,93(2/3):227-230.
[100]SNIJMAN PW,SWANEVELDER S,JOUBERT E,GREEN IR,GELDERBLOM WC.The antimutagenic activity of the major flavonoids of rooibos(Aspalathus linearis):some dose-response effects on mutagen activation-flavonoid interactions[J].Mutation Research,2007,631(2):111-123.
[101]KROGH R,KROTH R,BERTI C,MADEIRA AO,SOUZA MM,CECHINEL FILHO-V,DELLE,MONACHE-F,YUNES RA.Isolation and identification of compounds with antinociceptive action from Ipomoea pes-caprae(L.) R.Br.[J].Pharmazie,Die 1999,54(6):464-466.
[1]SOSA S,PACE R,BORNANCIN A,MORAZZONI P,RIVA A,TUBARO A,DELLA-LOGGIA R.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L[J].Journal of Pharmacy and Pharmacology,2007,59,703-709.
[2]VITOR RF,MOTA FILIPE H,TEIXEIRA G,BORGES C,RODRIGUES AI,TEIXEIRA A,PAULO A.Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury[J].Journal of Ethnopharmacology,200493(2/3):363-370.
[3]国家医药管理局中草药情报中心站编.植物有效成分手册[M].北京:人民卫生出版社,1986.
[4]Li Y J,LUO H F,WANG Y L,et al.Studies on the chemical constituents of flavonoids from polygonum capitatum[J].Chinese Pharmaceutical Journal,2000,35(5):300-302.
[5]KROGH R,KROTH R,BERTI C,MADEIRA AO,SOUZA MM,CECHINEL FILHO-V,DELLE,MONACHE-F,YUNES RA.Isolation and identification of compounds with antinocicepfive action from Ipomoea pes-caprae(L.) R.Br.[J].Pharmazie,Die 1999,54(6):464-466.
[6]SNIJMAN PW,SWANEVELDER S,JOUBERT E,GREEN IR,GELDERBLOM WC.The antimutagenic activity of the major flavonoids of rooibos(Aspalathus linearis):some dose-response effects on mutagen activation-flavonoid interactions[J].Mutation Research,2007,631(2):111-123.
[7]L QIAN,Y GUAN,H XIAO.Preparation and characterization of inclusion complexes of a cationic β-cyclodextrin polymer with butylparaben or triclosan[J].International Journal of Pharmaceutics,2008,357:244-251.
[8]LI-PING RUAN,BO-YANG YU,GUANG-MIAO FU,DAN-NI ZHU.Improving the solubility of ampelopsin by solid dispersions and inclusion complexes[J].Journal of Pharmaceutical and Biomedical Analysis,2005,38:457-464.
[9]LU Z,CHEN GB,HU YL,ZHANG YH,ZOU GL.Complexation of resveratrol with cyclodextrins:Solubility and antioxidant activity[J].Food Chemistry,2009,113:17-20.
[10]宋俊峰,王福民,何平.抗癌药物马蔺子素的β-环糊精包络物研究[J].药学学报,2002,37(12):963-966.
[11]R.FICARRA,S.TOMMASINI,D.RANERI,M.L.CALABRO,M.R.DIBELLA,C.RUSTICHELLI,M.C.GAMBERINI,P.FICARRA.Study of flavonoids/β-cyclodextrins inclusion complexes by NMR,FT-IR,DSC,X-ray investigation[J].Journal of Pharmaceutical and Biomedical Analysis,2002,29:1005-1014.
[12]SILVANA TOMMASINI,DANIELA RANERI,RITA FICARRA,MARIA LUISA CALABRO,ROSANNA STANCANELLI,PAOLA FICARRA.Improvement in solubility and dissolution rate of flavonoids by complexation with β-cyclodextrin[J].Journal of Pharmaceutical and Biomedical Analysis,2004,35:379-387.
[13]OMAIRA,BHANUDASK,YOGESHP,SAMEERL.Effect of β-cyclodextrin and hydroxypropyl-β-cyclodextrin complexation on physicochemical properties and antimicrobial activity of cefdinir[J].J Pharm Biomed Anal,2008,47:535-540.
[14]T HIGUCHI,K A CONNORS.Phase solubility techniques[J].Adv.Anal.Chem.Instrum.1965,4:117-212.
[15]国家药典委员会,中国药典2005二部[S].北京:化学工业出版社,2000.
[1]MAMORU FUKUDA,DAVE A MILLER,NICHOLAS A PEPPAS,JAMES W MCGINITY.International Influence of sulfobutyl ether β-cyclodextrin(Captisol(?)) on the dissolution properties of a poorly soluble drug from extrudates prepared by hot-melt extrusion[J].Journal of Pharmaceutics,2008,350:188-196.
[2]LI-PING RUAN,BO-YANG YU,GUANG-MIAO FU,DAN-NI ZHU.Improving the solubility of ampelopsin by solid dispersions and inclusion complexes[J].Journal of Pharmaceutical and Biomedical Analysis,2005,38:457-464.
[3]M L CALABRO,S TOMMASINI,P DONATO,D RANERI,R STANCANELLI,P FICARRA,R FICARRA,C COSTA,S CATANIA,C RUSTICHELLI,G GAMBERINI.Effects of α-and β-cyclodextrin complexation on the physico-chemical properties and antioxidant activity of some 3-hydroxyflavones[J].Journal of Pharmaceutical and Biomedical Analysis,2004,35:365-377.
[4]邵伟,王金山,王春香,米广太,王大庆.槲皮素-β-环糊精包合物的研究[J].高等学校化学学报,1998,19(7):1101-1103.
[5]CAROLINA JULLIAN,LORENA MOYANO,CLAUDIA YANEZ,CLAUDIO OLEA-AZAR.Complexation of quercetin with three kinds of cyclodextrins:An antioxidant study[J].Spectrochimica Acta Part A.2007,67:230-234.
[6]ML CALABRO,S TOMMASINI,P DONATO,R STANCANELLI,D RANERI,S CATANIA,C COSTA,V VILLARI,P FICARRA,R FICARRA.The rutin/β-cyclodextrin interactions in fully aqueous solution:spectroscopic studies and biological assays[J].Journal of Pharmaceutical and Biomedical Analysis,2005,36:1019-1027.
[7]DING HAIYUN,CHAO JIANBIN,ZHANG GUOMEI,SHUANG SHAOMIN,PAN JINHAO.Preparation and spectral investigation on inclusion complex of β-cyclodextrin with rutin[J].Spectrochimica Acta Part A,2003,59:3421-3429.
[8]张国权.应用概率统计[M].北京:科学出版社,2004.
[1]HATSUMI AKI,TOKIHIRO NIIYA,YUKIKO IWASE,MAGOBEI YAMAMOTO.Multimodal inclusion complexes between barbiturates and 2-hydroxypropyl-β-cyclodextrin in aqueous solution:Isothermal titration microcalorimetry,13C NMR spectrometry,and molecular dynamics simulation[J].Journal of Pharmaceutical Sciences,2001,98(8):1186-1197.
[2]WDAEA,WELLERPJ.Handbook of Phannaceutieal ExciPienis[M].Washington:American Phmaraceutical Association,1994.
[3]王亚南,王洪权,窦媛媛.羟丙基-β-环糊精在药剂学中的应用与研究[J].食品与药品,2007,9(04),47-50.
[4]陶涛.羟丙基倍他环糊精的特性及其药剂学应用[J].中国医药工业杂志,2002,33(6):304-306.
[5]SOSA S,PACE R,BORNANCIN A,MORAZZONI P,RIVA A,TUBARO A,DELLA-LOGGIA R.Topical anti-inflammatory activity of extracts and compounds from Hypericum perforatum L[J].Journal of Pharmacy and Pharmacology,2007,59,703-709.
[6]VITOR RF,MOTA FILIPE H,TEIXEIRA G;BORGES C,RODRIGUES AI,TEIXEIRA A,PAULO A.Flavonoids of an extract of Pterospartum tridentatum showing endothelial protection against oxidative injury[J].Journal of Ethnopharmacology,200493(2/3):363-370.
[7]国家医药管理局中草药情报中心站编.植物有效成分手册[M].北京:人民卫生出版社,1986.
[8]Li Y J,LUO H F,WANG Y L,et al.Studies on the chemical constituents of flavonoids from polygonum capitatum[J].Chinese Pharmaceutical Journal,2000,35(5):300-302.
[9]KROGH R,KROTH R,BERTI C,MADEIRA AO,SOUZA MM,CECHINEL FILHO-V,DELLE,MONACHE-F,YUNES RA.Isolation and identification of compounds with antinociceptive action from Ipomoea pes-caprae(L.) R.Br.[J].Pharmazie,Die 1999,54(6):464-466.
[10]SNIJMAN PW,SWANEVELDER S,JOUBERT E,GREEN IR,GELDERBLOM WC.The antimutagenic activity of the major flavonoids of rooibos(Aspalathus linearis):some dose-response effects on mutagen activation-flavonoid interactions[J].Mutation Research,2007,631(2):111-123.
[11]T HIGUCHI,K A CONNORS.Phase solubility techniques[J].Adv.Anal.Chem.Instrum.1965,4:117-212.
[12]国家药典委员会,中国药典2005二部[S].北京:化学工业出版社,2000.
[1]何仲贵.环糊精包合物技术[M].北京:人民卫生出版社,2008.
[2]卢毅,张彤,陶建生,林敏.京尼平-β-环糊精包合物制备工艺研究[J].中国药学杂志,2008,43(20):1568-1573.
[3]张学农,阎雪莹,唐丽华,龚金红,张强.马蔺子素-羟丙基-β-环糊精包合物的制备、鉴定及包合作用[J],药学学报,2005,40(4):369-372.
[4]宋俊峰,何平,王福民.抗癌药物马蔺子素的β-环糊精包络物研究[J].药学学报,2002,37(12):963-966.
[5]邵伟,谢清春,王春香,米广太,王大庆.槲皮素-羟丙基-β-环糊精包合物的研究[J].中药材 2002,25(2):121-123.
[6]邵伟,许伟,李爱国,席延伟,王春香.槲皮素与羟丙基-β-环糊精包合物的药物动力学研究[J].中药材,2005,28(1):47-50.