羟甲香豆素在家兔体内的药代动力学研究
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摘要
羟甲香豆素(hymecromone),化学名为7-羟基-4-甲基-2H-1-苯并吡喃-2-酮,被广泛应用于工业、农业、医药等领域。在医药领域,羟甲香豆素主要作为利胆药用于治疗胆囊炎、胆石症、胆道感染等。本实验室从菊科蒿属植物猪毛蒿(Artemisia scoparia Walds et kit)中提取得到具有高效杀螨活性的单体,结构鉴定为羟甲香豆素。羟甲香豆素属脂水难溶性化合物,国外对羟甲香豆素在人和大鼠体内的药代动力学研究均使用其钠盐,本试验首先进行羟甲香豆素钠盐的制备,建立家兔血浆内羟甲香豆素含量的反相高效液相测定法,进而研究羟甲香豆素在家兔体内的药代动力学规律。结果如下:
1.羟甲香豆素钠盐的制备:以10 mmol羟甲香豆素与9.5 mmol氢氧化钠为原料,92%的丙酮水溶液进行重结晶得到淡黄色针状晶体,产率75%。采用TLC,UV,IR,~1H NMR,~(13)C NMR和MS进行结构表征,确定所得化合物为羟甲香豆素钠盐;建立测定样品中羟甲香豆素钠盐含量的紫外分光光度法,标准曲线方程为y=0.0869x-0.3011(n=7),R~2=0.9976,在5~30μg/mL浓度范围内,线性关系良好。制备的样品中羟甲香豆素钠盐含量为98%。
2.家兔血浆中羟甲香豆素含量测定的RP-HPLC方法的建立:采用C18柱(4.6×150mm, 5μm),甲醇-水(55:45)为流动相,7-羟基香豆素为内标,乙腈沉淀蛋白,检测波长324 nm,柱温30℃,测定家兔血浆中的羟甲香豆素。在此色谱条件下,羟甲香豆素浓度在20~32000 ng/mL范围内与峰面积比呈良好的线性关系,标准曲线方程为y=0.0005x-0.0036(n=10),R~2=0.9998。日内和日间精密度(n=5)RSD<4%,平均回收率为100.02%,萃取回收率为95.78%。该法灵敏、简便、准确、快捷,特异性强,适用于羟甲香豆素在家兔体内的药代动力学研究。
3.羟甲香豆素在家兔体内的药代动力学研究:应用RP-HPLC方法研究静脉注射和经皮给药后,羟甲香豆素在家兔体内的药代动力学过程。结果表明,羟甲香豆素在家兔体内的药代动力学符合二室模型。静脉注射后,平均药动学方程为:C=14997.19e~(-3.957t)+ 161.72e~(-0.05t);药时曲线下面积(AUC)=3967.28±1554.60 ng/mL·h;分布半衰期(T_(1/2α))=0.18±0.04 h;消除半衰期(T_(1/2β))=15.99±5.25 h;表观分布容积(Vd)=5.19±2.10 L/(h·kg)。经皮给药后,平均药动学方程为C=210.13e~(-0.31)+108.02e~(-0.0032t)-318.15e~(-4.06t);AUC= 9295.16±3411.64 ng/mL·h;吸收半衰期(T1/2kα)=0.18±0.05 h;T_(1/2α)=2.27±0.24 h; T_(1/2β)=54.92±14.93 h;峰浓度(C_(max))=318.15±4367 ng/mL; Vd=493.21±65.29 L/(h·kg); CL=2030.62±691.41 ng/(kg·h)。
Hymecromone, the chemical name is 7- hydroxy -4- methyl-2H-1-Benzopyran-2- ketone, is widely used in industry, agriculture, medicine and other fields. In the ield of medicine, hymecromone are primarily used as a choleretic drug for the treatment of cholecystitis, cholelithiasis, biliary tract infections, gallbladder surgery syndrome, etc. A monomer which has a highly efficient of acaricidal activity has benn extracted from Artemisia scoparia Walds et kit, and it was identified as hymecromone. Hymecromone is insoluble in water and fat, its sodium salt was used in pharmacokinetics studies on hymecromone in humans and rats abroad. In this study, the hymecromone sodium salt was synthesized firstly, and a method of determining the concentration of hymecromone of blood plasma by reversed-phase high performance liquid chromatography in rabbits was established. Then, the pharmacokinetics of hymecromone in rabbits were studied. The results were as follows:
1. Synthesis of hymecromone sodium salt: Hymecromone sodium salt was prepared by reaction of hymecromone (10 mmol) with sodium hydroxide(9.5 mmol), recrystallization in the solution of 92% acetone in water provided pale yellow needle crystal with yield of 75%, The structure of the compound was characterized by TLC, UV, IR, 1H NMR, 13C NMR and MS, and was confirmed to be hymecromone sodium salt. The content of the product samples detected by the UV method was built, which the equation of standard curves was y=0.0869x-0.3011 (n=7), (R~2=0.9976) and the linear relations were good in the concentration range of 5~30μg/mL, and the mean content of hymecromone sodium salt synthesized by this new process was 98%.
2. A Method for determination content of hymecromone in rabbits blood plasma was established: the chromatographic conditions, which was used for determinating the content of hymecromone in rabbits blood plasma, were decided to be C18 column (4.6×150 mm, 5μm), Methanol and water (55:45) as mobile phase, 7-hydroxy coumarin as the internal standard and acetonitrile precipitation method for removing albumin with detective UV wavelength at 324 nm and column temperature at 30℃. Under these eonditions, the ratio of peak areas for hymecromone to internal standard 7-hydroxy coumarin was linear with the content of hymecromone in the range of 20~32000 ng/mL. The RSD of with-in day precision test and between-day precision test (n=5)were both less 4%. The average recovery and extraction recovery was 100.02% and 95.78%. This method is sensitive, simple, accurate, fast, specific for pharmacokinetics study on hymecromone in rabbits.
3. Pharmacokinetics study on hymecromone in rabbits: The pharmaeokineties study of hymecromone in rabbits was made after intravenous injection and transdermal drug delivery using RP-HPLC method. The results showed that hymecromone abided by two-compartment model in rabbits. After intravenous injection, its average pharmacokinetic equations was C=14997.19e~(-3.957)t+161.72e~(-0.05t); the area under the plasma concentration-time curve (AUC) was 3967.28±1554.60 ng/mL·h, the distribution half-life (T_(1/2α)) was 0.18±0.04h, the elimination half-life (T_(1/2β)) was 15.99±5.25 h, the apparent volume of distribution (Vd) was 5.19±2.10 L/(h·kg). After transdermal drug delivery, its average pharmacokinetic equations was C=210.13e~(-0.31)+108.02e~(-0.0032t)-318.15e~(-4.06t); AUC was 9295.16±3411.64 ng/mL·h, the absorption half-life (T1/2kα) was 0.18±0.05 h, T_(1/2α) was 2.27±0.24 h, T_(1/2β) was 54.92±14.93 h, the peak concentration (C_(max)) was 318.15±4367 ng/mL, Vd was 493.21±65.29 L/(h·kg), the CL was 2030.62±691.41 ng/(kg·h).
1.羟甲香豆素钠盐的制备:以10 mmol羟甲香豆素与9.5 mmol氢氧化钠为原料,92%的丙酮水溶液进行重结晶得到淡黄色针状晶体,产率75%。采用TLC,UV,IR,~1H NMR,~(13)C NMR和MS进行结构表征,确定所得化合物为羟甲香豆素钠盐;建立测定样品中羟甲香豆素钠盐含量的紫外分光光度法,标准曲线方程为y=0.0869x-0.3011(n=7),R~2=0.9976,在5~30μg/mL浓度范围内,线性关系良好。制备的样品中羟甲香豆素钠盐含量为98%。
2.家兔血浆中羟甲香豆素含量测定的RP-HPLC方法的建立:采用C18柱(4.6×150mm, 5μm),甲醇-水(55:45)为流动相,7-羟基香豆素为内标,乙腈沉淀蛋白,检测波长324 nm,柱温30℃,测定家兔血浆中的羟甲香豆素。在此色谱条件下,羟甲香豆素浓度在20~32000 ng/mL范围内与峰面积比呈良好的线性关系,标准曲线方程为y=0.0005x-0.0036(n=10),R~2=0.9998。日内和日间精密度(n=5)RSD<4%,平均回收率为100.02%,萃取回收率为95.78%。该法灵敏、简便、准确、快捷,特异性强,适用于羟甲香豆素在家兔体内的药代动力学研究。
3.羟甲香豆素在家兔体内的药代动力学研究:应用RP-HPLC方法研究静脉注射和经皮给药后,羟甲香豆素在家兔体内的药代动力学过程。结果表明,羟甲香豆素在家兔体内的药代动力学符合二室模型。静脉注射后,平均药动学方程为:C=14997.19e~(-3.957t)+ 161.72e~(-0.05t);药时曲线下面积(AUC)=3967.28±1554.60 ng/mL·h;分布半衰期(T_(1/2α))=0.18±0.04 h;消除半衰期(T_(1/2β))=15.99±5.25 h;表观分布容积(Vd)=5.19±2.10 L/(h·kg)。经皮给药后,平均药动学方程为C=210.13e~(-0.31)+108.02e~(-0.0032t)-318.15e~(-4.06t);AUC= 9295.16±3411.64 ng/mL·h;吸收半衰期(T1/2kα)=0.18±0.05 h;T_(1/2α)=2.27±0.24 h; T_(1/2β)=54.92±14.93 h;峰浓度(C_(max))=318.15±4367 ng/mL; Vd=493.21±65.29 L/(h·kg); CL=2030.62±691.41 ng/(kg·h)。
Hymecromone, the chemical name is 7- hydroxy -4- methyl-2H-1-Benzopyran-2- ketone, is widely used in industry, agriculture, medicine and other fields. In the ield of medicine, hymecromone are primarily used as a choleretic drug for the treatment of cholecystitis, cholelithiasis, biliary tract infections, gallbladder surgery syndrome, etc. A monomer which has a highly efficient of acaricidal activity has benn extracted from Artemisia scoparia Walds et kit, and it was identified as hymecromone. Hymecromone is insoluble in water and fat, its sodium salt was used in pharmacokinetics studies on hymecromone in humans and rats abroad. In this study, the hymecromone sodium salt was synthesized firstly, and a method of determining the concentration of hymecromone of blood plasma by reversed-phase high performance liquid chromatography in rabbits was established. Then, the pharmacokinetics of hymecromone in rabbits were studied. The results were as follows:
1. Synthesis of hymecromone sodium salt: Hymecromone sodium salt was prepared by reaction of hymecromone (10 mmol) with sodium hydroxide(9.5 mmol), recrystallization in the solution of 92% acetone in water provided pale yellow needle crystal with yield of 75%, The structure of the compound was characterized by TLC, UV, IR, 1H NMR, 13C NMR and MS, and was confirmed to be hymecromone sodium salt. The content of the product samples detected by the UV method was built, which the equation of standard curves was y=0.0869x-0.3011 (n=7), (R~2=0.9976) and the linear relations were good in the concentration range of 5~30μg/mL, and the mean content of hymecromone sodium salt synthesized by this new process was 98%.
2. A Method for determination content of hymecromone in rabbits blood plasma was established: the chromatographic conditions, which was used for determinating the content of hymecromone in rabbits blood plasma, were decided to be C18 column (4.6×150 mm, 5μm), Methanol and water (55:45) as mobile phase, 7-hydroxy coumarin as the internal standard and acetonitrile precipitation method for removing albumin with detective UV wavelength at 324 nm and column temperature at 30℃. Under these eonditions, the ratio of peak areas for hymecromone to internal standard 7-hydroxy coumarin was linear with the content of hymecromone in the range of 20~32000 ng/mL. The RSD of with-in day precision test and between-day precision test (n=5)were both less 4%. The average recovery and extraction recovery was 100.02% and 95.78%. This method is sensitive, simple, accurate, fast, specific for pharmacokinetics study on hymecromone in rabbits.
3. Pharmacokinetics study on hymecromone in rabbits: The pharmaeokineties study of hymecromone in rabbits was made after intravenous injection and transdermal drug delivery using RP-HPLC method. The results showed that hymecromone abided by two-compartment model in rabbits. After intravenous injection, its average pharmacokinetic equations was C=14997.19e~(-3.957)t+161.72e~(-0.05t); the area under the plasma concentration-time curve (AUC) was 3967.28±1554.60 ng/mL·h, the distribution half-life (T_(1/2α)) was 0.18±0.04h, the elimination half-life (T_(1/2β)) was 15.99±5.25 h, the apparent volume of distribution (Vd) was 5.19±2.10 L/(h·kg). After transdermal drug delivery, its average pharmacokinetic equations was C=210.13e~(-0.31)+108.02e~(-0.0032t)-318.15e~(-4.06t); AUC was 9295.16±3411.64 ng/mL·h, the absorption half-life (T1/2kα) was 0.18±0.05 h, T_(1/2α) was 2.27±0.24 h, T_(1/2β) was 54.92±14.93 h, the peak concentration (C_(max)) was 318.15±4367 ng/mL, Vd was 493.21±65.29 L/(h·kg), the CL was 2030.62±691.41 ng/(kg·h).
引文
陈红,张丹,邓晴源.2006.家兔血浆中替拉扎明的HPLC测定及药动学研究.生物医学工程学杂志,23(1):180~183
操继跃,卢笑丛.2005.兽医药代动力学.北京:中国农业出版社
陈晓冰,孙小强,熊敏秋,席海涛.2010.含氟香豆素荧光探针的合成及其荧光性能研究.化学通报,(10):949~952
豆传娜.2007.茵陈杀螨活性成分的分离纯化及结构鉴定.[硕士学位论文].杨凌:西北农林科技大学
邓世明,林强.2008.新药研究思路与方法.北京:人民卫生出版社
冯家钢,戴路明.2010.华法林的药理作用及在肺血栓栓塞中的应用.中外医学研究,8(29):193~195
高峰.2010.复方美托洛尔人体药代动力学研究.[硕士学位论文].吉林:吉林大学
高锦明.2003.植物化学.北京:科学出版社
国家药典委员会.2000.中华人民共和国药典2000年版二部.北京:化学工业出版社,776
郭书好.2008.有机化学实验.武汉:华中科技大学出版社
郭媛,陈康裕,倪小波,杨栋.2010.3-吡啶香豆素类化合物的合成及荧光性质研究.化学试剂,32(8):673~676
黄佳,李婷,史卫忠,赵志刚.2009.高效液相色谱法测定家兔血浆中红景天苷浓度及其药代动力学研究.吉林中医药,29(11):989~991
堪立巍,刘静,赵波,李宏,张梅.2008.紫外风光光度法测定川明参中总香豆素类成分含量.成都医学院学报,3(3):188~190
刘昌孝.2003.实用药代动力学.北京:中国医药科技出版社
李得堂,唐洪梅,蔡庆群,张丽娟,阎雪,丘振文.2011.疗筋涂膜剂的皮肤给药安全性评价.西北药学杂志,26(2):118~120
李华,史晓萍,张景云,肖玉平,王太一,王禄增.2006.新编实验动物学.辽宁:辽宁民族出版社
李好枝.2003.体内药物分析.北京:中国医药科技出版社
刘江,张小琴,韩隽,刘俊彪,黄锋,马彬彬,王宇.2010.香豆素类荧光探针在检测方面的研究进展.浙江化工,41(9):27~31
连其深,张志祖,胡晓,周俐,上官珠,叶和杨,何蔚,朱遵平.1996.花椒毒酚的药效学研究Ⅱ抗炎作用.赣南医学院学报,16(4):303~306
李欣.2007.痢菌净透皮剂在猪体内的药物动力学以及残留研究.[硕士学位论文].武汉:华中农业大学.
廉云飞,李娟,平其能,严菲.2005.吲哚美辛微乳的制备及经皮吸收研究.中国医药工业杂志,36(3):148~152
李在留,李凤兰,郑永唐,邹坤,张兴杰,汪鋆植.2007.文冠果种皮中的香豆素类化合物及抗HIV-1活性研究.北京林业大学学报,29(5):73~83
马文辉,彭孝军,徐群,宋波.2007.香豆素荧光传感器.化学进展,19(9):1258~1266
倪晨,冯彪,熊艺花,林吉,苏雪芬,赖小平.2004.HPLC法测定复方胆通片中羟甲香豆素的含量.中药新药与临床药理,15(6):420~421
邱艳,宋旭红,薛东,杨长举,林开春,韩波,谢令德,舒在习.2007.蛇床子素乳油对玉米象的防效及毒力分析.湖北农业科学,46(1):79~80
石琛.2006.石葺蒲有效单体β-细辛醚在家兔体内的药代动力学研究.[硕士学位论文].广州:广州中医药大学
上官珠,连其深,曾靖,周青,皮荣标,刘建新,杨敬格.1997.花椒毒酚的药效学研究Ⅲ镇痛作用.赣南医学院学报,17(3):201~204
孙令义.2008.香豆素化学.北京:化学工业出版社
孙佩鸣.2010.香豆素类化合物的应用研究进展.科技资讯,32(11):216
沈业寿,马金宝.2007.亮菌研究的现状与展望.安徽大学学报(自然科学版),31(1):82~86
石志琦,沈寿国,徐朗莱,范永坚.2004.蛇床子素对植物病原真菌抑制机制的初步研究.农药学学报,6(4):28~32
石志琦,王春梅,范永坚,李优琴,陈浩.2009.仿生新系列化合物7-烷氧基-8-(3,3'-二取代丙基)苯并吡喃-2-酮类合成及其作为农药的应用[P],CN,101456853A.
孙中武编著.2001.植物化学.哈尔滨:东北林业大学出版社
王春梅,崔新颖,李贺.2006.白芷香豆素的抗炎作用研究.北华大学学报(自然科学版),7(4):318~320
王春梅,关巍,刘志恒,房舒,陈浩,蔡春,石志琦.2010.蛇床子素结构修饰物JS-B对辣椒疫霉生物活性.农药,49(1):69~71
王春梅,吴桂本,王英姿,石志琦.2005.蛇床子素防治黄瓜白粉病研究.江苏农业科,(4):57~59
王广基,刘晓东,柳晓泉.2005.药物代谢动力学.北京:化学工业出版社
王敬旭,廖贵清.2004.透明质酸及透明质酸酶在肿瘤生长和转移中作用的研究进展.国外医学口腔医学分册,31(6):421~423
吴明明.2010.羟甲香豆素喷雾剂的研究.[硕士学位论文].杨凌:西北农林科技大学
王霞,马洪涛,温瑞兴.2009.抗HIV药物及其靶点的研究进展.中国中药杂志,34(11):1454~1459
王小蕊.2010.羟甲香豆素原料药的合成及质量控制研究.[硕士学位论文].杨凌:西北农林科技大学
王岩.2008.香豆素类利胆药物亮菌甲素的药代动力学研究.[博士学位论文].长春:吉林大学
王颖.2007.丹参酮IIA微乳制备及其在兔体内的药代动力学研究.[硕士学位论文].大连市:大连医科大学
肖崇厚.1997.中药化学.上海:上海科学技术出版社
夏长秀,李绍勤,蔡万伦,张宏宇.2009.蛇床子素粉剂对5种储粮害虫生物活性研究.中国粮油学报,24(9):108~111
熊敏秋,席海涛,付永胜,孙小强.2010.新型香豆素荧光探针的合成及其对三聚氰胺的识别性能研究.有机化学,30(6):908~911
徐淑永,曾和平,魏传晚,王晓娟,谢彦.2004.生物活性香豆素的研究进展.合成化学,12(4):340~348
熊雯.2004.盐酸阿扎司琼氯化钠注射液质量标准及其在家兔体内的药代动力学研究.[硕士学位论文].成都:四川大学
于世林.2005.高效液相色谱方法及应用(第二版).北京:化学工业出版社
杨旭建,江晓梅,吴爱发.2005.HPLC测定羟甲香豆素有关物质.广东药学,15(2):13~14.
杨秀伟,徐波,吴军,舟福香,王瑞卿,崔景荣.2006.40种香豆素类化合物对人胃癌细胞株BGC和人肝癌细胞株BEL-7402细胞生长抑制活性的筛选.中国现代中药,8(11):7~9
邹爱玲,阮健,付竹霓.2003.4-甲基伞形酮半乳糖苷快速检定药品中大肠菌群的方法研究.中国药学杂志,38(6):470~471
中国药学杂志编辑部.1989.新药手册.天津:天津科学技术出版社
郑晶,黄晓蓉,汤敏英,陈彬,张温玲,黄嫦娇.2006.荧光法快速检测蔬菜中大肠杆菌菌群.食品科学,27(10):480~483
周乐.2000.有机化学实验.西安:世界图书出版西安公司
张玲.2010.尼扎替丁注射液在健康人体内的药代动力学研究.[硕士学位论文].兰州:兰州大学
庄礼珂,朱文.2009.气相色谱-质谱法分析海芒果果实的挥发油化学成分.农药,48(7):504~505
郑丽容,梁丹,陈瑜.2008.高效液相色谱法测定复方胆通胶囊中羟甲香豆素的含量.药学与临床研究,16(4):333~334.
张庆林,赵精华,毕建进,曹菊荣,宋京,吴祖泽.2003.蛇床子中3种逆转肿瘤细胞多药耐药活性香豆素.中草药,34(2):104~106
张巧艳,秦路平,田野萍,郑汉臣,黄茅,刘祖德.2000.蛇床子素对新生大鼠颅盖骨成骨细胞的作用.第二军医大学学报,21(17):935~937
张巧艳,秦路平,黄宝康,郑汉臣,王寅,王昊,陈磊.2003.蛇床子总香豆素对去卵巢大鼠骨质疏松症的作用.中国药学杂志,38(2):101~103
张巧艳,秦路平,郑汉臣,田野苹,黄茅,刘祖德.2001.蛇床子总香豆素对新生大鼠成骨细胞的作用.中成药,2(2):111~113
张韶瑜,孟林,高文远.2005.香豆素类化合物生物学活性研究进展.中国中药杂志,30(6):410~414
张为民,施惠平,李贝特,赵时敏,戚庆炜,孙念怙,黄尚志.2006.黏多糖贮积症Ⅱ型的诊断与产前诊断.中华儿科杂志,44(9):644~647
张伟,孙宗科,鲁波,王友斌,丁培,郑萍,陈西平.2010.4-甲基伞形酮辛酯试验检测水中沙门菌方法研究.卫生研究,39(3):381~383
张旋,黄宁,郑永唐.2010.我国中药来源的抗HIV天然化合物研究进展.药学学报,45(2):141~153
张晓辉,孔蕾,王扬,郑天伦.2006.水产养殖饲料黄曲霉毒素B1的E Ll SA快速检测.中国动物检疫,23(6):41
赵学平,王强,吴长兴,吴声敢,陈丽萍.2005.蛇床子素防治菜青虫药效试验.浙江农业科学,(4):310~311
张志祖,胡晓,周俐,周青,上官珠,何晓南.1995.蛇床子总香豆素的抗炎作用.赣南医学院学报,15(2):87~89
Abate A, Dimartino V, Spina P, Costa PL, Lombardo C, Santini A, Del Piano M, Alimonti P. 2001. Hymecromone in the treatment of motor disorders of the bile ducts: a multicenter, double-blind, placebo-controlled clinical study. Drugs Exp Clin Res, 27(5-6): 223~231
Abdel-Rahman Susan M, Johnson Franklin K, Gauthier-Dubois Ginette, Weston Irving E, Kearns Gregory L.2003. The bioequivalence of nizatidine (Axid) in two extemporaneously and one commercially prepared oral liquid formulations compared with capsule. Journal of Clinical Pharmacology, 43(2): 148~153
Abuknesha Ramadan A, Darwish Fatima. 2005. Coupling of enzymatic and immunoassay steps to detect E. coli: a new, highly sensitive tandem technique for the analysis of low levels of bacteria. Talanta, 65(2): 343~348
Ajaykumar Kulkarni, Sangamesh A Patil, Prema S Badami. 2009. Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La (III), Th (IV) and VO (IV) complexes with Schiff bases of coumarin derivatives. European Journal of Medicinal Chemistry, 44(7): 2904~2912
Asres Kaleab, Seyoum Ameha, Veeresham Ciddi, Bucar Franz, Gibbons Simon. 2005. Naturally derivedanti-HIV agents. Phytother Res, 19: 557~581
Berson, S. A. and Yalow, R. S. Assay of plasma insulin in human subjects by immunolgical methods. Nature, 184: 1648
Bhattacharyya Soumya S, Paul Saili, Mandal Sushil K, Banerjee Antara, Naoual Boujedaini, Khuda-Bukhsh Anisur R. 2009. A synthetic coumarin (4-Methyl-7 hydroxy coumarin) has anti-cancer potentials against DMBA-induced skin cancer in mice. European Journal of Pharmacology, 614(1~3):128~136
Bosch Paula, Catalina Fernando, Corrales Teresa, Peinado Carmen. 2005. Fluorescent probes for sensing processes in polymers. chemistry, 11: 4314~4325
Cane Patricia A. 2009. New developments in HIV drug resistance. Journal of Antimicrobial Chemotherapy, 64(1): 137~140
Chen Keh-Shaw, Wu Chin-Chuang, Chang Fang-Rong, Chia Yi-Chen, Chiang Michael Y-N, Wang Wei-Ya, Wu Yang-Chang. 2003. Bioactive coumarins from the leaves of Murraya omphalocarpa. Planta Medica, 69(7): 654~657
Chia Yi-Chen, Chang Fang-Rong, Wang Jinn-Chyi, Wu Chin-Chung, Chiang Michael Y-N, Lan Yu-Hsuan, Chen Keh-Shaw, Wu Yang-Chang. 2008. Antiplatelet aggregation coumarins from the leaves of Murraya omphalocarpa. Molecules, 13: 122~128
Gutierrez-sanchez VC. Calvinoi-Casilda E. Perez-Mayoral R M,Martin-Aranda A J, Lopez-peinado M, Bejblova J Cejka. 2009. Coumarins preparation by Pechmann reaction under ultrasound irradiation. Synthesis of hymecromone as insecticide intermediate. Catal Lett, 128: 318~322
Collier Abby C, Tingle Malcolm D, Keelan Jeffrey A, Paxton James W, Mitchell Murray D. 2000. A highly sensitive fluorescent microplate method for the determination of UDP-glucuronosyl transferase activity in tissues and placental cell lines. Drug Metabolism and Disposition. 28(10): 1184~1186
Daisuke Kudo, Atsushi Kon, Shuichi Yoshihara, Ikuko Kakizaki, Mutsuo Sasaki, Masahiko Endo, Keiichi Takagaki. 2004 .Effect of a hyaluronan synthase suppressor, 4-methylumbelliferone, on B16F-10 melanoma cell adhesion and locomotion. Biochemical and Biophysical Research Communications, 321(4): 783~787
Deshmukh Madhavi, Pawar Pushpa, Joseph Mary, Phalgune Usha, Kashalkar Rajashree, Deshpande Nirmala R. 2008. Efficacy of 4-methyl-7-hydroxycoumarin derivatives against vectors Aedes aegypti and Culex quinquefasciatus. Indian Journal of Experimental Biology, 46(11): 788~792
Dinkelaar Jasper, Duivenvoorden Boudewijn A, Wennekes Tom, Overkleeft Herman S, Boot Rolf G, Aerts Johannes M. F. G, Codée Jeroen D. C, Mare Gijs A. van der. 2010. A Preparative synthesis of human chitinase fluorogenic substrate (4-Deoxychitobiosyl)-4-methylumbelliferone. European Journal of Organic Chemistry, (13): 2565~2570
Elmas M, Yazar E, Uney K, Karabacak A. 2006. Pharmacokinetics of flunixin after intravenous administration in healthy and endotoxaemic rabbits. Vet Res Commun, 30(1): 73~81.
Fujioka T, Furumi K, Fujii H, Okabe H, Mihashi K, Nakano Y, Matsunaga H, Katano M, Mori M. 1994. Antiproliferative constituents from umbelliferae plants.V.A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chem Pharm Bull, 47 (1): 96~100
Gao Wenzhong, Xing Bengang, Tsien Roger Y, Rao Jianghong. 2003. Novel fluorogenic substrates for imaging a-lactamase gene expression. Journal of the American Chemical Society, 125 (37):11146~11147
Garrett Edward R, Venitz Jurgen, Eberst Kathleen, Cerda James J. 1993. Pharmacokinetics and bioavailabilities of hymecromone in human volunteers. Biopharmaceutics and Drug disposition, 14:13~39
Heistermann HP, Krawzak HW, Andrejeweski K, Hohlbach G. 1997. Pharmacologic modification of postprandial bile duct kinetics—ultrasound measurement of the lumen of the bile duct. Ultraschall Med, 18(2): 84~87
Hideaki Nakazawa, Shuichi Yoshihara, Daisuke Kudo. 2006. 4-methylumbelliferone, a hyaluronan synthase suppressor, enhances the anticancer activity of gemcitabine in human pancreatic cancer cell. Cancer Chemother Pharmacol, 57: 165~170
Hoffmann RM, Schwarz G, Pohl C, Ziegenhagen DJ, Kruis W. 2005. Bile acid-independent effect of hymecromone on bile secretion and common bile duct motility. Dtsch Med Wochenschr. 130(34-35): 1938~1943
Ikuko Kakizaki, Keiichi Takagaki, Yasufumi Endo. 2001. Effect of 4-methylumbelliferone on hyaluronan synthesis of Streptococcus equi FM100. International Congress Series, 1223: 269~272
Johnson Mallory O, Charlebois Edwin, Morin Stephen F, Catz Sheryl L, Goldstein Rise B, Remien Robert H, Rotheram-Borus Mary Jane, Mickalian Joanne D. 2005. Perceived adverse effects of antiretroviral therapy. Journal of Pain and Symptom Management, 29(2): 193~205
Kanji Tanaka, Ryousuke Taniguchi, Tsuyoshi Higuchi, Takashi Ozaki, Hideki Mizunuma, Keiichi Takagaki. 2007. 4-Methylumbelliferone inhibits hyaluronate synthesis in human uterine cervical fibroblasts. Journal of Obstetrics and Gynaecology Research, 33(6): 772~776
Kashman Yoel, Gustafson Kirk R, Fuller Richard W, Cardellina John H, McMahon James B, Robert W Currens. 1992. The Calanolides, a Novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J.Med.Chem, 35: 2735~2743
Kostova Irena P, Manolov Ilia I, Nicolova Irina N, Danchev Nicolay D. 2001. New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity. Il Farmaco. 56: 707~713
Krawzak HW, Heistermann HP, Andrejewski K, Hohlbach G. Postprandial bile-duct kinetics under the influence of 4-methylumbelliferone (hymecromone). 1995. Int J Clin Pharmacol Ther, 33(10): 569~572
Kultti Anne, Pasonen-Sepp?nen Sanna, Jauhiainen Marjo. 2009. 4-Methylumbelliferone inhibits hyaluronan synthesis by depletion of cellular UDP-glucuronic acid and down regulation of hyaluronan synthasen 2 and 3. Experimental cell Research, 315(11): 1914~1923
Lee Thomas Tung-Ying Kashiwada Yoshiki, Huang Li, Snider James, Cosentino Mark, Lee Kuo-Hsiung. 1994. Suksdorfin: an anti-HIV principle from Lomatium suksdorfii, its structure-activity correlation with related coumarins, and synergistic effects with anti-AIDS nucleosides. Bioorg Med Chem, 2: 1051~1056.
Lu You You, Wang Yu Guang, Dai Bin, Dai Yi Qi, Wang Zhao, Fu Zheng Wei, Zhu Qing. 2008. A novel nuorogenic probe for monoamine oxidase assays. Chinese chemical letters, 19: 947~950
Makot Nakai, Shuichi Yoshihara, Hajime Morohashi. 2008. Effects of hyaluronan synthase inhibitors 4-methylumbelliferone and 4-methylesculetin on human pleural malignant mesothelioma cells (NCI-H2052). Hirosaki Med, 59: 118~127
Martino Sabata, Tiribuzi Roberto, Tortori Andrea, Conti Daniele, Visigalli Ilaria, Lattanzi Annalisa, Biffi Alessandra, Gritti Angela, Orlacchio Aldo. 2009. Specific determination of beta-galactocerebrosidase activity via competitive inhibition of beta-galactosidase. Clin Chem, 55(3): 541~548
Miyauchi Seiji, Sugiyama Yuichi, Iga Tatsuji, Hanano Manabu. 1989. The conjugative metabolism of 4-methylumbelliferone and deconjugation to the parent drug examined by isolated perfused liver and in vitro liver homogenate of rats. Chem Pharm Bull (Tokyo), 37(2): 475~480
Miyauchi Seiji, Sugiyama Yuichi, Sawada Yasufumi, Morita Kaname, Iga Tatsuji, Hanano Manabu. 1987. Kinetics of hepatic transport of 4-methylumbelliferone in rats. Analysis by multiple indicator dilution method. J Pharmacokinet Biopharm, 15(1): 25~38
Morita Kaname, Sugiyama Yuichi, Hanano Manabu. 1986. Pharmacokinetic study of 4-methylumbellifer
-one in rats: influence of dose on its first-pass hepatic elimination. J. Pharmacobio- Dyn, 9(2): 117~124
Mulder Gerard J, Brouwer Sybolt, Weitering Jeannette G, Scholtens Egbert, Pang K Sandy. 1985. Glucuronidation and sulfation in the rat in vivo. The role of the liver and the intestine in the in vivo clearance of 4-methylumbelliferone. Biochem Pharmacol, 34(8): 1325~1329
Nakamura Toshiya, Funahashi Masaru, Takagaki Keiichi, Munakata Hidekazu, Tanaka Kanji, Saito Yoshiharu, Endo Masahiko. 1997. Effect of 4-methylumbelliferone on cell-free synthesis of hyaluronic acid. Biochem Mol Biol Int, 43(2): 263~268
Nyberg SL, Mann HJ, Hu MY, Payne WD, Hu WS, Cerra FB, Remmel RP. 1996. Extrahepatic metabolism of 4-methylumbelliferone and lidocaine in the anhepatic rabbit. Drug Metab Dispos, 24(6): 643-648
Orhan Ilkay, Tosun Fatma, Sener Bilge. 2008. Coumarin, anthroquinone and stilbene derivatives with anticholinesterase activity. Z Naturforsch C, 63(5~6): 366~370
Ratna1 Sanjeev, Masato Chiba, Lopamudra Bandyopadhyay, Pang K. Sandy. 1993. Futile cycling between 4-methylumbelliferone and its conjugates in perfused rat liver. Hepatology, 17(5): 838~853
Rosskopf F, Kraus J, Franz G. 1992. Immunological and antitumor effects of coumarin and some derivatives.Pharmazie, 47(2): 139~142
Sabri Noor, Yassaa Narguess, Fazeli Mohammad Reza, Alavi Seyed Hamid Reza, Fouladi Fatemeh, Salimi Ladan, Manayi Azadeh, Tofighi Zahra. 2009. Antibacterial activity of Peucedanum ruthenicum, Johreniopsis seseloides and Cervaria cervariifolia extracts. Iranian Journal of Pharmaceutical Sciences, 5(1): 37~42
Schinkovitz A, Gibbons S, Stavri M, Cocksedge M J, Bucar F. 2003. Ostruthin: an antimycobacterial coumarin from the roots of Peucedanum ostruthium. Plantamedica, 69 (4): 369~371
Shetty M, Shivananda PG. 1994. Rapid identification of Salmonella typhimurium in stools by using 4-methylumbelliferone derivatives. Indian J Pathol Microbiol, 37(1): 91~95
Shigefumi Takeda, Masaki Aburada. 1981. The choleretic mechanism of coumarin compounds and phenolic compounds. Pharmacentical Society of Japan, 4: 724~734
Shuichi Yoshihara, Atsushi Kon, Daisuke Kudo, Hideaki Nakazawa, Ikuko Kakizaki, Mutsuo Sasaki, Masahiko Endo, Keiichi Takagaki. 2005. A hyaluronan synthase suppressor, 4-methylumbelliferone, inhibits liver metastasis of melanoma cells. Febs Letters, 579(12): 2722~2726
Suzuki Hiroshi, Sawada Yasufumi, Sugiyama Yuichi, Iga Tatsuji, Hanano, Manabu. 1987 . Pharmacokinetic study of 4-methylumbelliferone in mice. Pharmaceutical Society of Japan, 10(2): 195~200
Toshiya Nakamura, Takashi Ishikawa, Naoki Nanashima, Tomisato Miura, Hiroyuki Nozaka, Rie Nakaoka,Tatsusuke Sato. 2002. 4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts, Biochemical and Biophysical Research Communications, 298(5): 646~650
Twarock S?ren, Tammi Markku I, Savani Rashmin C, Fischer Jens W. 2010. Hyaluronan stabilizes focal adhesions, filopodia, and the proliferative phenotype in esophageal squamous carcinoma cells. The Journal of biological chemistry, 285(30): 23276~23284
Wang Liping, Yang Xiao-Feng, Zhao Minglei. 2009. A 4-Methylumbelliferone-based fluorescent probe for the sensitive detection of captopril. J Fluoresc, 19(4): 593~599
Widelski Jaroslaw, Popova Milena, Graikou Konstantia, Glowniak Kazimierz, Chinou Ioanna. 2009. Coumarins from Angelica lucida L. - antibacterial activities. molecules, 14: 2729~ 2734
Yang Xiaofeng, Wang Liping, Zhao Minglei, Qi Haiping, Wu Yao. 2010. A 4-Methylumbelliferone-based fluorescent probe for sodium new houttuyfonate. Chin. J. Chem, 28(8): 1469~1474
Yoshito Shibuya, Mikiko Nara, Akir Fukuoka, Tetsuo Takahashi, Yoshihisa Nishikawa. 1998. Induction of apoptosis and changes of macromolecule synthesis during differentiation of HL-60 cells by 4-methylumbelliferone. Tokai: Proceedings of the School of Engineering of Tokai University
Zhoua Ping, Takaishi Yoshihisa, Duana Hongquan, Chena Bei, Hondab Gisho, ItohbMichiho, Takedac Yoshio, KodzhimatoVd Olimjon K, Lee Kuo-Hsing. 2000. Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry, 53: 689~697
操继跃,卢笑丛.2005.兽医药代动力学.北京:中国农业出版社
陈晓冰,孙小强,熊敏秋,席海涛.2010.含氟香豆素荧光探针的合成及其荧光性能研究.化学通报,(10):949~952
豆传娜.2007.茵陈杀螨活性成分的分离纯化及结构鉴定.[硕士学位论文].杨凌:西北农林科技大学
邓世明,林强.2008.新药研究思路与方法.北京:人民卫生出版社
冯家钢,戴路明.2010.华法林的药理作用及在肺血栓栓塞中的应用.中外医学研究,8(29):193~195
高峰.2010.复方美托洛尔人体药代动力学研究.[硕士学位论文].吉林:吉林大学
高锦明.2003.植物化学.北京:科学出版社
国家药典委员会.2000.中华人民共和国药典2000年版二部.北京:化学工业出版社,776
郭书好.2008.有机化学实验.武汉:华中科技大学出版社
郭媛,陈康裕,倪小波,杨栋.2010.3-吡啶香豆素类化合物的合成及荧光性质研究.化学试剂,32(8):673~676
黄佳,李婷,史卫忠,赵志刚.2009.高效液相色谱法测定家兔血浆中红景天苷浓度及其药代动力学研究.吉林中医药,29(11):989~991
堪立巍,刘静,赵波,李宏,张梅.2008.紫外风光光度法测定川明参中总香豆素类成分含量.成都医学院学报,3(3):188~190
刘昌孝.2003.实用药代动力学.北京:中国医药科技出版社
李得堂,唐洪梅,蔡庆群,张丽娟,阎雪,丘振文.2011.疗筋涂膜剂的皮肤给药安全性评价.西北药学杂志,26(2):118~120
李华,史晓萍,张景云,肖玉平,王太一,王禄增.2006.新编实验动物学.辽宁:辽宁民族出版社
李好枝.2003.体内药物分析.北京:中国医药科技出版社
刘江,张小琴,韩隽,刘俊彪,黄锋,马彬彬,王宇.2010.香豆素类荧光探针在检测方面的研究进展.浙江化工,41(9):27~31
连其深,张志祖,胡晓,周俐,上官珠,叶和杨,何蔚,朱遵平.1996.花椒毒酚的药效学研究Ⅱ抗炎作用.赣南医学院学报,16(4):303~306
李欣.2007.痢菌净透皮剂在猪体内的药物动力学以及残留研究.[硕士学位论文].武汉:华中农业大学.
廉云飞,李娟,平其能,严菲.2005.吲哚美辛微乳的制备及经皮吸收研究.中国医药工业杂志,36(3):148~152
李在留,李凤兰,郑永唐,邹坤,张兴杰,汪鋆植.2007.文冠果种皮中的香豆素类化合物及抗HIV-1活性研究.北京林业大学学报,29(5):73~83
马文辉,彭孝军,徐群,宋波.2007.香豆素荧光传感器.化学进展,19(9):1258~1266
倪晨,冯彪,熊艺花,林吉,苏雪芬,赖小平.2004.HPLC法测定复方胆通片中羟甲香豆素的含量.中药新药与临床药理,15(6):420~421
邱艳,宋旭红,薛东,杨长举,林开春,韩波,谢令德,舒在习.2007.蛇床子素乳油对玉米象的防效及毒力分析.湖北农业科学,46(1):79~80
石琛.2006.石葺蒲有效单体β-细辛醚在家兔体内的药代动力学研究.[硕士学位论文].广州:广州中医药大学
上官珠,连其深,曾靖,周青,皮荣标,刘建新,杨敬格.1997.花椒毒酚的药效学研究Ⅲ镇痛作用.赣南医学院学报,17(3):201~204
孙令义.2008.香豆素化学.北京:化学工业出版社
孙佩鸣.2010.香豆素类化合物的应用研究进展.科技资讯,32(11):216
沈业寿,马金宝.2007.亮菌研究的现状与展望.安徽大学学报(自然科学版),31(1):82~86
石志琦,沈寿国,徐朗莱,范永坚.2004.蛇床子素对植物病原真菌抑制机制的初步研究.农药学学报,6(4):28~32
石志琦,王春梅,范永坚,李优琴,陈浩.2009.仿生新系列化合物7-烷氧基-8-(3,3'-二取代丙基)苯并吡喃-2-酮类合成及其作为农药的应用[P],CN,101456853A.
孙中武编著.2001.植物化学.哈尔滨:东北林业大学出版社
王春梅,崔新颖,李贺.2006.白芷香豆素的抗炎作用研究.北华大学学报(自然科学版),7(4):318~320
王春梅,关巍,刘志恒,房舒,陈浩,蔡春,石志琦.2010.蛇床子素结构修饰物JS-B对辣椒疫霉生物活性.农药,49(1):69~71
王春梅,吴桂本,王英姿,石志琦.2005.蛇床子素防治黄瓜白粉病研究.江苏农业科,(4):57~59
王广基,刘晓东,柳晓泉.2005.药物代谢动力学.北京:化学工业出版社
王敬旭,廖贵清.2004.透明质酸及透明质酸酶在肿瘤生长和转移中作用的研究进展.国外医学口腔医学分册,31(6):421~423
吴明明.2010.羟甲香豆素喷雾剂的研究.[硕士学位论文].杨凌:西北农林科技大学
王霞,马洪涛,温瑞兴.2009.抗HIV药物及其靶点的研究进展.中国中药杂志,34(11):1454~1459
王小蕊.2010.羟甲香豆素原料药的合成及质量控制研究.[硕士学位论文].杨凌:西北农林科技大学
王岩.2008.香豆素类利胆药物亮菌甲素的药代动力学研究.[博士学位论文].长春:吉林大学
王颖.2007.丹参酮IIA微乳制备及其在兔体内的药代动力学研究.[硕士学位论文].大连市:大连医科大学
肖崇厚.1997.中药化学.上海:上海科学技术出版社
夏长秀,李绍勤,蔡万伦,张宏宇.2009.蛇床子素粉剂对5种储粮害虫生物活性研究.中国粮油学报,24(9):108~111
熊敏秋,席海涛,付永胜,孙小强.2010.新型香豆素荧光探针的合成及其对三聚氰胺的识别性能研究.有机化学,30(6):908~911
徐淑永,曾和平,魏传晚,王晓娟,谢彦.2004.生物活性香豆素的研究进展.合成化学,12(4):340~348
熊雯.2004.盐酸阿扎司琼氯化钠注射液质量标准及其在家兔体内的药代动力学研究.[硕士学位论文].成都:四川大学
于世林.2005.高效液相色谱方法及应用(第二版).北京:化学工业出版社
杨旭建,江晓梅,吴爱发.2005.HPLC测定羟甲香豆素有关物质.广东药学,15(2):13~14.
杨秀伟,徐波,吴军,舟福香,王瑞卿,崔景荣.2006.40种香豆素类化合物对人胃癌细胞株BGC和人肝癌细胞株BEL-7402细胞生长抑制活性的筛选.中国现代中药,8(11):7~9
邹爱玲,阮健,付竹霓.2003.4-甲基伞形酮半乳糖苷快速检定药品中大肠菌群的方法研究.中国药学杂志,38(6):470~471
中国药学杂志编辑部.1989.新药手册.天津:天津科学技术出版社
郑晶,黄晓蓉,汤敏英,陈彬,张温玲,黄嫦娇.2006.荧光法快速检测蔬菜中大肠杆菌菌群.食品科学,27(10):480~483
周乐.2000.有机化学实验.西安:世界图书出版西安公司
张玲.2010.尼扎替丁注射液在健康人体内的药代动力学研究.[硕士学位论文].兰州:兰州大学
庄礼珂,朱文.2009.气相色谱-质谱法分析海芒果果实的挥发油化学成分.农药,48(7):504~505
郑丽容,梁丹,陈瑜.2008.高效液相色谱法测定复方胆通胶囊中羟甲香豆素的含量.药学与临床研究,16(4):333~334.
张庆林,赵精华,毕建进,曹菊荣,宋京,吴祖泽.2003.蛇床子中3种逆转肿瘤细胞多药耐药活性香豆素.中草药,34(2):104~106
张巧艳,秦路平,田野萍,郑汉臣,黄茅,刘祖德.2000.蛇床子素对新生大鼠颅盖骨成骨细胞的作用.第二军医大学学报,21(17):935~937
张巧艳,秦路平,黄宝康,郑汉臣,王寅,王昊,陈磊.2003.蛇床子总香豆素对去卵巢大鼠骨质疏松症的作用.中国药学杂志,38(2):101~103
张巧艳,秦路平,郑汉臣,田野苹,黄茅,刘祖德.2001.蛇床子总香豆素对新生大鼠成骨细胞的作用.中成药,2(2):111~113
张韶瑜,孟林,高文远.2005.香豆素类化合物生物学活性研究进展.中国中药杂志,30(6):410~414
张为民,施惠平,李贝特,赵时敏,戚庆炜,孙念怙,黄尚志.2006.黏多糖贮积症Ⅱ型的诊断与产前诊断.中华儿科杂志,44(9):644~647
张伟,孙宗科,鲁波,王友斌,丁培,郑萍,陈西平.2010.4-甲基伞形酮辛酯试验检测水中沙门菌方法研究.卫生研究,39(3):381~383
张旋,黄宁,郑永唐.2010.我国中药来源的抗HIV天然化合物研究进展.药学学报,45(2):141~153
张晓辉,孔蕾,王扬,郑天伦.2006.水产养殖饲料黄曲霉毒素B1的E Ll SA快速检测.中国动物检疫,23(6):41
赵学平,王强,吴长兴,吴声敢,陈丽萍.2005.蛇床子素防治菜青虫药效试验.浙江农业科学,(4):310~311
张志祖,胡晓,周俐,周青,上官珠,何晓南.1995.蛇床子总香豆素的抗炎作用.赣南医学院学报,15(2):87~89
Abate A, Dimartino V, Spina P, Costa PL, Lombardo C, Santini A, Del Piano M, Alimonti P. 2001. Hymecromone in the treatment of motor disorders of the bile ducts: a multicenter, double-blind, placebo-controlled clinical study. Drugs Exp Clin Res, 27(5-6): 223~231
Abdel-Rahman Susan M, Johnson Franklin K, Gauthier-Dubois Ginette, Weston Irving E, Kearns Gregory L.2003. The bioequivalence of nizatidine (Axid) in two extemporaneously and one commercially prepared oral liquid formulations compared with capsule. Journal of Clinical Pharmacology, 43(2): 148~153
Abuknesha Ramadan A, Darwish Fatima. 2005. Coupling of enzymatic and immunoassay steps to detect E. coli: a new, highly sensitive tandem technique for the analysis of low levels of bacteria. Talanta, 65(2): 343~348
Ajaykumar Kulkarni, Sangamesh A Patil, Prema S Badami. 2009. Synthesis, characterization, DNA cleavage and in vitro antimicrobial studies of La (III), Th (IV) and VO (IV) complexes with Schiff bases of coumarin derivatives. European Journal of Medicinal Chemistry, 44(7): 2904~2912
Asres Kaleab, Seyoum Ameha, Veeresham Ciddi, Bucar Franz, Gibbons Simon. 2005. Naturally derivedanti-HIV agents. Phytother Res, 19: 557~581
Berson, S. A. and Yalow, R. S. Assay of plasma insulin in human subjects by immunolgical methods. Nature, 184: 1648
Bhattacharyya Soumya S, Paul Saili, Mandal Sushil K, Banerjee Antara, Naoual Boujedaini, Khuda-Bukhsh Anisur R. 2009. A synthetic coumarin (4-Methyl-7 hydroxy coumarin) has anti-cancer potentials against DMBA-induced skin cancer in mice. European Journal of Pharmacology, 614(1~3):128~136
Bosch Paula, Catalina Fernando, Corrales Teresa, Peinado Carmen. 2005. Fluorescent probes for sensing processes in polymers. chemistry, 11: 4314~4325
Cane Patricia A. 2009. New developments in HIV drug resistance. Journal of Antimicrobial Chemotherapy, 64(1): 137~140
Chen Keh-Shaw, Wu Chin-Chuang, Chang Fang-Rong, Chia Yi-Chen, Chiang Michael Y-N, Wang Wei-Ya, Wu Yang-Chang. 2003. Bioactive coumarins from the leaves of Murraya omphalocarpa. Planta Medica, 69(7): 654~657
Chia Yi-Chen, Chang Fang-Rong, Wang Jinn-Chyi, Wu Chin-Chung, Chiang Michael Y-N, Lan Yu-Hsuan, Chen Keh-Shaw, Wu Yang-Chang. 2008. Antiplatelet aggregation coumarins from the leaves of Murraya omphalocarpa. Molecules, 13: 122~128
Gutierrez-sanchez VC. Calvinoi-Casilda E. Perez-Mayoral R M,Martin-Aranda A J, Lopez-peinado M, Bejblova J Cejka. 2009. Coumarins preparation by Pechmann reaction under ultrasound irradiation. Synthesis of hymecromone as insecticide intermediate. Catal Lett, 128: 318~322
Collier Abby C, Tingle Malcolm D, Keelan Jeffrey A, Paxton James W, Mitchell Murray D. 2000. A highly sensitive fluorescent microplate method for the determination of UDP-glucuronosyl transferase activity in tissues and placental cell lines. Drug Metabolism and Disposition. 28(10): 1184~1186
Daisuke Kudo, Atsushi Kon, Shuichi Yoshihara, Ikuko Kakizaki, Mutsuo Sasaki, Masahiko Endo, Keiichi Takagaki. 2004 .Effect of a hyaluronan synthase suppressor, 4-methylumbelliferone, on B16F-10 melanoma cell adhesion and locomotion. Biochemical and Biophysical Research Communications, 321(4): 783~787
Deshmukh Madhavi, Pawar Pushpa, Joseph Mary, Phalgune Usha, Kashalkar Rajashree, Deshpande Nirmala R. 2008. Efficacy of 4-methyl-7-hydroxycoumarin derivatives against vectors Aedes aegypti and Culex quinquefasciatus. Indian Journal of Experimental Biology, 46(11): 788~792
Dinkelaar Jasper, Duivenvoorden Boudewijn A, Wennekes Tom, Overkleeft Herman S, Boot Rolf G, Aerts Johannes M. F. G, Codée Jeroen D. C, Mare Gijs A. van der. 2010. A Preparative synthesis of human chitinase fluorogenic substrate (4-Deoxychitobiosyl)-4-methylumbelliferone. European Journal of Organic Chemistry, (13): 2565~2570
Elmas M, Yazar E, Uney K, Karabacak A. 2006. Pharmacokinetics of flunixin after intravenous administration in healthy and endotoxaemic rabbits. Vet Res Commun, 30(1): 73~81.
Fujioka T, Furumi K, Fujii H, Okabe H, Mihashi K, Nakano Y, Matsunaga H, Katano M, Mori M. 1994. Antiproliferative constituents from umbelliferae plants.V.A new furanocoumarin and falcarindiol furanocoumarin ethers from the root of Angelica japonica. Chem Pharm Bull, 47 (1): 96~100
Gao Wenzhong, Xing Bengang, Tsien Roger Y, Rao Jianghong. 2003. Novel fluorogenic substrates for imaging a-lactamase gene expression. Journal of the American Chemical Society, 125 (37):11146~11147
Garrett Edward R, Venitz Jurgen, Eberst Kathleen, Cerda James J. 1993. Pharmacokinetics and bioavailabilities of hymecromone in human volunteers. Biopharmaceutics and Drug disposition, 14:13~39
Heistermann HP, Krawzak HW, Andrejeweski K, Hohlbach G. 1997. Pharmacologic modification of postprandial bile duct kinetics—ultrasound measurement of the lumen of the bile duct. Ultraschall Med, 18(2): 84~87
Hideaki Nakazawa, Shuichi Yoshihara, Daisuke Kudo. 2006. 4-methylumbelliferone, a hyaluronan synthase suppressor, enhances the anticancer activity of gemcitabine in human pancreatic cancer cell. Cancer Chemother Pharmacol, 57: 165~170
Hoffmann RM, Schwarz G, Pohl C, Ziegenhagen DJ, Kruis W. 2005. Bile acid-independent effect of hymecromone on bile secretion and common bile duct motility. Dtsch Med Wochenschr. 130(34-35): 1938~1943
Ikuko Kakizaki, Keiichi Takagaki, Yasufumi Endo. 2001. Effect of 4-methylumbelliferone on hyaluronan synthesis of Streptococcus equi FM100. International Congress Series, 1223: 269~272
Johnson Mallory O, Charlebois Edwin, Morin Stephen F, Catz Sheryl L, Goldstein Rise B, Remien Robert H, Rotheram-Borus Mary Jane, Mickalian Joanne D. 2005. Perceived adverse effects of antiretroviral therapy. Journal of Pain and Symptom Management, 29(2): 193~205
Kanji Tanaka, Ryousuke Taniguchi, Tsuyoshi Higuchi, Takashi Ozaki, Hideki Mizunuma, Keiichi Takagaki. 2007. 4-Methylumbelliferone inhibits hyaluronate synthesis in human uterine cervical fibroblasts. Journal of Obstetrics and Gynaecology Research, 33(6): 772~776
Kashman Yoel, Gustafson Kirk R, Fuller Richard W, Cardellina John H, McMahon James B, Robert W Currens. 1992. The Calanolides, a Novel HIV-inhibitory class of coumarin derivatives from the tropical rainforest tree, Calophyllum lanigerum. J.Med.Chem, 35: 2735~2743
Kostova Irena P, Manolov Ilia I, Nicolova Irina N, Danchev Nicolay D. 2001. New metal complexes of 4-methyl-7-hydroxycoumarin sodium salt and their pharmacological activity. Il Farmaco. 56: 707~713
Krawzak HW, Heistermann HP, Andrejewski K, Hohlbach G. Postprandial bile-duct kinetics under the influence of 4-methylumbelliferone (hymecromone). 1995. Int J Clin Pharmacol Ther, 33(10): 569~572
Kultti Anne, Pasonen-Sepp?nen Sanna, Jauhiainen Marjo. 2009. 4-Methylumbelliferone inhibits hyaluronan synthesis by depletion of cellular UDP-glucuronic acid and down regulation of hyaluronan synthasen 2 and 3. Experimental cell Research, 315(11): 1914~1923
Lee Thomas Tung-Ying Kashiwada Yoshiki, Huang Li, Snider James, Cosentino Mark, Lee Kuo-Hsiung. 1994. Suksdorfin: an anti-HIV principle from Lomatium suksdorfii, its structure-activity correlation with related coumarins, and synergistic effects with anti-AIDS nucleosides. Bioorg Med Chem, 2: 1051~1056.
Lu You You, Wang Yu Guang, Dai Bin, Dai Yi Qi, Wang Zhao, Fu Zheng Wei, Zhu Qing. 2008. A novel nuorogenic probe for monoamine oxidase assays. Chinese chemical letters, 19: 947~950
Makot Nakai, Shuichi Yoshihara, Hajime Morohashi. 2008. Effects of hyaluronan synthase inhibitors 4-methylumbelliferone and 4-methylesculetin on human pleural malignant mesothelioma cells (NCI-H2052). Hirosaki Med, 59: 118~127
Martino Sabata, Tiribuzi Roberto, Tortori Andrea, Conti Daniele, Visigalli Ilaria, Lattanzi Annalisa, Biffi Alessandra, Gritti Angela, Orlacchio Aldo. 2009. Specific determination of beta-galactocerebrosidase activity via competitive inhibition of beta-galactosidase. Clin Chem, 55(3): 541~548
Miyauchi Seiji, Sugiyama Yuichi, Iga Tatsuji, Hanano Manabu. 1989. The conjugative metabolism of 4-methylumbelliferone and deconjugation to the parent drug examined by isolated perfused liver and in vitro liver homogenate of rats. Chem Pharm Bull (Tokyo), 37(2): 475~480
Miyauchi Seiji, Sugiyama Yuichi, Sawada Yasufumi, Morita Kaname, Iga Tatsuji, Hanano Manabu. 1987. Kinetics of hepatic transport of 4-methylumbelliferone in rats. Analysis by multiple indicator dilution method. J Pharmacokinet Biopharm, 15(1): 25~38
Morita Kaname, Sugiyama Yuichi, Hanano Manabu. 1986. Pharmacokinetic study of 4-methylumbellifer
-one in rats: influence of dose on its first-pass hepatic elimination. J. Pharmacobio- Dyn, 9(2): 117~124
Mulder Gerard J, Brouwer Sybolt, Weitering Jeannette G, Scholtens Egbert, Pang K Sandy. 1985. Glucuronidation and sulfation in the rat in vivo. The role of the liver and the intestine in the in vivo clearance of 4-methylumbelliferone. Biochem Pharmacol, 34(8): 1325~1329
Nakamura Toshiya, Funahashi Masaru, Takagaki Keiichi, Munakata Hidekazu, Tanaka Kanji, Saito Yoshiharu, Endo Masahiko. 1997. Effect of 4-methylumbelliferone on cell-free synthesis of hyaluronic acid. Biochem Mol Biol Int, 43(2): 263~268
Nyberg SL, Mann HJ, Hu MY, Payne WD, Hu WS, Cerra FB, Remmel RP. 1996. Extrahepatic metabolism of 4-methylumbelliferone and lidocaine in the anhepatic rabbit. Drug Metab Dispos, 24(6): 643-648
Orhan Ilkay, Tosun Fatma, Sener Bilge. 2008. Coumarin, anthroquinone and stilbene derivatives with anticholinesterase activity. Z Naturforsch C, 63(5~6): 366~370
Ratna1 Sanjeev, Masato Chiba, Lopamudra Bandyopadhyay, Pang K. Sandy. 1993. Futile cycling between 4-methylumbelliferone and its conjugates in perfused rat liver. Hepatology, 17(5): 838~853
Rosskopf F, Kraus J, Franz G. 1992. Immunological and antitumor effects of coumarin and some derivatives.Pharmazie, 47(2): 139~142
Sabri Noor, Yassaa Narguess, Fazeli Mohammad Reza, Alavi Seyed Hamid Reza, Fouladi Fatemeh, Salimi Ladan, Manayi Azadeh, Tofighi Zahra. 2009. Antibacterial activity of Peucedanum ruthenicum, Johreniopsis seseloides and Cervaria cervariifolia extracts. Iranian Journal of Pharmaceutical Sciences, 5(1): 37~42
Schinkovitz A, Gibbons S, Stavri M, Cocksedge M J, Bucar F. 2003. Ostruthin: an antimycobacterial coumarin from the roots of Peucedanum ostruthium. Plantamedica, 69 (4): 369~371
Shetty M, Shivananda PG. 1994. Rapid identification of Salmonella typhimurium in stools by using 4-methylumbelliferone derivatives. Indian J Pathol Microbiol, 37(1): 91~95
Shigefumi Takeda, Masaki Aburada. 1981. The choleretic mechanism of coumarin compounds and phenolic compounds. Pharmacentical Society of Japan, 4: 724~734
Shuichi Yoshihara, Atsushi Kon, Daisuke Kudo, Hideaki Nakazawa, Ikuko Kakizaki, Mutsuo Sasaki, Masahiko Endo, Keiichi Takagaki. 2005. A hyaluronan synthase suppressor, 4-methylumbelliferone, inhibits liver metastasis of melanoma cells. Febs Letters, 579(12): 2722~2726
Suzuki Hiroshi, Sawada Yasufumi, Sugiyama Yuichi, Iga Tatsuji, Hanano, Manabu. 1987 . Pharmacokinetic study of 4-methylumbelliferone in mice. Pharmaceutical Society of Japan, 10(2): 195~200
Toshiya Nakamura, Takashi Ishikawa, Naoki Nanashima, Tomisato Miura, Hiroyuki Nozaka, Rie Nakaoka,Tatsusuke Sato. 2002. 4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts, Biochemical and Biophysical Research Communications, 298(5): 646~650
Twarock S?ren, Tammi Markku I, Savani Rashmin C, Fischer Jens W. 2010. Hyaluronan stabilizes focal adhesions, filopodia, and the proliferative phenotype in esophageal squamous carcinoma cells. The Journal of biological chemistry, 285(30): 23276~23284
Wang Liping, Yang Xiao-Feng, Zhao Minglei. 2009. A 4-Methylumbelliferone-based fluorescent probe for the sensitive detection of captopril. J Fluoresc, 19(4): 593~599
Widelski Jaroslaw, Popova Milena, Graikou Konstantia, Glowniak Kazimierz, Chinou Ioanna. 2009. Coumarins from Angelica lucida L. - antibacterial activities. molecules, 14: 2729~ 2734
Yang Xiaofeng, Wang Liping, Zhao Minglei, Qi Haiping, Wu Yao. 2010. A 4-Methylumbelliferone-based fluorescent probe for sodium new houttuyfonate. Chin. J. Chem, 28(8): 1469~1474
Yoshito Shibuya, Mikiko Nara, Akir Fukuoka, Tetsuo Takahashi, Yoshihisa Nishikawa. 1998. Induction of apoptosis and changes of macromolecule synthesis during differentiation of HL-60 cells by 4-methylumbelliferone. Tokai: Proceedings of the School of Engineering of Tokai University
Zhoua Ping, Takaishi Yoshihisa, Duana Hongquan, Chena Bei, Hondab Gisho, ItohbMichiho, Takedac Yoshio, KodzhimatoVd Olimjon K, Lee Kuo-Hsing. 2000. Coumarins and bicoumarin from Ferula sumbul: anti-HIV activity and inhibition of cytokine release. Phytochemistry, 53: 689~697