苔类植物中双联苄化合物的质谱和核磁共振规律研究及其在高通量筛选中的应用
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摘要
苔藓植物(Bryophytes)是由水生向陆生过渡的高等植物,虽分布面积广,但密度很小,种间杂生,不易区别和分离,难以大量采集,给常规系统的化学成分分离研究工作带来困难。为快速掌握苔类植物中所含的已知和新联苄类化合物的结构信息,为苔藓植物植物化学研究提供指导,避免研究工作的盲目性,增强分离的目的性并提高分离的效率,同时为其他药用植物化学成分的高通量筛选提供有益的借鉴,建立一种快速高效准确的筛选方法势在必行。
质谱是一种有效地确定有机化合物结构信息的方法。一级质谱和多级质谱数据不仅能够提供分子量信息,结合元素组成数据还可以提供结构信息,因此在新的候选药物高通量筛选方面发挥着越来越重要的作用。
基于此,本文建立了采用气相色谱-质谱联用法(Gas chromatography-massspectrometry,GC-MS)和液相色谱-质谱联用法(Liquid chromatography-massspectrometry,LC-MS)快速筛选苔藓植物中联苄化合物的方法。
核磁共振波谱(NMR)技术在有机化合物结构确证和解析中发挥越来越重要的作用,而联苄化合物的NMR数据显示一定的规律性,本文总结了各种类型联苄化合物的波谱学规律,为联苄化合物的结构确证提供依据。
为了快速筛选苔类植物中已知联苄和微量的未知联苄,本文采用气相(GC)飞时间高分辨质谱(EI-TOF)和液相色谱(LC)电喷雾三重四极杆质谱(ESI-TQ-MS)对来源于苔类植物的双联苄化合物进行详细的质谱分析。首先,通过对1种单联苄和15种结构相似的双联苄化合物对照品进行质谱分析,获得其质谱裂解规律,推测了二级碎片离子的可能结构,并通过精确分子量的测定进行进一步验证;在此基础上对双联苄类化合物可能的裂解途径及裂解机制进行了推断。
本文所涉及的15种双联苄化合物根据单联苄间连接方式的不同分三种结构类型:单醚键相连(A类)、双醚键相连(B类)、以及单醚键和C-C键相连(C类),三种结构类型的双联苄具有不同的EI-MS和ESI-MS/MS质谱特征,通过比较这些信息可以确定双联苄化合物的结构类型和烷氧取代基的数量。本方法可以在一定程度上区分异构体,但是联苄间连接位点和联苄间醚键的连接位点难以确定。此外,在此基础上建立了一种简单快速的液相色谱-二极管阵列-串联质谱(LC-DAD/MS)方法,可用于筛选苔藓类粗提物中ppm水平的双联苄类化合物。本章采用LC-DAD/MS法对采自中国不同地区的三种苔类植物地钱(Marchantiapolymorpha),无纹紫背苔(Ptagiochasm intermedium)和花萼苔(Asterella angusta)进行了筛选,通过比较三种苔藓类植物的质谱数据,紫外吸收光谱特征和色谱保留行为,分别检测出7/12,8/5和8/9已知/未知的双联苄化合物。
联苄类化合物结构的相似性也体现在其核磁共振波谱数据呈现一定规律。本文总结了联苄化合物的核磁共振波谱数据规律。双联苄化合物都具有四个苯环,通过亚甲基或次甲基相连,其核磁共振波谱上表现出某些共性,~1H NMR谱中化学位移值(δ_H)位于5.10-7.40 ppm左右出现10-16个芳环质子信号,2.0-3.0 ppm左右有6-8个亚甲基质子信号。~(13)C NMR谱中芳环碳信号的化学位移值(δ_C)位于110-160ppm,而2-4个亚甲基碳信号则出现在δ_C 30-40 ppm附近。
苯环上取代基的引入可以引起其波谱数据的改变,与甲氧基、羟基及醚氧键相连的碳的化学位移值(δ_C)一般位于140-160 ppm左右,甲氧基、羟基的取代还可使其相邻碳的化学位移值(δ_C)较无取代时向高场移动5-10 ppm。不同取代模式下苯环上的氢具有不同的偶合裂分,苯环上二取代类型主要为对位取代,多出现在A环上,表现为AA'BB'偶合。苯环上三取代模式最为常见,而且多发生在B,D环,主要为1,2,4-三取代形式,许多化合物的氢谱可呈现两个二重峰(d)及一个双二重峰(dd)。苯环上的四取代和多取代形式较为容易确认,其氢谱上表现为位于δ_H 6.60以及6.90 ppm左右的两个单峰信号或δ_H 6.60-7.10 ppm范围内两个相互耦合的d峰氢信号。
不同连接位点下,双联苄类化合物表现出不同的NMR谱图特征。以醚氧键相连的苯环碳的化学位移较以C-C键直接相连苯环碳上的化学位移值低场位移20-30ppm。所有具有1-2′醚氧键的连接类型中,3′位的质子高场位移,δ_H位于4.84-5.60ppm之间。本文从A,C环通过醚氧键相连(A-O-C)、A,C环以C-C键直接相连(A-C)、B,D环以醚氧键相连(B-O-D)、以及B,D环以碳碳键直接相连(B-D)四个方面加以阐述。在分析双联苄化合物结构分类的基础上,分析此类化合物的波谱数据(~1H和~(13)CNMR)特征,找到快速有效的解析双联苄化合物结构的方法。
Bryophytes are higher plants from aquatic to terrestrial transition.Although the plants are widely distributed,it is difficult to collect enough amount for the conventional separation and isolation of the chemical compositions,due to the low density,mixed species,and difficult distinction.
Mass spectrometry(MS) is an effective method to determine the structural information of organic compounds.Multi-stage MS-MS data not only provide molecular weight information,but also give the structural information,combined with the data elements.Therefore,it has played an important role in the new high-throughput screening of new leads.
To provide a fast-track approach for discovering the known and new bibenzyl compounds form liverworts,guide the phytochemical study of bryophytes,prevent blindness,and enhance the purpose of separation and to improve the efficiency of separation,we established a method based on gas chromatography mass spectrometry (GC-MS) and liquid chromatography mass spectrometry(LC-MS) in the rapid screening of bibenzyl compounds from bryophytes.
To achieve a rapid screening of known and unknown bibenzyls from liverworts,a method using gas chromatography(GC) electron impact time-of-flight(EI-TOF) and liquid chromatography(LC) ESI triple quadrupole mass spectrometry(ESI-TQ-MS) was developed to detailedly analysize mass spectrometry of bisbibenzyl compounds. Firstly,one bibenzyl and 15 structurally similar compounds as bisbibenzyl standards were analyzed to obtain the mass spectrometry fragmentation patterns,and the possible secondary fragment ions were also carried out,to find the possible fragmentation rules and mechanism.
Fifteen bisbibenzyls were classified into three types according the connecting styles between two bibenzyl units:one C-O-C connection(group A);two C-O-C connections(group B);one C-O-C connection;and one C-C connection(group C).The above three types of bisbenzyls possessed different EI-MS and ESI-MS/MS fragments, and the connecting styles and substituents would be verified by MS fragments.The isomers were also distinguished,however,the connecting sites and C-O-C sites were unable to be assigned.On the basis of above results,a simple and rapid liquid chromatography diode array tandem mass spectrometry(LC-DAD/MS) method was developed for screening of benzyl compounds form the Bryophytes crude extracts in the ppm level.
Three China liverworts Marehantia polymorpha,Pagiochasma intermedium,and Asterella angusta colleted from three different regions were screened using the LC-DAD/MS method.By comparing their MS data,UV absorption spectra and retention characteristics,7/12,8/5 and 8/9(known/unknown) bisbibenzyl compounds were detected in the above three liverworts.
The bisbibenzyl,which comprise four benzene rings by methylene or methylene-linked,show some commonalities in its nuclear magnetic resonance spectroscopy.Chemical shift value in ~1H NMR(δ_H) presents ten to sixteen aromatic proton signals at about 5.10-7.40 ppm,with six to eight methylene proton signals atδ_H 2.0-3.0 ppm.In the ~(13)C NMR spectrum,chemical shift values ofδ_C 110-160 ppm indicate aromatic carbons,and two to four methylene carbon signals often appear at aboutδ_C 30-40 ppm.
The introduction of substituents on the benzene ring can cause changes in its spectral data.The chemical shift value of carbon linked to methoxy,hydroxyl,and biphenyl ether located at aboutδ_C 140-160 ppm,with a 5-10 ppm upfield shift to the carbon adjacent to it.Different substituted benzene ring has a different split coupling. Disubstituted benzene rings on the type of main-substituted with para-substituted appear AA'BB' coupling in ring A.Trisubstituted patterns on benzene rings,1,2,4-trisubstituted styles is encountered frequently and occurred mainly on the rings B and D. The pattern present two double peaks(d) and a double-double peak(dd) in the ~1H NMR spectrum.When there are more than three substituents,the pattern is easily identifiable with two singlets atδ_H 6.60-6.90 ppm or two doublets atδ_H 6.60-7.10 ppm.
With the different connection,the bisbibenzyl compounds show different characteristics of the NMR spectrum.Compared to the presence of biphenyl linkage,the chemical shift values of carbon linked to the biphenyl ether shift downfield by 20-30 ppm.Of all the bisbibenzyls with 1-2 'ether oxygen bond in connection type,show a highfield-shifted characteristic resonance for H-3' withδ_H at 4.84-5.60 ppm.The text display the result with four parts which are biphenyl ether linkage between A,C ring (A-O-C),biphenyl linkage between them(A-C),biphenyl ether linkage between B,D ring(B-O-D),as well as biphenyl linkage of B,D ring(B-D).Based on the analysis of the structure of bisbibenzyl compounds and the observation of the spectral data of these compounds(~1H and ~(13)C NMR),we could find a analysis approach for structure elucidation quickly and efficiently.
质谱是一种有效地确定有机化合物结构信息的方法。一级质谱和多级质谱数据不仅能够提供分子量信息,结合元素组成数据还可以提供结构信息,因此在新的候选药物高通量筛选方面发挥着越来越重要的作用。
基于此,本文建立了采用气相色谱-质谱联用法(Gas chromatography-massspectrometry,GC-MS)和液相色谱-质谱联用法(Liquid chromatography-massspectrometry,LC-MS)快速筛选苔藓植物中联苄化合物的方法。
核磁共振波谱(NMR)技术在有机化合物结构确证和解析中发挥越来越重要的作用,而联苄化合物的NMR数据显示一定的规律性,本文总结了各种类型联苄化合物的波谱学规律,为联苄化合物的结构确证提供依据。
为了快速筛选苔类植物中已知联苄和微量的未知联苄,本文采用气相(GC)飞时间高分辨质谱(EI-TOF)和液相色谱(LC)电喷雾三重四极杆质谱(ESI-TQ-MS)对来源于苔类植物的双联苄化合物进行详细的质谱分析。首先,通过对1种单联苄和15种结构相似的双联苄化合物对照品进行质谱分析,获得其质谱裂解规律,推测了二级碎片离子的可能结构,并通过精确分子量的测定进行进一步验证;在此基础上对双联苄类化合物可能的裂解途径及裂解机制进行了推断。
本文所涉及的15种双联苄化合物根据单联苄间连接方式的不同分三种结构类型:单醚键相连(A类)、双醚键相连(B类)、以及单醚键和C-C键相连(C类),三种结构类型的双联苄具有不同的EI-MS和ESI-MS/MS质谱特征,通过比较这些信息可以确定双联苄化合物的结构类型和烷氧取代基的数量。本方法可以在一定程度上区分异构体,但是联苄间连接位点和联苄间醚键的连接位点难以确定。此外,在此基础上建立了一种简单快速的液相色谱-二极管阵列-串联质谱(LC-DAD/MS)方法,可用于筛选苔藓类粗提物中ppm水平的双联苄类化合物。本章采用LC-DAD/MS法对采自中国不同地区的三种苔类植物地钱(Marchantiapolymorpha),无纹紫背苔(Ptagiochasm intermedium)和花萼苔(Asterella angusta)进行了筛选,通过比较三种苔藓类植物的质谱数据,紫外吸收光谱特征和色谱保留行为,分别检测出7/12,8/5和8/9已知/未知的双联苄化合物。
联苄类化合物结构的相似性也体现在其核磁共振波谱数据呈现一定规律。本文总结了联苄化合物的核磁共振波谱数据规律。双联苄化合物都具有四个苯环,通过亚甲基或次甲基相连,其核磁共振波谱上表现出某些共性,~1H NMR谱中化学位移值(δ_H)位于5.10-7.40 ppm左右出现10-16个芳环质子信号,2.0-3.0 ppm左右有6-8个亚甲基质子信号。~(13)C NMR谱中芳环碳信号的化学位移值(δ_C)位于110-160ppm,而2-4个亚甲基碳信号则出现在δ_C 30-40 ppm附近。
苯环上取代基的引入可以引起其波谱数据的改变,与甲氧基、羟基及醚氧键相连的碳的化学位移值(δ_C)一般位于140-160 ppm左右,甲氧基、羟基的取代还可使其相邻碳的化学位移值(δ_C)较无取代时向高场移动5-10 ppm。不同取代模式下苯环上的氢具有不同的偶合裂分,苯环上二取代类型主要为对位取代,多出现在A环上,表现为AA'BB'偶合。苯环上三取代模式最为常见,而且多发生在B,D环,主要为1,2,4-三取代形式,许多化合物的氢谱可呈现两个二重峰(d)及一个双二重峰(dd)。苯环上的四取代和多取代形式较为容易确认,其氢谱上表现为位于δ_H 6.60以及6.90 ppm左右的两个单峰信号或δ_H 6.60-7.10 ppm范围内两个相互耦合的d峰氢信号。
不同连接位点下,双联苄类化合物表现出不同的NMR谱图特征。以醚氧键相连的苯环碳的化学位移较以C-C键直接相连苯环碳上的化学位移值低场位移20-30ppm。所有具有1-2′醚氧键的连接类型中,3′位的质子高场位移,δ_H位于4.84-5.60ppm之间。本文从A,C环通过醚氧键相连(A-O-C)、A,C环以C-C键直接相连(A-C)、B,D环以醚氧键相连(B-O-D)、以及B,D环以碳碳键直接相连(B-D)四个方面加以阐述。在分析双联苄化合物结构分类的基础上,分析此类化合物的波谱数据(~1H和~(13)CNMR)特征,找到快速有效的解析双联苄化合物结构的方法。
Bryophytes are higher plants from aquatic to terrestrial transition.Although the plants are widely distributed,it is difficult to collect enough amount for the conventional separation and isolation of the chemical compositions,due to the low density,mixed species,and difficult distinction.
Mass spectrometry(MS) is an effective method to determine the structural information of organic compounds.Multi-stage MS-MS data not only provide molecular weight information,but also give the structural information,combined with the data elements.Therefore,it has played an important role in the new high-throughput screening of new leads.
To provide a fast-track approach for discovering the known and new bibenzyl compounds form liverworts,guide the phytochemical study of bryophytes,prevent blindness,and enhance the purpose of separation and to improve the efficiency of separation,we established a method based on gas chromatography mass spectrometry (GC-MS) and liquid chromatography mass spectrometry(LC-MS) in the rapid screening of bibenzyl compounds from bryophytes.
To achieve a rapid screening of known and unknown bibenzyls from liverworts,a method using gas chromatography(GC) electron impact time-of-flight(EI-TOF) and liquid chromatography(LC) ESI triple quadrupole mass spectrometry(ESI-TQ-MS) was developed to detailedly analysize mass spectrometry of bisbibenzyl compounds. Firstly,one bibenzyl and 15 structurally similar compounds as bisbibenzyl standards were analyzed to obtain the mass spectrometry fragmentation patterns,and the possible secondary fragment ions were also carried out,to find the possible fragmentation rules and mechanism.
Fifteen bisbibenzyls were classified into three types according the connecting styles between two bibenzyl units:one C-O-C connection(group A);two C-O-C connections(group B);one C-O-C connection;and one C-C connection(group C).The above three types of bisbenzyls possessed different EI-MS and ESI-MS/MS fragments, and the connecting styles and substituents would be verified by MS fragments.The isomers were also distinguished,however,the connecting sites and C-O-C sites were unable to be assigned.On the basis of above results,a simple and rapid liquid chromatography diode array tandem mass spectrometry(LC-DAD/MS) method was developed for screening of benzyl compounds form the Bryophytes crude extracts in the ppm level.
Three China liverworts Marehantia polymorpha,Pagiochasma intermedium,and Asterella angusta colleted from three different regions were screened using the LC-DAD/MS method.By comparing their MS data,UV absorption spectra and retention characteristics,7/12,8/5 and 8/9(known/unknown) bisbibenzyl compounds were detected in the above three liverworts.
The bisbibenzyl,which comprise four benzene rings by methylene or methylene-linked,show some commonalities in its nuclear magnetic resonance spectroscopy.Chemical shift value in ~1H NMR(δ_H) presents ten to sixteen aromatic proton signals at about 5.10-7.40 ppm,with six to eight methylene proton signals atδ_H 2.0-3.0 ppm.In the ~(13)C NMR spectrum,chemical shift values ofδ_C 110-160 ppm indicate aromatic carbons,and two to four methylene carbon signals often appear at aboutδ_C 30-40 ppm.
The introduction of substituents on the benzene ring can cause changes in its spectral data.The chemical shift value of carbon linked to methoxy,hydroxyl,and biphenyl ether located at aboutδ_C 140-160 ppm,with a 5-10 ppm upfield shift to the carbon adjacent to it.Different substituted benzene ring has a different split coupling. Disubstituted benzene rings on the type of main-substituted with para-substituted appear AA'BB' coupling in ring A.Trisubstituted patterns on benzene rings,1,2,4-trisubstituted styles is encountered frequently and occurred mainly on the rings B and D. The pattern present two double peaks(d) and a double-double peak(dd) in the ~1H NMR spectrum.When there are more than three substituents,the pattern is easily identifiable with two singlets atδ_H 6.60-6.90 ppm or two doublets atδ_H 6.60-7.10 ppm.
With the different connection,the bisbibenzyl compounds show different characteristics of the NMR spectrum.Compared to the presence of biphenyl linkage,the chemical shift values of carbon linked to the biphenyl ether shift downfield by 20-30 ppm.Of all the bisbibenzyls with 1-2 'ether oxygen bond in connection type,show a highfield-shifted characteristic resonance for H-3' withδ_H at 4.84-5.60 ppm.The text display the result with four parts which are biphenyl ether linkage between A,C ring (A-O-C),biphenyl linkage between them(A-C),biphenyl ether linkage between B,D ring(B-O-D),as well as biphenyl linkage of B,D ring(B-D).Based on the analysis of the structure of bisbibenzyl compounds and the observation of the spectral data of these compounds(~1H and ~(13)C NMR),we could find a analysis approach for structure elucidation quickly and efficiently.
引文
[1]J.Gorham,M.Tori,Y.Asakawa,The Biochemistry of the Stilbenoids,Chapman &Hall,London,1995,p.1
[2]Majumder,P.L.;Roychowdhury,M.;Chakraborty,S.Phytochemistry,1997,44,167-172.
[3]Hernandez-Romero,Y.;Rojas,J.I.;Castillo,R.;Rojas,A.;Mata,R.J.Nat.Prod.,2004,67,160.
[4]Majumder,P.L.;Guha,S.;Sen,S.Phytochemistry,1999,55,1365.
[5]Leong,Y.-W.;Kang,C.-C.;Harrison,L.J.;Powell,A.D.Phytochemistry,1997,44,157.
[6]Majumder,P.L.;Chakraborty,S.;Sen,S.J..Indian Chem.Soc.,2002,79,169.
[7]Bai,L.;Masukawa,N.;Yamaki,M.;Takagi,S.Phytochemistry,1997,44,1565.
[8]Estrada,S.;Rojas,A.;Mathison,Y.;Israel,A.;Mata,R.Planta Med.,1999,65,109.
[9]Lin,Y.-L.;Chen,W.-P.;Macabalang,A.D.Chem.Pharm.Bull.,2005,53,1111.
[10]Bai,L.;Masukawa,N.;Yamaki,M.;Takagi,S.Phytochemistry,1998,47,1637.
[11]Bai,L.;Masukawa,N.;Yamaki,M.;Takagi,S.Phytochemistry,1998,48,327.
[12]Anton,H.;Kraut,L.;Mues R.;Morales,Z.M.I.Phytochemistry,1997,46,1069.
[13]Baek,S.-H.,Phipps,R.K.;Perry,N.B.J..Nat.Prod.,2004,67,718.
[14]Ma,G.X.;Xu,G.J.;Xu,L.S.;Wang Z.T.;Kickuchi,T.Acta Pharm.Sin.,1996,31,222.
[15]Eloff,J.N.;Famakin,J.O.;Katerere,D.R.P.Afr.J.Biotechnol.,2005,4,1167.
[16]Ye,Q.;Zhao,W.Planta med.,2002,68,723.
[17]Fan,C.Q.;Zhao,W.M.;Qin,G.W.Chin.Chem.Lett.,2000,11,705.
[18]Kostecki,K.;Engelmeier,D.;Pacher,T.;Hofer,O.;Vajrodaya,S.;Greger,H.Phytochemistry,2004,65,99.
[19]Yoshida,T.;Hashimoto,T.;Takaoka,S.;Kan,Y.;Tori,M.;Asakawa,Y.Tetrahedron,1996,52,14487.
[20]Biondi,D.M.;Rocco,C.;Ruberto,G.J..Nat.Prod.,2005,68,1099.
[21]Bi,Z.M.;Yang,L.;Wang,Z.T.;Xu,L.S.;Xu,G.J.Chin.Chem.Lett.,2002,3,535.
[22]Bi,Z.;Wang,Z.;Xu,L.Acta Pharm.Sin..,2004,46,124.
[23]Anton,H.;Schoeneborn,R.;Mues,R.Phytochemistry,1999,52,1639.
[24]Rycroft,D.S.,Cole,W.J.;Aslam,N.Phytochemistry,1998,49,145.
[25]Zhao,W.,Qin,G.;Ye,Y.;Xu R.;Le,X.Phytochemistry.1995,38,711.
[26]Xiao,K.;Xuan,L.;Xu,Y.;Bai,D.;Zhong,D.Chem.Pharm.Bull.,2002,50,605.
[27]von Reuβ S.H.;K(o|¨)nig,W.A.Phytochemistry,2004,65,3113.
[28]Lou,H.X.;Li,G.Y.;Wang,F.Q.J..Asian Nat.Prod.Res.,2002,4,87.
[29]Fan,C.;Wang,W.;Wang,Y.;Qin,G.;Zhao.W.Phytochemistry,2001,57,1255
[30]Miyazawa,M.;Shimamura,H.;Nakamura,S.;Kameoka,H.J..Agric.Food Chem.,1997,45,2849.
[31]Zhang,G.-N.;Zhang,C.-F.;Wang,Z.-T.;Xu,L.-S.Chin.J.Nat.Med.,2004,2,78.
[32]Cullmann,F.;Becker,H.;Pandolfi,E.;Roeckner E.;Eicher,T.Phytochemistry,1997,45,1235.
[33]Jarevang,T.;Nilsson,M.-C.;Wallstedt,A.;Odham,G.;Sterner,O.Phytochemisty,1998,48,893.
[34]Han,G.X.;Wang,L.X.;Gu,Z.B.;Zhang,W.D.Acta Pharm.Sin..,2002,37,194.
[35]Han,G.X.;Wang,L.X.;Gu,Z.B.;Zhang,W.D.;Chen,H.S.Chin.Chem.Lett.,2002,13,231.
[36]Flegel,M.;Adam,K.-P.;Becker,H.Phytochemistry,1999,52,1633.
[37]Chen,C.-C.;Huang,Y.-L.;Teng,C.-M.Planta Med.,2000,66,372.
[38]Connolly,J.D.;Rycroft,D.S.;Srivastava,D.L.;Cole,W.J.;Ifeadike,P.;Kimbu,S.F.;Singh,J.;Hughes,M.;Thom,C.;Gerhard,U.;Organ,A.J.;Smith,R.J.;Harrison,L.J.Phytochemsitry,1999,50,1159.
[39]Miyazawa,M.;Shimamura,H.;Nakamura,S.;Sugiura,W.;Kosaka,H.;Kameoka,H.J.Agric.Food Chem.,1999,47,2163.
[40]Bai,L.;Yamaki,M.;Takagi,S.Phytochemistry,1996,42,853.
[41]Pacher,T.;Seger,C.;Engelmeier,D.;Vajrodaya,S.;Hofer,O.;Greger,H.J..Nat.Prod.,2002,65,820.
[42]Zidorn,C.;Lohwasser,U.;Pschorr,S.;Salvenmoser,D.;Ongania,K.H.;Ellmerer,E.P.;Borner,A.;Stuppner,H.Phytochemistry,2005,66,1691.
[43]Kunz,S.;Becker,H.Phytochemistry,1994,36,675.
[44]Bardon,A.;Mitre,G.B.;Kamiya,N.;Toyota,M.;Asakawa,Y.Phytochemistry,2002,59,205.
[45]Wu,P.-L.;Hsu,Y.-L.;Zao,C.-W.;Damu A.G.;Wu,T.-S.J.Nat.Prod.,2005,68,1180.
[46]Apisantiyakom,S.;Kittakoop,P.;Manyum,T.;Kirtikara,K.;Bremner,J.B.;Thebtaranonth,Y.Chem.Biodiv.,2004,1,1694.
[47]Kraut,L.;Mues,R.;Zinsmeister,H.D.Phytochemistry,1997,45,1249.
[48]Biondi,D.M.;Rocco,C.;Ruberto,G.J.Nat.Prod.,2003,66,477.
[49]Toyota,M.;Kinugawa,T.;Asakawa,Y.Phytochemistry,1994,37,859.
[50]Toyota,M.;Shimamura,T.;Ishii,H.;Renner,M.;Braggins,J.;Asakawa,Y.Chem.Pharm.Bull.,2002,50,1390.
[51]Nagashima,F.;Kuba,Y.;Asakawa,Y.Chem.Pharm.Bull.,2006,54,902.
[52]Toyota,M.;Nakaishi,E.;Asakawa,Y.Phytochemistry,1996,41,833.
[53]Manfredi,K.P.;Vallurupalli,V.;Demidova,M.;Kindscher,K.;Pannell,L.K.Phytochemistry,2001,58,153.
[54]Kittakoop,P.;Kirtikara,K.;Tanticharoen,M.;Thebtaranonth,Y.Phytochemistry,2000,55,349.
[55]Kunz,S.;Becker,H.Phytochemistry,1992,31,3981.
[56]Schwikkard,S.;Zhou,B.N.;Glass,T.E.;Sharp,J.L.;Mattern,M.R.;Johnson,R.K.;Kingston,D.G.J.Nat.Prod.,2000,63,457.
[57]Zhao,C.S.;Zhao,W.M.Chin.Chem.Lett.,2003,14,276.
[58]Han,G.;Wang,L.;Zhang,W.;Yang,Z.;Li,T.;Jiang T.;Liu,W.Acad.J.Sec.Mil.Med.Univ.,2002,23,443.
[59]Feng,W.;Cao,X.;Kuang,H.;Zheng,X.Acta Pharm.Sin.,2005,40,1131.
[60]Lee,K.Y.;Sung,S.H.;Kim,Y.C.J.Nat.Prod.,2006,69,679.
[61]Zidorn,C.;Ellmerer-M(u|¨)ller,E.P.;Stuppner,H.Helv.Chim.Acta,2000,83,2920.
[62]Zidorn,C.;Spitaler,R.;Ellmerer-M(u|¨)ller,E.P.;Perry,N.B.;Gerh(a|¨)user,C.;Stuppner,H.Z Naturforsch,2002,57C,614.
[63]Zidom,C.;Ellmerer-Miiller,E.P.;Sturm,S.;Stuppner,H.Phytochemistry,2003,63,61.
[64]Rycroft,D.S.;Cole,W.J.;Aslam,N.;Lamont,Y.M.;Gabriel,R.Phytochemistry,1999,50,1167.
[65]Heinrichs,J.;Anton,H.;Gradstein,S.R.;Mues,R.Plant Syst.Evol.,2000,220,115.
[66]Zheng,G.-Q.;Ho,D.K.;Cottrell,C.E.;Cassady,J.M.J.Nat.Prod.,1994,57,32
[67]Guo,X.-Y.;Wang,J.;Wang,N.-L.;Kitanaka,S.;Liu H.-W.;Yao,X.-S.Chem.Pharm.Bull.,2006,54,21.
[68]Siegel,U.;Mues,R.;D(o|¨)nig,R.;Eicher,T.Phytochemistry,1991,30,3643.
[69]Y.Asakawa,in'progress in the Chemistry of Organic Natural Products',ed.W.Herz,G.W.Kirby,R.E.Moore,W.Steglick,C.Tamm,Springer Verlag,New York,1995,Vol.65,p.1.
[70]Nagashima,F.;Izumo,H.;Takaoka,S.,Tori,M.;Asakawa Y.Phytochemistry,1994,37,433.
[71]Nagashima,F.;Momosaki,S.;Watanabe,Y.;Toyota,M.;Huneek,S.;Asakawa,Y.Phytochemistry,1996,41,207.
[72]Nabeta,K.;Ohkubo,S.;Hozumi,R.;Katoh,K.Phytochemistry,1998,49,1941.
[73]Tori,M.,Aold,M.,Asakawa,Y.Phytochemistry 1994,36,73.
[74]So,M.L.;Chan,W.H.;Xia,P.F.Natural Products Letters,2002,16,167.
[75]Asakawa,Y.;Tori,M.;Masuya,T.;Frahm,J.-P.Phytochemistry,1990,29,1577.
[76]牛冲,娄红祥.山东大学硕士学位论文 2004,苔类植物地钱中活性天然产物的筛选及分离.
[77]Toyota,M.,Nagashima,F.,Asakawa,Y.Phytochemistry,1988,27,2603.
[78]王风强,娄红祥.药学学报 2000,35,587.
[79]Hashimoto,T.;Ikeda,H.;Takaoka,S.;Toyota,M.;Asakawa,Y.Phytochemistry,1999,52,501.
[80]Wei,H.C.;Ma,S.J.;Wu,C.L.Phytochemistry,1995,39,91.
[81]Toyota,M.;Konoshima,M.;Asakawa,Y.Phytochemistry,1999,52,105.
[82]Yoshida,T.,Toyota,M.,Asakawa,Y.J.Nat.Prod.1997,60,145.
[83]Scher,J.M.;Burgess,E.J.;Lorimerb,S.D.;Perry,N.B.Tetrahedron,2002,58,7875.
[84]Hashimoto,T.;Irita,H.;Takaoka,S.;Toyota,M.;Asakawa,Y.Tetrahedron,2000,56,3153.
[85]Martini,U.;Zapp,J.,Becker,H.Phytochemistry,1998,47,89.
[86]Toyota,M.;Yoshida,T.;Kan,Y.;Takaoka,S.;Asakawa,Y.Tetrahedron Letters,1996,37,4745.
[87]Asakawa Y.1995,Chemical Constituent of Hepaticae.In “Progress in Chemistry of Organic Natural Products”.Springer.Wein.65:562
[88]Asakawa,Y.Bryophytes:Their Chemistry and Chemical Taxonomy.Oxford University Press,1990,369.
[89]Choma,I.M.;Choma,A.;Staszczuk K.J.liq.Chrom.& Rel.Technol.2002,25,1579.
[90]Williams,L.A.;Vasques,E.;Reid,W.Naturwissenschaften,2003,90,468.
[91]Asakawa,Y.Pure & Appl.Chem.1994,66,2193.
[92]Asakawa,Y.;Toyota.M;Tori,M.Spectroscopy,2000,14,149.
[93]Asakawa,Y.;Kondo,K.;Tori,M.;et al.Phytochemistry,1991,30,219.
[94]Asakawa Y,Hashimato T,Takikawa K,et al.Phytochemistry,1991,30,235.
[95]Schwartner C,Michel C,Stettmaier K,et al.Free Radical Biology & Medicine.1996,20,237.
[96]George,H.;Teng CM,Wu CL,et al.Archives of Biochemistry and Biophysics.1996,334,18.
[97]Gyorgy,M.K.;Mihaly,N.Bioorganic & Medicinal Chemistry,1995,3,1511.
[1]Harinantenaina,L.;Quang,D.N.;Takeshi,N.;Hashimoto,T.;Kohchi,C.;Soma,J.I.;Asakawa,Y.J..Nat.Prod.,2005,68,1779.
[2]Niu,C.;Qu,J.B.;Lou,H.X.Chem.Biodivers.2006,3,34.
[3]Lu,Z.Q.;Fan,P.H.;Ji,M.;Lou,H.X.J.Asian Nat.Prod.Res.2006,8,187.
[4]Asakawa,Y.Phytochemistry 2001,56,297.
[5]Zhong,D.F.;Xing,J.;Zhang,S.Q.;Sun,L.Rapid Commun.Mass Spectrom.2002,16,1836.
[6]Chen,X.Y.;Xing,J.;Zhong,D.F.J.Mass Spectrom.2004,39,145.
[7]Speicher,A.;Hollemeyer,K.;Heinzle,E.Rapid Commun.Mass Spectrom.2001,15,124.
[8]Asakawa,Y.;Toyota,M.;Tori,M.;Hashimoto,T.Spectroscropy 2000,14,149.
[1]Asakawa,Y.Progress in the Chemistry of Organic Natural Products,1995,65,pp.1-618.
[2]Asakawa,Y.Phytochemistry,2001,56,297
[3]Asakawa,Y.;Toyota,M.;Tori,M.;Hashimoto,T.Spectroscopy,2000,14,149.
[4]Oiso,Y.;Toyota,M.;Asakawa,Y.Chemical Pharmaceutical Bulletin,2001,49,126.
[5]Scher,J.M.;Burgess,E.J.;Lorimerb,S.D.;Perry,N.B.Tetrahedron,2002,58,7875
[6]Scher,J.M.;Speakman,J.B.;Zapp,J.;Becker,H.Phytochemistry,2004 65,2583
[7]Schwartner,C.;Bors,W.;Michel,C.;Franck,U.;Muller-Jakic,B.;Nenninger,A.;Asakawa,Y.Phytomedicine,1995,2,113
[8]Taira,Z.;Takei,M.;Endo,K.;Hashimoto,T.;Sakiya,Y.;Asakawa,Y.Chemical Pharmaceutical Bulletin,1994,42,52-56.
[9]Schwartner,C.;Michel,C.;Stettmaier,K.;Wagner,H.;Bors,W.Free Radical Biology & Medicine,1996,20,237
[10]Qu,J.;Xie,C.;Guo,H.;Yu,W.;Lou,H.Phytochemistry,2007,68,1767
[11]So,M.L.;Chan,W.H.;Xia,P.F.Naturalproducts letters,2002,16,167
[12]王风强;娄红祥;季梅.国外医药·植物药分册,1999,14,242
[13]Martini,U.;Zapp,J.;Becker,H.Phytochemistry,1998,47,89
[14]Asakawa,Y.;Toyota,M.;Matsuda,R.;Taldkawa,K.;Takemoto,T.Phytochemistry,1998,22,1413
[15]Asakawa,Y.;Tori,M.;Takikawa,K.;Krishnamurty,H.G.;Kar,S.K.Phytochemistry,1987,26,1811
[16]Tori,M.;Aoki,M.;Asakawa,Y.Phytochemistry.,1994,36,73
[17]Asakawa,Y.;Tori,M.;Masuya,T.Phytochemistry,1990,29,1577
[18]Hashimoto,T.;Ikeda,H.;Takaoka,S.Phytochemistry,1999,52,501
[19]Wei,H.C.;Ma,S.J.;Wu,C.L.Phytochemistry.,1995,39,91
[20]Yoshida,T.;Toyota,M.;Asakawa,Y.J.Nat.Prod.,1997,60,145.
[21]Nagashima,F.;Momosaki,S.;Watanabe,Y.Phytochemistry,1996,41,207
[22]Hashimoto,T.;Kananyama,S.;Kan,Y.;Tori,M.;Asakawa,Y.;Chem.Lett.,1996,9,741.
[23]Hashimoto,T.;Irita,H.;Takaoka,S.;Tanaka,M.;Asakawa,Y.Tetrahedron,2000,56,3153.
[24]Tori,M.;Masuya,T.;Asakawa,Y.J..Chem.Res.,1990,36.
[25]Nabeta,K.;Ohkubo,S.;Hozumi,R.;Katoh,K.Phytochemistry,1998,49,1941.
[26]Anton,H.;Schoeneborn,R.;Mues,R.Phytochemistry,1999,52,1639.
[27]曲建博;四种苔类植物的化学成分及其生物活性,2008,山东大学博士学位论文.
[2]Majumder,P.L.;Roychowdhury,M.;Chakraborty,S.Phytochemistry,1997,44,167-172.
[3]Hernandez-Romero,Y.;Rojas,J.I.;Castillo,R.;Rojas,A.;Mata,R.J.Nat.Prod.,2004,67,160.
[4]Majumder,P.L.;Guha,S.;Sen,S.Phytochemistry,1999,55,1365.
[5]Leong,Y.-W.;Kang,C.-C.;Harrison,L.J.;Powell,A.D.Phytochemistry,1997,44,157.
[6]Majumder,P.L.;Chakraborty,S.;Sen,S.J..Indian Chem.Soc.,2002,79,169.
[7]Bai,L.;Masukawa,N.;Yamaki,M.;Takagi,S.Phytochemistry,1997,44,1565.
[8]Estrada,S.;Rojas,A.;Mathison,Y.;Israel,A.;Mata,R.Planta Med.,1999,65,109.
[9]Lin,Y.-L.;Chen,W.-P.;Macabalang,A.D.Chem.Pharm.Bull.,2005,53,1111.
[10]Bai,L.;Masukawa,N.;Yamaki,M.;Takagi,S.Phytochemistry,1998,47,1637.
[11]Bai,L.;Masukawa,N.;Yamaki,M.;Takagi,S.Phytochemistry,1998,48,327.
[12]Anton,H.;Kraut,L.;Mues R.;Morales,Z.M.I.Phytochemistry,1997,46,1069.
[13]Baek,S.-H.,Phipps,R.K.;Perry,N.B.J..Nat.Prod.,2004,67,718.
[14]Ma,G.X.;Xu,G.J.;Xu,L.S.;Wang Z.T.;Kickuchi,T.Acta Pharm.Sin.,1996,31,222.
[15]Eloff,J.N.;Famakin,J.O.;Katerere,D.R.P.Afr.J.Biotechnol.,2005,4,1167.
[16]Ye,Q.;Zhao,W.Planta med.,2002,68,723.
[17]Fan,C.Q.;Zhao,W.M.;Qin,G.W.Chin.Chem.Lett.,2000,11,705.
[18]Kostecki,K.;Engelmeier,D.;Pacher,T.;Hofer,O.;Vajrodaya,S.;Greger,H.Phytochemistry,2004,65,99.
[19]Yoshida,T.;Hashimoto,T.;Takaoka,S.;Kan,Y.;Tori,M.;Asakawa,Y.Tetrahedron,1996,52,14487.
[20]Biondi,D.M.;Rocco,C.;Ruberto,G.J..Nat.Prod.,2005,68,1099.
[21]Bi,Z.M.;Yang,L.;Wang,Z.T.;Xu,L.S.;Xu,G.J.Chin.Chem.Lett.,2002,3,535.
[22]Bi,Z.;Wang,Z.;Xu,L.Acta Pharm.Sin..,2004,46,124.
[23]Anton,H.;Schoeneborn,R.;Mues,R.Phytochemistry,1999,52,1639.
[24]Rycroft,D.S.,Cole,W.J.;Aslam,N.Phytochemistry,1998,49,145.
[25]Zhao,W.,Qin,G.;Ye,Y.;Xu R.;Le,X.Phytochemistry.1995,38,711.
[26]Xiao,K.;Xuan,L.;Xu,Y.;Bai,D.;Zhong,D.Chem.Pharm.Bull.,2002,50,605.
[27]von Reuβ S.H.;K(o|¨)nig,W.A.Phytochemistry,2004,65,3113.
[28]Lou,H.X.;Li,G.Y.;Wang,F.Q.J..Asian Nat.Prod.Res.,2002,4,87.
[29]Fan,C.;Wang,W.;Wang,Y.;Qin,G.;Zhao.W.Phytochemistry,2001,57,1255
[30]Miyazawa,M.;Shimamura,H.;Nakamura,S.;Kameoka,H.J..Agric.Food Chem.,1997,45,2849.
[31]Zhang,G.-N.;Zhang,C.-F.;Wang,Z.-T.;Xu,L.-S.Chin.J.Nat.Med.,2004,2,78.
[32]Cullmann,F.;Becker,H.;Pandolfi,E.;Roeckner E.;Eicher,T.Phytochemistry,1997,45,1235.
[33]Jarevang,T.;Nilsson,M.-C.;Wallstedt,A.;Odham,G.;Sterner,O.Phytochemisty,1998,48,893.
[34]Han,G.X.;Wang,L.X.;Gu,Z.B.;Zhang,W.D.Acta Pharm.Sin..,2002,37,194.
[35]Han,G.X.;Wang,L.X.;Gu,Z.B.;Zhang,W.D.;Chen,H.S.Chin.Chem.Lett.,2002,13,231.
[36]Flegel,M.;Adam,K.-P.;Becker,H.Phytochemistry,1999,52,1633.
[37]Chen,C.-C.;Huang,Y.-L.;Teng,C.-M.Planta Med.,2000,66,372.
[38]Connolly,J.D.;Rycroft,D.S.;Srivastava,D.L.;Cole,W.J.;Ifeadike,P.;Kimbu,S.F.;Singh,J.;Hughes,M.;Thom,C.;Gerhard,U.;Organ,A.J.;Smith,R.J.;Harrison,L.J.Phytochemsitry,1999,50,1159.
[39]Miyazawa,M.;Shimamura,H.;Nakamura,S.;Sugiura,W.;Kosaka,H.;Kameoka,H.J.Agric.Food Chem.,1999,47,2163.
[40]Bai,L.;Yamaki,M.;Takagi,S.Phytochemistry,1996,42,853.
[41]Pacher,T.;Seger,C.;Engelmeier,D.;Vajrodaya,S.;Hofer,O.;Greger,H.J..Nat.Prod.,2002,65,820.
[42]Zidorn,C.;Lohwasser,U.;Pschorr,S.;Salvenmoser,D.;Ongania,K.H.;Ellmerer,E.P.;Borner,A.;Stuppner,H.Phytochemistry,2005,66,1691.
[43]Kunz,S.;Becker,H.Phytochemistry,1994,36,675.
[44]Bardon,A.;Mitre,G.B.;Kamiya,N.;Toyota,M.;Asakawa,Y.Phytochemistry,2002,59,205.
[45]Wu,P.-L.;Hsu,Y.-L.;Zao,C.-W.;Damu A.G.;Wu,T.-S.J.Nat.Prod.,2005,68,1180.
[46]Apisantiyakom,S.;Kittakoop,P.;Manyum,T.;Kirtikara,K.;Bremner,J.B.;Thebtaranonth,Y.Chem.Biodiv.,2004,1,1694.
[47]Kraut,L.;Mues,R.;Zinsmeister,H.D.Phytochemistry,1997,45,1249.
[48]Biondi,D.M.;Rocco,C.;Ruberto,G.J.Nat.Prod.,2003,66,477.
[49]Toyota,M.;Kinugawa,T.;Asakawa,Y.Phytochemistry,1994,37,859.
[50]Toyota,M.;Shimamura,T.;Ishii,H.;Renner,M.;Braggins,J.;Asakawa,Y.Chem.Pharm.Bull.,2002,50,1390.
[51]Nagashima,F.;Kuba,Y.;Asakawa,Y.Chem.Pharm.Bull.,2006,54,902.
[52]Toyota,M.;Nakaishi,E.;Asakawa,Y.Phytochemistry,1996,41,833.
[53]Manfredi,K.P.;Vallurupalli,V.;Demidova,M.;Kindscher,K.;Pannell,L.K.Phytochemistry,2001,58,153.
[54]Kittakoop,P.;Kirtikara,K.;Tanticharoen,M.;Thebtaranonth,Y.Phytochemistry,2000,55,349.
[55]Kunz,S.;Becker,H.Phytochemistry,1992,31,3981.
[56]Schwikkard,S.;Zhou,B.N.;Glass,T.E.;Sharp,J.L.;Mattern,M.R.;Johnson,R.K.;Kingston,D.G.J.Nat.Prod.,2000,63,457.
[57]Zhao,C.S.;Zhao,W.M.Chin.Chem.Lett.,2003,14,276.
[58]Han,G.;Wang,L.;Zhang,W.;Yang,Z.;Li,T.;Jiang T.;Liu,W.Acad.J.Sec.Mil.Med.Univ.,2002,23,443.
[59]Feng,W.;Cao,X.;Kuang,H.;Zheng,X.Acta Pharm.Sin.,2005,40,1131.
[60]Lee,K.Y.;Sung,S.H.;Kim,Y.C.J.Nat.Prod.,2006,69,679.
[61]Zidorn,C.;Ellmerer-M(u|¨)ller,E.P.;Stuppner,H.Helv.Chim.Acta,2000,83,2920.
[62]Zidorn,C.;Spitaler,R.;Ellmerer-M(u|¨)ller,E.P.;Perry,N.B.;Gerh(a|¨)user,C.;Stuppner,H.Z Naturforsch,2002,57C,614.
[63]Zidom,C.;Ellmerer-Miiller,E.P.;Sturm,S.;Stuppner,H.Phytochemistry,2003,63,61.
[64]Rycroft,D.S.;Cole,W.J.;Aslam,N.;Lamont,Y.M.;Gabriel,R.Phytochemistry,1999,50,1167.
[65]Heinrichs,J.;Anton,H.;Gradstein,S.R.;Mues,R.Plant Syst.Evol.,2000,220,115.
[66]Zheng,G.-Q.;Ho,D.K.;Cottrell,C.E.;Cassady,J.M.J.Nat.Prod.,1994,57,32
[67]Guo,X.-Y.;Wang,J.;Wang,N.-L.;Kitanaka,S.;Liu H.-W.;Yao,X.-S.Chem.Pharm.Bull.,2006,54,21.
[68]Siegel,U.;Mues,R.;D(o|¨)nig,R.;Eicher,T.Phytochemistry,1991,30,3643.
[69]Y.Asakawa,in'progress in the Chemistry of Organic Natural Products',ed.W.Herz,G.W.Kirby,R.E.Moore,W.Steglick,C.Tamm,Springer Verlag,New York,1995,Vol.65,p.1.
[70]Nagashima,F.;Izumo,H.;Takaoka,S.,Tori,M.;Asakawa Y.Phytochemistry,1994,37,433.
[71]Nagashima,F.;Momosaki,S.;Watanabe,Y.;Toyota,M.;Huneek,S.;Asakawa,Y.Phytochemistry,1996,41,207.
[72]Nabeta,K.;Ohkubo,S.;Hozumi,R.;Katoh,K.Phytochemistry,1998,49,1941.
[73]Tori,M.,Aold,M.,Asakawa,Y.Phytochemistry 1994,36,73.
[74]So,M.L.;Chan,W.H.;Xia,P.F.Natural Products Letters,2002,16,167.
[75]Asakawa,Y.;Tori,M.;Masuya,T.;Frahm,J.-P.Phytochemistry,1990,29,1577.
[76]牛冲,娄红祥.山东大学硕士学位论文 2004,苔类植物地钱中活性天然产物的筛选及分离.
[77]Toyota,M.,Nagashima,F.,Asakawa,Y.Phytochemistry,1988,27,2603.
[78]王风强,娄红祥.药学学报 2000,35,587.
[79]Hashimoto,T.;Ikeda,H.;Takaoka,S.;Toyota,M.;Asakawa,Y.Phytochemistry,1999,52,501.
[80]Wei,H.C.;Ma,S.J.;Wu,C.L.Phytochemistry,1995,39,91.
[81]Toyota,M.;Konoshima,M.;Asakawa,Y.Phytochemistry,1999,52,105.
[82]Yoshida,T.,Toyota,M.,Asakawa,Y.J.Nat.Prod.1997,60,145.
[83]Scher,J.M.;Burgess,E.J.;Lorimerb,S.D.;Perry,N.B.Tetrahedron,2002,58,7875.
[84]Hashimoto,T.;Irita,H.;Takaoka,S.;Toyota,M.;Asakawa,Y.Tetrahedron,2000,56,3153.
[85]Martini,U.;Zapp,J.,Becker,H.Phytochemistry,1998,47,89.
[86]Toyota,M.;Yoshida,T.;Kan,Y.;Takaoka,S.;Asakawa,Y.Tetrahedron Letters,1996,37,4745.
[87]Asakawa Y.1995,Chemical Constituent of Hepaticae.In “Progress in Chemistry of Organic Natural Products”.Springer.Wein.65:562
[88]Asakawa,Y.Bryophytes:Their Chemistry and Chemical Taxonomy.Oxford University Press,1990,369.
[89]Choma,I.M.;Choma,A.;Staszczuk K.J.liq.Chrom.& Rel.Technol.2002,25,1579.
[90]Williams,L.A.;Vasques,E.;Reid,W.Naturwissenschaften,2003,90,468.
[91]Asakawa,Y.Pure & Appl.Chem.1994,66,2193.
[92]Asakawa,Y.;Toyota.M;Tori,M.Spectroscopy,2000,14,149.
[93]Asakawa,Y.;Kondo,K.;Tori,M.;et al.Phytochemistry,1991,30,219.
[94]Asakawa Y,Hashimato T,Takikawa K,et al.Phytochemistry,1991,30,235.
[95]Schwartner C,Michel C,Stettmaier K,et al.Free Radical Biology & Medicine.1996,20,237.
[96]George,H.;Teng CM,Wu CL,et al.Archives of Biochemistry and Biophysics.1996,334,18.
[97]Gyorgy,M.K.;Mihaly,N.Bioorganic & Medicinal Chemistry,1995,3,1511.
[1]Harinantenaina,L.;Quang,D.N.;Takeshi,N.;Hashimoto,T.;Kohchi,C.;Soma,J.I.;Asakawa,Y.J..Nat.Prod.,2005,68,1779.
[2]Niu,C.;Qu,J.B.;Lou,H.X.Chem.Biodivers.2006,3,34.
[3]Lu,Z.Q.;Fan,P.H.;Ji,M.;Lou,H.X.J.Asian Nat.Prod.Res.2006,8,187.
[4]Asakawa,Y.Phytochemistry 2001,56,297.
[5]Zhong,D.F.;Xing,J.;Zhang,S.Q.;Sun,L.Rapid Commun.Mass Spectrom.2002,16,1836.
[6]Chen,X.Y.;Xing,J.;Zhong,D.F.J.Mass Spectrom.2004,39,145.
[7]Speicher,A.;Hollemeyer,K.;Heinzle,E.Rapid Commun.Mass Spectrom.2001,15,124.
[8]Asakawa,Y.;Toyota,M.;Tori,M.;Hashimoto,T.Spectroscropy 2000,14,149.
[1]Asakawa,Y.Progress in the Chemistry of Organic Natural Products,1995,65,pp.1-618.
[2]Asakawa,Y.Phytochemistry,2001,56,297
[3]Asakawa,Y.;Toyota,M.;Tori,M.;Hashimoto,T.Spectroscopy,2000,14,149.
[4]Oiso,Y.;Toyota,M.;Asakawa,Y.Chemical Pharmaceutical Bulletin,2001,49,126.
[5]Scher,J.M.;Burgess,E.J.;Lorimerb,S.D.;Perry,N.B.Tetrahedron,2002,58,7875
[6]Scher,J.M.;Speakman,J.B.;Zapp,J.;Becker,H.Phytochemistry,2004 65,2583
[7]Schwartner,C.;Bors,W.;Michel,C.;Franck,U.;Muller-Jakic,B.;Nenninger,A.;Asakawa,Y.Phytomedicine,1995,2,113
[8]Taira,Z.;Takei,M.;Endo,K.;Hashimoto,T.;Sakiya,Y.;Asakawa,Y.Chemical Pharmaceutical Bulletin,1994,42,52-56.
[9]Schwartner,C.;Michel,C.;Stettmaier,K.;Wagner,H.;Bors,W.Free Radical Biology & Medicine,1996,20,237
[10]Qu,J.;Xie,C.;Guo,H.;Yu,W.;Lou,H.Phytochemistry,2007,68,1767
[11]So,M.L.;Chan,W.H.;Xia,P.F.Naturalproducts letters,2002,16,167
[12]王风强;娄红祥;季梅.国外医药·植物药分册,1999,14,242
[13]Martini,U.;Zapp,J.;Becker,H.Phytochemistry,1998,47,89
[14]Asakawa,Y.;Toyota,M.;Matsuda,R.;Taldkawa,K.;Takemoto,T.Phytochemistry,1998,22,1413
[15]Asakawa,Y.;Tori,M.;Takikawa,K.;Krishnamurty,H.G.;Kar,S.K.Phytochemistry,1987,26,1811
[16]Tori,M.;Aoki,M.;Asakawa,Y.Phytochemistry.,1994,36,73
[17]Asakawa,Y.;Tori,M.;Masuya,T.Phytochemistry,1990,29,1577
[18]Hashimoto,T.;Ikeda,H.;Takaoka,S.Phytochemistry,1999,52,501
[19]Wei,H.C.;Ma,S.J.;Wu,C.L.Phytochemistry.,1995,39,91
[20]Yoshida,T.;Toyota,M.;Asakawa,Y.J.Nat.Prod.,1997,60,145.
[21]Nagashima,F.;Momosaki,S.;Watanabe,Y.Phytochemistry,1996,41,207
[22]Hashimoto,T.;Kananyama,S.;Kan,Y.;Tori,M.;Asakawa,Y.;Chem.Lett.,1996,9,741.
[23]Hashimoto,T.;Irita,H.;Takaoka,S.;Tanaka,M.;Asakawa,Y.Tetrahedron,2000,56,3153.
[24]Tori,M.;Masuya,T.;Asakawa,Y.J..Chem.Res.,1990,36.
[25]Nabeta,K.;Ohkubo,S.;Hozumi,R.;Katoh,K.Phytochemistry,1998,49,1941.
[26]Anton,H.;Schoeneborn,R.;Mues,R.Phytochemistry,1999,52,1639.
[27]曲建博;四种苔类植物的化学成分及其生物活性,2008,山东大学博士学位论文.