伞花木和白头翁中的醌还原酶诱导剂的快速发现
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摘要
伞花木(Eurycorymbus cavaleriei(Levl.)Rehd.et Hand.-Mazz.)收载于《中国植物志》,系无患子科伞花木属植物,为中国特有的单种属植物,属国家二级保护植物。伞花木的研究集中在生物遗传、组织培养、品种保护等方面,其化学成分及生物活性未见报道。白头翁(Pulsatilla chinensis(Bunge)Regel)是一种有着悠久药用历史的中药,用于治疗痢疾、疟疾、阴道滴虫和细菌感染等,化学及药理研究表明三萜皂苷是其重要的生物活性成分。
细胞二相代谢酶在化学致癌剂和其它有害氧化剂的代谢中具有重要作用。因而对醌还原酶具有诱导活性的成分被认为在肿瘤起始阶段具有潜在的癌症预防作用。二相酶水平的上调被认为是预防癌症发生的主要机制。
本文对两种植物的化学成分进行了研究,基于HPLC/ESI-MS~n分析手段,采用与还原型谷胱甘肽的结合方法快速发现两种植物提取物中具有醌还原酶(QR)诱导作用的化学成分,并用细胞筛选方法进行了验证;同时运用银离子复合法对两种植物的三萜类成分的质谱裂解规律进行了研究。主要研究内容及成果如下:
1.采用柱色谱对伞花木细枝的95%乙醇提取物的石油醚及二氯甲烷萃取部位进行了分离纯化。运用IR、UV、ESI-MS、HRESI-MS、~1H NMR、~(13)C NMR、HSQC、HMBC、~1H-~1H COSY、NOESY等波谱手段和理化性质鉴定了其中27个化合物的结构。这些化合物均为首次从该植物中分离得到,其中三萜类成分11个,全部为新发现的三萜,分别鉴定为3β,6β,7β,11α-tetrahydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T1),11α-acetyloxy-7β-benzoyloxy-3β,6β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T2),11α-acetyloxy-7β-caproyloxy-3β,6β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T3),7β-benzoyloxy-3β,6β,11α-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T4),6β-acetyloxy-3β,12β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T5),7β-benzoyloxy-3β,6β,11β-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T6),6β-acetyloxy-7β-benzoyloxy-3β,11β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T7),6β-acetyloxy-12β-benzoyloxy-3β-hydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T8),3β,12β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T9),6β-acetyloxy-3β,11β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T10),7β-benzoyloxy-3β,24ξ,25-trihydroxy-dammar-20(21)-ene(EU-T11),并命名为伞花木三萜A-K。另外发现新联苯1个,鉴定为4,4′-dihydroxy-5,5′-bis[(2S,4Z)-6-hydroxy-5-methyl-2-(1-methylethenyl)hex-4-en-l-yl]-3,3′-bis(3-methylbut-2-en-l-yl)-2,2′-biphenyl-1,1′-dicarboxaldehyde(EU-3),命名为cavalerol。
2.采用柱色谱对白头翁95%乙醇提取物的石油醚及二氯甲烷萃取部位进行了分离纯化。运用IR、UV、ESI-MS、HRESI-MS、~1H NMR、~(13)C NMR、HSQC、HMBC、~1H-~1H COSY、NOESY等波谱手段和理化性质鉴定了11个三萜皂苷、1个醌类和1个噻吩类的化学结构。
3.建立了伞花木95%乙醇提取物的二氯甲烷萃取部位中具有醌还原酶诱导活性的成分的HPLC/ESI-MS~n快速发现方法。首先对从伞花木中分得的9个香豆素对照品进行直接进样分析,根据多级质谱碎片离子推导其裂解规律,区分同分异构体。然后以这些规律为基础,对伞花木的95%乙醇提取物的二氯甲烷萃取部位与还原型谷胱甘肽反应前后化学成分的变化进行液质联用分析,推测出了具有QR诱导作用的2个香豆素类成分。
4.建立了白头翁95%乙醇提取物的石油醚萃取部位中具有醌还原酶诱导活性的成分的HPLC/ESI-MS~n快速发现方法。对白头翁的95%乙醇提取物的石油醚萃取部位与还原型谷胱甘肽反应前后化学成分的变化进行液质联用分析,推测出了具有QR诱导作用的1个醌类化合物和1个噻吩类化合物。
5.利用HPLC-ESI-MS~n分析发现了白头翁95%乙醇提取物的二氯甲烷萃取部位中的两类具相同分子量母核的三萜皂苷的银离子复合物在正离子模式下不同的质谱裂解行为。对银离子/三萜皂苷复合物进行直接进样分析,推导出齐墩果烷型三萜皂苷的两种裂解途径,并对白头翁95%乙醇提取物的二氯甲烷萃取部位进行液质联用分析,可区分植物粗提物中的两类皂苷。
6.利用ESI-MS~n分析发现了伞花木95%乙醇提取物的二氯甲烷萃取部位中分离得到的降藿烷型三萜银离子复合物在正离子模式下的裂解行为。对银离子/三萜复合物进行直接进样分析,区分其中的两对同分异构体,并推导出降藿烷型三萜的三条特征性裂解途径,为质谱鉴定该类罕见三萜提供了理论基础。
7.用小鼠Hepa 1c1c7细胞系对伞花木和白头翁95%乙醇提取物的各萃取部位及化学成分进行了醌还原酶诱导活性的筛选。
Eurycorymbus cavaleriei(Levl.) Rehd.et Hand.-Mazz.is a dioecious,rare and endemic tree species in China and there is only one species in this genus.The tissue culture,genetic diversity and properties of E.cavaleriei have been previously studied, but few investigations on its chemical components and pharmacological activities have been reported up to now.Pulsatilla chinensis(Bunge) Regel is one of the most important crude drugs in traditional Chinese medicine and have been used for the treatment of intestinal amebiasis,malaria,vaginal trichomoniasis,and bacterial infections.Chemical and pharmacological investigations have indicated that triterpenoid saponins are important bioactive components existing in this plant,which also have been reported to have antiproliferative activity.
PhaseⅡenzymes play an important role in the metabolism of chemical carcinogen and other harmful oxidants.The chemical components which can induct the quinone reductase(QR) are regarded having the chemopreventive effects in the initiation of many tumors.The increase of phaseⅡenzymes are considered as the major mechanism of prevention of cancer.
According to the above study background,the main target of this thesis is concentrated on characterization of the preventive agents through the reaction with GSH in the extract of E.cavaleriei and P.chinensis and the cleavage pathways of triterpenes by silver complexation using HPLC/ESI-MS~n method.And further,the Structure-activity relationship was discussed and validated through the assay of bioactivities,which provided scientific information for the discovery of new chemopreventive agents from the natural products.The main innovation and academic contributions of this thesis are presented as follows:
1.Column chromatography wass used to separate constituents from the petroleum ether and dichloromethane partitions in 95%ethanol extract of the twigs of E.cavaleriei and the structures of 27 compounds were elucidated by IR,UV,MS,NMR and physicochemical properties.All of them were isolated from this plant for the first time, eleven new triterpenes was identified as 3β,6β,7β,11α-tetrahydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T1),11α-acetyloxy-7β-benzoyloxy-3β,6β-dihydroxy -21αH-24-norhopa-4(23),22(29)-diene(EU-T2),11α-acetyloxy-7β-caproyloxy-3β,6β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T3),7β-benzoyloxy-3β,6β,11α-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T4),6β-acetyloxy-3β,12β-di hydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T5),7β-benzoyloxy-3β,6β,11β-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T6),6β-acetyloxy-7β-benzoy loxy-3β,11β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T7),6β-acetyloxy -12β-benzoyloxy-3β-hydroxyl-21αH-24-norhopa-4(23),22(29)-diene(EU-T8),3β, 12β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T9),6β-acetyloxy -3β,11β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T10),7β-benzoyloxy-3β,24ξ,25-trihydroxy-dammar-20(21)-ene(EU-T11),and named as cavalerol A-K(1-11).One novel meroterpene was identified as 5,5'-dihydroxy -4,4'-bis[(2S,4Z)-6-hydroxy-5-methyl-2-(1-methylethenyl)hex-4-en-l-yl]-6,6'-bis(3-me thylbut-2-en-l-yl)-1,1'-biphenyl-2,2'-dicarboxaldehyde(EU-3) and named as cavalerol.
2.Column chromatography was used to separate constituents from the petroleum ether and dichloromethane partitions in 95%ethanol extract of P.chinensis and the structures of eleven triterpenoid saponins,one quinone compound and one thiophene compound were elucidated by IR,UV,MS,NMR and physicochemical properties.
3.A HPLC/ESI-MS~n method was established to discover the chemical components which were able to induct QR in dichloromethane partitions of 95%ethanol extract of the twigs of E.cavaleriei.Firstly,MS~n experiments were carried out on the nine reference compounds to obtain the fragmentation patterns of the coumarin compounds and differentiate isomers according to the fragment ions.Based on the fragmentation patterns of the reference compounds,this method was applied to studies on the components change after reacting with GSH in dichloromethane partition of the 95% ethanol extracts of E.cavaleriei,two coumarin compounds which had QR induction effects were identified.
4.The above HPLC/ESI-MS~n method was employed to study the chemical components which were able to induct QR in petroleum ether partitions of 95%ethanol extract of P.chinensis based on components change after reacting with GSH and one quinone and one thiophene which had QR induction effects were identified.
5.The silver complexation of triterpenoid was employed to MS analysis and obvious differences were found in the fragmentation behavior of two types of triterpenoid saponins which had the same molecular basic aglycons separated from the dichloromethane partition of the 95%ethanol extracts of P.chinensis through HPLC-ESI-MS~n in positive ion mode.silver / triterpenoid saponin complexes of the type(Ag + triterpenoid saponin)~+ were analyzed and there were two main pathways of fragmentation in triterpenoid saponins which had aglycons of oleanane skeleton.These studies can assist the effective analysis of two kinds of saponins,and benefit the structural identification of similar constituents in crude plant extracts.
6.The silver complexation of triterpene was employed to MS analysis and the fragmentation behavior of triterpene compounds including isomers which had norhopene skeletons separated from dichloromethane partition of the 95%ethanol extracts of E.cavaleriei were studied through ESI-MS~n in positive ion mode.silver / triterpene complexes of the type(Ag + triterpene)~+ were analyzed to differentiate two pairs of isomers and three main pathways of fragmentation were also inferred.This method was quite helpful for characterization of these rare triterpene compounds.
7.Hepa 1c1c7 murine hepatoma cells were employed to assay the QR activity of the partitions and components from the 95%ethanol extract of E.cavaleriei and P. chinensis.
细胞二相代谢酶在化学致癌剂和其它有害氧化剂的代谢中具有重要作用。因而对醌还原酶具有诱导活性的成分被认为在肿瘤起始阶段具有潜在的癌症预防作用。二相酶水平的上调被认为是预防癌症发生的主要机制。
本文对两种植物的化学成分进行了研究,基于HPLC/ESI-MS~n分析手段,采用与还原型谷胱甘肽的结合方法快速发现两种植物提取物中具有醌还原酶(QR)诱导作用的化学成分,并用细胞筛选方法进行了验证;同时运用银离子复合法对两种植物的三萜类成分的质谱裂解规律进行了研究。主要研究内容及成果如下:
1.采用柱色谱对伞花木细枝的95%乙醇提取物的石油醚及二氯甲烷萃取部位进行了分离纯化。运用IR、UV、ESI-MS、HRESI-MS、~1H NMR、~(13)C NMR、HSQC、HMBC、~1H-~1H COSY、NOESY等波谱手段和理化性质鉴定了其中27个化合物的结构。这些化合物均为首次从该植物中分离得到,其中三萜类成分11个,全部为新发现的三萜,分别鉴定为3β,6β,7β,11α-tetrahydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T1),11α-acetyloxy-7β-benzoyloxy-3β,6β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T2),11α-acetyloxy-7β-caproyloxy-3β,6β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T3),7β-benzoyloxy-3β,6β,11α-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T4),6β-acetyloxy-3β,12β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T5),7β-benzoyloxy-3β,6β,11β-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T6),6β-acetyloxy-7β-benzoyloxy-3β,11β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T7),6β-acetyloxy-12β-benzoyloxy-3β-hydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T8),3β,12β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T9),6β-acetyloxy-3β,11β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T10),7β-benzoyloxy-3β,24ξ,25-trihydroxy-dammar-20(21)-ene(EU-T11),并命名为伞花木三萜A-K。另外发现新联苯1个,鉴定为4,4′-dihydroxy-5,5′-bis[(2S,4Z)-6-hydroxy-5-methyl-2-(1-methylethenyl)hex-4-en-l-yl]-3,3′-bis(3-methylbut-2-en-l-yl)-2,2′-biphenyl-1,1′-dicarboxaldehyde(EU-3),命名为cavalerol。
2.采用柱色谱对白头翁95%乙醇提取物的石油醚及二氯甲烷萃取部位进行了分离纯化。运用IR、UV、ESI-MS、HRESI-MS、~1H NMR、~(13)C NMR、HSQC、HMBC、~1H-~1H COSY、NOESY等波谱手段和理化性质鉴定了11个三萜皂苷、1个醌类和1个噻吩类的化学结构。
3.建立了伞花木95%乙醇提取物的二氯甲烷萃取部位中具有醌还原酶诱导活性的成分的HPLC/ESI-MS~n快速发现方法。首先对从伞花木中分得的9个香豆素对照品进行直接进样分析,根据多级质谱碎片离子推导其裂解规律,区分同分异构体。然后以这些规律为基础,对伞花木的95%乙醇提取物的二氯甲烷萃取部位与还原型谷胱甘肽反应前后化学成分的变化进行液质联用分析,推测出了具有QR诱导作用的2个香豆素类成分。
4.建立了白头翁95%乙醇提取物的石油醚萃取部位中具有醌还原酶诱导活性的成分的HPLC/ESI-MS~n快速发现方法。对白头翁的95%乙醇提取物的石油醚萃取部位与还原型谷胱甘肽反应前后化学成分的变化进行液质联用分析,推测出了具有QR诱导作用的1个醌类化合物和1个噻吩类化合物。
5.利用HPLC-ESI-MS~n分析发现了白头翁95%乙醇提取物的二氯甲烷萃取部位中的两类具相同分子量母核的三萜皂苷的银离子复合物在正离子模式下不同的质谱裂解行为。对银离子/三萜皂苷复合物进行直接进样分析,推导出齐墩果烷型三萜皂苷的两种裂解途径,并对白头翁95%乙醇提取物的二氯甲烷萃取部位进行液质联用分析,可区分植物粗提物中的两类皂苷。
6.利用ESI-MS~n分析发现了伞花木95%乙醇提取物的二氯甲烷萃取部位中分离得到的降藿烷型三萜银离子复合物在正离子模式下的裂解行为。对银离子/三萜复合物进行直接进样分析,区分其中的两对同分异构体,并推导出降藿烷型三萜的三条特征性裂解途径,为质谱鉴定该类罕见三萜提供了理论基础。
7.用小鼠Hepa 1c1c7细胞系对伞花木和白头翁95%乙醇提取物的各萃取部位及化学成分进行了醌还原酶诱导活性的筛选。
Eurycorymbus cavaleriei(Levl.) Rehd.et Hand.-Mazz.is a dioecious,rare and endemic tree species in China and there is only one species in this genus.The tissue culture,genetic diversity and properties of E.cavaleriei have been previously studied, but few investigations on its chemical components and pharmacological activities have been reported up to now.Pulsatilla chinensis(Bunge) Regel is one of the most important crude drugs in traditional Chinese medicine and have been used for the treatment of intestinal amebiasis,malaria,vaginal trichomoniasis,and bacterial infections.Chemical and pharmacological investigations have indicated that triterpenoid saponins are important bioactive components existing in this plant,which also have been reported to have antiproliferative activity.
PhaseⅡenzymes play an important role in the metabolism of chemical carcinogen and other harmful oxidants.The chemical components which can induct the quinone reductase(QR) are regarded having the chemopreventive effects in the initiation of many tumors.The increase of phaseⅡenzymes are considered as the major mechanism of prevention of cancer.
According to the above study background,the main target of this thesis is concentrated on characterization of the preventive agents through the reaction with GSH in the extract of E.cavaleriei and P.chinensis and the cleavage pathways of triterpenes by silver complexation using HPLC/ESI-MS~n method.And further,the Structure-activity relationship was discussed and validated through the assay of bioactivities,which provided scientific information for the discovery of new chemopreventive agents from the natural products.The main innovation and academic contributions of this thesis are presented as follows:
1.Column chromatography wass used to separate constituents from the petroleum ether and dichloromethane partitions in 95%ethanol extract of the twigs of E.cavaleriei and the structures of 27 compounds were elucidated by IR,UV,MS,NMR and physicochemical properties.All of them were isolated from this plant for the first time, eleven new triterpenes was identified as 3β,6β,7β,11α-tetrahydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T1),11α-acetyloxy-7β-benzoyloxy-3β,6β-dihydroxy -21αH-24-norhopa-4(23),22(29)-diene(EU-T2),11α-acetyloxy-7β-caproyloxy-3β,6β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T3),7β-benzoyloxy-3β,6β,11α-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T4),6β-acetyloxy-3β,12β-di hydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T5),7β-benzoyloxy-3β,6β,11β-trihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T6),6β-acetyloxy-7β-benzoy loxy-3β,11β-dihydroxy-21αH-24-norhopa-4(23),22(29)-diene(EU-T7),6β-acetyloxy -12β-benzoyloxy-3β-hydroxyl-21αH-24-norhopa-4(23),22(29)-diene(EU-T8),3β, 12β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T9),6β-acetyloxy -3β,11β-dihydroxy-21αH-hop-22(29)-ene-24-oic acid methyl ester(EU-T10),7β-benzoyloxy-3β,24ξ,25-trihydroxy-dammar-20(21)-ene(EU-T11),and named as cavalerol A-K(1-11).One novel meroterpene was identified as 5,5'-dihydroxy -4,4'-bis[(2S,4Z)-6-hydroxy-5-methyl-2-(1-methylethenyl)hex-4-en-l-yl]-6,6'-bis(3-me thylbut-2-en-l-yl)-1,1'-biphenyl-2,2'-dicarboxaldehyde(EU-3) and named as cavalerol.
2.Column chromatography was used to separate constituents from the petroleum ether and dichloromethane partitions in 95%ethanol extract of P.chinensis and the structures of eleven triterpenoid saponins,one quinone compound and one thiophene compound were elucidated by IR,UV,MS,NMR and physicochemical properties.
3.A HPLC/ESI-MS~n method was established to discover the chemical components which were able to induct QR in dichloromethane partitions of 95%ethanol extract of the twigs of E.cavaleriei.Firstly,MS~n experiments were carried out on the nine reference compounds to obtain the fragmentation patterns of the coumarin compounds and differentiate isomers according to the fragment ions.Based on the fragmentation patterns of the reference compounds,this method was applied to studies on the components change after reacting with GSH in dichloromethane partition of the 95% ethanol extracts of E.cavaleriei,two coumarin compounds which had QR induction effects were identified.
4.The above HPLC/ESI-MS~n method was employed to study the chemical components which were able to induct QR in petroleum ether partitions of 95%ethanol extract of P.chinensis based on components change after reacting with GSH and one quinone and one thiophene which had QR induction effects were identified.
5.The silver complexation of triterpenoid was employed to MS analysis and obvious differences were found in the fragmentation behavior of two types of triterpenoid saponins which had the same molecular basic aglycons separated from the dichloromethane partition of the 95%ethanol extracts of P.chinensis through HPLC-ESI-MS~n in positive ion mode.silver / triterpenoid saponin complexes of the type(Ag + triterpenoid saponin)~+ were analyzed and there were two main pathways of fragmentation in triterpenoid saponins which had aglycons of oleanane skeleton.These studies can assist the effective analysis of two kinds of saponins,and benefit the structural identification of similar constituents in crude plant extracts.
6.The silver complexation of triterpene was employed to MS analysis and the fragmentation behavior of triterpene compounds including isomers which had norhopene skeletons separated from dichloromethane partition of the 95%ethanol extracts of E.cavaleriei were studied through ESI-MS~n in positive ion mode.silver / triterpene complexes of the type(Ag + triterpene)~+ were analyzed to differentiate two pairs of isomers and three main pathways of fragmentation were also inferred.This method was quite helpful for characterization of these rare triterpene compounds.
7.Hepa 1c1c7 murine hepatoma cells were employed to assay the QR activity of the partitions and components from the 95%ethanol extract of E.cavaleriei and P. chinensis.
引文
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[8]Jang M,Cai L,Udeani GO.Cancer chemopreventive activity of resveratrol,a natural product derived from grapes.Science,1997,275(10):218-220
[9]Ann M.Benson,Markus J.Hunkeler,Talalay P.Increase of NAD(P)H:quinone reductase by dietary antioxidants:Possible role in protection against carcinogenesis and toxicity.Biochemistry,1980,77(9):5216-5220
[10]Su BN,Jung Park E,Vigo JS,et al.Activity-guided isolation of the chemical constituents of Muntingia calabura using a quinone reductase induction assay.Phytochemistry,2003,63(3):335-341
[11]Middleton E,Jr.,Kandaswami C,Theoharides TC.The effects of plant flavonoids on mammalian cells:implications for inflammation,heart disease,and cancer.Pharmacol Rev,2000,52(4):673-751
[12]Su BN,Park EJ,Nikolic D,et al.Activity-guided isolation of novel norwithanolides from Deprea subtriflora with potential cancer chemopreventive activity.J Org Chem,2003,68(6):2350-2361
[13]Su BN,Misico R,Park EJ,et al.Isolation and characterization of bioactive principles of the leaves and stems of Physalis philadelphica.Tetrahedron,2002,58(17):3453-3466
[14]Kwak MK,Egner PA,Dolan PM,et al.Role of phase 2 enzyme induction in chemoprotection by dithiolethiones.Mutat Res,2001,480-481:305-315
[15]McWalter G.K.,Higgins L.G.,McLellan L.I.Transcription factor nrf2 is essential for induction of NAD(P)H:quinone oxidoreductase 1,glutathione s-transferases,and glutamate cysteine ligase by Broccoli seeds and Isothiocyanates.The Journal of Nutrition,2004,3499-3506
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[20]Chen CL.The preliminary analysis of phsico-mechanical properties of Eurycorymbus cavaleriei wood.Journal of Fujian Forestry Science and Technology,2002,29:50-52
[21]Zhu HY,Kang M,Ye QG,et al.Allozymic genetic diversity in Eurycorymbus cavaleriei(Levl.)Rehd.et Hand.-Mazz.,an endemic and dioecious tree in China.Journal of Wuhan Botanical Research,2005,23:310-318
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[26]Kanchanapoom T,Kasai R,Yamasaki K.Acetylated triterpene saponins from the Thai medicinal plant,Sapindus emarginatus.Chem Pharm Bull(Tokyo),2001,49(9):1195-1197
[27]Teng RW,Ni W,Hua Y,et al.Two New Tirucallane-Type Triterpenoid Saponins from Sapindus mukorossi.Acta Botanica Sinica,2003,45:369-372
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[31]Kommalapati RR,Valsaraj KT,Constant WD.Soil flushing using colloidal gas aphron suspensions generated from a plant-based surfactant.J Hazardous Materials,1998,60:73-87
[32]Tamura Y.无患子果皮中皂苷的抗皮真菌活性.国外医学中医中药分册,2002,24:300-301
[33]Arulmozhi DK,Sridhar N,Bodhankar SL,et al.In vitro pharmacological investigations ot Sapindus trifoliatus in various migraine targets.J Ethnopharmacol,2004,95(2-3):239-245
[34]Arulmozhi DK,Veeranjaneyulu A,Bodhankar SL,et al.Pharmacological studies of the aqueous extract of Sapindus trifoliatus on central nervous system:possible antimigraine mechanisms.J Ethnopharmacol,2005,97(3):491-496
[35]Maikhuri JP,Dwivedi AK,Dhar JD,et al.Mechanism of action of some acrylophenones,quinolines and dithiocarbamate as potent,non-detergent spermicidal agents.Contraception,2003,67(5):403-408
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