1.三七有效部位药效物质基础研究 2.红花中抗脑缺血活性成分质谱裂解行为及分布研究
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摘要
本论文包括三七有效部位药效物质基础研究和红花中抗脑缺血活性成分质谱裂解行为及体内分布研究两个部分。
三七为五加科植物三七Panax notoginseng(Burk.)F.H.Chen的干燥根。具有散瘀止血,消肿定痛的功效。大量药物化学及药理学实验数据表明:皂苷类成分为三七的主要活性成分之一,其皂苷类型主要为达玛烷型四环三萜(人参皂苷)。目前国内外对该类成分的研究报道较多,包括质谱裂解行为、在线鉴定、定量分析方法及代谢研究等,其研究重点主要针对常量皂苷类成分。由于受常规分离方法所限,对其微量成分的信息知之甚少,然而中药是一个复杂体系,即使仅由皂苷类成分组成的有效部位,除常量成分外尚有很多微量甚至痕量成分客观存在,因此有必要对这些微量成分进行鉴定。本论文即主要针对三七有效部位中微量皂苷类成分进行研究,以进一步阐明其药效物质基础。
基于以上研究目的,本论文首先对12个皂苷对照品进行了ESI-MS~n和HPLC/ESI-MS~n裂解行为研究,总结了特征性碎片离子及其强度与结构的关系,并深入探讨了其裂解机理与结构间的内在联系,建立了可用于解析皂苷糖链、苷元及二者连接信息的在线鉴定策略。另外,在对三七有效部位中常量皂苷类成分含量测定的基础上,发现其量大成分对微量成分的检出存在较大干扰,据此提出利用色谱方法除去有效部位中量大成分,从而在现有条件下大大提高了微量成分的检出灵敏度。最后,运用以上总结的皂苷类成分裂解规律和在线鉴定策略,对富集微量皂苷类成分的部位进行HPLC/HRMS、HPLC/DAD/ESI-MS~n测定,鉴定或推测了151个常量及微量皂苷类成分的结构,其中56个为新化合物。
上述研究为快速、有效识别并鉴定植物提取物中的微量成分提供了有益的借鉴,同时为进一步开展三七指纹图谱、阐明三七有效部位中药效物质基础及其代谢研究奠定基础。
红花为菊科(Compositae)植物Carthamus tinctorius L.的干燥管状花。具有活血通经、散瘀止痛、降低胆固醇、降血压等功效。醌型查耳酮类化合物为其发挥活血化淤功效的主要活性成分,这类化合物属色素类成分极性较大,分离纯化过程比较困难,因此有必要对其UV、ESI-MS、ESI-MS~n等谱学特征进行研究,总结出可用于该类成分在线结构鉴定的谱学规律。
本论文利用ESI-MS~n及HPLC/DAD/ESI-MS~n等方法,研究了红花中醌型查耳酮类成分质谱裂解行为,通过分析该类化合物的UV吸收特征,正负离子模式下所表现的不同裂解特征,并以HPLC-HRMS~n数据对可能的裂解机制进行验证,总结了该类化合物的质谱裂解规律。为快速、有效识别并鉴定植物提取物中醌型查耳酮类化合物提供分析方法,并为进一步开展该类化合物代谢研究奠定基础。
羟基红花黄色素A(hydroxysafflor yellow A,HSYA)是从红花中分离得到的醌型查耳酮类化合物,该化合物具有较强的抗脑缺血活性。然而对于HSYA抗脑缺血可能的作用部位,是否可透过血脑屏障而发挥作用等方面的研究目前报道较少。本论文在对红花中醌型查耳酮类成分质谱裂解行为研究的基础上,开展了红花中抗脑缺血活性成分HSYA在血浆、脑组织及细胞中的分布研究。探讨了HSYA作为抗脑缺血药物,在不同组别大鼠(正常组与脑缺血模型组)、不同时间点(3、6、12、24h)、不同给药方式(单次给药与多次给药)及在不同部位脑组织(脑干、皮层、海马区、小脑)中的分布特征。研究表明,HSYA作为极性小分子化合物可以透过大鼠血脑屏障;其在不同组别动物、不同给药方式、不同部位脑组织及不同时间点的分布均存在显著性差异。该研究结果可为进一步探索HSYA抗脑缺血作用机制,寻找其作用靶标奠定基础。
The thesis included two parts of studies on pharmacodynamic substances studies of active fractions from Panax notoginseng(Burk.) F.H.Chen and studies of fragmentation behaviors of quinochalone constituents from Carthamus tinctorius L.and HSYA's internal distribution.
P.notoginseng(Burk.) F.H.Chen is one of the most commonly used traditional Chinese medicinal plants.Its roots(San-Qi) have been widely used for treatment of cardiovascular diseases,inflammation,fatigue,different body pains,and internal and external bleeding due to injury.Through extensive phytochemical and pharmacological studies,triterpenoid saponins have long been recognized as the main bioactive constituents of P.notoginseng.The type of saponins is mainly of dammarane-type (ginsenoside).Numerous studies,including fragmentation hehaviours,on-line analysis, determination and metabolism,have been reported which forcused on major constituents. However,the TCM is a complicated system,except for major constituents,there are a lot of minor or even trace constituents.Therefore,development of reliable analytical method for minor triterpenoid saponins is of great significance for elucidating pharmacodynamic substances of P.notoginseng and its related preparations.
In the study reported here,fragmentation behaviors of triterpenoid saponins from P. notoginseng were investigated by ESI-MS~n and high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry(HPLC/ESI-MS~n). Analyses revealed that fragment ions from glycosidic and cross-ring cleavages can give a wealth of structural information regarding the nature of the aglycone,sugar types,the sequence and linkage information of sugar units.According to the summarized fragmentation rules,identification of triterpenoid saponins from the roots of P. notoginseng could be fulfilled,even when reference standards were unavailable. Furthermore,minor and trace constituents were enriched and detected by eliminating the major constituents in one of the saponin fractions.As a result,a total of 151 saponins, including 56 new trace ones,were identified or tentatively characterized from saponin fractions based on their retention times,HPLC/HRMS,HPLC/ESI-MS~n fragmentation behaviors and comparison with data in the literatures.
These studies can assist in the effective analyses of saponins of this type and benefit the structural identification of similar trace constituents in fractions.This research provides a model for extensively screening and structural characterization of bioactive constituents in plant extracts.It also provides an informative fingerprint of P. notoginseng.
Carthamus tinctorius L.belongs to the family of Compositae,which is widely distributed in the province of Henan,Zhejing,and Sichuan,etc.in China,and its flowers are used as traditional Chinese medicine for treatment of heart and brain blood vessel diseases.Quinochalones are the major bioactive constituents of Carthamus tinctorius L. It shows higher polarity,therefore,it isolation and purification is difficult.ESI is a relatively new technique and is ideally suited to the introduction of polar,thermally labile compounds into a mass spectrometer.
In this study reported here,fragmentation behaviors of quinochalones from C. tinctorius were investigated by ESI-MS~n and HPLC/ESI-MS~n.And an efficient on-line identification system was established for constituents of this type.After the characteristic fragmentation patterns in positive and negative ion mode,and UV spectra of these compounds were summarized,HPLC-HR-MS,HPLC-DAD-ESI-MS~n of active fraction from C.tinctorius were measured.This technique can be utilized for the consecutive analysis of metabolites.
Hydroxysafflor yellow A(HSYA),a C-Glycosyl quinochalcones isolated from the safflower,exhibited extensive biological activities such as anti-cerebral ischemia effect. However the actual site of action of HSYA was still unclear and it was less study on whether the HSYA would travel through the BBB(blood brain barrier) or not.
Therefore,based on the mass spectrum schizolysis of C-Glycosyl quinochalcones, the anti-cerebral ischemia activities study of HSYA in plasma,different part of the brain and intra-cellular was developed.As an anti-cerebral ischemia drug,we investigated the distribution characteristics of HSYA in the brain at various group,different time,not alike take medicine way.The result showed the HSYA as low polarity compound,can travel through BBB at model animal and control group.In addition,the distribution of HSYA expressed significantly variance in the different part of brain,take medicine way and time.The research should do well to deeply mechanism study of anti-cerebral ischemia of HSYA.
三七为五加科植物三七Panax notoginseng(Burk.)F.H.Chen的干燥根。具有散瘀止血,消肿定痛的功效。大量药物化学及药理学实验数据表明:皂苷类成分为三七的主要活性成分之一,其皂苷类型主要为达玛烷型四环三萜(人参皂苷)。目前国内外对该类成分的研究报道较多,包括质谱裂解行为、在线鉴定、定量分析方法及代谢研究等,其研究重点主要针对常量皂苷类成分。由于受常规分离方法所限,对其微量成分的信息知之甚少,然而中药是一个复杂体系,即使仅由皂苷类成分组成的有效部位,除常量成分外尚有很多微量甚至痕量成分客观存在,因此有必要对这些微量成分进行鉴定。本论文即主要针对三七有效部位中微量皂苷类成分进行研究,以进一步阐明其药效物质基础。
基于以上研究目的,本论文首先对12个皂苷对照品进行了ESI-MS~n和HPLC/ESI-MS~n裂解行为研究,总结了特征性碎片离子及其强度与结构的关系,并深入探讨了其裂解机理与结构间的内在联系,建立了可用于解析皂苷糖链、苷元及二者连接信息的在线鉴定策略。另外,在对三七有效部位中常量皂苷类成分含量测定的基础上,发现其量大成分对微量成分的检出存在较大干扰,据此提出利用色谱方法除去有效部位中量大成分,从而在现有条件下大大提高了微量成分的检出灵敏度。最后,运用以上总结的皂苷类成分裂解规律和在线鉴定策略,对富集微量皂苷类成分的部位进行HPLC/HRMS、HPLC/DAD/ESI-MS~n测定,鉴定或推测了151个常量及微量皂苷类成分的结构,其中56个为新化合物。
上述研究为快速、有效识别并鉴定植物提取物中的微量成分提供了有益的借鉴,同时为进一步开展三七指纹图谱、阐明三七有效部位中药效物质基础及其代谢研究奠定基础。
红花为菊科(Compositae)植物Carthamus tinctorius L.的干燥管状花。具有活血通经、散瘀止痛、降低胆固醇、降血压等功效。醌型查耳酮类化合物为其发挥活血化淤功效的主要活性成分,这类化合物属色素类成分极性较大,分离纯化过程比较困难,因此有必要对其UV、ESI-MS、ESI-MS~n等谱学特征进行研究,总结出可用于该类成分在线结构鉴定的谱学规律。
本论文利用ESI-MS~n及HPLC/DAD/ESI-MS~n等方法,研究了红花中醌型查耳酮类成分质谱裂解行为,通过分析该类化合物的UV吸收特征,正负离子模式下所表现的不同裂解特征,并以HPLC-HRMS~n数据对可能的裂解机制进行验证,总结了该类化合物的质谱裂解规律。为快速、有效识别并鉴定植物提取物中醌型查耳酮类化合物提供分析方法,并为进一步开展该类化合物代谢研究奠定基础。
羟基红花黄色素A(hydroxysafflor yellow A,HSYA)是从红花中分离得到的醌型查耳酮类化合物,该化合物具有较强的抗脑缺血活性。然而对于HSYA抗脑缺血可能的作用部位,是否可透过血脑屏障而发挥作用等方面的研究目前报道较少。本论文在对红花中醌型查耳酮类成分质谱裂解行为研究的基础上,开展了红花中抗脑缺血活性成分HSYA在血浆、脑组织及细胞中的分布研究。探讨了HSYA作为抗脑缺血药物,在不同组别大鼠(正常组与脑缺血模型组)、不同时间点(3、6、12、24h)、不同给药方式(单次给药与多次给药)及在不同部位脑组织(脑干、皮层、海马区、小脑)中的分布特征。研究表明,HSYA作为极性小分子化合物可以透过大鼠血脑屏障;其在不同组别动物、不同给药方式、不同部位脑组织及不同时间点的分布均存在显著性差异。该研究结果可为进一步探索HSYA抗脑缺血作用机制,寻找其作用靶标奠定基础。
The thesis included two parts of studies on pharmacodynamic substances studies of active fractions from Panax notoginseng(Burk.) F.H.Chen and studies of fragmentation behaviors of quinochalone constituents from Carthamus tinctorius L.and HSYA's internal distribution.
P.notoginseng(Burk.) F.H.Chen is one of the most commonly used traditional Chinese medicinal plants.Its roots(San-Qi) have been widely used for treatment of cardiovascular diseases,inflammation,fatigue,different body pains,and internal and external bleeding due to injury.Through extensive phytochemical and pharmacological studies,triterpenoid saponins have long been recognized as the main bioactive constituents of P.notoginseng.The type of saponins is mainly of dammarane-type (ginsenoside).Numerous studies,including fragmentation hehaviours,on-line analysis, determination and metabolism,have been reported which forcused on major constituents. However,the TCM is a complicated system,except for major constituents,there are a lot of minor or even trace constituents.Therefore,development of reliable analytical method for minor triterpenoid saponins is of great significance for elucidating pharmacodynamic substances of P.notoginseng and its related preparations.
In the study reported here,fragmentation behaviors of triterpenoid saponins from P. notoginseng were investigated by ESI-MS~n and high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry(HPLC/ESI-MS~n). Analyses revealed that fragment ions from glycosidic and cross-ring cleavages can give a wealth of structural information regarding the nature of the aglycone,sugar types,the sequence and linkage information of sugar units.According to the summarized fragmentation rules,identification of triterpenoid saponins from the roots of P. notoginseng could be fulfilled,even when reference standards were unavailable. Furthermore,minor and trace constituents were enriched and detected by eliminating the major constituents in one of the saponin fractions.As a result,a total of 151 saponins, including 56 new trace ones,were identified or tentatively characterized from saponin fractions based on their retention times,HPLC/HRMS,HPLC/ESI-MS~n fragmentation behaviors and comparison with data in the literatures.
These studies can assist in the effective analyses of saponins of this type and benefit the structural identification of similar trace constituents in fractions.This research provides a model for extensively screening and structural characterization of bioactive constituents in plant extracts.It also provides an informative fingerprint of P. notoginseng.
Carthamus tinctorius L.belongs to the family of Compositae,which is widely distributed in the province of Henan,Zhejing,and Sichuan,etc.in China,and its flowers are used as traditional Chinese medicine for treatment of heart and brain blood vessel diseases.Quinochalones are the major bioactive constituents of Carthamus tinctorius L. It shows higher polarity,therefore,it isolation and purification is difficult.ESI is a relatively new technique and is ideally suited to the introduction of polar,thermally labile compounds into a mass spectrometer.
In this study reported here,fragmentation behaviors of quinochalones from C. tinctorius were investigated by ESI-MS~n and HPLC/ESI-MS~n.And an efficient on-line identification system was established for constituents of this type.After the characteristic fragmentation patterns in positive and negative ion mode,and UV spectra of these compounds were summarized,HPLC-HR-MS,HPLC-DAD-ESI-MS~n of active fraction from C.tinctorius were measured.This technique can be utilized for the consecutive analysis of metabolites.
Hydroxysafflor yellow A(HSYA),a C-Glycosyl quinochalcones isolated from the safflower,exhibited extensive biological activities such as anti-cerebral ischemia effect. However the actual site of action of HSYA was still unclear and it was less study on whether the HSYA would travel through the BBB(blood brain barrier) or not.
Therefore,based on the mass spectrum schizolysis of C-Glycosyl quinochalcones, the anti-cerebral ischemia activities study of HSYA in plasma,different part of the brain and intra-cellular was developed.As an anti-cerebral ischemia drug,we investigated the distribution characteristics of HSYA in the brain at various group,different time,not alike take medicine way.The result showed the HSYA as low polarity compound,can travel through BBB at model animal and control group.In addition,the distribution of HSYA expressed significantly variance in the different part of brain,take medicine way and time.The research should do well to deeply mechanism study of anti-cerebral ischemia of HSYA.
引文
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