丹参提取物中有效成分的质量控制及药动学研究
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摘要
丹参(Radix et Rhizoma Salviae Miltiorrhiza)为唇型科植物丹参(Salviamiltiorrhiza Bge.)的干燥根及根茎,主要药效成分包括脂溶性的丹参酮类和水溶性的丹酚酸类。本文通过对不同来源药材中两类主要成分的含量相关性研究,提取工艺研究,药材及提取物的主要组分及稳定性研究,探讨主要成分不同存在状态时的相互影响,在此基础上,研究了不同极性的两类物质的双向载药脂质微球制备工艺,并对其在单用和不同比例配伍时大鼠体内外药物动力学及相互作用进行了研究。
参照药典方法对来源于主产区的不同产地的栽培丹参及市售商品丹参进行了鉴别及化学成分含量测定。结果表明丹参药材来源单一,薄层色谱及红外光谱行为无明显差异,但其主要指标性成分含量差异较大;药材中脂溶性指标成分之间存在含量相关性,水溶性指标成份之间亦存在含量相关性,而水溶性成份及脂溶性成分之间含量无相关性。
对丹参不同极性有效成份的提取工艺进行了研究。结果显示,采用超临界二氧化碳萃取技术先提取丹参中的脂溶性成分,后对药渣进行水溶性成份提取的先进工艺,可使药材中的有效成分得以充分利用。确定了超临界提取的最佳工艺参数为:萃取压力为25MPa,萃取温度为50℃,萃取时间为2.5小时,携带剂为为95%的乙醇;水溶性成份提取工艺为:干燥药渣加8倍量水,浸泡4小时后,煎煮两次,每次2小时,滤液加95%乙醇使醇浓度达60%,冷藏静置40小时,滤液浓缩后上D101大孔吸附树脂吸附,50%乙醇洗脱,滤液浓缩后冷冻干燥。
通过对丹参药材、脂溶性提取物及对照品的甲醇提取物稳定性考察,表明丹参酮ⅡA及隐丹参酮易受温度、pH、光照的影响而发生降解。与纯品对比,药材及提取物中的其他成分对丹参酮ⅡA及隐丹参酮的降解有延缓作用,弱酸环境下其稳定性较好。
通过对丹参药材、水溶性提取物、脂溶性提取物及对照品UPLC-ESI-MS色谱及质谱行为研究,从中分离检定了20个化合物,其中水溶性成份10个,脂溶性成分7个,未知3个。对指标成分丹参酮ⅡA及丹酚酸B进行了不同碰撞能量下的ESI-MS裂解规律研究,指出丹参酮ⅡA的裂解特征是正离子模式下出现碎片m/z280、277、262、252、249;丹酚酸B的裂解特征是负离子模式下形成m/z519、321、339、295的碎片离子。
分别对丹参脂溶性提取物、水溶性提取物及不同比例的两种提取物混合物中丹参酮ⅡA、隐丹参酮及丹酚酸B的大鼠体外血浆及肝匀浆降解动力学进行了研究。结果表明,0.2mg/ml的脂溶性提取物中丹参酮ⅡA及隐丹参酮在血浆中随血浆浓度升高,降解速率减小;60mg/ml的水溶性提取物中丹酚酸B在不同浓度血浆中降解速率没有明显变化;在肝匀浆中三个化合物均随肝匀浆浓度上升降解速率增大。水溶性提取物与脂溶性提取物按不同比例(20∶1,10∶1,5∶1)混合后在20%血浆及20%肝匀浆中,丹参酮ⅡA的降解速率与混合前比较明显降低;隐丹参酮及丹酚酸B的降解速率与混合前比较,在20%血浆中略有上升,在20%肝匀浆中均显著下降。两种提取物混合后,在血浆和肝匀浆液中的确发生了代谢性药物的相互作用。
研究了丹参双相载药脂质微球注射液的处方、工艺及制剂的理化性质。结果显示,丹参双向载药脂质微球注射液呈现棕褐色,粒径分布在200nm左右,ζ-电位在-20——40mv之间,灭菌前后外观形态,粒径以及电位值均无明显变化,水溶性成份主要分布于水相当中,脂溶性成份主要分布于油相当中。
分别采用静脉及口服给药方式,对丹参脂溶性提取物、水溶性提取物及两种提取物混合物中丹参酮ⅡA、丹酚酸B的大鼠体内药物动力学进行了研究,建立了血浆中丹参酮ⅡA和丹酚酸B同时测定的UPLC/MS-MS分析方法。结果表明,静脉注射混合提取物乳剂比相应等剂量脂溶性提取物乳剂和水溶性提取物溶液剂的丹参酮ⅡA和丹酚酸B的AUC显著提高2～14倍,低剂量组和中剂量组提高至2倍,高剂量组分别提高至约14倍和5倍(p<0.01);血浆清除率(CLt)显著降低(p<0.01),达峰浓度(C_(0.083h))显著升高(p<0.01)。口服给高剂量和中剂量的混合提取物混悬液比相应等剂量脂溶性提取物混悬液和水溶性提取物溶液剂所测得丹参酮ⅡA和丹酚酸B的AUC显著性提高(p<0.05);高剂量和低剂量组测得丹参酮ⅡA和丹酚酸B的总血浆清除率CLt显著降低(p<0.01)。两种提取物混合后,在大鼠体内发生了代谢性药物的相互作用。
Radix Salvia Miltiorrhizae is the dried root of Salvia miltiorrhiza Bge.The main pharmacological active ingredients are the hydrosoluble components salvianolic acids and liposoluble components diterpenoid tanshinones.In this study,the correlativity of content from different sources,extraction technology,the main components and the stability of crude drug and extracts were investigated to reveal the interactions between the key components in different conditions.On the basis upon, formulation technology of bidirectional drug-loaded lipid microsphere of the two different polar components was studied.Also,the pharmacokinetics in rats after administration of single and mixed components in different ratios and components interactions were studied.
According to Chinese Pharmacopoeia,cultivated and commericall available Salvia Miltiorrhizae from different habitats were identified and assayed.It was found that the source of Salvia Miltiorrhizae was single and there was no significant difference in thin-layer chromatography(TLC) as well as infrared spectrum.However, differences in contents of main index components were of significance.It was also found that the content of diterpenoid tanshinones existed a correlativity,as well as salvianolic acids.But there was no correlativity of content between tanshinones and salvianolic acids.
Extraction technology of active ingredients with different polarity in Salvia Miltiorrhizae was investigated.The result showed that the active ingredients could be fully extracted after supercritical carbon dioxide extraction of diterpenoid tanshinones from Salvia Miltiorrhizae crude drug,then extracting alvianolic acids from the herb residue.The optimum condition of supercritical extraction was as follows:extracting pressure:25MPa,extracting temperature:50℃,extracting time:2.5h and ethanol was added as a cosolvent.The extraction process of salvianolic acids was discribed below. Soaking dry herb residue in 8 volumes of water for 4 hours,then decocting twice for 2 hours each time,95%ethanol was added to filtrate until the concentration of ethanol was 60%.After storage in cold for 40 hours,concentrated filtrate was eluted on a column of D101 macroporous resin by 50%ethanol.The eluate was finally freeze-dried.
By studying the stability of Salvia Miltiorrhizae crude drug,liposoluble extracts and the standard methanol solution,it indicated that tanshinoneⅡA and cryptotanshinone were vulnerable to temperature,pH and light and prone to degrade. Compared with pure substances,other components in crude drug and extracts could delay the degradation of tanshinoneⅡA and cryptotanshinone.In addition, tanshinoneⅡA and cryptotanshinone were more stable under weak acid condition.
According to the UPLC-ESI-MS chromatographic and mass spectral behaviors of Salvia Miltiorrhizae crude drug,salvianolic acids,diterpenoid tanshinones and reference substances,20 compounds have been separated and identified including 10 watersoluble components,7 liposoluble components,and 3 unknown components. Based on the research of ESI-MS fragmentation pathways of tanshinoneⅡA and salvianolic acid B at different collision energy,fragments of tanshinoneⅡA at m/z280, 277,262,252 and 249 in the positive ion mode were obtained.With respect to salvianolic acid B,fragments at m/z519,321,339 and 295 in the negative ion mode were formed.
The in vitro degradation kinetics in rat plasma and liver homogenate of tanshinoneⅡA,cryptotanshinone in diterpenoid tanshinones,salvianolic acid B in salvianolic acids and mixed extract in the different proportion were investigated.The result indicated that with the increasing of plasma concentration,the degradation rate of 0.5mg/ml tanshinoneⅡA and cryptotanshinone in plasma was was decreased;the degradation rate of salvianolic acid B in 2.97mg/ml salvianolic acids in different concentration of plasma had no obvious change;the degradation rates of the three compounds in liver homogenate was high with the increasing concentration of liver homogenate.After mixing diterpenoid tanshinones and salvianolic acids in different ratio(20:1,10:1,5:1),the degradation rate of tanshinoneⅡA was obviously lowered. The degradation rate of cryptotanshinone and salvianolic acid B was slightly increased in 20%plasma and decreased significantly in 20%liver homogenate.In summary,interaction of drugs metabolism in plasma and liver homogenate occurred.
Formulation,process and physicochemical properties of bidirectional Salvia Miltiorrhizae lipid microsphere injection were studied.It showed that the color of bidirectional drug-loaded lipid microsphere injection of Salvia Miltiorrhizae was dark brown.The particle size of the injectionwas about 200nm withζ-potential -20——40mv.The appearance,particle size andζ-potential had no significant change before and after sterilization.Salvianolic acids mainly distributed in water phase and diterpenoid tanshinones mainly distributed in oil phase.
By intravenous and oral administration,rats pharmacokinetics of tanshinoneⅡA and salvianolic acid B from diterpenoid tanshinones,salvianolic acids and mixed extracts were studied.A UPLC/MS-MS methods of simultaneously determining tanshinoneⅡA and salvianolic acid B in plasma was established. Compared mixed extracted emulsions with tanshinones emulsions and salvianolic acids emulsions isodose,AUC of tanshinoneⅡA and salvianolic acid B was obviously increased by 2-14 times,where the AUC of low dosage group and middle dosage group increased to 2 times and the AUC of high dose group was increased to about 14 times and 5 times respectively(P<0.01).Furthermore,plasma clearance(CLt) decreased significantly(p<0.01) and the peak concentration(C_(0.083h)) significant increased(p<0.01).Compared oral high dose and middle dose mixed extracts with tanshinones suspension and salvianolic acids suspension isodose,AUC of tanshinoneⅡA and salvianolic acid B significant increased(p<0.05),total plasma clearance(CLt) of tanshinoneⅡA and salvianolic acid B in high dose group and low dose group decreased significantly(p<0.01).In conclude,there existed interaction of drugs in metabolism in rats after mixing of the two extracts.
参照药典方法对来源于主产区的不同产地的栽培丹参及市售商品丹参进行了鉴别及化学成分含量测定。结果表明丹参药材来源单一,薄层色谱及红外光谱行为无明显差异,但其主要指标性成分含量差异较大;药材中脂溶性指标成分之间存在含量相关性,水溶性指标成份之间亦存在含量相关性,而水溶性成份及脂溶性成分之间含量无相关性。
对丹参不同极性有效成份的提取工艺进行了研究。结果显示,采用超临界二氧化碳萃取技术先提取丹参中的脂溶性成分,后对药渣进行水溶性成份提取的先进工艺,可使药材中的有效成分得以充分利用。确定了超临界提取的最佳工艺参数为:萃取压力为25MPa,萃取温度为50℃,萃取时间为2.5小时,携带剂为为95%的乙醇;水溶性成份提取工艺为:干燥药渣加8倍量水,浸泡4小时后,煎煮两次,每次2小时,滤液加95%乙醇使醇浓度达60%,冷藏静置40小时,滤液浓缩后上D101大孔吸附树脂吸附,50%乙醇洗脱,滤液浓缩后冷冻干燥。
通过对丹参药材、脂溶性提取物及对照品的甲醇提取物稳定性考察,表明丹参酮ⅡA及隐丹参酮易受温度、pH、光照的影响而发生降解。与纯品对比,药材及提取物中的其他成分对丹参酮ⅡA及隐丹参酮的降解有延缓作用,弱酸环境下其稳定性较好。
通过对丹参药材、水溶性提取物、脂溶性提取物及对照品UPLC-ESI-MS色谱及质谱行为研究,从中分离检定了20个化合物,其中水溶性成份10个,脂溶性成分7个,未知3个。对指标成分丹参酮ⅡA及丹酚酸B进行了不同碰撞能量下的ESI-MS裂解规律研究,指出丹参酮ⅡA的裂解特征是正离子模式下出现碎片m/z280、277、262、252、249;丹酚酸B的裂解特征是负离子模式下形成m/z519、321、339、295的碎片离子。
分别对丹参脂溶性提取物、水溶性提取物及不同比例的两种提取物混合物中丹参酮ⅡA、隐丹参酮及丹酚酸B的大鼠体外血浆及肝匀浆降解动力学进行了研究。结果表明,0.2mg/ml的脂溶性提取物中丹参酮ⅡA及隐丹参酮在血浆中随血浆浓度升高,降解速率减小;60mg/ml的水溶性提取物中丹酚酸B在不同浓度血浆中降解速率没有明显变化;在肝匀浆中三个化合物均随肝匀浆浓度上升降解速率增大。水溶性提取物与脂溶性提取物按不同比例(20∶1,10∶1,5∶1)混合后在20%血浆及20%肝匀浆中,丹参酮ⅡA的降解速率与混合前比较明显降低;隐丹参酮及丹酚酸B的降解速率与混合前比较,在20%血浆中略有上升,在20%肝匀浆中均显著下降。两种提取物混合后,在血浆和肝匀浆液中的确发生了代谢性药物的相互作用。
研究了丹参双相载药脂质微球注射液的处方、工艺及制剂的理化性质。结果显示,丹参双向载药脂质微球注射液呈现棕褐色,粒径分布在200nm左右,ζ-电位在-20——40mv之间,灭菌前后外观形态,粒径以及电位值均无明显变化,水溶性成份主要分布于水相当中,脂溶性成份主要分布于油相当中。
分别采用静脉及口服给药方式,对丹参脂溶性提取物、水溶性提取物及两种提取物混合物中丹参酮ⅡA、丹酚酸B的大鼠体内药物动力学进行了研究,建立了血浆中丹参酮ⅡA和丹酚酸B同时测定的UPLC/MS-MS分析方法。结果表明,静脉注射混合提取物乳剂比相应等剂量脂溶性提取物乳剂和水溶性提取物溶液剂的丹参酮ⅡA和丹酚酸B的AUC显著提高2～14倍,低剂量组和中剂量组提高至2倍,高剂量组分别提高至约14倍和5倍(p<0.01);血浆清除率(CLt)显著降低(p<0.01),达峰浓度(C_(0.083h))显著升高(p<0.01)。口服给高剂量和中剂量的混合提取物混悬液比相应等剂量脂溶性提取物混悬液和水溶性提取物溶液剂所测得丹参酮ⅡA和丹酚酸B的AUC显著性提高(p<0.05);高剂量和低剂量组测得丹参酮ⅡA和丹酚酸B的总血浆清除率CLt显著降低(p<0.01)。两种提取物混合后,在大鼠体内发生了代谢性药物的相互作用。
Radix Salvia Miltiorrhizae is the dried root of Salvia miltiorrhiza Bge.The main pharmacological active ingredients are the hydrosoluble components salvianolic acids and liposoluble components diterpenoid tanshinones.In this study,the correlativity of content from different sources,extraction technology,the main components and the stability of crude drug and extracts were investigated to reveal the interactions between the key components in different conditions.On the basis upon, formulation technology of bidirectional drug-loaded lipid microsphere of the two different polar components was studied.Also,the pharmacokinetics in rats after administration of single and mixed components in different ratios and components interactions were studied.
According to Chinese Pharmacopoeia,cultivated and commericall available Salvia Miltiorrhizae from different habitats were identified and assayed.It was found that the source of Salvia Miltiorrhizae was single and there was no significant difference in thin-layer chromatography(TLC) as well as infrared spectrum.However, differences in contents of main index components were of significance.It was also found that the content of diterpenoid tanshinones existed a correlativity,as well as salvianolic acids.But there was no correlativity of content between tanshinones and salvianolic acids.
Extraction technology of active ingredients with different polarity in Salvia Miltiorrhizae was investigated.The result showed that the active ingredients could be fully extracted after supercritical carbon dioxide extraction of diterpenoid tanshinones from Salvia Miltiorrhizae crude drug,then extracting alvianolic acids from the herb residue.The optimum condition of supercritical extraction was as follows:extracting pressure:25MPa,extracting temperature:50℃,extracting time:2.5h and ethanol was added as a cosolvent.The extraction process of salvianolic acids was discribed below. Soaking dry herb residue in 8 volumes of water for 4 hours,then decocting twice for 2 hours each time,95%ethanol was added to filtrate until the concentration of ethanol was 60%.After storage in cold for 40 hours,concentrated filtrate was eluted on a column of D101 macroporous resin by 50%ethanol.The eluate was finally freeze-dried.
By studying the stability of Salvia Miltiorrhizae crude drug,liposoluble extracts and the standard methanol solution,it indicated that tanshinoneⅡA and cryptotanshinone were vulnerable to temperature,pH and light and prone to degrade. Compared with pure substances,other components in crude drug and extracts could delay the degradation of tanshinoneⅡA and cryptotanshinone.In addition, tanshinoneⅡA and cryptotanshinone were more stable under weak acid condition.
According to the UPLC-ESI-MS chromatographic and mass spectral behaviors of Salvia Miltiorrhizae crude drug,salvianolic acids,diterpenoid tanshinones and reference substances,20 compounds have been separated and identified including 10 watersoluble components,7 liposoluble components,and 3 unknown components. Based on the research of ESI-MS fragmentation pathways of tanshinoneⅡA and salvianolic acid B at different collision energy,fragments of tanshinoneⅡA at m/z280, 277,262,252 and 249 in the positive ion mode were obtained.With respect to salvianolic acid B,fragments at m/z519,321,339 and 295 in the negative ion mode were formed.
The in vitro degradation kinetics in rat plasma and liver homogenate of tanshinoneⅡA,cryptotanshinone in diterpenoid tanshinones,salvianolic acid B in salvianolic acids and mixed extract in the different proportion were investigated.The result indicated that with the increasing of plasma concentration,the degradation rate of 0.5mg/ml tanshinoneⅡA and cryptotanshinone in plasma was was decreased;the degradation rate of salvianolic acid B in 2.97mg/ml salvianolic acids in different concentration of plasma had no obvious change;the degradation rates of the three compounds in liver homogenate was high with the increasing concentration of liver homogenate.After mixing diterpenoid tanshinones and salvianolic acids in different ratio(20:1,10:1,5:1),the degradation rate of tanshinoneⅡA was obviously lowered. The degradation rate of cryptotanshinone and salvianolic acid B was slightly increased in 20%plasma and decreased significantly in 20%liver homogenate.In summary,interaction of drugs metabolism in plasma and liver homogenate occurred.
Formulation,process and physicochemical properties of bidirectional Salvia Miltiorrhizae lipid microsphere injection were studied.It showed that the color of bidirectional drug-loaded lipid microsphere injection of Salvia Miltiorrhizae was dark brown.The particle size of the injectionwas about 200nm withζ-potential -20——40mv.The appearance,particle size andζ-potential had no significant change before and after sterilization.Salvianolic acids mainly distributed in water phase and diterpenoid tanshinones mainly distributed in oil phase.
By intravenous and oral administration,rats pharmacokinetics of tanshinoneⅡA and salvianolic acid B from diterpenoid tanshinones,salvianolic acids and mixed extracts were studied.A UPLC/MS-MS methods of simultaneously determining tanshinoneⅡA and salvianolic acid B in plasma was established. Compared mixed extracted emulsions with tanshinones emulsions and salvianolic acids emulsions isodose,AUC of tanshinoneⅡA and salvianolic acid B was obviously increased by 2-14 times,where the AUC of low dosage group and middle dosage group increased to 2 times and the AUC of high dose group was increased to about 14 times and 5 times respectively(P<0.01).Furthermore,plasma clearance(CLt) decreased significantly(p<0.01) and the peak concentration(C_(0.083h)) significant increased(p<0.01).Compared oral high dose and middle dose mixed extracts with tanshinones suspension and salvianolic acids suspension isodose,AUC of tanshinoneⅡA and salvianolic acid B significant increased(p<0.05),total plasma clearance(CLt) of tanshinoneⅡA and salvianolic acid B in high dose group and low dose group decreased significantly(p<0.01).In conclude,there existed interaction of drugs in metabolism in rats after mixing of the two extracts.
引文
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