黄精降血糖活性成分的提取、分离及结构鉴定
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摘要
黄精(Rhizoma polygonati)为百合科(Liliaceae)黄精属(Polygonatum Mill.)多年生草本植物。黄精含有多种对人体有益的化学成分,如多糖、甾体皂苷、蒽醌类、生物碱、强心苷、木脂素、维生素和氨基酸等。
本文对黄精的化学成分进行了系统的研究;进行了黄精皂苷及其苷元的分离、纯化及结构鉴定;确立黄精总皂苷的提取工艺,并筛选出适合分离纯化黄精总皂苷的大孔吸附树脂型号;建立了黄精总皂苷的ELISA的检测方法;并对黄精提取物降血糖活性进行了研究。
通过气相色谱-质谱联用技术,对黄精中的脂肪酸、挥发性成分进行了测定,结果表明:黄精中的脂肪酸主要是亚油酸、棕榈油酸、硬脂酸、亚麻酸、花生酸,其相对质量分数分别是38.79%、33.20%、10.45%、9.74%、2.73%。黄精挥发性成分的组成较复杂,有羧酸类、醛类、醇类、芳香类、烷烃类、酸酐等多类别的化合物,其中主要有己醛、己烯酸、正己醇,相对质量分数分别为:29.13%、14.7%、4.89%。黄精所含的氨基酸种类齐全,氨基酸总量为5.778 g/100g,必需氨基酸总含量为1.075g/100g。
通过与标准品对照及利用NMR等手段确定了从黄精中提纯的皂苷元为薯蓣皂苷元。
通过琥珀酸酐法进行了半抗原的改造,碳二亚胺法进行了半抗原和大分子蛋白的偶联,成功地合成了免疫原和包被原。半抗原和牛血清白蛋白及卵清蛋白的结合比分别是21:1和11:1。利用合成的免疫原免疫新西兰大白兔,获得效价为1:12800的多克隆抗体。方阵滴定法确定抗体的最佳稀释度为1:3000;包被原的最佳稀释度为1:10000,包被原工作浓度为1.25μg/mL。
首次利用所制备的兔抗薯蓣皂苷多克隆抗体建立检测黄精皂苷的ELISA方法。其标准曲线在5.105×10~(-3)～3.972×10~(-1)μg/ml线性范围内呈相关性,回归方程I=32.021LogC+189.02,相关系数R~2=0.9974。最低检测下限I10为2.468×10~(-3)μg/ ml。并进行了ELISA分析条件的优化。ELISA检测方法测定黄精皂苷的结果表明:批内误差和批间误差的变异系数皆小于10%;样品的回收率在80.33～103.88%之间,变异系数﹤3%。与人参皂苷和强心甙的交叉反应率分别为3.24%和7.68%,对黄精总皂苷的特异性较高。通过ELISA方法,测得黄精中总皂苷含量为0.1366%(以薯蓣皂苷记)。
通过正交实验,确定了黄精总皂苷提取最优工艺参数为:提取温度80oC、乙醇浓度80%、提取时间180min、料液比1:20。
通过对8种大孔吸附树脂静态吸附特性的研究,确定了LSA-30大孔吸附树脂是一种黄精总皂苷理想的吸附剂。通过进一步对LSA-30型树脂的动态吸附特性的研究,LSA-30型树脂在上样液浓度0.5～0.85mg/ml,洗脱剂流速3ml/min时,对黄精总皂苷
Rhizoma polygonati belongs to the Polygonatum Mill family. It is perennial herbageplant which contained rich in polysaccharides, steroids saponins, anthraquinone, alkaloids,cardiac saponins, lignans, vitamine, and amino acid, etc, all of components are benefit tohuman bodies. However no information about volatile components has been reported.
In this paper, systematic studies were carried out on the basic chemical components andcontents of Rhizoma polygonati,and also concludes isolation, purification, identification,and quantification of Rhizoma polygonati, saponins. A ELISA method was also set up toinvestigate total saponins of the Rhizoma polygonati. Extraction procedure for total saponinswas established, and the macro-reticular resin that was suitable for absorption of the totalsaponins was screened. Saponins monomers were isolated, prettified and identified. We alsostudied the effect of monomers on reduce the blood sugar.
Components and contents of the fatty acids, volatile components were analyzed byGC-MS. Experiment results showed that fatty acids of saponins mainly consisted linoleic acid,opalmitic acid, stearic acid、linolenic acid and peanut acid. Their relative quality masses were38.79%, 33.20%, 10.45%, 9.74%, 2.73%, respectively. The volatile components werecomplicated and included hexa-dehyde n-heptoic acid, n-hexanol, their relative quality masseswere 29.13%、14.7%、4.89%,respectively. Rhizoma polygonati almost contain all the aminoacid, the total content of amino acid was 5.778 g/100g. Among them, the total content ofindispensable amino acid was 1.075g/100g.
Hapten was modified by the succinicanhydride method, and Hapten combined withbig molecular protein by the carbodiimide activation, then the coating antigen weresuccessfully synesized. Ratios of hapten intergraded with BSA and OVA were 21:1 and11:1, respectively. Multi-clone antibody was created by immunity of New Zealand rabbitsusing synthesized coating antigen. The optimum of diluted ratio of antibody, coatingantigen was 1:3000 and 1:3000 respectively by phalanx titration method, and theoptimum work concentration was 1.25μg/mL.
ELISA method that can determine the saponins of Rhizoma polygonati wasconstructed by the rabbit with multi-clone antibody of yam saponins. The standard curvewas positive relativity between 5.105×10~(-3) and 3.972×10~(-1)μg/ml, and the equation wasI=32.021LogC+189.02. The correlation coefficient was R2=0.9974 and the lowest limitwas 2.468×10~(-3)μg/ ml. The analysis terms of ELISA were optimized. The saponins ofRhizoma polygonati results which determined by ELISA showed that variation coefficientwas less than 10% between errors of the same batch and that of different batch. Therecovery rate of samples was between 80.33 and 103.88%, the variation coefficient was
less than 3%. However the ginseng saponins and cardiac saponins was 3.24% and 7.68%,respectively. From the result, we can deduced that the specificity is higher for saponins ofRhizoma polygonati, compared with ginseng saponins and cardiac saponins. The totalcontent of saponins in Rhizoma polygonati was 0.1366%(according to saponins of yam).The optimum terms of process extracting total saponins of Rhizoma polygonati wereinvestigated by orthogonal design experiment and the temperature of extraction,concentration of alcohol, time of extraction and ration of materials and liquid were 80oC,80%, 180min and 1:20, respectively.Macro-reticular resin, LSA-30, was selected and identified to use as the sorbent fortotal saponins by investigating static state absorption characters of eight kinds ofMacro-reticular resin. When the concentration of added samples was between 0.5mg/ml and0.85mg/ml, and the flow velocity of eluting reagent was 3ml/min, the volumetric absorptionwas the biggest. When the eluting reagent was alcohol and the concentration was more than50%, the eluting rate could reach 83.5%. But when the alcohol with concentration 95% , theeluting result was best.Activities reducing blood sugar of all kinds of eluting sample were investigated byconstructing the animal model with diaetes. The test results showed that activity ofRhizoma polygonati reducing the blood sugar was remarkable, and the best componentwas further isolated and purified. Structures of five kinds of monomers of purificationproducts by alcohol were identified, they were compounds B,C,D,E,F, and the compoundD and compound E were isolated from Rhizoma polygonati for the first time. Four kinds ofcomponents among of five monomers were tri-terpenes. So we deduced that the bestcomponents reducing blood sugar were tri-terpenes of Rhizoma polygonati.The extraction products were no influence on weight of mice, blood sugar of limosismice, and blood sugar of mice with taking food and endure content for sugar, but it couldimprove the symptom of mice with diabetes induced by 4-O-pyrimidine. After the animalstook the extraction products, the contents taken were 0.8g and 1.6g respectively perkilogram,the blood sugar value of animals is lower than that of control samples, it showedthat the mid and high dosage could reduce the blood sugar value of limosis mice, and theyalso could adjust the endure content of model mice with diabetes, at the same time, they couldcontrol the influence on the blood sugar value by extrinsic glucose.
本文对黄精的化学成分进行了系统的研究;进行了黄精皂苷及其苷元的分离、纯化及结构鉴定;确立黄精总皂苷的提取工艺,并筛选出适合分离纯化黄精总皂苷的大孔吸附树脂型号;建立了黄精总皂苷的ELISA的检测方法;并对黄精提取物降血糖活性进行了研究。
通过气相色谱-质谱联用技术,对黄精中的脂肪酸、挥发性成分进行了测定,结果表明:黄精中的脂肪酸主要是亚油酸、棕榈油酸、硬脂酸、亚麻酸、花生酸,其相对质量分数分别是38.79%、33.20%、10.45%、9.74%、2.73%。黄精挥发性成分的组成较复杂,有羧酸类、醛类、醇类、芳香类、烷烃类、酸酐等多类别的化合物,其中主要有己醛、己烯酸、正己醇,相对质量分数分别为:29.13%、14.7%、4.89%。黄精所含的氨基酸种类齐全,氨基酸总量为5.778 g/100g,必需氨基酸总含量为1.075g/100g。
通过与标准品对照及利用NMR等手段确定了从黄精中提纯的皂苷元为薯蓣皂苷元。
通过琥珀酸酐法进行了半抗原的改造,碳二亚胺法进行了半抗原和大分子蛋白的偶联,成功地合成了免疫原和包被原。半抗原和牛血清白蛋白及卵清蛋白的结合比分别是21:1和11:1。利用合成的免疫原免疫新西兰大白兔,获得效价为1:12800的多克隆抗体。方阵滴定法确定抗体的最佳稀释度为1:3000;包被原的最佳稀释度为1:10000,包被原工作浓度为1.25μg/mL。
首次利用所制备的兔抗薯蓣皂苷多克隆抗体建立检测黄精皂苷的ELISA方法。其标准曲线在5.105×10~(-3)～3.972×10~(-1)μg/ml线性范围内呈相关性,回归方程I=32.021LogC+189.02,相关系数R~2=0.9974。最低检测下限I10为2.468×10~(-3)μg/ ml。并进行了ELISA分析条件的优化。ELISA检测方法测定黄精皂苷的结果表明:批内误差和批间误差的变异系数皆小于10%;样品的回收率在80.33～103.88%之间,变异系数﹤3%。与人参皂苷和强心甙的交叉反应率分别为3.24%和7.68%,对黄精总皂苷的特异性较高。通过ELISA方法,测得黄精中总皂苷含量为0.1366%(以薯蓣皂苷记)。
通过正交实验,确定了黄精总皂苷提取最优工艺参数为:提取温度80oC、乙醇浓度80%、提取时间180min、料液比1:20。
通过对8种大孔吸附树脂静态吸附特性的研究,确定了LSA-30大孔吸附树脂是一种黄精总皂苷理想的吸附剂。通过进一步对LSA-30型树脂的动态吸附特性的研究,LSA-30型树脂在上样液浓度0.5～0.85mg/ml,洗脱剂流速3ml/min时,对黄精总皂苷
Rhizoma polygonati belongs to the Polygonatum Mill family. It is perennial herbageplant which contained rich in polysaccharides, steroids saponins, anthraquinone, alkaloids,cardiac saponins, lignans, vitamine, and amino acid, etc, all of components are benefit tohuman bodies. However no information about volatile components has been reported.
In this paper, systematic studies were carried out on the basic chemical components andcontents of Rhizoma polygonati,and also concludes isolation, purification, identification,and quantification of Rhizoma polygonati, saponins. A ELISA method was also set up toinvestigate total saponins of the Rhizoma polygonati. Extraction procedure for total saponinswas established, and the macro-reticular resin that was suitable for absorption of the totalsaponins was screened. Saponins monomers were isolated, prettified and identified. We alsostudied the effect of monomers on reduce the blood sugar.
Components and contents of the fatty acids, volatile components were analyzed byGC-MS. Experiment results showed that fatty acids of saponins mainly consisted linoleic acid,opalmitic acid, stearic acid、linolenic acid and peanut acid. Their relative quality masses were38.79%, 33.20%, 10.45%, 9.74%, 2.73%, respectively. The volatile components werecomplicated and included hexa-dehyde n-heptoic acid, n-hexanol, their relative quality masseswere 29.13%、14.7%、4.89%,respectively. Rhizoma polygonati almost contain all the aminoacid, the total content of amino acid was 5.778 g/100g. Among them, the total content ofindispensable amino acid was 1.075g/100g.
Hapten was modified by the succinicanhydride method, and Hapten combined withbig molecular protein by the carbodiimide activation, then the coating antigen weresuccessfully synesized. Ratios of hapten intergraded with BSA and OVA were 21:1 and11:1, respectively. Multi-clone antibody was created by immunity of New Zealand rabbitsusing synthesized coating antigen. The optimum of diluted ratio of antibody, coatingantigen was 1:3000 and 1:3000 respectively by phalanx titration method, and theoptimum work concentration was 1.25μg/mL.
ELISA method that can determine the saponins of Rhizoma polygonati wasconstructed by the rabbit with multi-clone antibody of yam saponins. The standard curvewas positive relativity between 5.105×10~(-3) and 3.972×10~(-1)μg/ml, and the equation wasI=32.021LogC+189.02. The correlation coefficient was R2=0.9974 and the lowest limitwas 2.468×10~(-3)μg/ ml. The analysis terms of ELISA were optimized. The saponins ofRhizoma polygonati results which determined by ELISA showed that variation coefficientwas less than 10% between errors of the same batch and that of different batch. Therecovery rate of samples was between 80.33 and 103.88%, the variation coefficient was
less than 3%. However the ginseng saponins and cardiac saponins was 3.24% and 7.68%,respectively. From the result, we can deduced that the specificity is higher for saponins ofRhizoma polygonati, compared with ginseng saponins and cardiac saponins. The totalcontent of saponins in Rhizoma polygonati was 0.1366%(according to saponins of yam).The optimum terms of process extracting total saponins of Rhizoma polygonati wereinvestigated by orthogonal design experiment and the temperature of extraction,concentration of alcohol, time of extraction and ration of materials and liquid were 80oC,80%, 180min and 1:20, respectively.Macro-reticular resin, LSA-30, was selected and identified to use as the sorbent fortotal saponins by investigating static state absorption characters of eight kinds ofMacro-reticular resin. When the concentration of added samples was between 0.5mg/ml and0.85mg/ml, and the flow velocity of eluting reagent was 3ml/min, the volumetric absorptionwas the biggest. When the eluting reagent was alcohol and the concentration was more than50%, the eluting rate could reach 83.5%. But when the alcohol with concentration 95% , theeluting result was best.Activities reducing blood sugar of all kinds of eluting sample were investigated byconstructing the animal model with diaetes. The test results showed that activity ofRhizoma polygonati reducing the blood sugar was remarkable, and the best componentwas further isolated and purified. Structures of five kinds of monomers of purificationproducts by alcohol were identified, they were compounds B,C,D,E,F, and the compoundD and compound E were isolated from Rhizoma polygonati for the first time. Four kinds ofcomponents among of five monomers were tri-terpenes. So we deduced that the bestcomponents reducing blood sugar were tri-terpenes of Rhizoma polygonati.The extraction products were no influence on weight of mice, blood sugar of limosismice, and blood sugar of mice with taking food and endure content for sugar, but it couldimprove the symptom of mice with diabetes induced by 4-O-pyrimidine. After the animalstook the extraction products, the contents taken were 0.8g and 1.6g respectively perkilogram,the blood sugar value of animals is lower than that of control samples, it showedthat the mid and high dosage could reduce the blood sugar value of limosis mice, and theyalso could adjust the endure content of model mice with diabetes, at the same time, they couldcontrol the influence on the blood sugar value by extrinsic glucose.
引文
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