马铃薯糖苷生物碱的提取与纯化
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摘要
本文根据近年来国内外的研究动态,简要论述了糖苷生物碱的分布、糖苷生物碱化学结构及分类和药理学活性；介绍了马铃薯糖苷生物碱的化学结构,概括了糖苷生物碱的定性方法,从不同提取溶剂和不同的提取方法阐述了糖苷生物碱提取的进展,归纳了糖苷生物碱的纯化方法,比较了含量测定的各种方法,为马铃薯糖苷生物碱的综合开发利用指出了新途径。
根据参考文献和所选择材料的特点,考虑到提取材料的经济性(市场上方便易购买),发绿的马铃薯薯皮中糖苷生物碱的含量要明显高于正常的马铃薯薯皮,以发绿的马铃薯薯皮为提取材料,本课题旨在考察不同的提取方法、不同的提取溶剂,对马铃薯糖苷生物碱含量的影响,并探讨粗产物柱层析分离纯化的条件。主要内容概括如下：
1.原料化学成分的检验及提取方法的筛选
马铃薯绿皮干样粉末的化学成分为生物碱类、多糖及其苷类、皂苷、氨基酸、多肽及蛋白质、酚类、内酯、香豆素及其苷、甾体(植物甾醇)和萜类、挥发油和有机酸,可能含有黄酮及其苷类、强心苷和蒽醌及苷,没有油脂和鞣质。考察了马铃薯糖苷生物碱的紫外光谱分析方法的适用性；从不同的提取方法中筛选出最优的提取方法,提取效果为索氏提取<回流提取<超声波提取,粗样品质量分别为0.0126g/g、0.00152g/g、0.0306g/g, TGA含量分别为2.18mg/g、2.76mg／g、4.45mg/g,超声波的提取率最高。
2.超声波提取马铃薯TGA
通过超声波提取的正交设计试验,直观分析得第12号实验提取率最高。方差分析得显著影响提取率的因素依次为提取温度>提取溶剂种类>超声波频率>提取时间>料液比,根据效应分析确定最佳因素水平组合为A3B4C3D1E3(提取时间2h、提取温度50℃、超声波频率45Hz、溶剂种类乙醇-乙酸、料液比(m／v)1：12)。进一步作了单因素实验,筛选出最优条件为超声波频率45Hz,提取时间2.5 h,料液比(m／v)1：14,提取温度50℃,乙醇-乙酸配比(100：30,v／v)。在最优的条件下,测定不同试材中马铃薯糖苷生物碱的含量,提取效果为正常的马铃薯薯肉<发绿的马铃薯薯肉<正常的马铃薯薯皮<发绿的马铃薯薯皮<马铃薯薯芽,粗样品质量分别为0.0067g/g、0.0124g/g、0.0234g／g、0.0700g／g、0.1150g／g,TGA含量分别为1.02mg/g、2.64mg／g、3.24mg／g、11.80mg／g、21.23mg／g,马铃薯薯芽中糖苷生物碱的含量最高。
3.微波-超声波联用提取马铃薯TGA
首先对微波作为前处理的手段进行了分析,正交设计微波提取马铃薯糖苷生物碱,筛选出最优条件为95%乙醇-36%乙酸配比为100：40,料液比(m／v)1：20,60℃下提取7min。其次,以乙醇-离子液体为提取溶剂,正交设计微波-超声波提取马铃薯糖苷生物碱,先经过微波预处理,筛选出超声波提取最优条件为温度70℃,溶剂配比(v／v)600：1,提取时间20min,料液比(m／v)6：1。
4.超临界CO2提取马铃薯TGA
通过均匀设计试验和单因素实验,筛选出最优提取条件为萃取压力30Mpa、温度55℃、萃取时间90min、夹带剂乙醇含量10%。当HPLC色谱条件为Zorbax edclipsexdb C8(4.6mm×150mm,5.0um),柱温30℃,流动相为乙腈与KH2PO4～K2HPO4缓冲液(pH=7.6)配比为(60：40,v／v)时,α-茄碱的保留时间为t=6.4。
5.柱层析分离纯化马铃薯TGA
考察了索氏提取物的纯化条件,以硅胶为吸附剂,乙酸乙酯-95%乙醇-10%氨水(80：30：4,v／v)洗脱部位得到茄碱单体。探讨了超声波提取物的纯化条件,对三种洗脱溶剂系统进行了筛选,以三氧化二铝为吸附剂,流动相为氯仿-无水甲醇溶剂系统时,茄碱在氯仿-无水甲醇(20：80,v／v)、(10：90,v／v)、(0：100,v／v)洗脱部位,将这三种洗脱液合并,通过制备薄层层析分离得到茄碱和另外一个化合物。最后对得到的三种化合物进行结构表征。
According to research trends at home and abroad in recent years, briefly discussed the distribution of glycoalkaloids, chemical structure and types of glycoalkaloids, pharmacological activity of glycoalkaloids, introduced chemical structure of potato glycoalkaloids, summarizes qualitative methods of glycoalkaloids, describes the extraction progress of glycoalkaloids from different extraction solvents and different extraction methods, summarizes the purification methods of glycoalkaloids, compared various methods of content determination, indicated a new approach for comprehensive development and utilization of potato glycoalkaloids.
According to references and characteristics of the selected material, considering the extraction of the material economy (convenient to purchase), compared normal potato skins with green potato skin, the content of glycoalkaloids in green potatoskin was significantly high. Therefore, using green potato skin as the extracting materials, In this article, aiming to explore influence factors of potato glycoalkaloids in the aspects of different extraction methods and different extraction solvents, and discusses separation and purification conditions of coarse product using column chromatography.
The major contents are described as follows:
1.Inspection of chemical composition from raw material and screening of different extraction methods
chemical composition of potatoes green skin powder:alkaloids, polysaccharide and nucleoside, saponins, amino acids, peptides and protein, phenols, lactones, coumarin and glycosides, sterols (phytosterols) and terpenoids, volatile oil, triterpenes and glycosides, organic acids, probably contained flavonoids and glycosides, cardiac glycosides, anthraquinones, but oil and tannins is without. Investigated the ultraviolet spectrum analysis method applicability of potato glycoalkaloids, choosing the best extraction method from different extraction methods, extraction efficiency:soxhlet extraction 2. Ultrasonic extraction of potato TGA
according to orthogonal design experiment of ultrasonic extraction, extraction efficiency of the 12th experiment is the highest by intuitive analysis. significant influence factors of extraction efficiency extraction temperature>type of extraction solvent>ultrasonic frequency>extraction time> ratio of solid-liquid, determine the optimal factor level combination A3B4C3D1E3 (extraction time 2h, extraction temperature 50℃, ultrasonic frequency 45Hz, type of extraction solvent ethanol-acid extraction solution, ratio of solid-liquid (m/v) 1:12). In further research of single factors experiment, the optimal conditions of potato glycoalkaloids extraction:ultrasonic frequency 45Hz, extraction time 2.5h, ratio of solid-liquid (m/v) 1:14, extraction temperature 50℃, volume ratio of ethanol-acetic acid (100:30, v/v), Under optimal conditions,, determinated TGA content of potato from different materials. extraction efficiency:tuber of normal potato 3. Combined extraction of microwave-ultrasonic for potato TGA
firstly, microwave extraction as the pretreatment method was analyzed, doing the orthogonal design experiment of potato glycoalkaloids which was extracted by microwave, selected the optimal conditions, volume ratio of acid 95% ethanol-36% acetic acid(100:40, v/v), ratio of solid-liquid(m/v) 1:20, extraction temperature 60℃, extraction time 7min. Secondly, ethanol-ionic liquid is a new kind of solvent system, orthogonal design experiment of potato TGA which was combined extraction of microwave-ultrasonic, firstly, microwave pretreatment, and selected the optimal conditions for ultrasonic extraction:extraction temperature 70℃, volume ratio of solvent 600:1 (v/v), extraction time 20min, ratio of solid-liquid (m/v)1:6.
4. Supercritical CO2 extraction of potato TGA
Based on the experiment of uniform design and single factors experiment, the optimal extraction conditions:extraction pressure 30Mpa, temperature 55℃, extraction time 90min, dosage of entrainer 10%. HPLC chromatographic conditions:Zorbax edclipsexdb C8(4.6mm×150mm,5.0um), column temperature30℃, mobile phase:Volume ratio of acetonitrile and buffer solution of KH2PO4～K2HPO4 ((pH=7.6) (60:40, v/v), retention time ofα-solanine is t=6.4.
5. Separated and purification of potato TGA by column chromatography
Investigated purification of soxhlet extraction, using silica gel column, finally obtained a-solanine monomer from ethylacetate-95% ethanol-10% ammonia (80:30:4, v/v) elution part. Discussed purification of ultrasonic extraction, three kinds of solvent elution were screened, using Al2O3 column chromatography, mobile phase was solvent systems of chloroform-methanol without water,α-solanine is in elution parts of chloroform-methanol without water (20:80, v/v), (10:90, v/v), (0:100, v/v), mergerded the three kinds of eluent solvents. Obtained a-solanine and another kind of compound by the preparation thin-layer chromatography separation. Finally, determined structure characterization of three compounds which were obtained.
根据参考文献和所选择材料的特点,考虑到提取材料的经济性(市场上方便易购买),发绿的马铃薯薯皮中糖苷生物碱的含量要明显高于正常的马铃薯薯皮,以发绿的马铃薯薯皮为提取材料,本课题旨在考察不同的提取方法、不同的提取溶剂,对马铃薯糖苷生物碱含量的影响,并探讨粗产物柱层析分离纯化的条件。主要内容概括如下：
1.原料化学成分的检验及提取方法的筛选
马铃薯绿皮干样粉末的化学成分为生物碱类、多糖及其苷类、皂苷、氨基酸、多肽及蛋白质、酚类、内酯、香豆素及其苷、甾体(植物甾醇)和萜类、挥发油和有机酸,可能含有黄酮及其苷类、强心苷和蒽醌及苷,没有油脂和鞣质。考察了马铃薯糖苷生物碱的紫外光谱分析方法的适用性；从不同的提取方法中筛选出最优的提取方法,提取效果为索氏提取<回流提取<超声波提取,粗样品质量分别为0.0126g/g、0.00152g/g、0.0306g/g, TGA含量分别为2.18mg/g、2.76mg／g、4.45mg/g,超声波的提取率最高。
2.超声波提取马铃薯TGA
通过超声波提取的正交设计试验,直观分析得第12号实验提取率最高。方差分析得显著影响提取率的因素依次为提取温度>提取溶剂种类>超声波频率>提取时间>料液比,根据效应分析确定最佳因素水平组合为A3B4C3D1E3(提取时间2h、提取温度50℃、超声波频率45Hz、溶剂种类乙醇-乙酸、料液比(m／v)1：12)。进一步作了单因素实验,筛选出最优条件为超声波频率45Hz,提取时间2.5 h,料液比(m／v)1：14,提取温度50℃,乙醇-乙酸配比(100：30,v／v)。在最优的条件下,测定不同试材中马铃薯糖苷生物碱的含量,提取效果为正常的马铃薯薯肉<发绿的马铃薯薯肉<正常的马铃薯薯皮<发绿的马铃薯薯皮<马铃薯薯芽,粗样品质量分别为0.0067g/g、0.0124g/g、0.0234g／g、0.0700g／g、0.1150g／g,TGA含量分别为1.02mg/g、2.64mg／g、3.24mg／g、11.80mg／g、21.23mg／g,马铃薯薯芽中糖苷生物碱的含量最高。
3.微波-超声波联用提取马铃薯TGA
首先对微波作为前处理的手段进行了分析,正交设计微波提取马铃薯糖苷生物碱,筛选出最优条件为95%乙醇-36%乙酸配比为100：40,料液比(m／v)1：20,60℃下提取7min。其次,以乙醇-离子液体为提取溶剂,正交设计微波-超声波提取马铃薯糖苷生物碱,先经过微波预处理,筛选出超声波提取最优条件为温度70℃,溶剂配比(v／v)600：1,提取时间20min,料液比(m／v)6：1。
4.超临界CO2提取马铃薯TGA
通过均匀设计试验和单因素实验,筛选出最优提取条件为萃取压力30Mpa、温度55℃、萃取时间90min、夹带剂乙醇含量10%。当HPLC色谱条件为Zorbax edclipsexdb C8(4.6mm×150mm,5.0um),柱温30℃,流动相为乙腈与KH2PO4～K2HPO4缓冲液(pH=7.6)配比为(60：40,v／v)时,α-茄碱的保留时间为t=6.4。
5.柱层析分离纯化马铃薯TGA
考察了索氏提取物的纯化条件,以硅胶为吸附剂,乙酸乙酯-95%乙醇-10%氨水(80：30：4,v／v)洗脱部位得到茄碱单体。探讨了超声波提取物的纯化条件,对三种洗脱溶剂系统进行了筛选,以三氧化二铝为吸附剂,流动相为氯仿-无水甲醇溶剂系统时,茄碱在氯仿-无水甲醇(20：80,v／v)、(10：90,v／v)、(0：100,v／v)洗脱部位,将这三种洗脱液合并,通过制备薄层层析分离得到茄碱和另外一个化合物。最后对得到的三种化合物进行结构表征。
According to research trends at home and abroad in recent years, briefly discussed the distribution of glycoalkaloids, chemical structure and types of glycoalkaloids, pharmacological activity of glycoalkaloids, introduced chemical structure of potato glycoalkaloids, summarizes qualitative methods of glycoalkaloids, describes the extraction progress of glycoalkaloids from different extraction solvents and different extraction methods, summarizes the purification methods of glycoalkaloids, compared various methods of content determination, indicated a new approach for comprehensive development and utilization of potato glycoalkaloids.
According to references and characteristics of the selected material, considering the extraction of the material economy (convenient to purchase), compared normal potato skins with green potato skin, the content of glycoalkaloids in green potatoskin was significantly high. Therefore, using green potato skin as the extracting materials, In this article, aiming to explore influence factors of potato glycoalkaloids in the aspects of different extraction methods and different extraction solvents, and discusses separation and purification conditions of coarse product using column chromatography.
The major contents are described as follows:
1.Inspection of chemical composition from raw material and screening of different extraction methods
chemical composition of potatoes green skin powder:alkaloids, polysaccharide and nucleoside, saponins, amino acids, peptides and protein, phenols, lactones, coumarin and glycosides, sterols (phytosterols) and terpenoids, volatile oil, triterpenes and glycosides, organic acids, probably contained flavonoids and glycosides, cardiac glycosides, anthraquinones, but oil and tannins is without. Investigated the ultraviolet spectrum analysis method applicability of potato glycoalkaloids, choosing the best extraction method from different extraction methods, extraction efficiency:soxhlet extraction
according to orthogonal design experiment of ultrasonic extraction, extraction efficiency of the 12th experiment is the highest by intuitive analysis. significant influence factors of extraction efficiency extraction temperature>type of extraction solvent>ultrasonic frequency>extraction time> ratio of solid-liquid, determine the optimal factor level combination A3B4C3D1E3 (extraction time 2h, extraction temperature 50℃, ultrasonic frequency 45Hz, type of extraction solvent ethanol-acid extraction solution, ratio of solid-liquid (m/v) 1:12). In further research of single factors experiment, the optimal conditions of potato glycoalkaloids extraction:ultrasonic frequency 45Hz, extraction time 2.5h, ratio of solid-liquid (m/v) 1:14, extraction temperature 50℃, volume ratio of ethanol-acetic acid (100:30, v/v), Under optimal conditions,, determinated TGA content of potato from different materials. extraction efficiency:tuber of normal potato
firstly, microwave extraction as the pretreatment method was analyzed, doing the orthogonal design experiment of potato glycoalkaloids which was extracted by microwave, selected the optimal conditions, volume ratio of acid 95% ethanol-36% acetic acid(100:40, v/v), ratio of solid-liquid(m/v) 1:20, extraction temperature 60℃, extraction time 7min. Secondly, ethanol-ionic liquid is a new kind of solvent system, orthogonal design experiment of potato TGA which was combined extraction of microwave-ultrasonic, firstly, microwave pretreatment, and selected the optimal conditions for ultrasonic extraction:extraction temperature 70℃, volume ratio of solvent 600:1 (v/v), extraction time 20min, ratio of solid-liquid (m/v)1:6.
4. Supercritical CO2 extraction of potato TGA
Based on the experiment of uniform design and single factors experiment, the optimal extraction conditions:extraction pressure 30Mpa, temperature 55℃, extraction time 90min, dosage of entrainer 10%. HPLC chromatographic conditions:Zorbax edclipsexdb C8(4.6mm×150mm,5.0um), column temperature30℃, mobile phase:Volume ratio of acetonitrile and buffer solution of KH2PO4～K2HPO4 ((pH=7.6) (60:40, v/v), retention time ofα-solanine is t=6.4.
5. Separated and purification of potato TGA by column chromatography
Investigated purification of soxhlet extraction, using silica gel column, finally obtained a-solanine monomer from ethylacetate-95% ethanol-10% ammonia (80:30:4, v/v) elution part. Discussed purification of ultrasonic extraction, three kinds of solvent elution were screened, using Al2O3 column chromatography, mobile phase was solvent systems of chloroform-methanol without water,α-solanine is in elution parts of chloroform-methanol without water (20:80, v/v), (10:90, v/v), (0:100, v/v), mergerded the three kinds of eluent solvents. Obtained a-solanine and another kind of compound by the preparation thin-layer chromatography separation. Finally, determined structure characterization of three compounds which were obtained.
引文
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