烟叶中茄尼醇的提取与分离研究
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摘要
茄尼醇(Solanesol)是一种不饱和的九聚异戊二烯醇，主要存在于茄科植物中，其中以烟叶中茄尼醇含量为最高。茄尼醇是合成生物活性的泛醌类物质如辅酶Q_(10)和维生素K_2类的原料，是一种重要的药物中间体。烟叶中化学成分复杂，有许多与茄尼醇结构相近的物质与茄尼醇共同存在，提取与分离茄尼醇具有一定的难度。本文主要研究了以烟叶为原料提取分离纯化茄尼醇的工艺过程。
本文首先研究了烟叶中茄尼醇的分析与检测，建立了以固相萃取技术对茄尼醇样品进行处理，结合HPLC分析检测茄尼醇的方法。采用固相萃取代替传统的多步液-液萃取进行分析样品的制备，减少了样品处理时间，提高了分析效率。采用LC-APCI(+)-MS对烟叶中结合态茄尼醇进行了分析检测，并探讨了结合态茄尼醇在皂化过程中存在形态的变化进行了分析探讨，对其存在的结合态作了初步推断。认为与茄尼醇结合成酯的有机酸的分子量范围在110～170之间。
本文研究了柱浸法浸提烟叶中茄尼醇。经过几种常用试剂的筛选，发现石油醚浸提茄尼醇与其它试剂相比具有提取率高，产物中杂质少的特点。对柱浸法的浸取时间、烟草填充床高径比对茄尼醇的提取效率以及有机溶剂的消耗量进行了考察，采用柱浸提取方法从烟叶粉末中浸提茄尼醇，可以减少浸提单位体积烟叶粉末的石油醚消耗量。同时柱浸法时原料中的粉尘固定在填充床中，不会在过滤过程中产生滤饼，使生产过程变得容易，尤其是采用卷烟厂的烟草粉尘浸提茄尼醇时更加有优势。在制备茄尼醇不皂化物时，采用冷冻处理，使浸膏中的蜡质析出而除去后再皂化，可以使制备茄尼醇不皂化物变得容易，而且茄尼醇损失小。
本文研究了吸附层析分离的过程。在相同溶液浓度和等量吸附介质的条件下，硅胶的穿透点是氧化铝的2倍，表明硅胶对茄尼醇的吸附容量要远高于氧化铝，采用硅胶作为吸附剂，可以增大单位吸附剂的茄尼醇原料处理量。采用硅胶吸附层析从烟叶中分离茄尼醇时，经过TLC分析对洗脱液组成进行初步筛选，然后将筛选得到的吸附剂填料装入不锈钢色谱柱(100mm×6mm..i.d)，利用液相色谱系统对溶剂进行系统优化。通过溶剂组成对茄尼醇在硅胶柱上的容量因子、茄尼醇与杂质峰之间的分离度和洗脱剂组成对茄尼醇在硅胶柱上的保留时间进行了考察，发现乙醇／正己烷(1.5／98.5)作为洗脱剂最好。
采用Van Deemter方程考察了在不同洗脱剂流速的情况下，茄尼醇层析分离的理论塔板高度(HETP)，确定了最小理论塔板高度和获得最小理论塔板高度时的洗脱剂流速。对两种不同颗粒大小的硅胶填充柱所得到的流速与计算得到的塔板数数据进行拟合，得到Van Deemter方程分别为：粒径200～300目硅胶：H=-19.019+13.191／u+7.46u，当流速为1.3ml／min时，获得最小理论塔板高度0.82mm；粒径300～400目硅胶：H=0.147+0.156／u+0.103u，当流速为1.2ml／min时获得最小理论塔板高度为0.40mm。从理论塔板高度的计算结果可以看出，粒径小的硅胶比粒径大的硅胶理论塔板高度小，即在相同柱高的情况下，采用粒径小的硅胶可以获得更多的理论塔板数，达到更好的分离效果。采用300～400目硅胶对作为吸附剂一次分离得到茄尼醇，纯度为83.0％，得率76.1％。
通过二次层析，采用石油醚洗涤上样后的层析柱，使样品中的色素被洗脱，当色素被去除后，采用丙酮—石油醚(10-90，v／v)将茄尼醇洗脱下来。此方法脱色效果较好，所获得的样品为白色蜡状物质，纯度为91.4％，平均回收率87.4％。
采用自己填装的硅胶色谱柱，在高效液相色谱仪上对茄尼醇的层析过程动力学进行了考察。采用普通速率模型分析了影响茄尼醇分离过程以及茄尼醇分离纯化的因素：1)茄尼醇在硅胶上的吸附采用二次浓度梯度进样获得的色谱图数据，通过计算得到，与静态吸附实验测定物质等温吸附线的方法相比要简单而且容易操作；2)通过模型计算的图谱与实验获得的色谱图进行比较，发现计算与实验结果比较一致。但实验获得的色谱峰有拖尾现象，表明孔内扩散影响比较大；3)通过对色谱峰半峰宽的考察发现，考察发现，当Peclet准数值超过1000时，色谱峰的半峰宽几乎不再随Peclet准数的变化而改变，表明此时轴向扩散系数对色谱峰扩展的影响可以忽略；4)通过分析发现普通速率模型中两个参数Bi和η的乘积在一定的流速下为恒定值，表明物质的液膜传质系数和孔内扩散系数对物质层析过程的贡献的总量是一定的，定义该恒定值为T，其数量级为10~2。并以此考察了Bi和η值的变化对茄尼醇与杂质的色谱峰之间的分离度的影响。当η减小时，Bi增大，孔内扩散成为主要控制因素；当η值增大时则液膜传质系数成为主要影响因素。当孔扩散成为主要控制因素时，物质的色谱峰会出现拖尾，影响物质间的分离；5)采用制备层析一般是在超载的情况下操作的。通过上样量对茄尼醇与杂质色谱峰之间的考察，建立了分离度与上样量之间的线性关系，由此关系可以预测达到理想分离的最大上样量。
以纳滤和亲水膜蒸馏为基础，研究了膜分离过程在茄尼醇提取分离过程中有机溶剂回收中的应用。考察了不同膜材料对茄尼醇制备过程的有机溶剂的通量。发现：1)在0.3MPa的压力条件下，石油醚能够透过聚酰胺纳滤膜，而不能透过聚PAN超滤膜和PVA／PAN复合膜；2)对聚酰胺纳滤膜，通量随压力增加而逐渐增加，当压力增加到0.3MPa时，膜通量达到3.07L／m~2h；3)料液中乙醇的增加减使膜通量减小，而丙酮的含量对膜通量的影响较小；4)对PAN膜和PVA／PAN复合膜，采用膜蒸馏回收有机溶剂，随着铸膜液中PVA浓度的增加，膜的通量逐渐下降。
Solanesol, a polyisoprenoid alcohol, was first isolated from flue-cured tobacco and it is an important source of isoprene units for the synthesis of metabolically active quinones such as coenzyme Q_(10) and vitamin K_2 analogs. Extraction and separation of solanesol from tobacco leaves were studied in this dissertation.
The first part of this dissertation is the summary of bibliographic information of solanesol including the application of solanesol as an important intermediate in the synthesis of medical substances, the form in which solanesol occurred in tobacco, the resource which can be used as materials for extraction solanesol, the technical development in extraction and separation of solanesol. Furthermore, the project of this dissertation was raised and discussed.
In the second part, analysis for solanesol was studied. Including solid-phase extraction (SPE) of solanesol from tobacco leaves coupled high performance liquid chromatography-UV detector (HPLC-UV) for quantitative analysis of solanesol, analysis of solanesol in tobacco leaves. The free and esterified forms of solanesol was studied employed LC-APCI(+)-MS and the bound solanesol was conferred, the molecular weight of fatty acid bounded with solanesol was between 110 and 170.
Extraction of solanesol from tobacco powder employing Column Leaching was studied. The extracting ability of organic solvent, the contact time of solvent with tobacco powder and the ratio of the height of tobacco power column to the diameter were investigated. In the optimized extraction condition, the solvents volume needed to the weight of tobacco was 5:1 (v/v), much smaller than conventional methods.
Enrichment of solanesol from the tobacco extract was studied. The adsorbent was selected through the breakthrough curve of solanesol. The selected adsorbent was put into column and the elution was optimized using HPLC system. Effect of elution consistent on the retention factor, resolution and retention time of solanesol was investigated. Effect of the flow rate of elution on the height equivalent to a theoretical
plate (HETP) was studied to obtain an optimized flow rate during chromatography separation solanesol.
Methods for purifying solanesol was studied. The possibility of using high-speed countercurrent chromatography (HSCCC) was investigated. And solanesol was obtained through rechromatography and crystallization.
Separation process of solanesol on silica gel column was studied using general rate model of chromatography. The range of Peclet number (Pe) was evaluated in which axial dispersion effect could be ignored. Relationship between parameters of
Biot number (Bi ) and η value was studied, and through this relationship the effect
of film mass transfer and pore diffusion was investigated. The sample volume was calculated through the linear relationship between sample and resolution.
The performance of nanofiltration membrane and membrane distillation for organic solvents recovery was investigated. The influence of operation pressure, the consistent of feedstock on the permeation flux of solvent was studied. The results indicated that the permeation flux increased along with the rising of operation pressure. The ascent of ethanol concentration in feedstock decreased the permeation influx . When recovery of organic solvents using membrane distillation, the permeation influx decreased with the concentration increasing of PVA from which the PVA/PAN complex membranes were prepared.
本文首先研究了烟叶中茄尼醇的分析与检测，建立了以固相萃取技术对茄尼醇样品进行处理，结合HPLC分析检测茄尼醇的方法。采用固相萃取代替传统的多步液-液萃取进行分析样品的制备，减少了样品处理时间，提高了分析效率。采用LC-APCI(+)-MS对烟叶中结合态茄尼醇进行了分析检测，并探讨了结合态茄尼醇在皂化过程中存在形态的变化进行了分析探讨，对其存在的结合态作了初步推断。认为与茄尼醇结合成酯的有机酸的分子量范围在110～170之间。
本文研究了柱浸法浸提烟叶中茄尼醇。经过几种常用试剂的筛选，发现石油醚浸提茄尼醇与其它试剂相比具有提取率高，产物中杂质少的特点。对柱浸法的浸取时间、烟草填充床高径比对茄尼醇的提取效率以及有机溶剂的消耗量进行了考察，采用柱浸提取方法从烟叶粉末中浸提茄尼醇，可以减少浸提单位体积烟叶粉末的石油醚消耗量。同时柱浸法时原料中的粉尘固定在填充床中，不会在过滤过程中产生滤饼，使生产过程变得容易，尤其是采用卷烟厂的烟草粉尘浸提茄尼醇时更加有优势。在制备茄尼醇不皂化物时，采用冷冻处理，使浸膏中的蜡质析出而除去后再皂化，可以使制备茄尼醇不皂化物变得容易，而且茄尼醇损失小。
本文研究了吸附层析分离的过程。在相同溶液浓度和等量吸附介质的条件下，硅胶的穿透点是氧化铝的2倍，表明硅胶对茄尼醇的吸附容量要远高于氧化铝，采用硅胶作为吸附剂，可以增大单位吸附剂的茄尼醇原料处理量。采用硅胶吸附层析从烟叶中分离茄尼醇时，经过TLC分析对洗脱液组成进行初步筛选，然后将筛选得到的吸附剂填料装入不锈钢色谱柱(100mm×6mm..i.d)，利用液相色谱系统对溶剂进行系统优化。通过溶剂组成对茄尼醇在硅胶柱上的容量因子、茄尼醇与杂质峰之间的分离度和洗脱剂组成对茄尼醇在硅胶柱上的保留时间进行了考察，发现乙醇／正己烷(1.5／98.5)作为洗脱剂最好。
采用Van Deemter方程考察了在不同洗脱剂流速的情况下，茄尼醇层析分离的理论塔板高度(HETP)，确定了最小理论塔板高度和获得最小理论塔板高度时的洗脱剂流速。对两种不同颗粒大小的硅胶填充柱所得到的流速与计算得到的塔板数数据进行拟合，得到Van Deemter方程分别为：粒径200～300目硅胶：H=-19.019+13.191／u+7.46u，当流速为1.3ml／min时，获得最小理论塔板高度0.82mm；粒径300～400目硅胶：H=0.147+0.156／u+0.103u，当流速为1.2ml／min时获得最小理论塔板高度为0.40mm。从理论塔板高度的计算结果可以看出，粒径小的硅胶比粒径大的硅胶理论塔板高度小，即在相同柱高的情况下，采用粒径小的硅胶可以获得更多的理论塔板数，达到更好的分离效果。采用300～400目硅胶对作为吸附剂一次分离得到茄尼醇，纯度为83.0％，得率76.1％。
通过二次层析，采用石油醚洗涤上样后的层析柱，使样品中的色素被洗脱，当色素被去除后，采用丙酮—石油醚(10-90，v／v)将茄尼醇洗脱下来。此方法脱色效果较好，所获得的样品为白色蜡状物质，纯度为91.4％，平均回收率87.4％。
采用自己填装的硅胶色谱柱，在高效液相色谱仪上对茄尼醇的层析过程动力学进行了考察。采用普通速率模型分析了影响茄尼醇分离过程以及茄尼醇分离纯化的因素：1)茄尼醇在硅胶上的吸附采用二次浓度梯度进样获得的色谱图数据，通过计算得到，与静态吸附实验测定物质等温吸附线的方法相比要简单而且容易操作；2)通过模型计算的图谱与实验获得的色谱图进行比较，发现计算与实验结果比较一致。但实验获得的色谱峰有拖尾现象，表明孔内扩散影响比较大；3)通过对色谱峰半峰宽的考察发现，考察发现，当Peclet准数值超过1000时，色谱峰的半峰宽几乎不再随Peclet准数的变化而改变，表明此时轴向扩散系数对色谱峰扩展的影响可以忽略；4)通过分析发现普通速率模型中两个参数Bi和η的乘积在一定的流速下为恒定值，表明物质的液膜传质系数和孔内扩散系数对物质层析过程的贡献的总量是一定的，定义该恒定值为T，其数量级为10~2。并以此考察了Bi和η值的变化对茄尼醇与杂质的色谱峰之间的分离度的影响。当η减小时，Bi增大，孔内扩散成为主要控制因素；当η值增大时则液膜传质系数成为主要影响因素。当孔扩散成为主要控制因素时，物质的色谱峰会出现拖尾，影响物质间的分离；5)采用制备层析一般是在超载的情况下操作的。通过上样量对茄尼醇与杂质色谱峰之间的考察，建立了分离度与上样量之间的线性关系，由此关系可以预测达到理想分离的最大上样量。
以纳滤和亲水膜蒸馏为基础，研究了膜分离过程在茄尼醇提取分离过程中有机溶剂回收中的应用。考察了不同膜材料对茄尼醇制备过程的有机溶剂的通量。发现：1)在0.3MPa的压力条件下，石油醚能够透过聚酰胺纳滤膜，而不能透过聚PAN超滤膜和PVA／PAN复合膜；2)对聚酰胺纳滤膜，通量随压力增加而逐渐增加，当压力增加到0.3MPa时，膜通量达到3.07L／m~2h；3)料液中乙醇的增加减使膜通量减小，而丙酮的含量对膜通量的影响较小；4)对PAN膜和PVA／PAN复合膜，采用膜蒸馏回收有机溶剂，随着铸膜液中PVA浓度的增加，膜的通量逐渐下降。
Solanesol, a polyisoprenoid alcohol, was first isolated from flue-cured tobacco and it is an important source of isoprene units for the synthesis of metabolically active quinones such as coenzyme Q_(10) and vitamin K_2 analogs. Extraction and separation of solanesol from tobacco leaves were studied in this dissertation.
The first part of this dissertation is the summary of bibliographic information of solanesol including the application of solanesol as an important intermediate in the synthesis of medical substances, the form in which solanesol occurred in tobacco, the resource which can be used as materials for extraction solanesol, the technical development in extraction and separation of solanesol. Furthermore, the project of this dissertation was raised and discussed.
In the second part, analysis for solanesol was studied. Including solid-phase extraction (SPE) of solanesol from tobacco leaves coupled high performance liquid chromatography-UV detector (HPLC-UV) for quantitative analysis of solanesol, analysis of solanesol in tobacco leaves. The free and esterified forms of solanesol was studied employed LC-APCI(+)-MS and the bound solanesol was conferred, the molecular weight of fatty acid bounded with solanesol was between 110 and 170.
Extraction of solanesol from tobacco powder employing Column Leaching was studied. The extracting ability of organic solvent, the contact time of solvent with tobacco powder and the ratio of the height of tobacco power column to the diameter were investigated. In the optimized extraction condition, the solvents volume needed to the weight of tobacco was 5:1 (v/v), much smaller than conventional methods.
Enrichment of solanesol from the tobacco extract was studied. The adsorbent was selected through the breakthrough curve of solanesol. The selected adsorbent was put into column and the elution was optimized using HPLC system. Effect of elution consistent on the retention factor, resolution and retention time of solanesol was investigated. Effect of the flow rate of elution on the height equivalent to a theoretical
plate (HETP) was studied to obtain an optimized flow rate during chromatography separation solanesol.
Methods for purifying solanesol was studied. The possibility of using high-speed countercurrent chromatography (HSCCC) was investigated. And solanesol was obtained through rechromatography and crystallization.
Separation process of solanesol on silica gel column was studied using general rate model of chromatography. The range of Peclet number (Pe) was evaluated in which axial dispersion effect could be ignored. Relationship between parameters of
Biot number (Bi ) and η value was studied, and through this relationship the effect
of film mass transfer and pore diffusion was investigated. The sample volume was calculated through the linear relationship between sample and resolution.
The performance of nanofiltration membrane and membrane distillation for organic solvents recovery was investigated. The influence of operation pressure, the consistent of feedstock on the permeation flux of solvent was studied. The results indicated that the permeation flux increased along with the rising of operation pressure. The ascent of ethanol concentration in feedstock decreased the permeation influx . When recovery of organic solvents using membrane distillation, the permeation influx decreased with the concentration increasing of PVA from which the PVA/PAN complex membranes were prepared.
引文
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