新型羧基键合硅胶高效液相色谱固定相的合成及应用
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摘要
自高效液相色谱法建立以来,关于色谱固定相的研究一直是色谱工作者的一个重要研究领域。近年来,由于人们对中草药的重新重视,使中药得以迅速发展并被广泛应用于多种疾病的预防和治疗中。但中药结构复杂,对其进行分离研究需要具有多种分离功能的色谱固定相。中药活性成分由于具有独特的结构,能与多种物质发生作用,其用作分离材料更适用于中草药的分离。为此,人们制备了一系列新型中药有效成分高效液相色谱键合固定相。本论文在前人研究的基础上,以大黄酸为原料制备了两种固定相,分别对它们进行了结构表征和高效液相色谱性能评价,初步探讨了其色谱保留机理,并对两种新固定相进行了色谱应用研究。主要研究内容包括：1、以γ-氨丙基三乙氧基硅烷为偶联剂制备了酰胺型大黄酸键合硅胶固定相。2、以γ-缩水甘油醚氧丙基三甲氧基硅烷为偶联剂制备了酯型大黄酸键合硅胶固定相。3、研究了新制备的酰胺型固定相在简单流动相甲醇-水条件下对两种异黄酮化合物的分离测定。4、用常见的两种生物碱基研究了新制酯型固定相的分离性能。
1.酰胺型大黄酸键合硅胶固定相的简便制备及色谱性能评价
以大黄酸为原料,γ-氨丙基三乙氧基硅烷为偶联剂,简便制备了一种酰胺型羧基键合硅胶固定相(RBSP),并用红外光谱、热重分析及元素分析对其结构进行表征。考察了流动相中甲醇含量对键合固定相的影响,并以含酸性、中性和碱性化合物的混合物为溶质,评价了RBSP的色谱性能。以甲醇-水为流动相,用C18柱作参比,研究了该键合固定相对两种大豆异黄酮化合物和几种生物碱基的分离,并对其色谱分离机理进行了初步探讨。实验结果表明,该固定相(RBSP)具有较好的反相色谱性能,同时由于键合相中含有酚羟基及酰胺基团,能为多种溶质提供作用位点,对极性化合物的分离具有明显优势,且分离速度快,可有效用于极性化合物的分离分析。
2.酯型大黄酸键合硅胶固定相的制备及其色谱性能评价
本研究以γ-缩水甘油醚氧丙基三甲氧基硅烷为偶联剂与大黄酸反应,制备了酯型大黄酸键合硅胶固定相(RESP),用多种手段对其结构进行了表征,以多种溶质探针对其色谱性能进行了综合评价,并与传统C18柱相比较。结果表明,由于键合相上存在酯基和大黄酸的蒽醌结构单元,能抑制硅胶上残存硅醇基的活性,可有效实现对多种化合物的分离。
3.酰胺型大黄酸键合硅胶固定相对两种异黄酮化合物的分析应用
研究了两种异黄酮化合物大豆甙和黄豆黄甙在酰胺型大黄酸键合相(RBSP)上的色谱行为,并与C18柱相比较,通过改变流动相的组成考察了两种化合物在该固定相上的保留行为。实验结果表明,与C18相比,在相同色谱条件下,RBSP在以简单流动相甲醇-水(V／V=75／25)条件下,能实现对两种异黄酮化合物的快速分离,但洗脱顺序与C18柱相反,说明RBSP柱与C18柱存在不同的保留机理。4.酯型大黄酸键合硅胶固定相对两种碱基的分离测定
本文以新制键合固定相(RESP)对碱基尿嘧啶(Uracil)和腺嘌呤(Adenine)进行分离研究,并与C18相比较。通过优化色谱条件,实现了对两种碱基的较好分离,并对尿样中尿嘧啶和腺嘌呤进行了分离测定。实验发现,两种碱基在RESP和C18上的出峰顺序一致,表明RESP的分离也主要基于疏水作用。
Since the establishment of HPLC, the study of chromatographic stationary phase has become an important area for chromatography researchers. In the past few years, because of people's renewed attention on the Chinese herbal medicine, traditional Chinese herbs have got a rapid development and widely used in prevention and treatment of a variety of diseases. But the structures of traditional Chinese herbs are complicated, it demands some chromatography stationary phases which have kinds of functions separating them. As the active ingredients of Chinese Herbs have their own unique structure, it can play a role with a variety of substances, which could be used as separation materials of Chinese herbal medicine, a series of new high performance liquid chromatography bonded stationary on Chinese herbal ingredients were prepared. On the basis of the previous literatures, we prepared two kinds of bonded stationary phases which all used rhein as the raw material in this dissertation. Their chemical structures were characterized, and the chromatographic performances of them were also investigated. The chromatographic separation mechanism was initially discussed, and some chromatographic exploratory developments were done on the two new stationary phases. The major content contains:1.γ-aminopropyltriethoxy silane was used as the coupling agent to prepare a amide rhein-bonded silica gel stationary phase.2. y-glycidoxypropyltrimethoxy silane was used as the coupling agent to prepare a ester rhein-bonded silica gel stationary phase.3. The new amide rhein-bonded silica gel stationary phase was used to separate two isoflavone compounds under the simple mobile phase of methanol-water.4. The separation performance of the new ester rhein-bonded silica gel stationary phase was researched by two bio-basic groups.
1. Simple preparation and evaluations of amide rhein-bonded silica gel stationary phase
A new amide carboxy bonded silica gel stationary phase (RBSP) was prepared which was used rhein as the raw material and y-aminopropyltriethoxy silane as the coupling agent. The structure of RBSP was characterized by infrared spectroscopy, thermal analysis and elemental analysis. The effect of methanol content in the mobile phase on chromatographic performance of the bonded stationary phase was investigated. The chromatographic performance of RBSP was also evaluated using the mixture of acidic, neutral and basic compounds as solute. The separating property of bonded stationary phase was carried out using methanol-water as the mobile phase by separating two kinds of soy isoflavones and several biological bases compared with C18. The chromatographic separation mechanism was also initially discussed. The results demonstrated that RBSP possessed good reversed-phase chromatographic behavior. At the same time, because of the bonded stationary phase containing phenolic hydroxyl and amide groups which can provide action sites for multiple compounds, it has the obvious advantage in separating polar compounds especially the fast separating rate. So the RBSP could be efficiently used for the separation of polar compounds.
2. Preparation and evaluations of ester rhein-bonded silica gel stationary phase
In this study, y-glycidoxypropyltrimethoxy silane was used as the coupling agent reacting with rhein to prepare a ester rhein-bonded silica gel stationary phase(RESP). The structure of RESP was characterized by multiple methods. And the chromatographic performance was also evaluated using various solutes compared with C18. The results indicated that the bonded stationary phase can hold-back the alcohol groups of silica gel because of the esterfunction and anthraquinones on RESP. So it could separate many compounds efficiently.
3. The analytical application of amide rhein-bonded silica gel stationary phase to two isoflavone compounds.
A amide rhein bonded silica gel stationary phase (RBSP) was used for the separation of two isoflavones which named daidzin and glycitin, and the chromatographic behavior of the two isoflavones was studied in comparison with conventional C18. The retention behavior of the two isoflavones on this stationary phase was investigated through changing the construction of mobile phase.The experiments showed that under the same chromatographic condition, RBSP could tacho-separate the two isoflavones when using methanol-water (V/V=75/25) as the mobile phase, but the elution order opposited compared to C18. And the results illustrate that RBSP is different from C18 at the retention mechanism.
4. Separation and determination of two bio-basic groups on the ester rhein-bonded silica gel stationary phase.
The analytical research was carried out by comparing the chromatographic behavior of uracil and adenine on the new bonded stationary phase (RESP) with the conventional C18.It could efficiently separate the two basic groups under the optimized chromatographic conditions. And uracil and adenine in urine were determined on RESP. It was found that the elution order of the two basic groups on RESP was unanimously compared to C18. It indicates that the separation mechanism of RBSP is mainly in view of hydrophobic interaction.
1.酰胺型大黄酸键合硅胶固定相的简便制备及色谱性能评价
以大黄酸为原料,γ-氨丙基三乙氧基硅烷为偶联剂,简便制备了一种酰胺型羧基键合硅胶固定相(RBSP),并用红外光谱、热重分析及元素分析对其结构进行表征。考察了流动相中甲醇含量对键合固定相的影响,并以含酸性、中性和碱性化合物的混合物为溶质,评价了RBSP的色谱性能。以甲醇-水为流动相,用C18柱作参比,研究了该键合固定相对两种大豆异黄酮化合物和几种生物碱基的分离,并对其色谱分离机理进行了初步探讨。实验结果表明,该固定相(RBSP)具有较好的反相色谱性能,同时由于键合相中含有酚羟基及酰胺基团,能为多种溶质提供作用位点,对极性化合物的分离具有明显优势,且分离速度快,可有效用于极性化合物的分离分析。
2.酯型大黄酸键合硅胶固定相的制备及其色谱性能评价
本研究以γ-缩水甘油醚氧丙基三甲氧基硅烷为偶联剂与大黄酸反应,制备了酯型大黄酸键合硅胶固定相(RESP),用多种手段对其结构进行了表征,以多种溶质探针对其色谱性能进行了综合评价,并与传统C18柱相比较。结果表明,由于键合相上存在酯基和大黄酸的蒽醌结构单元,能抑制硅胶上残存硅醇基的活性,可有效实现对多种化合物的分离。
3.酰胺型大黄酸键合硅胶固定相对两种异黄酮化合物的分析应用
研究了两种异黄酮化合物大豆甙和黄豆黄甙在酰胺型大黄酸键合相(RBSP)上的色谱行为,并与C18柱相比较,通过改变流动相的组成考察了两种化合物在该固定相上的保留行为。实验结果表明,与C18相比,在相同色谱条件下,RBSP在以简单流动相甲醇-水(V／V=75／25)条件下,能实现对两种异黄酮化合物的快速分离,但洗脱顺序与C18柱相反,说明RBSP柱与C18柱存在不同的保留机理。4.酯型大黄酸键合硅胶固定相对两种碱基的分离测定
本文以新制键合固定相(RESP)对碱基尿嘧啶(Uracil)和腺嘌呤(Adenine)进行分离研究,并与C18相比较。通过优化色谱条件,实现了对两种碱基的较好分离,并对尿样中尿嘧啶和腺嘌呤进行了分离测定。实验发现,两种碱基在RESP和C18上的出峰顺序一致,表明RESP的分离也主要基于疏水作用。
Since the establishment of HPLC, the study of chromatographic stationary phase has become an important area for chromatography researchers. In the past few years, because of people's renewed attention on the Chinese herbal medicine, traditional Chinese herbs have got a rapid development and widely used in prevention and treatment of a variety of diseases. But the structures of traditional Chinese herbs are complicated, it demands some chromatography stationary phases which have kinds of functions separating them. As the active ingredients of Chinese Herbs have their own unique structure, it can play a role with a variety of substances, which could be used as separation materials of Chinese herbal medicine, a series of new high performance liquid chromatography bonded stationary on Chinese herbal ingredients were prepared. On the basis of the previous literatures, we prepared two kinds of bonded stationary phases which all used rhein as the raw material in this dissertation. Their chemical structures were characterized, and the chromatographic performances of them were also investigated. The chromatographic separation mechanism was initially discussed, and some chromatographic exploratory developments were done on the two new stationary phases. The major content contains:1.γ-aminopropyltriethoxy silane was used as the coupling agent to prepare a amide rhein-bonded silica gel stationary phase.2. y-glycidoxypropyltrimethoxy silane was used as the coupling agent to prepare a ester rhein-bonded silica gel stationary phase.3. The new amide rhein-bonded silica gel stationary phase was used to separate two isoflavone compounds under the simple mobile phase of methanol-water.4. The separation performance of the new ester rhein-bonded silica gel stationary phase was researched by two bio-basic groups.
1. Simple preparation and evaluations of amide rhein-bonded silica gel stationary phase
A new amide carboxy bonded silica gel stationary phase (RBSP) was prepared which was used rhein as the raw material and y-aminopropyltriethoxy silane as the coupling agent. The structure of RBSP was characterized by infrared spectroscopy, thermal analysis and elemental analysis. The effect of methanol content in the mobile phase on chromatographic performance of the bonded stationary phase was investigated. The chromatographic performance of RBSP was also evaluated using the mixture of acidic, neutral and basic compounds as solute. The separating property of bonded stationary phase was carried out using methanol-water as the mobile phase by separating two kinds of soy isoflavones and several biological bases compared with C18. The chromatographic separation mechanism was also initially discussed. The results demonstrated that RBSP possessed good reversed-phase chromatographic behavior. At the same time, because of the bonded stationary phase containing phenolic hydroxyl and amide groups which can provide action sites for multiple compounds, it has the obvious advantage in separating polar compounds especially the fast separating rate. So the RBSP could be efficiently used for the separation of polar compounds.
2. Preparation and evaluations of ester rhein-bonded silica gel stationary phase
In this study, y-glycidoxypropyltrimethoxy silane was used as the coupling agent reacting with rhein to prepare a ester rhein-bonded silica gel stationary phase(RESP). The structure of RESP was characterized by multiple methods. And the chromatographic performance was also evaluated using various solutes compared with C18. The results indicated that the bonded stationary phase can hold-back the alcohol groups of silica gel because of the esterfunction and anthraquinones on RESP. So it could separate many compounds efficiently.
3. The analytical application of amide rhein-bonded silica gel stationary phase to two isoflavone compounds.
A amide rhein bonded silica gel stationary phase (RBSP) was used for the separation of two isoflavones which named daidzin and glycitin, and the chromatographic behavior of the two isoflavones was studied in comparison with conventional C18. The retention behavior of the two isoflavones on this stationary phase was investigated through changing the construction of mobile phase.The experiments showed that under the same chromatographic condition, RBSP could tacho-separate the two isoflavones when using methanol-water (V/V=75/25) as the mobile phase, but the elution order opposited compared to C18. And the results illustrate that RBSP is different from C18 at the retention mechanism.
4. Separation and determination of two bio-basic groups on the ester rhein-bonded silica gel stationary phase.
The analytical research was carried out by comparing the chromatographic behavior of uracil and adenine on the new bonded stationary phase (RESP) with the conventional C18.It could efficiently separate the two basic groups under the optimized chromatographic conditions. And uracil and adenine in urine were determined on RESP. It was found that the elution order of the two basic groups on RESP was unanimously compared to C18. It indicates that the separation mechanism of RBSP is mainly in view of hydrophobic interaction.
引文
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