微生物脂肽制备条件优化及其衍生化反应的特征
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摘要
微生物脂肽(Lipopeptide)是一类重要的生物表面活性剂,因其突出的表/界面活性和生物活性,在生物医药、食品、化妆品和石油等领域有着重要的应用前景。由于脂肽是一类结构多样的物质,目前对脂肽制备条件及其衍生化反应的认识还非常有限。本文以表面活性素(Surfactin)为主要研究对象,改进了现有制备条件,获得了较高纯度的Surfactin样品,研究了Surfactin水解反应条件及酯化反应动力学,取得了以下主要成果。
以枯草芽孢杆菌Bacillus subtilis HSO121为脂肽产生菌,经过发酵、离心、酸沉、洗涤、乙醚浸提及高效液相纯化等步骤,获得了Surfactin样品。在上述制备过程中,严格控制酸性溶剂和醇溶剂与样品接触的时间,缩短制备的步骤及操作的时间,样品纯度为98.6%。通过高效液相色谱分离得到一系列脂肪酸碳链长度分别为13、14、15的Surfactin同系物,研究比较了它们的表面活性。
通过对水解方法和反应条件的研究,确定了Surfactin酸性水解的最佳条件：6.0mol/L盐酸、90℃下反应24h。当酸性水解温度由常用的110℃降低至90℃,β-羟基脂肪酸脱水率由34%降低至5%,样品中羟基脂肪酸的完好度得到了提高。此外,脂肽水解温度能够降低至水的沸点以下,使得操作更为安全和便利,且释放的脂肪酸总量不变。确定了Surfactin内酯键断裂发生部分水解反应的条件为0.1mol/L NaOH、80℃下反应60mmin。利用高效液相色谱分离得到一组脂肪酸碳链长度分别为13、14、15的线性Surfactin样品,并分别测定了样品的表面活性。
建立了一种准确定量测定Surfactin及其各个组分含量的方法。酸性水解后的Surfactin样品经由三甲基硅烷化试剂(BSTFA)在60℃下反应20mmin,再利用气质联用对样品进行检测,确定样品中氨基酸和脂肪酸的组成。根据氨基酸标准浓度工作曲线及Surfactin各个组分与氨基酸、脂肪酸的对应关系,确定该样品的总摩尔量为4.80×10-7moo1。积分分析谱图中所识别到的羟基脂肪酸峰,分别得到该样品中9种同系物的比例：n C12(0.32%)、iso C13(4.89%)、anteisoC13(6.27%)、iso C14(23.05%)、nC14(8.95%)、iso C15(17.69%)、anteisoC15(38.69%)、iso C16(0.07%)和n C16(0.07%)。结合样品总摩尔量、同系物比例及其对应的分子量,得出每个同系物的质量,加合后得到该Surfactin样品的质量为493μg(纯度98.6%)。该定量方法是目前唯一可测定Surfactin异构体含量的方法,并且适用于已知肽链组成的其他微生物脂肽。
研究了脂肽的酯化反应动力学。对脂肪酸部分碳链长度不同的Surfactin,以酸性甲醇为溶剂,分别分析了其生成单酯化或双酯化Surfactin的反应过程。在4℃、25℃和45℃三个温度下,利用高效液相色谱检测多组反应时间不同的酯化样品,建立了在三氟乙酸的催化下,Surfactin在甲醇溶剂中的酯化动力学模型。结果表明,Surfactin单酯化的反应速率系数远大于双酯化的反应速率系数；Surfactin脂肪酸碳链长度越大,反应速率系数越大,活化能越小。根据实验的结果,确定了在这三个温度下,脂肪酸碳链长度不同的Surfactin可储存的最长时间,即样品的酯化度低于10%的时间。该结果对单酯化或双酯化Surfactin的制备及脂肽的保存有着重要的参考价值。
本文的研究成果丰富了Surfactin制备、提取和分离的方法,获得了高纯度的样品；提供了一种可以测定Surfactin及其同系物含量的方法,对微生物菌种的筛选、发酵条件的改进和理化性质的测定均具有重要的参考价值；明确了脂肽衍生化反应的特征,为脂肽的结构修饰奠定了基础。
Surfactin is a family of lipopeptide produced by various strain.It is important in scientific and industrial fields such as medicine, food, cosmetics and enhancement of oil recovery due to its excellent surface-active and specific bio-active properties. The studies focused on the improvement of the extraction procedure, optimization of hydrolysis condition, the quantification method and the kinetics of esterification of surfactin. The results could be described as follow.
The surfactin sample was obtained from Bacillus subtilis HSO121in our laboratory. The surfactin, with the purity of98.6%, was obtained after separation from the cell-free broth, acid precipitation, solvent extraction, and purification by reverse-phase HPLC through shortening the operation process and time. A series of isoforms of surfactin, with fatty acid chains of C13, C14and C15, respectively, was isolated by HPLC. And the surface activities of these surfactins were studied.
An optimum hydrolysis condition, in6.0mol/L HCl at90℃for24h, was established. The relative dehydration rate was decreased from34%to5%when the reaction temperature changed from110℃to90℃. It showed that at90℃, the temperature lower than the water boiling point, more β-hydroxy fatty acids and less unsaturated fatty acids were produced and the operation might be more safe and convenient. When the partially hydrolysis was performed at80℃in0.1mol/L NaOH for60min, more linear surfactin could be obtained. A series of isoforms of linear surfactin, with fatty acid chains of C13, C14and C15, was isolated by HPLC. And their surface activities were studied.
A new method for quantitative determination of each isoform in surfactin family has been established. The surfactin was firstly hydrolyzed in acid solution at90℃for24h, dried and treated with bio (trimethylsilyl) trifluoroacetamide at60℃for20min, and the derived hydrolysates were then analyzed by GC-MS. The composition of the peptide part and the fatty acid part of surfactin was recognized. The amount of surfactin,4.80×10-7mol, was detected through the working curves made with the amino acids and the relationship between surfactin varants, amino acid residues and fatty acid residues. The mole fractions of nine surfactin isoforms with different fatty acid chains were, n C12(0.32%), iso C13(4.89%), anteiso C13(6.27%), iso C14(23.05%), n C14(8.95%), iso C15(17.69%), anteiso C15(38.69%), iso C16 (0.07%), n C16(0.07%), respectively. The mass of these nine isoforms would be obtained according to each molecular weight and the matter quantity. Finally, the accurate mass of the surfactin in this original sample was493μg (the purity was98.6%). This approach was the only method which could quantify the accurate mass of the isoforms of surfactin and might be applied to the quantitative analyses for other families of lipopeptides as long as the sequence of amino acid residues in peptide was determined.
The reaction, by which surfactins in methanol solution with acid was esterified into the mono-or dimethyl-esters, was studied. At4℃,25℃and45℃, the kinetic model of surfactin esterification in TFA methanol was established via the HPLC. Results showed that the reaction rate of mono-esterification of surfactin was much larger than the double-esterification; the longer the carbon chain was, the smaller the activation energy was. We obtained the storage time at the three temperatures, when the surfactin less than10%was esterified. The results might help confirm that the condition for storage and treatment of surfactin.
The results of this thesis that enriched the methods of preparation, extraction and separation of surfactin in order to enhance the purity of the sample; provided a new method to determine the content of each isoform of surfactin which had important reference value to screen the microorganism species, determine the fermentation conditions and the physical and chemical properties; made clear the characteristics of the derivative reaction and provided firm foundation for structure modification of surfactin.
以枯草芽孢杆菌Bacillus subtilis HSO121为脂肽产生菌,经过发酵、离心、酸沉、洗涤、乙醚浸提及高效液相纯化等步骤,获得了Surfactin样品。在上述制备过程中,严格控制酸性溶剂和醇溶剂与样品接触的时间,缩短制备的步骤及操作的时间,样品纯度为98.6%。通过高效液相色谱分离得到一系列脂肪酸碳链长度分别为13、14、15的Surfactin同系物,研究比较了它们的表面活性。
通过对水解方法和反应条件的研究,确定了Surfactin酸性水解的最佳条件：6.0mol/L盐酸、90℃下反应24h。当酸性水解温度由常用的110℃降低至90℃,β-羟基脂肪酸脱水率由34%降低至5%,样品中羟基脂肪酸的完好度得到了提高。此外,脂肽水解温度能够降低至水的沸点以下,使得操作更为安全和便利,且释放的脂肪酸总量不变。确定了Surfactin内酯键断裂发生部分水解反应的条件为0.1mol/L NaOH、80℃下反应60mmin。利用高效液相色谱分离得到一组脂肪酸碳链长度分别为13、14、15的线性Surfactin样品,并分别测定了样品的表面活性。
建立了一种准确定量测定Surfactin及其各个组分含量的方法。酸性水解后的Surfactin样品经由三甲基硅烷化试剂(BSTFA)在60℃下反应20mmin,再利用气质联用对样品进行检测,确定样品中氨基酸和脂肪酸的组成。根据氨基酸标准浓度工作曲线及Surfactin各个组分与氨基酸、脂肪酸的对应关系,确定该样品的总摩尔量为4.80×10-7moo1。积分分析谱图中所识别到的羟基脂肪酸峰,分别得到该样品中9种同系物的比例：n C12(0.32%)、iso C13(4.89%)、anteisoC13(6.27%)、iso C14(23.05%)、nC14(8.95%)、iso C15(17.69%)、anteisoC15(38.69%)、iso C16(0.07%)和n C16(0.07%)。结合样品总摩尔量、同系物比例及其对应的分子量,得出每个同系物的质量,加合后得到该Surfactin样品的质量为493μg(纯度98.6%)。该定量方法是目前唯一可测定Surfactin异构体含量的方法,并且适用于已知肽链组成的其他微生物脂肽。
研究了脂肽的酯化反应动力学。对脂肪酸部分碳链长度不同的Surfactin,以酸性甲醇为溶剂,分别分析了其生成单酯化或双酯化Surfactin的反应过程。在4℃、25℃和45℃三个温度下,利用高效液相色谱检测多组反应时间不同的酯化样品,建立了在三氟乙酸的催化下,Surfactin在甲醇溶剂中的酯化动力学模型。结果表明,Surfactin单酯化的反应速率系数远大于双酯化的反应速率系数；Surfactin脂肪酸碳链长度越大,反应速率系数越大,活化能越小。根据实验的结果,确定了在这三个温度下,脂肪酸碳链长度不同的Surfactin可储存的最长时间,即样品的酯化度低于10%的时间。该结果对单酯化或双酯化Surfactin的制备及脂肽的保存有着重要的参考价值。
本文的研究成果丰富了Surfactin制备、提取和分离的方法,获得了高纯度的样品；提供了一种可以测定Surfactin及其同系物含量的方法,对微生物菌种的筛选、发酵条件的改进和理化性质的测定均具有重要的参考价值；明确了脂肽衍生化反应的特征,为脂肽的结构修饰奠定了基础。
Surfactin is a family of lipopeptide produced by various strain.It is important in scientific and industrial fields such as medicine, food, cosmetics and enhancement of oil recovery due to its excellent surface-active and specific bio-active properties. The studies focused on the improvement of the extraction procedure, optimization of hydrolysis condition, the quantification method and the kinetics of esterification of surfactin. The results could be described as follow.
The surfactin sample was obtained from Bacillus subtilis HSO121in our laboratory. The surfactin, with the purity of98.6%, was obtained after separation from the cell-free broth, acid precipitation, solvent extraction, and purification by reverse-phase HPLC through shortening the operation process and time. A series of isoforms of surfactin, with fatty acid chains of C13, C14and C15, respectively, was isolated by HPLC. And the surface activities of these surfactins were studied.
An optimum hydrolysis condition, in6.0mol/L HCl at90℃for24h, was established. The relative dehydration rate was decreased from34%to5%when the reaction temperature changed from110℃to90℃. It showed that at90℃, the temperature lower than the water boiling point, more β-hydroxy fatty acids and less unsaturated fatty acids were produced and the operation might be more safe and convenient. When the partially hydrolysis was performed at80℃in0.1mol/L NaOH for60min, more linear surfactin could be obtained. A series of isoforms of linear surfactin, with fatty acid chains of C13, C14and C15, was isolated by HPLC. And their surface activities were studied.
A new method for quantitative determination of each isoform in surfactin family has been established. The surfactin was firstly hydrolyzed in acid solution at90℃for24h, dried and treated with bio (trimethylsilyl) trifluoroacetamide at60℃for20min, and the derived hydrolysates were then analyzed by GC-MS. The composition of the peptide part and the fatty acid part of surfactin was recognized. The amount of surfactin,4.80×10-7mol, was detected through the working curves made with the amino acids and the relationship between surfactin varants, amino acid residues and fatty acid residues. The mole fractions of nine surfactin isoforms with different fatty acid chains were, n C12(0.32%), iso C13(4.89%), anteiso C13(6.27%), iso C14(23.05%), n C14(8.95%), iso C15(17.69%), anteiso C15(38.69%), iso C16 (0.07%), n C16(0.07%), respectively. The mass of these nine isoforms would be obtained according to each molecular weight and the matter quantity. Finally, the accurate mass of the surfactin in this original sample was493μg (the purity was98.6%). This approach was the only method which could quantify the accurate mass of the isoforms of surfactin and might be applied to the quantitative analyses for other families of lipopeptides as long as the sequence of amino acid residues in peptide was determined.
The reaction, by which surfactins in methanol solution with acid was esterified into the mono-or dimethyl-esters, was studied. At4℃,25℃and45℃, the kinetic model of surfactin esterification in TFA methanol was established via the HPLC. Results showed that the reaction rate of mono-esterification of surfactin was much larger than the double-esterification; the longer the carbon chain was, the smaller the activation energy was. We obtained the storage time at the three temperatures, when the surfactin less than10%was esterified. The results might help confirm that the condition for storage and treatment of surfactin.
The results of this thesis that enriched the methods of preparation, extraction and separation of surfactin in order to enhance the purity of the sample; provided a new method to determine the content of each isoform of surfactin which had important reference value to screen the microorganism species, determine the fermentation conditions and the physical and chemical properties; made clear the characteristics of the derivative reaction and provided firm foundation for structure modification of surfactin.
引文
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