磁场影响有机介质中酶促合成柚皮苷酯机理及其特性研究
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摘要
黄酮类化合物(如柚皮苷)具有多种生理活性,在医药、食品、精细化工等行业中已有广泛应用。对天然来源的黄酮类化合物进行结构修饰,可改善黄酮类化合物的水溶性或脂溶性,或提高其生理活性、增加新的功能等,成为新药研制的有效途径之一。本文以柚皮苷为研究对象,通过脂肪酸酯化反应提高柚皮苷的脂溶性,以改善其生物利用度。引入物理场强化技术,重点研究利用磁场强化有机溶剂中固定化脂肪酶催化合成柚皮苷棕榈酸酯的反应,深入探讨磁场作用下酶结构与活性的变化规律,为实际生产提供理论依据;同时,利用现代光谱分析技术研究了柚皮苷棕榈酸酯与蛋白质分子之间相互作用的特性,为黄酮脂肪酸酯的药物利用提供启发与指导。主要研究内容和结果如下:
一、有机介质中酶催化合成柚皮苷棕榈酸酯的研究
较为系统地研究了有机介质中固定化脂肪酶催化合成柚皮苷脂肪酸酯的影响因素,探讨了柚皮苷与棕榈酸酯化反应动力学和反应机制。研究结果表明,脂肪酸链长、酶的种类和加酶量、有机溶剂的种类、初始水分活度、反应温度、振荡速度、底物比例等因素对柚皮苷与脂肪酸的酯化反应有着不同程度的影响。较适宜的反应条件为:以叔戊醇为反应介质,Novozym 435固定化脂肪酶为催化剂,反应温度60℃、振荡速度150 r/min。在此条件下,以柚皮苷和棕榈酸浓度为50 mmol/L和250 mmol/L进行反应,加酶量10 g/L,采用分子筛为脱水剂脱除反应过程中生成的水,反应48 h酯化率为34.80%。在叔戊醇中,Novozym 435催化柚皮苷与棕榈酸的酯化反应为动力学控制,反应遵循Michaelis-Menton方程,符合Ping-Pong Bi-Bi机制。
二、磁场-酶耦合催化合成柚皮苷棕榈酸酯的研究
采用磁场预处理耦合酶催化的方式合成柚皮苷棕榈酸酯,研究磁场强度和磁化时间对酶活力以及酯化率的影响。结果表明,适宜的磁处理条件可以显著提高酶活和酯化率。采用磁场预处理有机溶剂和酶的方式,不同场强(100、300、500 mT)处理不同时间(1、2、3 h)后,酶活力均有所提高。500 mT,3 h的磁处理条件下,48 h酯化率从34.80%提高到45.31%,增幅37.4%。采用磁场预处理酶的方式,适宜的场强和时间(500 mT,2 h)可以使酶活力较大幅度地提高,24 h酯化率从18.66%提高到24.10%,增幅为29.2%。
采用红外光谱研究Novozym 435的游离酶南极假丝酵母脂肪酶B(Candida antartica lipse B,CALB)在磁场作用下二级结构的变化情况,结果表明,磁化作用对CALB二级结构影响不明显,Novozym 435经过磁场处理后催化活力的变化不是由于酶的二级结构发生显著变化引起的,可能是酶活性中心发生了局部的细微的构象变化,即酶的柔性发生了变化所致。
三、柚皮苷棕榈酸酯的分离纯化及结构表征
采用硅胶柱层析法分离纯化柚皮苷棕榈酸酯化产物,洗脱剂为乙酸乙酯:乙醇:甲酸(15:1:1,V/V/V)。采用制备高效液相色谱法分离纯化柚皮苷棕榈酸酯化产物,色谱条件为:色谱柱:C18柱(21.5×250 mm);流动相:甲醇;流速:20 mL/min;进样浓度:30 mg/mL;进样体积3 mL;紫外检测波长λ=283 nm。
用IR、MS、1H-NMR、13C-NMR对磁场-酶催化合成的酯化产物进行结构表征,结果表明生成产物为柚皮苷棕榈酸单酯,酰化反应选择性地发生在葡萄糖基的C-6′′位羟基上。磁场作用没有改变酶催化合成柚皮苷棕榈酸酯的区域选择性。四、柚皮苷棕榈酸酯与蛋白质相互作用的研究
采用荧光光谱法对柚皮苷及其酯化衍生物柚皮苷棕榈酸酯与牛血清白蛋白(BSA)、溶菌酶的相互作用进行研究。结果表明,柚皮苷棕榈酸酯与蛋白质相互作用符合黄酮类化合物的一般规律。柚皮苷棕榈酸酯对BSA和溶菌酶的荧光猝灭机理都是静态猝灭,与蛋白质结合是自发进行的,对蛋白质内源荧光的猝灭由分子间能量转移引起,柚皮苷棕榈酸酯与BSA和溶菌酶的结合位点数(37℃)分别为0.7和0.6。柚皮苷棕榈酸酯与BSA之间的作用力主要为静电作用力;而柚皮苷棕榈酸酯与溶菌酶二者之间的作用力类型主要为氢键和范德华力。柚皮苷棕榈酸酯与BSA、溶菌酶相互作用的解离常数分别小于柚皮苷与二者的解离常数,提示柚皮苷棕榈酸酯在被蛋白质贮留和转运的过程中,贮留时间比柚皮苷长,有助于药物持久缓释发挥药效。
Flavonoids, such as naringin, are widely used in pharmaceutical, food and cosmetic industry. The bioavailability and bioactivity of natural flavonoids are improved after proper modification. Naringin, one of flavonoids, was employed in this study, and modified by esterification to improve its lipophilicity and bioavailability. Magnetic field was introduced to strengthen the enzymatically synthesis of naringin palmitat in organic solvent with immobilized lipase. Besides, the effect of magnetic field on the lipase was discussed. Furthermore, the interaction between naringin palmitate and protein molecules was investigated so as to obtain the information about drug actions of the esterified naringin. The main contents and results are as follows:
1. Enzymatically synthesis of naringin palmitate in organic solvent.
Effect of the chain length of the fatty acids, the origin and concentration of the enzyme, the type of organic solvent, the initial water activity, the reaction temperature, the shaking speed or the molar ratio between the substrates on the the enzymatically reaction of naringin with fatty acids were studied. The proper operation conditions were: immobilized lipase Novozym 435 in t-amyl alchohol at 60℃, with the orbitally shaking speed of 150 r/min. Molecular sieves were used to removed the water produced during the the esterifiation. At the fixed conditions, naringin(50 mmol/L) was esterified with palmitic acid(250 mmol/L), the enzyme concentration of 10 g/L. The conversion rate of naringin reached 34.80% after 48 h. A kinetic study showed that the reaction followed the Michaelis-Menton kinetic and a Ping-Pong Bi-Bi mechanism.
2. Synthesis of naringin palmitate catalyzed by enzyme under magnetic field.
Novozym 435, and Novozym 435 and the organic solvent were separately pretreated by magnetic field. The effects of magnetic field intensity and magnetic pretreatment time on the enzyme activity and conversion rate were studied. The results showed that when with proper magnetic field intensity and pretreatment time magnetical pretreatment would improve the enzyme activity as well as the conversion rate. When the enzyme and the organic solvent were pretreated with magnetic field intensity of 100, 300 or 500 mT and pretreatment time of 1, 2 or 3 h, the enzyme activity was raised. The conversion rate was reached 45.31% from 34.80% after 48 h at the ratio of 37.4%. When only Novozym 435 was pretreated by magnetic field, at 500 mT for 2 h, the enzyme activity was greatly increased and the conversion rate reached 24.20% from 18.66% after 24 h, increased by 29.2%.
The secondary structure of Candida antarctica lipse B(CALB), which is the free form of Novozym 435, was investigated with FT-IR after magnetic pretreatment. The results showed that the secondary structure of CALB after magnetically pretreated was almost indistinguishable from the origin. It seemed that the change of enzyme activity was not induced by the secondary structure change of the molecule, but by the subtle change at the active site of the enzyme, that is, the change of the flexibility of the protein.
3. Purification and structrual identification of enzymatically synthesized naringin palmitate.
Naringin palmitate was purification by a silica column using a solvent mixture system of acetic acetate: ethnol: formic acid(15:1:1) as the eluent or by preparative HPLC with a C18 column(21.5×250 mm) and a UV detector(283 nm) using methanol as the eluent. The injection volume of samples was 3 mL at the concentration of 30 mg/mL, and the flow rare of 20 mL/min.
The product prepared by magnetically assisted enzyme catalysis was purified. The structure of the purified product was identified as mono-ester of naringin and palmitic acid by IR spectra and mass spectra. 1H NMR and 13C NMR data showed the regioselective acylation preferred to the 6′′-hydroxyl group of the naringin glucose. It indicated that the regioselectivity of the enzyme did not change after magnetic pretreatment.
4. Interaction between naringin palmitate and protein.
Fluorescence quenching technique was used to investigate the interaction of naringin or its esterified derivative naringin palmitate with bovine serum albumin(BSA) or lysozyme. The results showed that the interaction between naringin palmitate and protein followed the regular principles as other flvonoids. Naringin palmitate caused the flurescence quenching of BSA or lysozyme through a static quenching procedure. The binding of naringin palmitate with BSA or lysozyme was spontaneous and the energy transfer from the protein to naringin palmitate occurred with high probability. The number of binding sites was calculated as 0.7 and 0.6 at 37℃with BSA and lysozyme respectively. It was more likely that electrostatic interaction was involved in the binding process with BSA, while the binding with lysozyme might mainly account for hydrogen bonding force and Van der Waals force. The decomposing constant of naringin palmitate binding with BSA or lysozyme was lower than that of naringin, which indicated that naringin palmitate might perform longer retention when transported by protein and exert pharmacological effect persistly due to slow release.
一、有机介质中酶催化合成柚皮苷棕榈酸酯的研究
较为系统地研究了有机介质中固定化脂肪酶催化合成柚皮苷脂肪酸酯的影响因素,探讨了柚皮苷与棕榈酸酯化反应动力学和反应机制。研究结果表明,脂肪酸链长、酶的种类和加酶量、有机溶剂的种类、初始水分活度、反应温度、振荡速度、底物比例等因素对柚皮苷与脂肪酸的酯化反应有着不同程度的影响。较适宜的反应条件为:以叔戊醇为反应介质,Novozym 435固定化脂肪酶为催化剂,反应温度60℃、振荡速度150 r/min。在此条件下,以柚皮苷和棕榈酸浓度为50 mmol/L和250 mmol/L进行反应,加酶量10 g/L,采用分子筛为脱水剂脱除反应过程中生成的水,反应48 h酯化率为34.80%。在叔戊醇中,Novozym 435催化柚皮苷与棕榈酸的酯化反应为动力学控制,反应遵循Michaelis-Menton方程,符合Ping-Pong Bi-Bi机制。
二、磁场-酶耦合催化合成柚皮苷棕榈酸酯的研究
采用磁场预处理耦合酶催化的方式合成柚皮苷棕榈酸酯,研究磁场强度和磁化时间对酶活力以及酯化率的影响。结果表明,适宜的磁处理条件可以显著提高酶活和酯化率。采用磁场预处理有机溶剂和酶的方式,不同场强(100、300、500 mT)处理不同时间(1、2、3 h)后,酶活力均有所提高。500 mT,3 h的磁处理条件下,48 h酯化率从34.80%提高到45.31%,增幅37.4%。采用磁场预处理酶的方式,适宜的场强和时间(500 mT,2 h)可以使酶活力较大幅度地提高,24 h酯化率从18.66%提高到24.10%,增幅为29.2%。
采用红外光谱研究Novozym 435的游离酶南极假丝酵母脂肪酶B(Candida antartica lipse B,CALB)在磁场作用下二级结构的变化情况,结果表明,磁化作用对CALB二级结构影响不明显,Novozym 435经过磁场处理后催化活力的变化不是由于酶的二级结构发生显著变化引起的,可能是酶活性中心发生了局部的细微的构象变化,即酶的柔性发生了变化所致。
三、柚皮苷棕榈酸酯的分离纯化及结构表征
采用硅胶柱层析法分离纯化柚皮苷棕榈酸酯化产物,洗脱剂为乙酸乙酯:乙醇:甲酸(15:1:1,V/V/V)。采用制备高效液相色谱法分离纯化柚皮苷棕榈酸酯化产物,色谱条件为:色谱柱:C18柱(21.5×250 mm);流动相:甲醇;流速:20 mL/min;进样浓度:30 mg/mL;进样体积3 mL;紫外检测波长λ=283 nm。
用IR、MS、1H-NMR、13C-NMR对磁场-酶催化合成的酯化产物进行结构表征,结果表明生成产物为柚皮苷棕榈酸单酯,酰化反应选择性地发生在葡萄糖基的C-6′′位羟基上。磁场作用没有改变酶催化合成柚皮苷棕榈酸酯的区域选择性。四、柚皮苷棕榈酸酯与蛋白质相互作用的研究
采用荧光光谱法对柚皮苷及其酯化衍生物柚皮苷棕榈酸酯与牛血清白蛋白(BSA)、溶菌酶的相互作用进行研究。结果表明,柚皮苷棕榈酸酯与蛋白质相互作用符合黄酮类化合物的一般规律。柚皮苷棕榈酸酯对BSA和溶菌酶的荧光猝灭机理都是静态猝灭,与蛋白质结合是自发进行的,对蛋白质内源荧光的猝灭由分子间能量转移引起,柚皮苷棕榈酸酯与BSA和溶菌酶的结合位点数(37℃)分别为0.7和0.6。柚皮苷棕榈酸酯与BSA之间的作用力主要为静电作用力;而柚皮苷棕榈酸酯与溶菌酶二者之间的作用力类型主要为氢键和范德华力。柚皮苷棕榈酸酯与BSA、溶菌酶相互作用的解离常数分别小于柚皮苷与二者的解离常数,提示柚皮苷棕榈酸酯在被蛋白质贮留和转运的过程中,贮留时间比柚皮苷长,有助于药物持久缓释发挥药效。
Flavonoids, such as naringin, are widely used in pharmaceutical, food and cosmetic industry. The bioavailability and bioactivity of natural flavonoids are improved after proper modification. Naringin, one of flavonoids, was employed in this study, and modified by esterification to improve its lipophilicity and bioavailability. Magnetic field was introduced to strengthen the enzymatically synthesis of naringin palmitat in organic solvent with immobilized lipase. Besides, the effect of magnetic field on the lipase was discussed. Furthermore, the interaction between naringin palmitate and protein molecules was investigated so as to obtain the information about drug actions of the esterified naringin. The main contents and results are as follows:
1. Enzymatically synthesis of naringin palmitate in organic solvent.
Effect of the chain length of the fatty acids, the origin and concentration of the enzyme, the type of organic solvent, the initial water activity, the reaction temperature, the shaking speed or the molar ratio between the substrates on the the enzymatically reaction of naringin with fatty acids were studied. The proper operation conditions were: immobilized lipase Novozym 435 in t-amyl alchohol at 60℃, with the orbitally shaking speed of 150 r/min. Molecular sieves were used to removed the water produced during the the esterifiation. At the fixed conditions, naringin(50 mmol/L) was esterified with palmitic acid(250 mmol/L), the enzyme concentration of 10 g/L. The conversion rate of naringin reached 34.80% after 48 h. A kinetic study showed that the reaction followed the Michaelis-Menton kinetic and a Ping-Pong Bi-Bi mechanism.
2. Synthesis of naringin palmitate catalyzed by enzyme under magnetic field.
Novozym 435, and Novozym 435 and the organic solvent were separately pretreated by magnetic field. The effects of magnetic field intensity and magnetic pretreatment time on the enzyme activity and conversion rate were studied. The results showed that when with proper magnetic field intensity and pretreatment time magnetical pretreatment would improve the enzyme activity as well as the conversion rate. When the enzyme and the organic solvent were pretreated with magnetic field intensity of 100, 300 or 500 mT and pretreatment time of 1, 2 or 3 h, the enzyme activity was raised. The conversion rate was reached 45.31% from 34.80% after 48 h at the ratio of 37.4%. When only Novozym 435 was pretreated by magnetic field, at 500 mT for 2 h, the enzyme activity was greatly increased and the conversion rate reached 24.20% from 18.66% after 24 h, increased by 29.2%.
The secondary structure of Candida antarctica lipse B(CALB), which is the free form of Novozym 435, was investigated with FT-IR after magnetic pretreatment. The results showed that the secondary structure of CALB after magnetically pretreated was almost indistinguishable from the origin. It seemed that the change of enzyme activity was not induced by the secondary structure change of the molecule, but by the subtle change at the active site of the enzyme, that is, the change of the flexibility of the protein.
3. Purification and structrual identification of enzymatically synthesized naringin palmitate.
Naringin palmitate was purification by a silica column using a solvent mixture system of acetic acetate: ethnol: formic acid(15:1:1) as the eluent or by preparative HPLC with a C18 column(21.5×250 mm) and a UV detector(283 nm) using methanol as the eluent. The injection volume of samples was 3 mL at the concentration of 30 mg/mL, and the flow rare of 20 mL/min.
The product prepared by magnetically assisted enzyme catalysis was purified. The structure of the purified product was identified as mono-ester of naringin and palmitic acid by IR spectra and mass spectra. 1H NMR and 13C NMR data showed the regioselective acylation preferred to the 6′′-hydroxyl group of the naringin glucose. It indicated that the regioselectivity of the enzyme did not change after magnetic pretreatment.
4. Interaction between naringin palmitate and protein.
Fluorescence quenching technique was used to investigate the interaction of naringin or its esterified derivative naringin palmitate with bovine serum albumin(BSA) or lysozyme. The results showed that the interaction between naringin palmitate and protein followed the regular principles as other flvonoids. Naringin palmitate caused the flurescence quenching of BSA or lysozyme through a static quenching procedure. The binding of naringin palmitate with BSA or lysozyme was spontaneous and the energy transfer from the protein to naringin palmitate occurred with high probability. The number of binding sites was calculated as 0.7 and 0.6 at 37℃with BSA and lysozyme respectively. It was more likely that electrostatic interaction was involved in the binding process with BSA, while the binding with lysozyme might mainly account for hydrogen bonding force and Van der Waals force. The decomposing constant of naringin palmitate binding with BSA or lysozyme was lower than that of naringin, which indicated that naringin palmitate might perform longer retention when transported by protein and exert pharmacological effect persistly due to slow release.
引文
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