基于分子印迹技术的大蒜功能成分的分离提取及药理活性研究
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摘要
大蒜(Allium sativum L.)为百合科葱属植物的地下鳞茎，是著名的食药两用植物，富含有机硫化物、黄酮类化合物、皂苷类化合物和多糖等药用功能成分。近代医学研究表明，大蒜功能成分具有抑菌、降血脂、抗肿瘤、防衰老、提高机体免疫力等功效，在医药和保健品领域具有很大的开发潜力。本论文利用分子印迹技术，从大蒜中分离提取出蒜氨酸、大蒜素和大蒜黄酮类化合物等大蒜功能成分，研究了4种大蒜提取物的药理活性。本论文主要包括以下五个部分：
一、模板分子和功能单体的设计与预组装
针对从水相体系中分离提取大蒜功能成分存在的工艺复杂和分离困难等问题，以寻找能够在水相体系中有效分离蒜氨酸、大蒜素和大蒜黄酮类化合物的功能材料为目标，将分子印迹原理与现代配位化学理论相结合，构建了两种分子印迹识别模型。采用GAMESS软件包中的PM3基组优化了模板分子和功能单体的结构，分别采用非共价键和配位键两种结合模式计算了模板分子和功能单体组成的系列复合物的结合能(ΔE)，通过比较复合物结合能的大小，探讨了采用不同结合方式所形成复合物的稳定性差异。在量化计算结果指导下，设计了基于金属配位识别模式的大蒜功能成分分子印迹分离体系，并采用光谱法实验对模板分子和功能单体进行预组装筛选，优化出用于分离大蒜功能成分的金属配位分子印迹识别模型用于指导功能配体和聚合物材料的合成。
二、蒜氨酸配位分子印迹聚合物合成和性能研究
合成了新型N (4苯乙烯基)草酰胺功能配体，以S丙基L半胱氨酸亚砜替代蒜氨酸作为“伪模板分子”，合成了S丙基L半胱氨酸亚砜Zn草酰胺配位单体，并以此配合物为功能配位单体，构筑对目标分离物蒜氨酸选择性识别的双金属配位分子印迹聚合物模型；采用悬浮聚合工艺，定向合成了对蒜氨酸具有较好识别性能的配位分子印迹聚合物微球；通过评价蒜氨酸配位分子印迹聚合物对目标分离物的识别性能和分离效果，从中筛选出分离度高、吸附容量大的配位分子印迹聚合物材料，并应用于从水溶液中分离提取蒜氨酸。与目前所采用的普通阳离子树脂法相比，采用蒜氨酸配位分子印迹聚合物微球提取的蒜氨酸产品纯度达到73.6%。该方法为水相体系中氨基酸的分离提取研究开辟了新的途径。
三、大蒜素配位分子印迹聚合物合成和性能研究
合成了新型N (3丙氨基) N’(4苯乙烯基)草酰胺功能配体，以二丙基硫醚替代大蒜素作为“伪模板分子”，构筑对目标分离物大蒜素选择性识别的金属配位分子印迹聚合物模型；采用悬浮聚合工艺，定向合成了对大蒜素具有良好识别性能的配位分子印迹聚合物微球；通过评价大蒜素配位分子印迹聚合物对目标分离物的识别性能和分离效果，从中筛选出分离度高、吸附容量大的配位分子印迹聚合物材料，并应用于从水溶液中提取大蒜素。采用大蒜素配位分子印迹聚合物微球提取的大蒜素产品纯度达到89.5%。为水相体系中微量硫醚类化合物的分离富集提供新的方法学支撑。
四、大蒜黄酮配位分子印迹聚合物合成和性能研究
以大蒜黄酮类化合物中含量最大的杨梅黄酮为模板分子，4乙烯基吡啶为功能单体，在Zn(II)介导下，采用悬浮聚合工艺合成了对模板分子类似物具有选择性吸附的大蒜黄酮配位分子印迹聚合物微球；通过评价这些配位分子印迹聚合物对杨梅黄酮、槲皮素、芹菜素和山奈酚等黄酮类化合物的分离效果，从中筛选出分离度适宜、吸附容量大的大蒜黄酮配位分子印迹聚合物材料，用于对大孔树脂提取的大蒜黄酮粗提物的分离纯化。大蒜黄酮粗提物经大蒜黄酮配位分子印迹聚合物微球分离纯化后，大蒜总黄酮含量达到81.2%,为大蒜黄酮的纯化和规模化制备奠定了基础。
五、大蒜功能成分药理活性研究
分别采用H1N1流感病毒神经氨酸酶抑制剂筛选模型和MDCK细胞模型，从分子水平上和细胞水平上研究了蒜氨酸、大蒜素、大蒜黄酮和大蒜皂苷4个大蒜功能成分对H1N1流感病毒神经氨酸酶抑制活性和抗甲型流感病毒活性。结果显示：大蒜黄酮的抗氧化活性IC50为2.064±0.026μg/mL，优于阳性对照药维生素C(3.876±0.203μg/mL)；大蒜黄酮在H1N1流感病毒神经氨酸酶抑制剂筛选模型中的IC50值为10.922±2.651μg/mL，在MDCK细胞模型的IC50值为3.15μg/mL，在细胞水平抗流感活性实验中与阳性药物扎那米韦处于同一水平，而选择性和最大无毒浓度均低于阳性药物。显示了良好的体外抗流感活性和潜在的应用前景，为新型抗流感活性化合物的发现提供了新思路。采用DPPH抗氧化模型和乙、丁酰胆碱酯酶抑制剂模型，研究了蒜氨酸、大蒜素、大蒜黄酮和大蒜皂苷4个大蒜功能成分抗氧化和对乙、丁酰胆碱酯酶的抑制活性.利用荧光光谱法，从分子水平上研究大蒜黄酮类化合物(杨梅黄酮、槲皮素和山奈酚)与DNA的相互作用。以上这些药理活性研究为大蒜功能成分的药用开发奠定了科学基础。
上述研究不仅开辟了大蒜功能成分分离提取的新途径，而且为大蒜黄酮类化合物在抗氧化和抗流感病毒等的应用奠定了基础，对提升我国大蒜药用功能成分开发的水平具有重要的现实意义。
Garlic (Allium sativum L.), the underground bulbs of a kind of liliaceous alliumplants, is very popular for its edible and medicinal properties. It contains variousmedicinal components such as organic sulphides, flavonoids, saponins andpolysaccharides, etc. According to recent medical studies, garlic’s functionalcomponents possess many beneficial effects on antibacteria, lowering blood,antitumor, anti aging, enhancing immunity and so on, and consequently have manypotential applications in health care products. In this thesis, we extract alliin, allicin,flavonoid compounds, etc. functional components from garlic via molecularimprinting technique. Subsequently, we investigate their pharmacological activity.The main results are outlined as follows:
1. Design and pre-assembly of template molecule and functional monomers
Because it is a complicated, hard process to separate the garlic’s functionalcomponents from aqueous system, we seek to find a kind of functional material whichcan effectively separate alliin, allicin and flavonoid compounds from aqueous system.With the combination of the principle of molecular imprinting and the theory ofmodern coordination chemistry, we established two molecular imprinting recognitionmodels, in which the structure of template molecule and functional monomers hasbeen optimized via PM3groups of GAMESS software packages. In addition, thebinding energy (ΔE) of the monomer template conjugates has been calculated withthe binding modes of noncovalent and coordinate bonds, respectively. The stabilitydiversities of the conjugates in different binding ways also were discussed bycomparing the binding energy of the conjugates. According to the results ofquantitative calculation, we designed the molecularly imprinted separation system ofgarlic’s functional components based on the metallic coordinate recognition model.Finally, In order to optimize the metallic coordinate molecular imprinting recognitionmodel for the separation of garlic’s functional components, we prescreened thetemplate molecule and functional monomers by the spectroscopy experiments toguide the synthesis of functional ligands and polymers.
2. Synthesis and property of coordinate molecularly imprinted polymers for alliin
A new type of functional ligand N (4styryl) oxamide has been designed andsynthesized. Replacing alliin with S propyl L cysteine sulfoxide as a“pseudo template molecule”, the coordinate monomer named S propyl L cysteinesulfoxide Zn oxamide has been synthesized and considered as a functionalcoordinate monomer to establish the bimetallic coordinate molecularly imprintedpolymer model which can selectively recognize the target alliin separated from garlic.With suspension polymerization technique, the directed synthesis of coordinatemolecularly imprinted polymer microspheres which can recognize alliin effectivelyhas been achieved. Through evaluating the recognition and separation effect of alliincoordinate molecularly imprinted polymers on the separated target, the coordinatemolecularly imprinted polymers with satisfying separation ability and largeadsorption capacity have been selected and applied to separate alliin in aqueoussolution. Compared with common cationic resin used presently, the purity of alliinseparated by alliin coordinate molecularly imprinted polymer microspheres can reach73.6%. This method will open a new way to develop the extraction and separation ofamino acid in aqueous solution.
3. Synthesis and property of coordinate molecularly imprinted polymers for allicin
A new type of functional ligand N (3propylamino) N'(4styryl) oxamide hasbeen designed and synthesized. Replacing allicin with dipropyl thioether as a“pseudo template molecule”, the bimetallic coordinate molecularly imprintedpolymer model which can selectively recognize the target allicin separated from garlichas been established. With suspension polymerization technique, the directedsynthesis of coordinate molecularly imprinted polymer microspheres which canrecognize allicin effectively has been achieved. Through evaluating the recognitionand separation effect of allicin coordinate molecularly imprinted polymers on theseparated target, the coordinate molecularly imprinted polymers with satisfyingseparation ability and large adsorption capacity have been selected and applied toseparate allicin in aqueous solution. The purity of allicin separated by allicincoordinate molecularly imprinted polymer microspheres can reach89.5%. Thismethod will provide a new methodological support for the separation andconcentration of trace thioethers compounds in aqueous solution.
4. Synthesis and property of coordinate molecularly imprinted polymers for garlic’s flavonoid
With the major component myricetin in garlic flavonoids as template molecular, 4vinylpyridine as functional monomer and Zn(II) mediated，the garlic flavonoidcoordinate molecularly imprinted polymer microspheres, which can selectively adsorbthe template molecule analogues have been synthesized with the suspensionpolymerization technique. Through evaluating the separation effect of thesecoordinate molecularly imprinted polymers on several flavonoid compounds likemyricetin, quercetin, apigenin and kaempferol, the garlic’s flavonoids coordinatemolecularly imprinted polymers with proper separation ability and large adsorptioncapacity have been selected and applied to separate and purify the flavonoids crudeextract obtained by macroporous resin. And after the purification, the content ofgarlic’s flavonoids can reach81.2%. This method will lay a foundation for thepurification and large-scale preparation of garlic’s flavonoid.
5. The pharmacological activity studies of garlic’s functional components
The inhibition activities of the four garlic’s functional components on H1N1influenza virus neuraminidase and the influenza A virus have been studied at themolecular and cellular level with H1N1influenza virus neuraminidase inhibitorscreening model and MDCK cellular model. The results indicated that theantioxidative activity IC50of the garlic’s flavonoids is2.064±0.026μg/mL, which issuperior to the positive control vitamin C (3.876±0.203μg/mL). The IC50values ofgarlic’s flavonoids in H1N1influenza virus neuraminidase inhibitor screening modeland MDCK cellular model are10.922±2.651μg/mL and3.15μg/mL, respectively,which are at the same level with the positive drug zanamivir in evaluating theanti influenza activities at the cellular level, while lower than the positive drug withselectivity and the largest non toxic concentration. Consequently garlic’s flavonoidshave good in vitro anti-influenza activities and potential application prospect, whichwill provide a new idea for the discovery of novel anti-influenza activecompounds.The oxidative stability and inhibition activities of the four garlic’sfunctional components (alliin, allicin, garlic’s flavonoids and saponins) onacetylcholinesterase and butyrocholinesterase have been studied with the DPPHanti oxidation model and the acetylcholinesterase and butyrocholinesterase inhibitormodel. The interaction between garlic’s flavonoids (myricetin, quercetin andKaempferol) and some biological macromolecules, such as DNA, has beeninvestigated at the molecular level with ultraviolet and fluorescence spectroscopy.These pharmacological studies have provided a substantial basis for the pharmaceutical development of garlic’s functional components.
In conclusion, our researches built a new approach to separate and extractgarlic’s functional components. The results indicated that garlic’s flavonoidcompounds exhibited several pharmacological activities, such as oxidative stabilityand anti influenza virus, etc, which will not only provide important scientific data forthe research of China's garlic medicinal functional components, but also are beneficialto the sustained and efficient development and utilization of China's garlic resources.
一、模板分子和功能单体的设计与预组装
针对从水相体系中分离提取大蒜功能成分存在的工艺复杂和分离困难等问题，以寻找能够在水相体系中有效分离蒜氨酸、大蒜素和大蒜黄酮类化合物的功能材料为目标，将分子印迹原理与现代配位化学理论相结合，构建了两种分子印迹识别模型。采用GAMESS软件包中的PM3基组优化了模板分子和功能单体的结构，分别采用非共价键和配位键两种结合模式计算了模板分子和功能单体组成的系列复合物的结合能(ΔE)，通过比较复合物结合能的大小，探讨了采用不同结合方式所形成复合物的稳定性差异。在量化计算结果指导下，设计了基于金属配位识别模式的大蒜功能成分分子印迹分离体系，并采用光谱法实验对模板分子和功能单体进行预组装筛选，优化出用于分离大蒜功能成分的金属配位分子印迹识别模型用于指导功能配体和聚合物材料的合成。
二、蒜氨酸配位分子印迹聚合物合成和性能研究
合成了新型N (4苯乙烯基)草酰胺功能配体，以S丙基L半胱氨酸亚砜替代蒜氨酸作为“伪模板分子”，合成了S丙基L半胱氨酸亚砜Zn草酰胺配位单体，并以此配合物为功能配位单体，构筑对目标分离物蒜氨酸选择性识别的双金属配位分子印迹聚合物模型；采用悬浮聚合工艺，定向合成了对蒜氨酸具有较好识别性能的配位分子印迹聚合物微球；通过评价蒜氨酸配位分子印迹聚合物对目标分离物的识别性能和分离效果，从中筛选出分离度高、吸附容量大的配位分子印迹聚合物材料，并应用于从水溶液中分离提取蒜氨酸。与目前所采用的普通阳离子树脂法相比，采用蒜氨酸配位分子印迹聚合物微球提取的蒜氨酸产品纯度达到73.6%。该方法为水相体系中氨基酸的分离提取研究开辟了新的途径。
三、大蒜素配位分子印迹聚合物合成和性能研究
合成了新型N (3丙氨基) N’(4苯乙烯基)草酰胺功能配体，以二丙基硫醚替代大蒜素作为“伪模板分子”，构筑对目标分离物大蒜素选择性识别的金属配位分子印迹聚合物模型；采用悬浮聚合工艺，定向合成了对大蒜素具有良好识别性能的配位分子印迹聚合物微球；通过评价大蒜素配位分子印迹聚合物对目标分离物的识别性能和分离效果，从中筛选出分离度高、吸附容量大的配位分子印迹聚合物材料，并应用于从水溶液中提取大蒜素。采用大蒜素配位分子印迹聚合物微球提取的大蒜素产品纯度达到89.5%。为水相体系中微量硫醚类化合物的分离富集提供新的方法学支撑。
四、大蒜黄酮配位分子印迹聚合物合成和性能研究
以大蒜黄酮类化合物中含量最大的杨梅黄酮为模板分子，4乙烯基吡啶为功能单体，在Zn(II)介导下，采用悬浮聚合工艺合成了对模板分子类似物具有选择性吸附的大蒜黄酮配位分子印迹聚合物微球；通过评价这些配位分子印迹聚合物对杨梅黄酮、槲皮素、芹菜素和山奈酚等黄酮类化合物的分离效果，从中筛选出分离度适宜、吸附容量大的大蒜黄酮配位分子印迹聚合物材料，用于对大孔树脂提取的大蒜黄酮粗提物的分离纯化。大蒜黄酮粗提物经大蒜黄酮配位分子印迹聚合物微球分离纯化后，大蒜总黄酮含量达到81.2%,为大蒜黄酮的纯化和规模化制备奠定了基础。
五、大蒜功能成分药理活性研究
分别采用H1N1流感病毒神经氨酸酶抑制剂筛选模型和MDCK细胞模型，从分子水平上和细胞水平上研究了蒜氨酸、大蒜素、大蒜黄酮和大蒜皂苷4个大蒜功能成分对H1N1流感病毒神经氨酸酶抑制活性和抗甲型流感病毒活性。结果显示：大蒜黄酮的抗氧化活性IC50为2.064±0.026μg/mL，优于阳性对照药维生素C(3.876±0.203μg/mL)；大蒜黄酮在H1N1流感病毒神经氨酸酶抑制剂筛选模型中的IC50值为10.922±2.651μg/mL，在MDCK细胞模型的IC50值为3.15μg/mL，在细胞水平抗流感活性实验中与阳性药物扎那米韦处于同一水平，而选择性和最大无毒浓度均低于阳性药物。显示了良好的体外抗流感活性和潜在的应用前景，为新型抗流感活性化合物的发现提供了新思路。采用DPPH抗氧化模型和乙、丁酰胆碱酯酶抑制剂模型，研究了蒜氨酸、大蒜素、大蒜黄酮和大蒜皂苷4个大蒜功能成分抗氧化和对乙、丁酰胆碱酯酶的抑制活性.利用荧光光谱法，从分子水平上研究大蒜黄酮类化合物(杨梅黄酮、槲皮素和山奈酚)与DNA的相互作用。以上这些药理活性研究为大蒜功能成分的药用开发奠定了科学基础。
上述研究不仅开辟了大蒜功能成分分离提取的新途径，而且为大蒜黄酮类化合物在抗氧化和抗流感病毒等的应用奠定了基础，对提升我国大蒜药用功能成分开发的水平具有重要的现实意义。
Garlic (Allium sativum L.), the underground bulbs of a kind of liliaceous alliumplants, is very popular for its edible and medicinal properties. It contains variousmedicinal components such as organic sulphides, flavonoids, saponins andpolysaccharides, etc. According to recent medical studies, garlic’s functionalcomponents possess many beneficial effects on antibacteria, lowering blood,antitumor, anti aging, enhancing immunity and so on, and consequently have manypotential applications in health care products. In this thesis, we extract alliin, allicin,flavonoid compounds, etc. functional components from garlic via molecularimprinting technique. Subsequently, we investigate their pharmacological activity.The main results are outlined as follows:
1. Design and pre-assembly of template molecule and functional monomers
Because it is a complicated, hard process to separate the garlic’s functionalcomponents from aqueous system, we seek to find a kind of functional material whichcan effectively separate alliin, allicin and flavonoid compounds from aqueous system.With the combination of the principle of molecular imprinting and the theory ofmodern coordination chemistry, we established two molecular imprinting recognitionmodels, in which the structure of template molecule and functional monomers hasbeen optimized via PM3groups of GAMESS software packages. In addition, thebinding energy (ΔE) of the monomer template conjugates has been calculated withthe binding modes of noncovalent and coordinate bonds, respectively. The stabilitydiversities of the conjugates in different binding ways also were discussed bycomparing the binding energy of the conjugates. According to the results ofquantitative calculation, we designed the molecularly imprinted separation system ofgarlic’s functional components based on the metallic coordinate recognition model.Finally, In order to optimize the metallic coordinate molecular imprinting recognitionmodel for the separation of garlic’s functional components, we prescreened thetemplate molecule and functional monomers by the spectroscopy experiments toguide the synthesis of functional ligands and polymers.
2. Synthesis and property of coordinate molecularly imprinted polymers for alliin
A new type of functional ligand N (4styryl) oxamide has been designed andsynthesized. Replacing alliin with S propyl L cysteine sulfoxide as a“pseudo template molecule”, the coordinate monomer named S propyl L cysteinesulfoxide Zn oxamide has been synthesized and considered as a functionalcoordinate monomer to establish the bimetallic coordinate molecularly imprintedpolymer model which can selectively recognize the target alliin separated from garlic.With suspension polymerization technique, the directed synthesis of coordinatemolecularly imprinted polymer microspheres which can recognize alliin effectivelyhas been achieved. Through evaluating the recognition and separation effect of alliincoordinate molecularly imprinted polymers on the separated target, the coordinatemolecularly imprinted polymers with satisfying separation ability and largeadsorption capacity have been selected and applied to separate alliin in aqueoussolution. Compared with common cationic resin used presently, the purity of alliinseparated by alliin coordinate molecularly imprinted polymer microspheres can reach73.6%. This method will open a new way to develop the extraction and separation ofamino acid in aqueous solution.
3. Synthesis and property of coordinate molecularly imprinted polymers for allicin
A new type of functional ligand N (3propylamino) N'(4styryl) oxamide hasbeen designed and synthesized. Replacing allicin with dipropyl thioether as a“pseudo template molecule”, the bimetallic coordinate molecularly imprintedpolymer model which can selectively recognize the target allicin separated from garlichas been established. With suspension polymerization technique, the directedsynthesis of coordinate molecularly imprinted polymer microspheres which canrecognize allicin effectively has been achieved. Through evaluating the recognitionand separation effect of allicin coordinate molecularly imprinted polymers on theseparated target, the coordinate molecularly imprinted polymers with satisfyingseparation ability and large adsorption capacity have been selected and applied toseparate allicin in aqueous solution. The purity of allicin separated by allicincoordinate molecularly imprinted polymer microspheres can reach89.5%. Thismethod will provide a new methodological support for the separation andconcentration of trace thioethers compounds in aqueous solution.
4. Synthesis and property of coordinate molecularly imprinted polymers for garlic’s flavonoid
With the major component myricetin in garlic flavonoids as template molecular, 4vinylpyridine as functional monomer and Zn(II) mediated，the garlic flavonoidcoordinate molecularly imprinted polymer microspheres, which can selectively adsorbthe template molecule analogues have been synthesized with the suspensionpolymerization technique. Through evaluating the separation effect of thesecoordinate molecularly imprinted polymers on several flavonoid compounds likemyricetin, quercetin, apigenin and kaempferol, the garlic’s flavonoids coordinatemolecularly imprinted polymers with proper separation ability and large adsorptioncapacity have been selected and applied to separate and purify the flavonoids crudeextract obtained by macroporous resin. And after the purification, the content ofgarlic’s flavonoids can reach81.2%. This method will lay a foundation for thepurification and large-scale preparation of garlic’s flavonoid.
5. The pharmacological activity studies of garlic’s functional components
The inhibition activities of the four garlic’s functional components on H1N1influenza virus neuraminidase and the influenza A virus have been studied at themolecular and cellular level with H1N1influenza virus neuraminidase inhibitorscreening model and MDCK cellular model. The results indicated that theantioxidative activity IC50of the garlic’s flavonoids is2.064±0.026μg/mL, which issuperior to the positive control vitamin C (3.876±0.203μg/mL). The IC50values ofgarlic’s flavonoids in H1N1influenza virus neuraminidase inhibitor screening modeland MDCK cellular model are10.922±2.651μg/mL and3.15μg/mL, respectively,which are at the same level with the positive drug zanamivir in evaluating theanti influenza activities at the cellular level, while lower than the positive drug withselectivity and the largest non toxic concentration. Consequently garlic’s flavonoidshave good in vitro anti-influenza activities and potential application prospect, whichwill provide a new idea for the discovery of novel anti-influenza activecompounds.The oxidative stability and inhibition activities of the four garlic’sfunctional components (alliin, allicin, garlic’s flavonoids and saponins) onacetylcholinesterase and butyrocholinesterase have been studied with the DPPHanti oxidation model and the acetylcholinesterase and butyrocholinesterase inhibitormodel. The interaction between garlic’s flavonoids (myricetin, quercetin andKaempferol) and some biological macromolecules, such as DNA, has beeninvestigated at the molecular level with ultraviolet and fluorescence spectroscopy.These pharmacological studies have provided a substantial basis for the pharmaceutical development of garlic’s functional components.
In conclusion, our researches built a new approach to separate and extractgarlic’s functional components. The results indicated that garlic’s flavonoidcompounds exhibited several pharmacological activities, such as oxidative stabilityand anti influenza virus, etc, which will not only provide important scientific data forthe research of China's garlic medicinal functional components, but also are beneficialto the sustained and efficient development and utilization of China's garlic resources.
引文
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