CN106858601A - The covalent thing of Epigallo-catechin gallate (EGCG) ovalbumin stabilizes fish oil preparation and preparation method - Google Patents
The covalent thing of Epigallo-catechin gallate (EGCG) ovalbumin stabilizes fish oil preparation and preparation method Download PDFInfo
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- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 title claims abstract description 83
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 title claims abstract description 82
- 229940030275 epigallocatechin gallate Drugs 0.000 title claims abstract description 82
- 108010058846 Ovalbumin Proteins 0.000 title claims abstract description 73
- 229940092253 ovalbumin Drugs 0.000 title claims abstract description 73
- 238000002360 preparation method Methods 0.000 title claims abstract description 57
- 235000021323 fish oil Nutrition 0.000 title claims abstract description 52
- 239000002994 raw material Substances 0.000 claims abstract description 8
- 238000009472 formulation Methods 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 6
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 6
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- 239000000126 substance Substances 0.000 claims description 29
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 claims description 18
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 14
- 229960005070 ascorbic acid Drugs 0.000 claims description 9
- 239000002211 L-ascorbic acid Substances 0.000 claims description 7
- 235000000069 L-ascorbic acid Nutrition 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 238000000502 dialysis Methods 0.000 claims description 6
- 108010088751 Albumins Proteins 0.000 claims description 3
- 102000009027 Albumins Human genes 0.000 claims description 3
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- 239000011668 ascorbic acid Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- WMBWREPUVVBILR-GHTZIAJQSA-N (+)-gallocatechin gallate Chemical compound O([C@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-GHTZIAJQSA-N 0.000 claims 1
- LVJJFMLUMNSUFN-UHFFFAOYSA-N gallocatechin gallate Natural products C1=C(O)C=C2OC(C=3C=C(O)C(O)=CC=3)C(O)CC2=C1OC(=O)C1=CC(O)=C(O)C(O)=C1 LVJJFMLUMNSUFN-UHFFFAOYSA-N 0.000 claims 1
- 239000000839 emulsion Substances 0.000 abstract description 12
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- 239000003963 antioxidant agent Substances 0.000 description 9
- 235000006708 antioxidants Nutrition 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- MBMBGCFOFBJSGT-KUBAVDMBSA-N docosahexaenoic acid Natural products CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O MBMBGCFOFBJSGT-KUBAVDMBSA-N 0.000 description 8
- 235000020669 docosahexaenoic acid Nutrition 0.000 description 7
- 235000020673 eicosapentaenoic acid Nutrition 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 239000002245 particle Substances 0.000 description 5
- 235000014103 egg white Nutrition 0.000 description 4
- 210000000969 egg white Anatomy 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QCVGEOXPDFCNHA-UHFFFAOYSA-N 5,5-dimethyl-2,4-dioxo-1,3-oxazolidine-3-carboxamide Chemical compound CC1(C)OC(=O)N(C(N)=O)C1=O QCVGEOXPDFCNHA-UHFFFAOYSA-N 0.000 description 3
- 108010000912 Egg Proteins Proteins 0.000 description 3
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- 210000004204 blood vessel Anatomy 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000004438 eyesight Effects 0.000 description 2
- 238000000265 homogenisation Methods 0.000 description 2
- 108090000623 proteins and genes Proteins 0.000 description 2
- 102000004169 proteins and genes Human genes 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- JAZBEHYOTPTENJ-JLNKQSITSA-N all-cis-5,8,11,14,17-icosapentaenoic acid Chemical compound CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O JAZBEHYOTPTENJ-JLNKQSITSA-N 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003064 anti-oxidating effect Effects 0.000 description 1
- 230000000975 bioactive effect Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001765 catechin Chemical class 0.000 description 1
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 description 1
- 235000005487 catechin Nutrition 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 229960001231 choline Drugs 0.000 description 1
- OEYIOHPDSNJKLS-UHFFFAOYSA-N choline Chemical compound C[N+](C)(C)CCO OEYIOHPDSNJKLS-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 229940090949 docosahexaenoic acid Drugs 0.000 description 1
- 235000013345 egg yolk Nutrition 0.000 description 1
- 210000002969 egg yolk Anatomy 0.000 description 1
- 229960005135 eicosapentaenoic acid Drugs 0.000 description 1
- JAZBEHYOTPTENJ-UHFFFAOYSA-N eicosapentaenoic acid Natural products CCC=CCC=CCC=CCC=CCC=CCCCC(O)=O JAZBEHYOTPTENJ-UHFFFAOYSA-N 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 235000004626 essential fatty acids Nutrition 0.000 description 1
- 210000003754 fetus Anatomy 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 235000003084 food emulsifier Nutrition 0.000 description 1
- 235000013376 functional food Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 235000013402 health food Nutrition 0.000 description 1
- 238000009775 high-speed stirring Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 235000010445 lecithin Nutrition 0.000 description 1
- 239000000787 lecithin Substances 0.000 description 1
- 229940067606 lecithin Drugs 0.000 description 1
- 235000020667 long-chain omega-3 fatty acid Nutrition 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
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- 230000002035 prolonged effect Effects 0.000 description 1
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- 230000000087 stabilizing effect Effects 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000005480 straight-chain fatty acid group Chemical group 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/04—Animal proteins
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
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- Chemical & Material Sciences (AREA)
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- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Biochemistry (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Fats And Perfumes (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
技术领域technical field
本发明属于功能食品和健康食品领域，具体涉及一种表没食子儿茶素没食子酸酯卵清蛋白共价物稳定化鱼油制剂及其制备方法。The invention belongs to the field of functional food and health food, in particular to an epigallocatechin gallate ovalbumin covalent substance stabilized fish oil preparation and a preparation method thereof.
背景技术Background technique
鱼油中富含多不饱和脂肪酸，是一种优质的动物油脂资源。多不饱和脂肪酸指含有两个或两个以上双键且碳链长度为18～22个碳原子的直链脂肪酸，可分为ω-3和ω-6多不饱和脂肪酸。ω-3多不饱和脂肪酸中对人体最重要的两种不饱和脂肪酸是DHA和EPA。EPA是二十碳五烯酸，具有清理血管中的垃圾(胆固醇和甘油三酯)的功能。DHA是二十二碳六烯酸，具有软化血管、健脑益智、改善视力的功效。Fish oil is rich in polyunsaturated fatty acids and is a high-quality animal oil resource. Polyunsaturated fatty acids refer to straight-chain fatty acids containing two or more double bonds and a carbon chain length of 18 to 22 carbon atoms, which can be divided into ω-3 and ω-6 polyunsaturated fatty acids. Among the omega-3 polyunsaturated fatty acids, the two most important unsaturated fatty acids for the human body are DHA and EPA. EPA is eicosapentaenoic acid, which has the function of cleaning up garbage (cholesterol and triglycerides) in blood vessels. DHA is docosahexaenoic acid, which has the effects of softening blood vessels, strengthening brain and improving intelligence, and improving eyesight.
许多研究显示食用具有长链ω-3多不饱和脂肪酸的食物与减少冠心病的风险有关。必需脂肪酸对胎儿及婴儿的生长发育极其重要，特别是脑部和视力的发育。但是鱼油中多不饱和脂肪酸，极易发生氧化，并且鱼油的水不溶性也极大的限制了其在食品中的应用。因此鱼油在食品中应用需要添加乳化剂和抗氧化剂以实现其加工和储运稳定性。Numerous studies have shown that eating foods with long-chain omega-3 polyunsaturated fatty acids is associated with a reduced risk of coronary heart disease. Essential fatty acids are extremely important for the growth and development of the fetus and infant, especially the development of the brain and vision. However, polyunsaturated fatty acids in fish oil are prone to oxidation, and the water insolubility of fish oil also greatly limits its application in food. Therefore, the application of fish oil in food requires the addition of emulsifiers and antioxidants to achieve its processing and storage stability.
鸡蛋因其营养价值高、味道鲜美等优点成为日常生活的主要食物之一，由于蛋黄中富含卵磷脂、ω-3多不饱和脂肪酸、胆碱等生物活性物质，实现了其高效利用。但人们对蛋清重视不够，甚至废弃不用。拓宽蛋清的应用范围意义重大。鸡蛋清中的主要蛋白是卵清蛋白，为鸡蛋中的贮藏蛋白，具有发泡性、凝胶性及乳化性等功能性质，是一种优良的食品乳化剂。不足之处是卵清蛋白的抗氧化性比较弱，通常需要额外添加抗氧化剂，但是二者结合效果有时不理想。因此利用我国特色茶叶资源中的天然抗氧化物质表没食子儿茶素没食子酸酯，开发一种具有抗氧化功能的卵清蛋白获得稳定的鱼油制剂，具有重要价值。Eggs have become one of the main foods in daily life because of their high nutritional value and delicious taste. Egg yolks are rich in bioactive substances such as lecithin, omega-3 polyunsaturated fatty acids, and choline, and their efficient utilization has been realized. But people don't pay enough attention to egg whites, and even discard them. It is of great significance to broaden the application range of egg white. The main protein in egg white is ovalbumin, which is a storage protein in eggs. It has functional properties such as foaming, gelling, and emulsifying properties. It is an excellent food emulsifier. The disadvantage is that the antioxidant activity of ovalbumin is relatively weak, and it is usually necessary to add additional antioxidants, but the combination of the two is sometimes unsatisfactory. Therefore, it is of great value to use the natural antioxidant substance epigallocatechin gallate in our country's characteristic tea resources to develop an ovalbumin with antioxidant function to obtain a stable fish oil preparation.
发明内容Contents of the invention
本发明提供了一种表没食子儿茶素没食子酸酯卵清蛋白共价物及其制备方法，该表没食子儿茶素没食子酸酯卵清蛋白共价物可作为稳定剂，尤其可作为抗氧化剂使用，且制备方法简单，原料来源广泛易得。The invention provides a covalent epigallocatechin gallate ovalbumin and a preparation method thereof, the covalent epigallocatechin gallate ovalbumin can be used as a stabilizer, especially as an antioxidant The preparation method is simple, and the sources of raw materials are widely available.
本发明提供了一种表没食子儿茶素没食子酸酯卵清蛋白共价物稳定化鱼油制剂及其制备方法，该鱼油制剂的氧化稳定性大大提高，延长了货架期，且制备方法简单，原料来源广泛易得。The invention provides an epigallocatechin gallate ovalbumin covalent stabilized fish oil preparation and a preparation method thereof. The oxidation stability of the fish oil preparation is greatly improved, the shelf life is prolonged, and the preparation method is simple, and the raw materials Sources are widely available.
一种表没食子儿茶素没食子酸酯卵清蛋白共价物的制备方法，包括：以表没食子儿茶素没食子酸酯和卵清蛋白为原料通过接枝制备表没食子儿茶素没食子酸酯卵清蛋白共价物。A method for preparing covalent epigallocatechin gallate ovalbumin, comprising: preparing epigallocatechin gallate ovalbumin by grafting epigallocatechin gallate and ovalbumin as raw materials Albumin covalents.
一种表没食子儿茶素没食子酸酯卵清蛋白共价物稳定化鱼油制剂的制备方法，包括以下配方和制作步骤：A preparation method of epigallocatechin gallate ovalbumin covalent stabilized fish oil preparation, comprising the following formula and preparation steps:
(1)以表没食子儿茶素没食子酸酯和卵清蛋白为原料通过接枝制备表没食子儿茶素没食子酸酯卵清蛋白共价物；(1) using epigallocatechin gallate and ovalbumin as raw materials to prepare epigallocatechin gallate ovalbumin covalents by grafting;
(2)利用得到的表没食子儿茶素没食子酸酯卵清蛋白共价物制备稳定化的鱼油制剂。(2) Prepare a stabilized fish oil preparation using the obtained epigallocatechin gallate ovalbumin covalent substance.
作为优选，所述的接枝为将表没食子儿茶素没食子酸酯接枝到卵清蛋白上。所述儿茶素通过自由基反应接枝到卵清蛋白上。Preferably, the grafting is grafting epigallocatechin gallate onto ovalbumin. The catechins are grafted onto ovalbumin by free radical reaction.
作为优选，所述的表没食子儿茶素没食子酸酯通过自由基方法引发到卵清蛋白上的接枝反应。Preferably, the grafting reaction of the epigallocatechin gallate on the ovalbumin is initiated by a free radical method.
作为优选，所述的自由基通过L-抗坏血酸与过氧化氢氧化还原对产生。Preferably, the free radicals are generated by the redox pair of L-ascorbic acid and hydrogen peroxide.
作为优选，所述的L-抗坏血酸与过氧化氢氧化摩尔比为1:(5-50)，优选为1:(5-10)；As preferably, the molar ratio of L-ascorbic acid to hydrogen peroxide oxidation is 1:(5-50), preferably 1:(5-10);
作为优选，所述的表没食子儿茶素没食子酸酯与抗坏血酸的摩尔比为1:(1-50)，优选为1:(1-5)。Preferably, the molar ratio of epigallocatechin gallate to ascorbic acid is 1:(1-50), preferably 1:(1-5).
作为优选，所述的表没食子儿茶素没食子酸酯与卵清蛋白的质量比为(0.1-5):5，优选为(0.2-2.5)：5。Preferably, the mass ratio of epigallocatechin gallate to ovalbumin is (0.1-5):5, preferably (0.2-2.5):5.
作为优选，所述表没食子儿茶素没食子酸酯卵清蛋白共价物可以通过透析进行精制提纯，透析选用半透膜截留分子量为12000-14000道尔顿，通过该过程脱除未接枝的表没食子儿茶素没食子酸酯。As a preference, the epigallocatechin gallate ovalbumin covalent substance can be refined and purified by dialysis, and the dialysis selects a semipermeable membrane with a molecular weight cut-off of 12000-14000 Daltons, and removes ungrafted Epigallocatechin gallate.
作为优选，步骤(2)中，利用得到的表没食子儿茶素没食子酸酯卵清蛋白共价物制备稳定化的鱼油制剂，具体包括如下步骤：As preferably, in step (2), the stabilized fish oil preparation is prepared by utilizing the obtained epigallocatechin gallate ovalbumin covalent substance, which specifically includes the following steps:
(2-1)鱼油与制备好的表没食子儿茶素没食子酸酯卵清蛋白共价物进行高速搅拌混合，制备得到粗乳液；(2-1) The fish oil and the prepared epigallocatechin gallate ovalbumin covalent substance are stirred and mixed at high speed to prepare a coarse emulsion;
(2-2)将粗乳液进行高压均质制备得到最终的稳定化鱼油制剂；(2-2) The crude emulsion is subjected to high-pressure homogenization to obtain the final stabilized fish oil preparation;
作为优选，上述步骤(2-1)中，所述表没食子儿茶素没食子酸酯卵清蛋白共价物可以采用表没食子儿茶素没食子酸酯卵清蛋白共价物水溶液的方式与鱼油混合，所述表没食子儿茶素没食子酸酯卵清蛋白共价物水溶液的质量百分比浓度为0.5-5％，进一步优选为1-2％。作为优选，所述鱼油与表没食子儿茶素没食子酸酯卵清蛋白共价物的质量比为1:(1-0.01)，优选为1:(0.5-0.05)；进一步优选为1：(0.05-0.2)。As a preference, in the above step (2-1), the epigallocatechin gallate ovalbumin covalent substance can be mixed with fish oil in the form of an aqueous solution of the epigallocatechin gallate ovalbumin covalent substance The mass percent concentration of the epigallocatechin gallate ovalbumin covalent aqueous solution is 0.5-5%, more preferably 1-2%. As preferably, the mass ratio of the fish oil to the epigallocatechin gallate ovalbumin covalent substance is 1:(1-0.01), preferably 1:(0.5-0.05); more preferably 1:(0.05 -0.2).
上述步骤(2-1)中，所述高速搅拌混合可以采用机械搅拌，搅拌速度一般为8000-15000rpm。搅拌时间为10-40分钟。In the above step (2-1), mechanical stirring may be used for the high-speed stirring and mixing, and the stirring speed is generally 8000-15000 rpm. Stirring time is 10-40 minutes.
作为优选，所述高压均质是在50-80MPa条件下进行。Preferably, the high-pressure homogenization is carried out under the condition of 50-80MPa.
本发明所用的鱼油可从市场上购得，比如可以是市购的70％的EPA/DHA(20/50)等。The fish oil used in the present invention can be purchased from the market, such as commercially available 70% EPA/DHA (20/50).
本发明还提供了一种由上述任一方法制备得到的表没食子儿茶素没食子酸酯卵清蛋白共价物，可作为稳定剂，比如抗氧化剂等使用。作为优选，所述得到的表没食子儿茶素没食子酸酯卵清蛋白共价物可作为鱼油抗氧化剂使用。The present invention also provides a covalent substance of epigallocatechin gallate ovalbumin prepared by any of the above methods, which can be used as a stabilizer, such as an antioxidant. Preferably, the obtained epigallocatechin gallate ovalbumin covalent substance can be used as a fish oil antioxidant.
本发明还提供了一种由上述任一方法制备得到的表没食子儿茶素没食子酸酯卵清蛋白共价物稳定化鱼油制剂。所述制剂一般为乳液制剂；当然也可为其他容易制得的制剂剂型，比如颗粒剂，丸剂等。本发明的反应在室温下进行。The present invention also provides an epigallocatechin gallate ovalbumin covalent substance-stabilized fish oil preparation prepared by any one of the above methods. The formulation is generally an emulsion formulation; of course, it can also be in other easily prepared formulations, such as granules, pills and the like. The reactions of the present invention are carried out at room temperature.
本发明相对于现有鱼油制剂稳定化方法具有如下优点及效果：The present invention has the following advantages and effects relative to the existing method for stabilizing fish oil preparations:
(1)本发明的表没食子儿茶素没食子酸酯卵清蛋白共价物有很好的抗氧化性能。(1) The epigallocatechin gallate ovalbumin covalent substance of the present invention has good antioxidant properties.
(2)本发明的表没食子儿茶素没食子酸酯卵清蛋白共价物能够很容易与鱼油形成稳定的乳液制剂。鱼油制剂粒径稳定性和抗氧化稳定性均明显提高；特别是粒径稳定性更是显著提高，根据实施例检测结果，本发明制得的表没食子儿茶素没食子酸酯卵清蛋白共价物鱼油制剂的14天粒径稳定性是未改性的卵清蛋白的93倍。(2) The epigallocatechin gallate ovalbumin covalent substance of the present invention can easily form a stable emulsion preparation with fish oil. The particle size stability and anti-oxidation stability of the fish oil preparation are significantly improved; especially the particle size stability is significantly improved. According to the test results of the examples, the epigallocatechin gallate ovalbumin covalent The 14-day particle size stability of the biological fish oil formulation was 93 times that of unmodified ovalbumin.
(3)本发明的表没食子儿茶素没食子酸酯、卵清蛋白，原料来源广泛、价格便宜、制作工艺简便，适用于工业化生产应用。(3) The epigallocatechin gallate and ovalbumin of the present invention have wide sources of raw materials, low price and simple manufacturing process, and are suitable for industrial production and application.
具体实施方式detailed description
下面结合实施例对本发明作进一步详细的描述，但本发明的实施方式不限于此。The present invention will be further described in detail below in conjunction with examples, but the embodiments of the present invention are not limited thereto.
实施例1Example 1
将1克卵清蛋白溶解于100mL水中，氮气保护下加入1毫升过氧化氢(10M)和0.25克L-抗坏血酸，25摄氏度反应2小时后，加入表没食子儿茶素没食子酸酯(0.7mmol)再反应24小时。反应结束后透析(截留分子量：12000-14000道尔顿)除去未反应的表没食子儿茶素没食子酸酯，冷冻干燥得到表没食子儿茶素没食子酸酯卵清蛋白共价物(收率为78％)。然后将得到的表没食子儿茶素没食子酸酯卵清蛋白共价物配制成1％水溶液，鱼油与该水溶液以质量比1:9进行加料，在10000rpm转速下高速混合10分钟，形成粗乳液。在此基础上，进行60MPa高压均质制备得到最终鱼油乳液制剂。Dissolve 1 gram of ovalbumin in 100 mL of water, add 1 milliliter of hydrogen peroxide (10M) and 0.25 grams of L-ascorbic acid under nitrogen protection, and react for 2 hours at 25 degrees Celsius, then add epigallocatechin gallate (0.7 mmol) React for another 24 hours. Dialysis (molecular weight cut-off: 12000-14000 Daltons) after the reaction finishes removes unreacted epigallocatechin gallate, and freeze-drying obtains epigallocatechin gallate ovalbumin covalent product (yield is 78 %). Then the obtained covalent epigallocatechin gallate ovalbumin was formulated into a 1% aqueous solution, fish oil and the aqueous solution were added at a mass ratio of 1:9, and mixed at a high speed of 10000 rpm for 10 minutes to form a coarse emulsion. On this basis, 60MPa high pressure homogeneous preparation was carried out to obtain the final fish oil emulsion preparation.
所用的鱼油从市场上购得，包括70％的EPA/DHA(20/50)。The fish oil used was commercially available and comprised 70% EPA/DHA (20/50).
实施例2Example 2
将1克卵清蛋白溶解于100mL水中，氮气保护下加入1毫升过氧化氢(10M)和0.30克L-抗坏血酸，25摄氏度反应2小时后，加入表没食子儿茶素没食子酸酯(0.8mmol)再反应24小时。反应结束后透析(截留分子量：12000-14000道尔顿)除去未反应的表没食子儿茶素没食子酸酯，冷冻干燥得到表没食子儿茶素没食子酸酯卵清蛋白共价物(收率为79％)。然后将得到的表没食子儿茶素没食子酸酯卵清蛋白共价物配制成1.1％水溶液，鱼油与该水溶液以质量比1:9进行加料，在10000rpm转速下高速混合10分钟，形成粗乳液。在此基础上，进行60MPa高压均质制备得到最终鱼油乳液制剂。Dissolve 1 gram of ovalbumin in 100 mL of water, add 1 mL of hydrogen peroxide (10M) and 0.30 g of L-ascorbic acid under nitrogen protection, and react at 25 degrees Celsius for 2 hours, then add epigallocatechin gallate (0.8 mmol) React for another 24 hours. Dialysis (molecular weight cut-off: 12000-14000 Daltons) after the reaction finishes removes unreacted epigallocatechin gallate, and freeze-drying obtains epigallocatechin gallate ovalbumin covalent product (yield is 79 %). Then the obtained covalent epigallocatechin gallate ovalbumin was formulated into a 1.1% aqueous solution, fish oil and the aqueous solution were added at a mass ratio of 1:9, and mixed at a high speed of 10000 rpm for 10 minutes to form a coarse emulsion. On this basis, 60MPa high pressure homogeneous preparation was carried out to obtain the final fish oil emulsion preparation.
所用的鱼油从市场上购得，包括70％的EPA/DHA(20/50)。The fish oil used was commercially available and comprised 70% EPA/DHA (20/50).
实施例3Example 3
将1克卵清蛋白溶解于100mL水中，氮气保护下加入1毫升过氧化氢(10M)和0.20克L-抗坏血酸，25摄氏度反应2小时后，加入表没食子儿茶素没食子酸酯(0.7mmol)再反应24小时。反应结束后透析(截留分子量：12000-14000道尔顿)除去未反应的表没食子儿茶素没食子酸酯，冷冻干燥得到表没食子儿茶素没食子酸酯卵清蛋白共价物(收率为75％)。然后将得到的表没食子儿茶素没食子酸酯卵清蛋白共价物配制成1.2％水溶液，鱼油与该水溶液以质量比1:9进行加料，在10000rpm转速下高速混合10分钟，形成粗乳液。在此基础上，进行60MPa高压均质制备得到最终鱼油乳液制剂。Dissolve 1 gram of ovalbumin in 100 mL of water, add 1 mL of hydrogen peroxide (10M) and 0.20 g of L-ascorbic acid under nitrogen protection, and react at 25 degrees Celsius for 2 hours, then add epigallocatechin gallate (0.7 mmol) React for another 24 hours. Dialysis (molecular weight cut-off: 12000-14000 Dalton) after the reaction finishes removes unreacted epigallocatechin gallate, and freeze-drying obtains epigallocatechin gallate ovalbumin covalent product (yield is 75 %). Then the obtained covalent epigallocatechin gallate ovalbumin was formulated into a 1.2% aqueous solution, fish oil and the aqueous solution were added at a mass ratio of 1:9, and mixed at a high speed of 10000 rpm for 10 minutes to form a coarse emulsion. On this basis, 60MPa high pressure homogeneous preparation was carried out to obtain the final fish oil emulsion preparation.
所用的鱼油从市场上购得，包括70％的EPA/DHA(20/50)。The fish oil used was commercially available and comprised 70% EPA/DHA (20/50).
性能测试例Performance test case
实施例1制备得到的表没食子儿茶素没食子酸酯卵清蛋白共价物结构测定数据：质谱显示表没食子儿茶素没食子酸酯卵清蛋白共价物分子离子峰为45182.77，相对于卵清蛋白原料44561.32有显著增加，证明了表没食子儿茶素没食子酸酯成功接枝。针对实施例1～3制备得到的表没食子儿茶素没食子酸酯卵清蛋白共价物抗氧化活性测试：使用经典ORAC方法对实施例1～3制备得到的表没食子儿茶素没食子酸酯卵清蛋白共价物的抗氧化活性进行测试，结果表明表没食子儿茶素没食子酸酯卵清蛋白共价物的ORAC抗氧化活性分别是是未改性的卵清蛋白的12.7倍，13.5倍，11.5倍，抗氧化性能显著提高。Structural determination data of the epigallocatechin gallate ovalbumin covalent substance prepared in Example 1: mass spectrometry shows that the molecular ion peak of the epigallocatechin gallate ovalbumin covalent substance is 45182.77, relative to egg white There was a significant increase in protein material 44561.32, demonstrating the successful grafting of epigallocatechin gallate. Antioxidant activity test for the covalent substance of epigallocatechin gallate ovalbumin prepared in Examples 1-3: the epigallocatechin gallate egg prepared in Examples 1-3 was tested using the classical ORAC method The antioxidant activity of albumin covalent was tested, and the results showed that the ORAC antioxidant activity of epigallocatechin gallate ovalbumin covalent was 12.7 times and 13.5 times that of unmodified ovalbumin, respectively. 11.5 times, the antioxidant performance is significantly improved.
鱼油制剂稳定性测试：针对实施例1-3制备得到的表没食子儿茶素没食子酸酯卵清蛋白共价物稳定化鱼油乳液制剂，对形成鱼油制剂粒径和抗氧化稳定性等指标进行测试，结果表明表没食子儿茶素没食子酸酯卵清蛋白共价物稳定化鱼油制剂的14天粒径稳定性分别为是未改性的卵清蛋白的93倍(实施例1)，95倍(实施例2)，93倍(实施例3)，氧化稳定性分别是未修饰的卵清蛋白的3倍(实施例1)，4倍(实施例2)，3倍(实施例3)，制剂稳定性显著提高。Stability test of fish oil preparations: for the fish oil emulsion preparations stabilized by the epigallocatechin gallate ovalbumin covalent substance prepared in Examples 1-3, the indicators such as particle size and antioxidant stability of the formed fish oil preparations were tested , the results show that the 14-day particle size stability of the epigallocatechin gallate ovalbumin covalent stabilized fish oil preparation is 93 times (embodiment 1), 95 times ( Example 2), 93 times (Example 3), oxidation stability is respectively 3 times (Example 1), 4 times (Example 2), 3 times (Example 3) of unmodified ovalbumin, preparation Stability has been significantly improved.
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