High-content phosphatidylcholine phospholipid and preparation method thereof

Abstract

The invention discloses a high-content phosphatidylcholine phospholipid and a preparation method thereof, and belongs to the technical field of phospholipid preparation, the preparation method comprises the following steps: S1, adding soybean powder phospholipid into an organic solvent, stirring at 50-65 DEG C for 80-120 minutes, and filtering to obtain filtrate and filter residues; s2, loading the filtrate into an extraction column filled with a selective adsorbent, eluting with an eluent after loading, collecting an eluted mixture, and carrying out vacuum concentration and drying on the eluted mixture to obtain high-content phosphatidylcholine phospholipid; according to the method, soybean powder phospholipid is adopted as a raw material, the soybean powder phospholipid is firstly extracted with an organic solvent and then subjected to molecularly imprinted solid-phase extraction, the high-content phosphatidylcholine phospholipid is obtained, the purity of phosphatidylcholine in the phospholipid is larger than or equal to 85%, the preparation method is simple, and production equipment is saved.

Description

Technical Field

[0001] The present invention belongs to the technical field of phospholipid preparation, and particularly relates to a phospholipid with a high content of phosphatidylcholine and a preparation method thereof. Background Art

[0002] Soybean phospholipid is a by-product during the hydration degumming of crude soybean oil in the refining process of soybean oil. After further dehydration and deoiling purification treatment, it is made into yellow solid soybean powder phospholipid. According to the content of phosphatidylcholine, soybean powder phospholipid can be further purified into oral or injectable grade soybean phospholipid, which has a wide application as a pharmaceutical excipient in the preparation of liposomes and intravenous fat emulsions. Injectable grade soybean phospholipid generally requires a phosphatidylcholine content of more than 70%.

[0003] Phosphatidylcholine is one of the main components of phospholipids. Its structure includes a glycerol group, a phosphate group, a choline group, and a fatty acid group, and it is an amphiphilic molecule. In industry, the organic solvent extraction method is commonly used for extraction, but the extraction effect is poor. Moreover, since phosphatidylcholine is a substance with a relatively large polarity, polar substances such as lysophospholipids and glycolipids are accompanied during the purification process, and the separation and purification are difficult, resulting in a low purity. In this regard, Chinese Patent with Publication No. CN101792461 B discloses a preparation process of injectable soybean lecithin, which prepares an injectable soybean phosphatidylcholine by using the methods of acetone deoiling, membrane separation, adsorption decolorization, column chromatography separation, and filtration sterilization, with a purity > 98.0%. However, the production process is cumbersome, a large amount of solid waste is formed by aluminum oxide used for adsorption, the yield of phosphatidylcholine is low, and the production cost is high, and it is only applicable to the pharmaceutical field; the current most mainstream process for phosphatidylcholine is obtained by extracting phospholipids with solvents such as ethanol and acetone. The process is simple, and the yield and net extraction rate are high, but the purity of phosphatidylcholine is only 50.0 - 60.0%. Therefore, how to obtain a phospholipid with a high content of phosphatidylcholine through a simple process is a technical problem that needs to be solved currently. Summary of the Invention

[0004] The purpose of the present invention is to provide a phospholipid with a high content of phosphatidylcholine and a preparation method thereof, so as to solve the problem of the complex preparation process of existing phospholipids with a high content of phosphatidylcholine.

[0005] The purpose of the present invention can be achieved through the following technical solutions:

[0006] A preparation method of a phospholipid with a high content of phosphatidylcholine, comprising the following steps:

[0007] S1. Add soybean powder phospholipid into an organic solvent, stir at 50 - 65°C for 80 - 120 min, filter to obtain a filtrate and a filter residue; dry the filter residue in an oven at 60 - 70°C for 5 - 8 h to obtain a crude phosphatidylserine product;

[0008] S2. Load the filtrate onto an extraction column filled with a selective adsorbent. After loading, elute with an eluent, collect the elution mixture, transfer the elution mixture to a concentration tank for vacuum concentration at a vacuum degree of -0.06 to -0.07 MPa. Concentrate to 1 / 10 to 1 / 5 of the original volume and then dry in a vacuum drying oven at 60 to 70 °C until constant weight to obtain phosphatidylcholine phospholipid with high content.

[0009] In the selective adsorbent of the present invention, there are cavities with multiple action points that match the spatial configuration of phosphatidylcholine molecules. When the filtrate containing phosphatidylcholine contacts the selective adsorbent, phosphatidylcholine enters the cavities, and other substances remain in the filtrate due to factors such as mismatched spatial configurations, thereby achieving specific adsorption of phosphatidylcholine. Then, it is eluted with an eluent to obtain an elution mixture rich in phosphatidylcholine. Finally, it is vacuum concentrated and dried to obtain phosphatidylcholine phospholipid with high content.

[0010] Further, the selective adsorbent is a phosphatidylcholine molecularly imprinted polymer. The phosphatidylcholine molecularly imprinted polymer is prepared by a thermal polymerization method using silica modified with double bonds as the substrate, 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine as the template molecule, methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate as functional monomers, and ethylene glycol dimethacrylate as the crosslinking agent.

[0011] Since there are double bonds in the phosphatidylcholine molecular chain, it is easy to polymerize with other vinyl monomers during the preparation of the molecularly imprinted polymer. Therefore, when using phosphatidylcholine as the template molecule to synthesize the polymer, it is difficult to elute it from the imprinted polymer, affecting the selective adsorption effect. Based on this, the present invention selects 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, which is similar to phosphatidylcholine in terms of spatial structure, size, and functional groups, as the template molecule to synthesize the molecularly imprinted polymer.

[0012] Further, the preparation process of the selective adsorbent includes the following steps:

[0013] Add 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate to N,N-dimethylformamide, mix evenly by ultrasound, let it stand for 12 h, then add silica modified with double bonds, continue to mix by ultrasound for 5 - 10 min, then add ethylene glycol dimethacrylate and azobisisobutyronitrile. After ultrasonic degassing, place it at 60 °C for reaction for 24 h, then centrifuge, dry the precipitate for 24 h, crush the dried product through a 200-mesh sieve and transfer it to the eluent, clean it by ultrasound for 2 h, oscillate for 12 h, filter, wash the filter cake with distilled water and then dry to obtain the selective adsorbent.

[0014] Further, in the above preparation process, the dosage ratio of 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, methacrylic acid, unsaturated sulfonate, hydrophobic acrylate, N,N-dimethylformamide, double bond modified silica, ethylene glycol dimethacrylate and azobisisobutyronitrile is 0.4 mol: 0.4 - 0.8 mol: 0.4 mol: 0.4 mol: 400 mL: 1 g: 8 mol: 0.2 g.

[0015] Further, the unsaturated sulfonate is at least one of sodium vinyl sulfonate, sodium allyl sulfonate, sodium styrene sulfonate, 2-acrylamido-2-methylpropanesulfonic acid, potassium allyl sulfonate, ammonium allyl sulfonate, sodium methallyl sulfonate, potassium methallyl sulfonate and ammonium methallyl sulfonate.

[0016] Further, the hydrophobic acrylate is at least one of vinyl neopentanoate, vinyl laurate, vinyl novonate, vinyl neodecanoate and vinyl versatate.

[0017] Further, the eluent is composed of methanol and acetic acid according to a volume ratio of 9:1.

[0018] Further, the double bond modified silica is methacryloxypropyltriethoxysilane modified silica.

[0019] Further, the preparation method of the double bond modified silica includes the following steps:

[0020] Add silica into the ethanol solution. After ultrasonic treatment for 30 min, under the stirring condition of a rotation speed of 500 r / min, add ammonia water and methacryloxypropyltriethoxysilane, and stir and react at 65 °C for 24 h. Then centrifuge, repeatedly wash the centrifuged product with absolute ethanol, and finally vacuum dry at 40 °C to constant weight to obtain the double bond modified silica.

[0021] Further, in the above preparation process, the dosage ratio of silica, ethanol solution, ammonia water and methacryloxypropyltriethoxysilane is 0.4 g: 100 mL: 3 mL: 1.2 - 1.6 mL, and the mass fraction of the ethanol solution is 80 - 90%.

[0022] Further, the particle size of the silica is 100 - 200 mesh.

[0023] Further, the dosage ratio of soybean powder phospholipid and organic solvent is 5 - 30 g: 1 L.

[0024] Further, the acetone insoluble matter content in the soybean powder phospholipid is > 95%, and the phosphatidylcholine content is 18 - 23%.

[0025] Further, the organic solvent is one of methanol, ethanol with a mass concentration of 75-90%, n-hexane, petroleum ether, and ether.

[0026] Further, the dosage ratio of the filtrate to the selective adsorbent in S2 is 100-500 mL: 1 g.

[0027] Further, the loading rate in S2 is 1-5 mL / min, the flow rate of the eluent is 1-3 mL / min, and the dosage of the eluent is 3-5 times the volume of the filtrate.

[0028] A phosphatidylcholine phospholipid with a high content is prepared by the above preparation method.

[0029] Advantages of the present invention:

[0030] The present invention uses soybean powder phospholipid as a raw material, first extracts it with an organic solvent, and then combines it with molecularly imprinted solid-phase extraction to obtain a phosphatidylcholine phospholipid with a high content. The purity of phosphatidylcholine in the phospholipid is ≥85%, and the preparation method is simple, saving production equipment.

[0031] The present invention uses double-bond modified silica as a substrate, and constructs a molecularly imprinted polymer on the surface of the double-bond modified silica to obtain a selective adsorbent. Compared with the molecularly imprinted material without a substrate, this design can use the rigid surface of silica to limit the disordered cross-linking of polymer chains, significantly improving the spatial uniformity of imprinting sites. At the same time, its high specific surface area enhances the mass transfer efficiency of the template molecule (phosphatidylcholine). In addition, methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate are selected as functional monomers. The carboxyl group in methacrylic acid can form a hydrogen bond with the phosphate group in the phosphatidylcholine structure, the sulfonic acid group in unsaturated sulfonate can form an ion pair with the choline structure in the phosphatidylcholine structure, and the hydrophobic acrylate can form a hydrophobic stacking interaction with the hydrophobic long chain in the phosphatidylcholine structure. The three work synergistically to significantly improve the adsorption performance and selectivity of the selective adsorbent for phosphatidylcholine. Specific embodiments

[0032] In order to make the technical problems, technical solutions, and beneficial effects to be solved by the present application clearer, the following further details the present application in conjunction with examples. It should be understood that the specific examples described herein are only used to explain the present application and are not used to limit the present application.

[0033] In this application, "at least one" means one or more, and "a plurality" means two or more. "At least one of the following" or a similar expression means any combination of these items, including any combination of single item or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can both represent: a, b, c, a~b (i.e., a and b), a~c, b~c, or a~b~c, where a, b, and c can be single or multiple respectively.

[0034] The terms used in the embodiments of this application are only for the purpose of describing specific embodiments and are not intended to limit this application. The singular forms "a", "the", and "said" used in the embodiments of this application and the appended claims are also intended to include the plural forms unless the context clearly indicates otherwise.

[0035] It should be understood that in various embodiments of this application, the magnitude of the sequence numbers of each process does not mean the order of execution. Some or all of the steps can be executed in parallel or successively. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation to the implementation process of the embodiments of this application.

[0036] The weights of the relevant components mentioned in the specification of the embodiments of this application can not only refer to the specific contents of each component, but also represent the proportional relationship of the weights between each component. Therefore, as long as the contents of the relevant components in the specification of the embodiments of this application are enlarged or reduced in proportion, they are within the scope disclosed in the specification of the embodiments of this application. Specifically, the mass described in the specification of the embodiments of this application can be mass units well-known in the chemical industry such as μg, mg, g, kg, etc.

[0037] Unless otherwise defined, all the technical terms used hereinafter have the same meaning as commonly understood by those skilled in the art. The technical terms used herein are only for the purpose of describing specific embodiments and are not intended to limit the protection scope of the present invention.

[0038] Unless otherwise specifically stated, various raw materials, reagents, instruments, equipment, etc. used in this application can be obtained through the market or can be prepared by existing methods.

[0039] The technical solutions of this application will be described below through specific examples and comparative examples.

[0040] Preparation Example 1

[0041] A selective adsorbent is prepared according to the following steps:

[0042] 0.4 mol of 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, 0.4 mol of methacrylic acid, 0.4 mol of sodium vinylsulfonate, and 0.4 mol of vinyl laurate were added to 400 mL of N,N-dimethylformamide, and the mixture was ultrasonically mixed evenly and allowed to stand for 12 h. Then, 1 g of double bond-modified silica was added, and the mixture was continuously ultrasonically mixed for 5 min. After that, 8 mol of ethylene glycol dimethacrylate and 0.2 g of azobisisobutyronitrile were added. After ultrasonic degassing, the mixture was placed at 60 °C and reacted for 24 h. Then, it was centrifuged, and the precipitate was dried for 24 h. The dried product was crushed and passed through a 200-mesh sieve and then transferred to an eluent. The eluent was composed of methanol and acetic acid in a volume ratio of 9:1. It was ultrasonically cleaned for 2 h, shaken for 12 h, filtered, and the filter cake was washed with distilled water and then dried to obtain the selective adsorbent.

[0043] The preparation method of the double bond-modified silica includes the following steps:

[0044] 4 g of silica (100 - 200 mesh) was added to 1 L of 80 wt% ethanol solution. After ultrasonic treatment for 30 min, 30 mL of ammonia water and 12 mL of methacryloxypropyltriethoxysilane were added under the stirring condition of 500 r / min. The mixture was stirred and reacted at 65 °C for 24 h. Then, it was centrifuged, and the centrifuged product was repeatedly washed with absolute ethanol. Finally, it was vacuum dried at 40 °C to constant weight to obtain the double bond-modified silica.

[0045] Preparation Example 2

[0046] A selective adsorbent was prepared as follows:

[0047] 0.4 mol of 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, 0.6 mol of methacrylic acid, 0.4 mol of sodium methallylsulfonate, and 0.4 mol of vinyl neodecanoate were added to 400 mL of N,N-dimethylformamide, and the mixture was ultrasonically mixed evenly and allowed to stand for 12 h. Then, 1 g of double bond-modified silica was added, and the mixture was continuously ultrasonically mixed for 5 - 10 min. After that, 8 mol of ethylene glycol dimethacrylate and 0.2 g of azobisisobutyronitrile were added. After ultrasonic degassing, the mixture was placed at 60 °C and reacted for 24 h. Then, it was centrifuged, and the precipitate was dried for 24 h. The dried product was crushed and passed through a 200-mesh sieve and then transferred to an eluent. The eluent was composed of methanol and acetic acid in a volume ratio of 9:1. It was ultrasonically cleaned for 2 h, shaken for 12 h, filtered, and the filter cake was washed with distilled water and then dried to obtain the selective adsorbent.

[0048] The preparation method of the double bond-modified silica is the same as that in Preparation Example 1.

[0049] Preparation Example 3

[0050] A selective adsorbent was prepared as follows:

[0051] 0.4 mol of 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, 0.8 mol of methacrylic acid, 0.4 mol of potassium methallylsulfonate and 0.4 mol of vinyl versatate were added to 400 mL of N,N-dimethylformamide. After ultrasonic mixing and standing for 12 h, 1 g of double bond modified silica was added, and ultrasonic mixing was continued for 10 min. Then, 8 mol of ethylene glycol dimethacrylate and 0.2 g of azobisisobutyronitrile were added. After ultrasonic degassing, the mixture was reacted at 60 °C for 24 h. Then, centrifugation was carried out, and the precipitate was dried for 24 h. After the dried product was pulverized and passed through a 200-mesh sieve, it was transferred to an eluent. The eluent was composed of methanol and acetic acid in a volume ratio of 9:1. After ultrasonic cleaning for 2 h and shaking for 12 h, filtration was carried out. The filter cake was washed with distilled water and then dried to obtain the selective adsorbent.

[0052] The preparation method of the double bond modified silica was the same as that in Preparation Example 1.

[0053] Preparation Example 4

[0054] A selective adsorbent, which is different from Example 1 only in that "sodium vinyl sulfonate" in Example 1 was replaced with an equimolar amount of "2-acrylamido-2-methylpropanesulfonic acid".

[0055] Preparation Example 5

[0056] A selective adsorbent, which is different from Example 1 only in that "vinyl laurate" in Example 1 was replaced with an equimolar amount of "vinyl neodecanoate".

[0057] Control Example 1

[0058] A selective adsorbent, which is different from Example 1 only in that the double bond modified silica in Example 1 was removed.

[0059] Control Example 2

[0060] A selective adsorbent, which is different from Example 1 only in that "0.4 mol of methacrylic acid" in Example 1 was replaced with "0.2 mol of sodium vinyl sulfonate and 0.2 mol of vinyl laurate".

[0061] Control Example 3

[0062] A selective adsorbent, which is different from Example 1 only in that "0.4 mol of sodium vinyl sulfonate" in Example 1 was replaced with "0.2 mol of methacrylic acid and 0.2 mol of vinyl laurate".

[0063] Control Example 4

[0064] A selective adsorbent, which is different from Example 1 only in that "0.4 mol vinyl laurate" in Example 1 is replaced by "0.2 mol methacrylic acid and 0.2 mol sodium vinyl sulfonate".

[0065] Example 1

[0066] A method for preparing phosphatidylcholine phospholipids with a high content, comprising the following steps:

[0067] S1. Add 5 g of soy powder phospholipids to 1 L of an organic solvent, stir at 50 °C for 80 min, filter to obtain a filtrate and a filter residue; dry the filter residue in an oven at 60 °C for 5 h to obtain a crude phosphatidylserine product;

[0068] S2. Load the filtrate onto an extraction column filled with the selective adsorbent of Preparation Example 1. The dosage ratio of the filtrate to the selective adsorbent is 100 mL:1 g, the loading rate is 1 mL / min. After loading, elute with an eluent, which is composed of methanol and acetic acid in a volume ratio of 9:1. The flow rate of the eluent is 1 mL / min, and the amount of the eluent used is 3 times the volume of the filtrate. Collect the elution mixture, transfer the elution mixture to a concentration tank for vacuum concentration, with a vacuum degree of -0.06 MPa. After concentrating to 1 / 10 of the original volume, dry it in a vacuum drying oven at 60 °C to constant weight to obtain phosphatidylcholine phospholipids with a high content.

[0069] The acetone-insoluble matter content in the soy powder phospholipids is >95%, and the phosphatidylcholine content is 18-23%.

[0070] Example 2

[0071] A method for preparing phosphatidylcholine phospholipids with a high content, comprising the following steps:

[0072] S1. Add 10 g of soy powder phospholipids to 1 L of an organic solvent, stir at 60 °C for 80-120 min, filter to obtain a filtrate and a filter residue; dry the filter residue in an oven at 65 °C for 7 h to obtain a crude phosphatidylserine product;

[0073] S2. Load the filtrate onto an extraction column filled with the selective adsorbent of Preparation Example 1. The dosage ratio of the filtrate to the selective adsorbent is 200 mL:1 g, the loading rate is 3 mL / min. After loading, elute with an eluent, which is composed of methanol and acetic acid in a volume ratio of 9:1. The flow rate of the eluent is 2 mL / min, and the amount of the eluent used is 4 times the volume of the filtrate. Collect the elution mixture, transfer the elution mixture to a concentration tank for vacuum concentration, with a vacuum degree of -0.06 MPa. After concentrating to 1 / 5 of the original volume, dry it in a vacuum drying oven at 70 °C to constant weight to obtain phosphatidylcholine phospholipids with a high content.

[0074] The content of acetone-insoluble matter in the soybean powder phospholipid is >95%, and the content of phosphatidylcholine is 18-23%.

[0075] Example 3

[0076] A preparation method of phospholipid with high content of phosphatidylcholine, comprising the following steps:

[0077] S1. Add 30 g of soybean powder phospholipid into 1 L of organic solvent, stir at 65 °C for 120 min, filter to obtain a filtrate and a filter residue; dry the filter residue in an oven at 70 °C for 8 h to obtain a crude phosphatidylserine product;

[0078] S2. Load the filtrate onto an extraction column filled with the selective adsorbent prepared in Preparation Example 1. The dosage ratio of the filtrate to the selective adsorbent is 500 mL:1 g, the loading rate is 5 mL / min. After loading, elute with an eluent. The eluent is composed of methanol and acetic acid in a volume ratio of 9:1, the flow rate of the eluent is 3 mL / min, the dosage of the eluent is 5 times the volume of the filtrate. Collect the elution mixture, transfer the elution mixture to a concentration tank for vacuum concentration. The vacuum degree is -0.07 MPa. After concentrating to 1 / 5 of the original volume, dry it in a vacuum drying oven at 70 °C to constant weight to obtain phospholipid with high content of phosphatidylcholine.

[0079] The content of acetone-insoluble matter in the soybean powder phospholipid is >95%, and the content of phosphatidylcholine is 18-23%.

[0080] Example 4

[0081] A preparation method of phospholipid with high content of phosphatidylcholine, compared with Example 1, the difference is only that the "selective adsorbent" in Example 1 is replaced with the product prepared in Preparation Example 2.

[0082] Example 5

[0083] A preparation method of phospholipid with high content of phosphatidylcholine, compared with Example 1, the difference is only that the "selective adsorbent" in Example 1 is replaced with the product prepared in Preparation Example 3.

[0084] Example 6

[0085] A preparation method of phospholipid with high content of phosphatidylcholine, compared with Example 1, the difference is only that the "selective adsorbent" in Example 1 is replaced with the product prepared in Preparation Example 4.

[0086] Example 7

[0087] A preparation method of phospholipid with high content of phosphatidylcholine, compared with Example 1, the difference is only that the "selective adsorbent" in Example 1 is replaced with the product prepared in Preparation Example 5.

[0088] Example 8

[0089] A preparation method of phosphatidylcholine phospholipid with high content. Compared with Example 2, the only difference is that the "selective adsorbent" in Example 2 is replaced with the product prepared in Preparation Example 4.

[0090] Comparative Example 1

[0091] A preparation method of phosphatidylcholine phospholipid with high content. Compared with Example 1, the only difference is that the "selective adsorbent" in Example 1 is replaced with the product prepared in Control Example 1.

[0092] Comparative Example 2

[0093] A preparation method of phosphatidylcholine phospholipid with high content. Compared with Example 1, the only difference is that the "selective adsorbent" in Example 1 is replaced with the product prepared in Control Example 2.

[0094] Comparative Example 3

[0095] A preparation method of phosphatidylcholine phospholipid with high content. Compared with Example 1, the only difference is that the "selective adsorbent" in Example 1 is replaced with the product prepared in Control Example 3.

[0096] Comparative Example 4

[0097] A preparation method of phosphatidylcholine phospholipid with high content. Compared with Example 1, the only difference is that the "selective adsorbent" in Example 1 is replaced with the product prepared in Control Example 4.

[0098] The phosphatidylcholine phospholipid with high content obtained in Examples 1 - 8 and Comparative Examples 1 - 4 was detected. The phosphatidylcholine content in the phospholipid was detected, and the net extraction rate of phosphatidylcholine (%) was calculated. The net extraction rate = [(phospholipid weight) * (phosphatidylcholine content in the phospholipid) * 100%] / (phosphatidylcholine weight in soybean powder phospholipid). The results are shown in Table 1:

[0099] Table 1

[0100]

[0101]

[0102] Analyzing the data recorded in Table 1, it can be seen that the phosphatidylcholine content in the phospholipid products obtained in Examples 1 - 8 is 85.6 - 87.4%, and the net extraction rate of phosphatidylcholine is 87.2 - 88.6%. This shows that the preparation method provided by the present invention can obtain phospholipids with high phosphatidylcholine content and large extraction rate.

[0103] As can be seen from the test results of Example 1 and Comparative Example 1, during the preparation of the selective adsorbent, removing the double-bond modified silica as the substrate significantly decreases the extraction rate and purity of phosphatidylcholine.

[0104] As can be seen from the test results of Example 1 and Comparative Examples 2, 3, and 4, using any two of methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate as functional monomers to prepare the selective adsorbent results in significantly inferior application effects compared to the selective adsorbent prepared with methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate used together as functional monomers.

[0105] It should be noted that in this text, relational terms such as first and second are only used to distinguish one entity or operation from another entity or operation, and do not necessarily require or imply any actual relationship or order between these entities or operations. Moreover, the term "comprising", "including" or any other variant thereof is intended to cover non-exclusive inclusion, such that a process, method, article or device comprising a series of elements includes not only those elements but also other elements not expressly listed, or elements inherent to such process, method, article or device.

[0106] Although the embodiments of the present invention have been shown and described, for those of ordinary skill in the art, it can be understood that various changes, modifications, substitutions, and variations can be made to these embodiments without departing from the principles and spirit of the present invention. The scope of the present invention is defined by the appended claims and their equivalents.

Claims

1. A preparation method of phosphatidylcholine phospholipids with high content, characterized in that, It includes the following steps: S1. Add soybean powder phospholipid into an organic solvent, stir at 50 - 65 °C for 80 - 120 min, filter to obtain a filtrate and a filter residue; S2. Load the filtrate onto an extraction column filled with a selective adsorbent, after loading, elute with an eluent, collect the elution mixture, vacuum concentrate and dry the elution mixture to obtain a phospholipid with a high content of phosphatidylcholine; The selective adsorbent is a phosphatidylcholine molecularly imprinted polymer.

2. The preparation method of a phosphatidylcholine phospholipid with high content according to claim 1, characterized in that, The phosphatidylcholine molecularly imprinted polymer is prepared by a thermal polymerization method using silica modified with double bonds as the substrate, 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine as the template molecule, methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate as functional monomers, and ethylene glycol dimethacrylate as the crosslinking agent.

3. The preparation method of a phosphatidylcholine phospholipid with a high content according to claim 2, wherein, The unsaturated sulfonate is at least one of sodium vinyl sulfonate, sodium allyl sulfonate, sodium p-styrene sulfonate, 2-acrylamido-2-methylpropanesulfonic acid, potassium allyl sulfonate, ammonium allyl sulfonate, sodium methallyl sulfonate, potassium methallyl sulfonate, and ammonium methallyl sulfonate.

4. A method for preparing a phospholipid with a high content of phosphatidylcholine according to claim 2, characterized in that, The hydrophobic acrylate is at least one of vinyl neodecanoate, vinyl laurate, vinyl neodecanoate, vinyl neodecanoate, and vinyl versatate.

5. The preparation method of a phosphatidylcholine phospholipid with a high content according to claim 1, characterized in that, The preparation process of the selective adsorbent includes the following steps: Add 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, methacrylic acid, unsaturated sulfonate, and hydrophobic acrylate into N,N-dimethylformamide, mix evenly by ultrasonic wave, let it stand for 12 h, then add silica modified with double bonds, continue to mix by ultrasonic wave for 5 - 10 min, then add ethylene glycol dimethacrylate and azobisisobutyronitrile, after ultrasonic degassing, place it at 60 °C for reaction for 24 h, then centrifuge, dry the precipitate for 24 h, crush the dried product through a 200-mesh sieve and transfer it to the eluent, clean it by ultrasonic wave for 2 h, oscillate for 12 h, filter, wash the filter cake with distilled water and then dry it to obtain the selective adsorbent.

6. The preparation method of a phosphatidylcholine phospholipid with a high content according to claim 5, characterized in that, The dosage ratio of 1-palmitoyl-2-stearoyl-sn-glycero-3-phosphocholine, methacrylic acid, unsaturated sulfonate, hydrophobic acrylate, N,N-dimethylformamide, silica modified with double bonds, ethylene glycol dimethacrylate, and azobisisobutyronitrile is 0.4 mol : 0.4 - 0.8 mol : 0.4 mol : 0.4 mol : 400 mL : 1 g : 8 mol : 0.2 g.

7. The preparation method of a phosphatidylcholine phospholipid with a high content according to claim 1 or 5, characterized in that, The eluent is composed of methanol and acetic acid according to a volume ratio of 9 :

1.

8. A method for preparing a high-content phosphatidylcholine phospholipid according to claim 2 or 5, characterized in that, The silica modified with double bonds is silica modified with 3-methacryloxypropyltriethoxysilane.

9. The preparation method of a phosphatidylcholine phospholipid with a high content according to claim 1, characterized in that, The dosage ratio of soybean powder phospholipid and the organic solvent is 5 - 30 g : 1 L.

10. A phosphatidylcholine phospholipid with a high content, characterized in that, Prepared by the preparation method according to any one of claims 1 - 9.

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