CN102633832A - Method for preparing high-purity phosphatidylcholine - Google Patents
Method for preparing high-purity phosphatidylcholine Download PDFInfo
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Abstract
The invention relates to a method for preparing high-purity phosphatidylcholine, and is characterized in that the method comprises the following steps of: an alcohol treatment step, wherein crude phospholipids are used as raw materials, low carbon alcohol and water are used as mixed solvents, an alcohol soluble product is separated by extraction separation; a silicagel column chromatography step, wherein the product obtained in the previous step is subject to silicagel column chromatography, ethanol is used for gradient elution, and the product solution is collected; a drying step, wherein the product solution is subject to vacuum concentration and freeze drying to obtain the high-purity phosphatidylcholine. The method of the invention adopts a single elution solvent, which allows the production process to be nontoxic, free of pollution, and free of three wastes. The separated fillers can be recycled, which saves labor and time, and cause no harmful solvent introduction; the raw materials are not limited within certain sources, and can be derived from phospholipids of various plants and animals.
Description
Technical field
The present invention relates to a kind of method for preparing the high-purity phospholipid phatidylcholine.
Background technology
Phosphatide is prevalent in vegeto-animal protoplasma and the microbial film, and the homergy of biomembranous physiologically active and body is had important adjustment function, and it has good emulsifying property and oxidation-resistance simultaneously, is widely used in food, medicine, fields such as makeup.Phosphatidylcholine (phosphatidylcholine is called for short PC) is wherein important phosphatide.
Yelkin TTS is the staple that constitutes the human body cell film, is one of life basic substance that keeps the cell normal function, and the homergy of human body is had important regulatory role.The elasticity and the perviousness that keep heart and cerebrovascular wall, vessel softening, the content of increase RHDL prevents blood pool; Make nerves reaction sharp, memory prevents forgetful and senile dementia; But prevention of liver disease and diabetes-alleviating; Can promote damaging cells, enhance immunity power.The shortage of Yelkin TTS is the one of the main reasons that causes modern civilization sick.
Have hydrophilic group and hydrophobic group in the lecithin molecules structure simultaneously, this bipolar character makes Yelkin TTS show good surfactivity, belongs to application phosphatic type amphoterics more widely, has emulsification, thickening; Stable, disperse, solubilising, wetting, function such as lubricated; Can be widely used in food, feed, medicine, makeup, coating; Printing ink, weaving, leather, industrial and agricultural productions such as petroleum product and plant protection.High purity lecithin is meant that PC content is greater than 90% lecithin products.Because high purity lecithin purity is high, free from extraneous odour, emulsifying capacity is strong, and interpolation that not only can be more a large amount of in foodstuffs industry is used, and also can make healthcare products, pharmaceuticals etc.Especially pharmaceutically, can be used as intravenous liposome,, reduce toxicity, increase drug effect as the carrier of active ingredient.High-load phosphatidylcholine has the effect of prevention hepatitis and fatty liver, reducing cholesterol, the effect of preventing cardiovascular disease simultaneously.
The raw material of the highly purified natural phosphatidyl choline of preparation is mainly derived from animal and plant at present.The former mainly is yolk and animal tissues, and the latter is some vegetable oil materials, like soybean, vegetable seed.The quality of from yolk, extracting high purity lecithin is better, but cost is high.And the phosphatide in the vegetable oil material is a kind of fatty accompaniment, and stripping separates with grease as oil foot in the aquation operation of oil and fat refining along with greasy extraction.These oil foots such as untimely processing are very easily grown mikrobe and are caused environmental pollution.Oil foot through dehydration, obtains concentrated phosphatide, i.e. the raw phospholipid of plant origin earlier.The raw phospholipid of plant origin also contains glyceryl ester except containing the phosphatidyl choline, single glyceric acid three ester, two glycerates; Glyceric acid three ester (referring to oils here), peptide class, amino acid, stearin; Phosphatidyl inositide, phosphatidylethanolamine, and glucide.The general high-purity phospholipid phatidylcholine of obtaining is to be starting raw material with such raw phospholipid.The first step of general purifying phosphatide is with acetone deoiling (U.S.Pat.No.3,268,335), and second step was with extraction using alcohol (U.S.Pat.No.2,724,649) then, and the 3rd step was that the phosphatide that is dissolved in the ethanol part carries out adsorption chromatography, was no more than 35 ℃.When using the acetone method separating oil, produced acetone derivatives, like mesityl oxide, Pyranton, other material such as sym.-diisopropylideneacetone produces.Not only the smell is awful for these by products, and be deleterious.And the superoxide that with acetone deoiling the time, produces also can cause bad influence to Human Physiology.In addition, there is potential safety hazard in a large amount of uses of industrial production acetone.
When the purifying phosphatidylcholine, remove lyso-phosphatidylcholine also is the difficult problem of production injection stage phosphatidylcholine always.A kind of compound that lyso-phosphatidylcholine (lysophosphatidylcholine) is a Yelkin TTS to be generated by the phospholipase A hydrolysis has strong hemolytic action, mainly is through destroying cytolemma, causing haemolysis.The existence of lyso-phosphatidylcholine in the injection liquid causes that hemolytic sign, threat to life appear in patient.
High-purity phosphatidylcholine technology of preparing mainly contains: acetylation method, the inorganic salt precipitator method, supercritical extraction method, membrane separation process, tlc (TCL), HPLC (HPLC), column chromatography etc.The inorganic salt precipitator method and acetylation method can only obtain Phosphorylcholine, owing to added reaction reagent, the technical difficulty of aftertreatment strengthens; Commonly used in the supercutical fluid method is supercritical CO 2, the ability that its dissolves the strong and dissolving phosphatide of oily ability a little less than, only is fit to preparation mixed phosphatide product and is not suitable for the fractional separation of phosphatide, and cost of equipment is relatively more expensive; The cost of equipment of membrane separation process is also higher, realizes that the single component fractional separation of phosphatide also exists certain difficulty; Tlc (TCL) and HPLC (HPLC) all can obtain purity height, the measured single phosphatide product of matter, but the treatment capacity of HPLC method is little, and equipment and maintenance cost are higher, and tlc is difficult for changing developping agent, and aftertreatment is more loaded down with trivial details;
These methods are not enough to remove harmful lyso-phosphatidylcholine; Simultaneously raw materials used; Generally, the content of phosphatidylcholine is reached more than 90%, waste time and energy through removing grease with acetone; The lyso-phosphatidylcholine in the product of producing and the by product of acetone can not get effective control, are difficult to satisfy the basic demand as injection stage phosphatide.
In addition, part prepares in the technology of high-purity phospholipid phatidylcholine, uses toxic reagent, like CN1709895A, uses ETHYLE ACETATE, and silica gel needs activation, and operation is very loaded down with trivial details.
Summary of the invention
In order to solve the problems of the prior art; The invention provides a kind of method for preparing the high-purity phospholipid phatidylcholine; It is raw material that this preparation method adopts the plant concentrated phosphatide; Alcohol water is solvent, has solved key technical problems such as continuous extraction in the suitability for industrialized production, separation continuously, continuous chromatography separation, has solved the low difficult problem of phosphatidylcholine content; Can produce the phosphatide of phosphatidylcholine content more than 90%, solve phosphatidylcholine simultaneously as the high problem of detrimental impurity content in the injection stage phospholipid prod.This Technology is produced the phospholipid prod of phosphatidylcholine content more than 90%, and low lyso-phosphatidylcholine, the phospholipid prod of low phosphatidyl thanomin.Present device is simple, does not introduce toxic reagent, and separating effect is desirable, and is easy and simple to handle, can reach and work continuously, and is convenient to expand the scale of production.And this method is easy to extension, is to prepare the high-purity phospholipid phatidylcholine one of method of development potentiality is arranged most.
The preparation method of high-purity phospholipid phatidylcholine of the present invention comprises following technological process:
The alcohol treatment step: with the plant concentrated phosphatide is raw material, and alcohol and water is a mixed solvent, through extracting and separating, isolates pure soluble product;
Silica gel column chromatography step: the back products therefrom is carried out silica gel column chromatography, use pure gradient elution, collect product solution;
Drying step: silica gel column chromatography products therefrom solution is carried out vacuum concentration, and lyophilize obtains the high purity lecithin product.
Can further add the alumina column chromatography treatment step in preparing method's technological process of high-purity phospholipid phatidylcholine of the present invention; This treatment step before being placed on silica gel column chromatography is: adsorb pure soluble product with the alumina column chromatography method; Use the alcohol and water gradient elution, collect product solution; Silica gel column chromatography is collected high-content phosphorus acyl choline solution then, further carries out vacuum concentration, and lyophilize obtains the high purity lecithin product.
This treatment step after being placed on silica gel column chromatography is: with the product solution that alumina column chromatography method absorption silica gel column chromatography is collected, use the alcohol and water gradient elution, collect product solution; Further carry out vacuum concentration, lyophilize obtains the high purity lecithin product.
According to method of the present invention, wherein, the purity of said phosphatidylcholine is more than 90%.
According to method of the present invention, wherein, the purity of said phosphatidylcholine is more than 95%.
According to method of the present invention, wherein, the purity of said phosphatidylcholine is more than 98%.
According to method of the present invention, wherein, the determining alcohol that said gradient elution is used is between 40%-100%.In one embodiment of the invention, be sorbent material with silica gel, adopt 60%; 85%, 95% ethanol is when the content that has improved phosphatidylcholine is 90.0%; Removed oil; Lyso-phosphatidylcholine (content is 5%), phosphatidylethanolamine (content is 5%) reduces these foreign matter contents; In another embodiment of the present invention, adopt 40%, 80%; 100% methanol-eluted fractions alumina column cooperates silica gel column chromatography, when the content that has improved phosphatidylcholine is 96.7%; Removed oil; Lyso-phosphatidylcholine (content is 0.1%), phosphatidylethanolamine (content is 0.2%) reduces these foreign matter contents.
According to method of the present invention, wherein, the said raw material that contains phosphatidylcholine is selected from the group that comprises that soybean lecithin, Ovum Gallus domesticus Flavus lecithin, rapeseed oil phospholipid are formed; As concentrating soybean lecithin, powder soybean phospholipid, decolouring phosphatide; Sunflower Receptacle phosphatide, rapeseed oil phospholipid, peanut phosphatide.
According to method of the present invention, wherein, said alcohol is to comprise methyl alcohol, ethanol, propyl alcohol, Virahol, propyl carbinol, the group of isopropylcarbinol.
According to method of the present invention, wherein, said alcohol is methyl alcohol, the group that ethanol and Virahol are formed.
According to method of the present invention, wherein, the lysophospholipid content in the said high-purity phospholipid phatidylcholine product is below 3%.
According to method of the present invention, wherein, the thanomin content in the said high-purity phospholipid phatidylcholine product is below 5%.
According to method of the present invention, wherein, alumina column chromatography method in the said pre-treatment step and the silica gel column chromatography in the chromatographic step exchange.
The preparation method of high purity lecithin provided by the invention has proposed one from concentrated phosphatide, uses extraction using alcohol; The new technology route that silica gel column chromatography organically combines, whole process step is only used alcohol and water, is obtaining high purity PC product simultaneously; Guaranteed that this product hangs down LPC, PE content.The entire operation process adopts the single solvent alcoholic solution, makes production process nontoxic, and is nuisanceless, the no three wastes.Separating filler can recycle, and is time saving and energy saving, the entering of no hazardous solvent, and raw material is not confined to certain source, the phosphatide of the various plants of can originating and animal.
The high-purity phospholipid phatidylcholine product of aforesaid method preparation according to the present invention, wherein, said product contains phosphatidylcholine 90-100%, phosphatidylethanolamine 0-5%, lyso-phosphatidylcholine 0-5%.Further; The high-purity phospholipid phatidylcholine product of aforesaid method preparation according to the present invention, wherein, said product contains phosphatidylcholine 90-100%; Phosphatidylethanolamine 0-3%; Lyso-phosphatidylcholine 0-3% and other type phosphatide, like phosphatidyl-4 alcohol ester, phosphatidylserine, and phosphatidic acid.
The present invention provides high-content Yelkin TTS at medicine, healthcare products, and the application of cosmetic industry is particularly as the application of injection stage phosphatide.
The aluminum oxide that the present invention uses comprises neutral alumina, alkali alumina, and acidic alumina, size range is the 30-200 order; The silica gel size range that the present invention uses is the 30-700 order; The rate of load condensate of aluminum oxide and silica gel (per-cent of absorption soup) is 5-30%.Column chromatography service temperature of the present invention is 20-70 degree centigrade.
Embodiment
Embodiment 1
25.63 the thick beans concentrating liquid phosphatide of kilogram stirs with 128 kilogram of 95% methyl alcohol at 35 ℃, extracts, the room temperature state cold analysis separates, and isolates supernatant; Repetitive operation 2 times merges the second extraction supernatant, and (reduced vacuum concentrates; The HPLC detection level: phosphatidylcholine content is 44.2%, and the content of phosphatidylethanolamine is 15.2%, and the content of oil is 12.3%; The content of lyso-phosphatidylcholine is 10%), carry out alumina column chromatography (salic 40 kilograms), 80% methanol-eluted fractions; Thin-layer chromatography detects (TLC), collects the flow point that is rich in Yelkin TTS, and product is carried out silica gel column chromatography (containing 40 kilograms in silica gel); With 70%, 85%, 100% methyl alcohol gradient elution.The monitoring of TLC analytical procedure, the identical single phosphatidylcholine spot stream part that contains merges vacuum concentration; Lyophilize, 2.41 kilograms of the products that obtains, phosphatidylcholine (being called for short PC) content 97.5%; Lyso-phosphatidylcholine (being called for short LPC) is 0.8%; Phosphatidylethanolamine (being called for short PE) is 0.25%, and the content of oil is 0, phosphatidic acid content 1.45%.
Embodiment 2
16.8 the thick Ovum Gallus domesticus Flavus lecithin of kilogram stirs at 35 degrees centigrade of 95% Virahols with 170 kilograms, extracts, the room temperature state cold analysis separates; Isolate supernatant, repetitive operation 2 times, (reduced vacuum concentrates to merge the second extraction supernatant; Phosphatidylcholine content is: 43.2%, and phosphatidylethanolamine content 14.3%, the content 10.0% of oil; The content of lyso-phosphatidylcholine is: 15%) product is carried out alumina column absorption, 40%, 80%; 100% Virahol gradient elution, the flow point that is rich in Yelkin TTS is collected in the monitoring of TLC analytical procedure.Product is added silica gel column chromatography absorption, 80% Virahol wash-out.Thin-layer chromatography detects (TLC), and the identical single phosphatidylcholine spot stream part that contains merges vacuum concentration, lyophilize; The product 2.31Kg that obtains, PC content 96.7%, LPC are 0.1%; PE is 0.2%, and the content of oil is 0 and 3% phosphatidyl-4 alcohol ester composition.
Embodiment 3
6.38 kilogram powdered soybean Yelkin TTS (derive from commercially available, phosphatidylcholine content 53.2%, the content 15% of phosphatidylethanolamine; The content of lyso-phosphatidylcholine is 8%, and the content of oil is 0) be dissolved in 25 liters of industrial alcohols, directly add alumina column chromatography (containing 30 kilograms in 100-200 purpose aluminum oxide); Use 40%, 70%, 90% ethanol gradient elution then; The flow point that is rich in Yelkin TTS is collected in the monitoring of TLC analytical procedure.Product is added silica gel column chromatography absorption (containing 10 kilograms of 200-300 order silica gel), amalgamation liquid is carried out silica gel column chromatography, use ethanol: water (70: 30) mixed solvent gradient elution.Thin-layer chromatography detects (TLC), and the identical single phosphatidylcholine spot stream part that contains merges, vacuum concentration, and lyophilize, 2.55 kilograms of the products that obtains, PC content 98.5%, LPC are 0.8%, and PE is 0.7%, and the content of oil is 0.
Embodiment 4
16.8 the thick Ovum Gallus domesticus Flavus lecithin of kilogram stirs with 170 kilogram of 95% ethanol at 35 degrees centigrade, extracts, the room temperature state cold analysis separates; Isolate supernatant, repetitive operation 2 times, (reduced vacuum concentrates to merge the second extraction supernatant; Phosphatidylcholine content 43.2%, phosphatidylethanolamine content 14.3%, the content 10.0% of oil; The content of lyso-phosphatidylcholine is: 9%) add alumina column chromatography (containing 20 kilograms of 100-200 purpose neutral aluminas); Use 100% ethanol elution, the flow point that is rich in Yelkin TTS is collected in the monitoring of TLC analytical procedure.Product is carried out silica gel column chromatography (containing 8 kilograms of 60-100 order silica gel), the ethanol gradient elution with 80%, 95%.Thin-layer chromatography detects (TLC), and the identical single phosphatidylcholine spot stream part that contains merges, vacuum concentration, and lyophilize, 2.16 kilograms of the products that obtains, PC content 98%, LPC are 1%, PE is 1%.
Embodiment 5
25.63 the thick beans concentrating liquid phosphatide of kilogram stirs with 128 kilogram of 95% ethanol at 35 degrees centigrade, extracts, the room temperature state cold analysis separates, and isolates supernatant; Repetitive operation 2 times merges the second extraction supernatant, and reduced vacuum concentrates, and enriched material HPLC detection level: phosphatidylcholine content is 44.2%; The content of phosphatidylethanolamine is 15.2%, and the content of oil is 12.3%, and the content of lyso-phosphatidylcholine is 8%; Carry out alumina column chromatography (containing 25 kilograms in 30-60 purpose aluminum oxide), 50%, 75%; 90% ethanol elution, thin-layer chromatography detects (TLC), collects the flow point that is rich in Yelkin TTS.Product is added silica gel column chromatography (containing 15 kilograms of 60-100 order silica gel), with 50%, 80%, 100% ethanol gradient elution.The monitoring of TLC analytical procedure, the identical single phosphatidylcholine spot stream part that contains merges vacuum concentration; Lyophilize, 2.41 kilograms of the products that obtains, PC content 93.5%; LPC is 0.8%, and PE is 0.25%, and the content of oil is 0; With the capable composition of other phosphatide such as phosphatidyl-4 alcohol ester, phosphatidylserine, and phosphatidic acid 5.45%.
Embodiment 6
21.61 the thick beans concentrating liquid phosphatide of kilogram stirs with 108 kilogram of 95% ethanol at 35 degrees centigrade, extracts, the room temperature state cold analysis separates, and isolates supernatant; Repetitive operation 2 times merges the second extraction supernatant, and (reduced vacuum concentrates, and the HPLC detection level: phosphatidylcholine content is 44.2%; The content of phosphatidylethanolamine is 15.2%, and the content of oil is 12.3%, and the content of lyso-phosphatidylcholine is 10%); Carry out alumina column chromatography (containing 18 kilograms in 100-200 order aluminum oxide), 60%, 80%; 100% ethanol elution, thin-layer chromatography detects (TLC), collects the flow point that is rich in Yelkin TTS.Product is added silica gel column chromatography (containing 12 kilograms of 200-300 order silica gel), with 65%, 80%, 100% ethanol gradient elution.The monitoring of TLC analytical procedure, the identical single phosphatidylcholine spot stream part that contains merges vacuum concentration; Lyophilize, 2.41 kilograms of the products that obtains, PC content 95.5%; LPC is 1%, and PE is 0.25%, and the content of oil is 0; With other phosphatide property composition such as phosphatidyl-4 alcohol ester, phosphatidylserine, and phosphatidic acid.
Embodiment 7
15.36 the rapeseed oil phospholipid of kilogram stirs with 155 kilogram of 95% ethanol at 35 degrees centigrade, extracts, the room temperature state cold analysis separates, and isolates supernatant; Repetitive operation 2 times merges the second extraction supernatant, and (reduced vacuum concentrates, phosphatidylcholine content 40.2%; The content 15% of phosphatidylethanolamine, the content of oil is 14%, the content 8% of lyso-phosphatidylcholine), carry out silica gel column chromatography (100-200 order); 70%, 90% ethanol elution, thin-layer chromatography detects (TLC), collects the flow point that is rich in Yelkin TTS.Product is added alumina column chromatography (containing 20 kilograms in 30-60 order aluminum oxide), the ethanol gradient elution with 70%, 90%.The monitoring of TLC analytical procedure, the identical single phosphatidylcholine spot stream part that contains merges vacuum concentration; Lyophilize, 2.41 kilograms of the products that obtains, PC content 90.5%; LPC is 3%, and PE is 5.0%, and the content of oil is 0; With other phosphatide property composition such as phosphatidyl-4 alcohol ester, phosphatidylserine, and phosphatidic acid.
Embodiment 8
21.61 the thick beans concentrating liquid phosphatide of kilogram stirs with 108 kilogram of 95% ethanol at 35 degrees centigrade, extracts, the room temperature state cold analysis separates; Isolate supernatant, repetitive operation 2 times merges the second extraction supernatant; (reduced vacuum concentrates, and the HPLC detection level: phosphatidylcholine content is 44.2%, and the content of phosphatidylethanolamine is 15.2%; The content of oil is 12.3%, and the content of lyso-phosphatidylcholine is 10%), carry out silica gel column chromatography (containing 8 kilograms in 300-400 purpose silica gel); With 60%, 85%, 95% ethanol gradient elution.The monitoring of TLC analytical procedure, the identical single phosphatidylcholine spot stream part that contains merges, vacuum concentration, lyophilize, 2.51 kilograms of the products that obtains, PC content 90.0%, LPC are 5%, PE is 5%.
Claims (14)
1. a method for preparing the high-purity phospholipid phatidylcholine is characterized in that, said method comprises:
The alcohol treatment step: with the raw phospholipid is raw material, and the low-carbon (LC) alcohol and water is a mixed solvent, through extracting and separating, isolates pure soluble product;
Chromatographic step: the back products therefrom is carried out silica gel column chromatography, use pure gradient elution, collect product solution;
Drying step: products therefrom solution is carried out vacuum concentration, and lyophilize obtains the high-purity phospholipid phatidylcholine.
2. method according to claim 1 further adds the alumina treatment step in silica gel column chromatography step front: the product after handling with alumina column chromatography method absorption alcohol, use ethanol gradient elution, and collect product solution.
3. method according to claim 1 further adds the alumina treatment step at the back in the silica gel column chromatography step: with the product solution of alumina column chromatography absorption silica gel column chromatography, use ethanol gradient elution, collect product solution.
4. according to the described method of claim 1-3, wherein, the purity of said phosphatidylcholine is more than 90%.
5. according to the described method of claim 1-3, wherein, the purity of said phosphatidylcholine is more than 95%.
6. according to the described method of claim 1-3, wherein, the purity of said phosphatidylcholine is more than 98%.
7. according to the described method of claim 1-3, wherein, the determining alcohol that said gradient elution is used is between 40%-100%.
8. according to the described method of claim 1-3, wherein, said raw phospholipid is selected from the group that comprises that soybean lecithin, Ovum Gallus domesticus Flavus lecithin and rape oil Yelkin TTS are formed.
9. according to the described method of claim 1-3, wherein, said alcohol comprises methyl alcohol, ethanol, the group that Virahol is formed.
10. according to the described method of claim 1-9, wherein, the lyso-phosphatidylcholine content in the said high-purity phospholipid phatidylcholine product is below 3%.
11. according to the described method of claim 1-9, wherein, the phosphatidylethanolamine content in the said high-purity phospholipid phatidylcholine product is below 5%.
12. the application of high-purity phospholipid phatidylcholine in injection stage phosphatide of method preparation according to claim 1.
13. the high-purity phospholipid phatidylcholine product according to the described method preparation of claim 1-11, wherein, said product contains phosphatidylcholine 90-100%, phosphatidylethanolamine 0-5%, lyso-phosphatidylcholine 0-5%.
14. high-purity phospholipid phatidylcholine product according to claim 13, wherein, said product contains phosphatidylcholine 90-100%, phosphatidylethanolamine 0-3%, lyso-phosphatidylcholine 0-3% and other type phosphatide.
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| CN102924506A (en) * | 2012-11-20 | 2013-02-13 | 江南大学 | Preparation method of high-purity lecithin |
| CN103131736A (en) * | 2013-02-25 | 2013-06-05 | 上海艾韦特医药科技有限公司 | Preparation and application of high-purity lysophosphatidylcholine |
| CN103613612A (en) * | 2013-11-29 | 2014-03-05 | 广东省食品工业研究所 | Preparation method of high-purity phosphatidylcholine |
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| CN103131736A (en) * | 2013-02-25 | 2013-06-05 | 上海艾韦特医药科技有限公司 | Preparation and application of high-purity lysophosphatidylcholine |
| CN103131736B (en) * | 2013-02-25 | 2015-08-05 | 上海艾韦特医药科技有限公司 | The preparations and applicatio of high purity lyso-phosphatidylcholine |
| CN105377247B (en) * | 2013-03-26 | 2019-04-26 | 脂质治疗有限公司 | For treating pharmaceutical preparation of the ulcerative colitis containing phosphatidyl choline |
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| CN111039976A (en) * | 2019-12-26 | 2020-04-21 | 江苏汉斯通药业有限公司 | Method for purifying soybean phosphatidylcholine by gradient method |
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| CN115010750B (en) * | 2022-07-22 | 2023-09-12 | 山东欣康药业有限公司 | Soybean lecithin with high PC (polycarbonate) and PE (polyethylene) ratio and preparation method thereof |
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