WO2012150839A2 - 포스파티딜세린의 마이크로캡슐화 방법 - Google Patents

포스파티딜세린의 마이크로캡슐화 방법 Download PDF

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Publication number
WO2012150839A2
WO2012150839A2 PCT/KR2012/003504 KR2012003504W WO2012150839A2 WO 2012150839 A2 WO2012150839 A2 WO 2012150839A2 KR 2012003504 W KR2012003504 W KR 2012003504W WO 2012150839 A2 WO2012150839 A2 WO 2012150839A2
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Prior art keywords
phosphatidylserine
oil
starch
lecithin
emulsion
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PCT/KR2012/003504
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English (en)
French (fr)
Korean (ko)
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WO2012150839A3 (ko
Inventor
한지영
한정준
이관형
정국훈
황성기
Original Assignee
주식회사 두산
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Priority to CN201280033216.7A priority Critical patent/CN103635181A/zh
Publication of WO2012150839A2 publication Critical patent/WO2012150839A2/ko
Publication of WO2012150839A3 publication Critical patent/WO2012150839A3/ko

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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5089—Processes
    • 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
    • A23J7/00—Phosphatide compositions for foodstuffs, e.g. lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/66—Phosphorus compounds
    • A61K31/683—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols
    • A61K31/685—Diesters of a phosphorus acid with two hydroxy compounds, e.g. phosphatidylinositols one of the hydroxy compounds having nitrogen atoms, e.g. phosphatidylserine, lecithin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5015—Organic compounds, e.g. fats, sugars
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/48—Preparations in capsules, e.g. of gelatin, of chocolate
    • A61K9/50—Microcapsules having a gas, liquid or semi-solid filling; Solid microparticles or pellets surrounded by a distinct coating layer, e.g. coated microspheres, coated drug crystals
    • A61K9/5005—Wall or coating material
    • A61K9/5021—Organic macromolecular compounds
    • A61K9/5036—Polysaccharides, e.g. gums, alginate; Cyclodextrin
    • 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

Definitions

  • PS phosphatidlyserine
  • Microencapsulation technology is a method to protect the core material from the external environment or to release it at a desired rate under certain conditions by forming a film using a coating material on the core material in a solid, liquid, or gas phase. It can be applied to a wide range of fields such as medicine, food, and cosmetics.It can protect unstable cores from external factors, reduce losses, isolate highly reactive cores, and conceal or solidify toxic, odor and taste. It is used for the purpose of simplifying, controlling the elution rate of the contents, and the like.
  • microencapsulation of highly reactive bioactive ingredients and food materials has the advantages of preventing oxidation and preservation, blocking unwanted flavors, controlling release, enhancing bioavailability, and improving handling and processability by changing physical properties.
  • the coating material of the capsule used in food must be edible, excellent in dissolution, high in emulsification, and easy to operate during microencapsulation. It should also be less reactive with the core material during processing and storage, protect the core material from the external environment, and be economical due to its low price.
  • Carbohydrates, gelatin, cellulose, fats, proteins, gums and the like are used as coating materials, and microencapsulation methods for coating with various coating materials have been studied to overcome disadvantages of highly reactive materials.
  • Phosphatidylserine is a kind of phospholipid (Phospholipid) existing in nature, and is composed of a serine group (hydrophilic moiety), a phosphate group, glycerol and two fatty acid groups (hydrophobic moiety).
  • lecithin In the human brain, lecithin accounts for almost half of the dry weight, and most of the lecithin is contained in the membranes of nerve cells. Lecithin, an important component of the cell membrane, contains phosphatidylserine, which is particularly present in the brain, and constitutes a neural cell membrane, releasing energy for life-sustaining activity, releasing neurotransmitters or synapses. It is known that he is deeply involved in the expression of neurons' function, such as information transmission. For this reason, phosphatidylserine is sometimes called the "nutrient of the brain.”
  • Phosphatidylserine has been subject to dozens of clinical trials since it was first isolated by Jordi Folch in 1942. As a result, phosphatidylserine has been shown to be effective in improving Alzheimer's dementia and in reducing brain function due to aging. have. In addition to the effects of improving brain function, it has been reported to show effects such as improvement in epilepsy, stress tolerance, and recovery of hormone secretion rhythm.
  • Phosphatidylserine has been reported to be effective only when ingested from 100 to 300 mg / day (day), but the supply through food is limited, and the supply through a variety of manufacturing is actively considered (Korea Patent Publication No. 2002-0085756 Reference).
  • Korean Patent Laid-Open Publication No. 2003-0058839 discloses a liquid composition in which medium chain fat is further added to a composition including phosphatidylserine and fats and oils. Such liquid compositions are described as being able to prevent phenomena of increasing viscosity or curing when phosphatidylserine is dissolved in an oil containing unsaturated fatty acids, and furthermore, it can be used in health foods and medicines in the form of soft capsules and the like.
  • the water dispersibility of phosphatidylserine is not good, and even when dispersed in an aqueous solution, the ester bond of phosphatidylserine is gradually hydrolyzed naturally in the aqueous phase, and also has a relatively low oxidation stability.
  • An object of the present invention is to provide a method for microencapsulating phosphatidylserine using starch as a coating material, to improve dispersibility, solubility, and stability in an aqueous solution of phosphatidylserine, and to prevent oxidation by oxygen in light or air. Can improve the long-term preservation and transport properties while maintaining the intrinsic function of phosphatidylserine.
  • Another object of the present invention is to provide a microcapsule preparation preparable by the above method.
  • the present invention comprises the steps of (a) dissolving phosphatidylserine in edible oil to prepare a phosphatidylserine liquid composition; (b) preparing a starch aqueous solution by mixing the processed starch modified with lipophilic and hydrophilicity with water before, after or simultaneously with step (a); (c) mixing and homogenizing the aqueous starch solution and the phosphatidylserine liquid composition to emulsify; And (d) provides a method for microencapsulation of phosphatidylserine, comprising the step of drying the obtained emulsion.
  • the present invention provides a microcapsule formulation comprising phosphatidylserine suitable for food or pharmaceutical use, which can be prepared by the above-described method.
  • the microencapsulation method of phosphatidylserine according to the present invention can prevent phosphatidylserine from being oxidized by oxygen in light or air, improve dispersibility, solubility, stability in water, and improve storage and transport characteristics.
  • phosphatidylserine can be effectively formulated into capsule formulations such as health functional foods (particularly beverages) and medicines while maintaining phosphatidylserine-specific functions such as preventing cognitive decline and reducing stress.
  • the present invention is a method for microencapsulating phosphatidylserine having a function such as improvement of memory, dementia improvement, improvement of epilepsy, stress resistance, recovery of hormonal secretion rhythm using starch which is a biodegradable polymer material.
  • phosphatidylserine having a function such as improvement of memory, dementia improvement, improvement of epilepsy, stress resistance, recovery of hormonal secretion rhythm using starch which is a biodegradable polymer material.
  • starch which is a biodegradable polymer material.
  • it provides a method of microencapsulating in powder form.
  • the phosphatidylserine liquid composition according to the present invention is prepared by dissolving phosphatidylserine in powder or granule form in an edible oil and fat.
  • Phosphatidylserine in the form of a powder is difficult to be incorporated into lipophilic modified starch because the powder particles do not dissolve well in water and have a hydrophilic part and a hydrophobic part together due to the nature of phospholipids. Therefore, it is important to dissolve phosphatidylserine using edible oils and oils to make the oil type closer to lipophilic.
  • the phosphatidylserine is a natural phosphatidylserine derived from animal tissues; Natural phosphatidylserine derived from plant tissues; A phosphatidylserine obtained by reacting lecithin selected from the group consisting of soybean lecithin, rapeseed lecithin, fish-derived lecithin, mollusk-derived lecithin and egg yolk lecithin with serine in the presence of phospholipase D, a saturated fatty acid having 6 to 30 carbon atoms, mono- Unsaturated fatty acids or polyunsaturated fatty acids, or phosphatidylserine, including sodium salts, potassium salts, magnesium salts, ammonium salts, phosphate salts, hydrochloride salts or sulfate salts thereof.
  • Edible oil and fat may be at least one selected from medium chain fat, soybean oil, sunflower oil, grape seed oil, rapeseed oil, olive oil, corn oil, pumpkin seed oil, safflower seed oil, palm oil and the like.
  • medium chain fat refers to an oil or fat consisting of fatty acids having 6 to 10 carbon atoms.
  • Medium chain fat can be absorbed without pancreatic lipase and bile, and has an advantage that the absorption rate is four times faster than long chain fat and does not become accumulated fat. It is also more polar than long chain fats and is well suited for solubilizing phosphatidylserine.
  • the phosphatidylserine liquid composition may further include one or more functional ingredients such as fish oil, saw palmetto fruit extract, vitamins, fragrances including DHA or EPA.
  • Powdered or granular phosphatidylserine and edible oils used in the present invention may be used by removing all organic solvents by concentration under reduced pressure after dissolving in an organic solvent.
  • the organic solvent may be used alone or in combination of two or more common organic solvents, such as ethanol, propanol, hexane, cyclohexane.
  • Phosphatidylserine may be included in 10 to 50% by weight based on the total weight of the composition, but is not limited thereto.
  • Starch is used as the outer wall material of the phosphatidylserine powder capsule of the present invention.
  • the use of starch makes the film constituting the surface rough, but has a firm and flexible elasticity and impact resistance, and a formulation having excellent properties of protecting internal materials from oxidation is obtained.
  • Processed starch used as coating material can be used to heat unmodified starch, enzymes (e.g. hydrolases, isomerases, oxidases, branching enzymes, etc.), acids (e.g. succinic acid, succinic acid, acetic acid).
  • (Modified) starch obtained by treatment with hydrochloric acid, etc.) unlike ordinary starch, it has both hydrophilic and lipophilic properties, and has stable emulsion formation and excellent film forming ability.
  • the starch may be used at about 5 to 30 times (w / w), preferably 5 to 15 times (w / w) of water at 50 to 90 ° C, preferably at 80 ° C.
  • Preparation of the starch aqueous solution may be carried out before, after or simultaneously with the step of preparing the phosphatidylserine liquid composition described above.
  • the starch aqueous solution may contain maltodextrin, arabic gum, guar gum, xanthan gum, sodium casein, gelatin, lecithin, sodium alginate, etc. to suppress elution of phosphatidylserine incorporated into starch and at the same time improve dispersibility in aqueous solution. It may further comprise one or more excipients.
  • the first starch aqueous solution and the phosphatidylserine liquid composition prepared above are mixed and homogenized at 1,000 to 10,000 rpm for 5 to 10 minutes to obtain a first emulsion, and then a high pressure homogenizer, an ultrasonic emulsifier, etc. is used to increase the composition stability.
  • the first emulsion may be further homogenized for 10 to 30 minutes at a pressure condition of 200 to 300 bar to obtain a secondary emulsion.
  • phosphatidylserine may be mixed in an amount of 20 to 50 parts by weight based on 100 parts by weight of starch.
  • Phosphatidylserine may be 1 to 30% by weight, preferably 3 to 20% by weight, based on the total weight of the mixture. If the phosphatidylserine content is less than 1% by weight, it is difficult to maintain the concentration that exerts the bioactive function in the final product, and if it exceeds 30% by weight, the emulsion stability may be deteriorated.
  • Secondary emulsification may be carried out one or more times to stabilize the composition.
  • Heat may be generated during the first and second emulsification, but the homogenization temperature may be generally 30 to 60 ° C, preferably 50 ° C. If the homogenization temperature exceeds 60 °C, the rancidity of phosphatidylserine can be promoted, if less than 30 °C the coating material can be hardened to reduce the stability of the capsule. At about 50 ° C., the degree of gelatinization of the internal and coating materials can be kept uniform, and is particularly effective in suppressing the rancidity of phosphatidylserine.
  • At least one of the primary emulsion and the secondary emulsion is maltodextrin, arabic gum, guar gum, xanthan gum, casein sodium, gelatin, lecithin to inhibit elution of phosphatidylserine incorporated into starch and at the same time improve dispersibility in aqueous solution.
  • excipients such as sodium alginate.
  • secondary encapsulation may be performed with another coating to improve acid resistance, shelf life, transportability, and the ability to protect the internals from oxidation.
  • Coating materials used for secondary encapsulation include, but are not limited to, whey protein, cyclodextrin, maltodextrin, sodium casein, gelatin, starch, and the like.
  • phosphatidylserine may be microencapsulated and powdered at the same time as it is dried.
  • Continuous powder drying or fluidized bed drying may be used to powder the final product.
  • spray drying is performed by using a nozzle having a size of 1 to 5 mm at a temperature of 150 to 200 ° C. of a hot air blower, a temperature of 100 to 150 ° C. of a nozzle part, and a temperature of 40 to 100 ° C. of a cyclone part. It can be carried out by spraying.
  • the average particle diameter of the microcapsules obtained after drying may range from approximately 400 to 700 nm.
  • the microcapsules prepared by the above method can improve dispersibility, solubility and stability in aqueous solution of phosphatidylserine, prevent oxidation by oxygen in light or air, and maintain the intrinsic function of phosphatidylserine for a long time. It is possible to improve the preservation and transport properties, and furthermore, to contain phosphatidylserine at high concentrations, thereby increasing the ability to be used as medicines, foods (health functional foods), etc., which are mainly composed of phosphatidylserine.
  • the present invention therefore also provides a microcapsule formulation comprising phosphatidylserine suitable for food or pharmaceutical use, which may be prepared by the methods described above.
  • phosphatidylserine suitable for food or pharmaceutical use, which may be prepared by the methods described above.
  • the content of phosphatidylserine may vary depending on the effective amount in the end use, but may be 1 to 25% by weight based on the total weight of the microcapsules.
  • phosphatidylserine powder PS40SW of Doosan Co., Ltd.
  • 60 g of soybean oil Welga Co., Ltd.
  • the mixture was stirred until completely clear and dried under reduced pressure to prepare a liquid composition containing 25% by weight of phosphatidylserine.
  • the processed starch substituted with 40 g of succinic acid was mixed with 540 g of sterile water, gelatinized at 80 ° C, and then cooled to 50 ° C.
  • An emulsion was prepared.
  • the primary emulsion was further homogenized by two passes of a 250 bar high pressure homogenizer to increase the stability of the composition. Then at 180 ° C Spray drying for 2 hours and powdered to prepare microcapsules (containing 10% by weight of phosphatidylserine) having an average particle diameter of 527 nm.
  • the average particle diameter of the microcapsules is a value measured after diluting the aqueous capsule solution with sterile tertiary distilled water using Zeta PALS.
  • the processed starch substituted with 60 g of succinic acid was mixed with 520 g of sterile water, gelatinized at 80 ° C, and then cooled to 50 ° C.
  • the primary emulsion was further homogenized by two passes of a 250 bar high pressure homogenizer to increase the stability of the composition. After spray drying for 2 hours at 180 °C to powder to prepare a microcapsules (containing 6% by weight of phosphatidylserine) with an average particle diameter of 542 nm.
  • the processed starch substituted with 60 g of succinic acid was mixed with 520 g of an aqueous solution added with 3% by weight of arabic gum, gelatinized at 80 ° C, and then cooled to 50 ° C.
  • the primary emulsion was further homogenized by two passes of a 250 bar high pressure homogenizer to increase the stability of the composition. After spray drying at 180 ° C for 2 hours to form a microcapsules (containing 6% by weight of phosphatidylserine) with an average particle diameter of 487 nm.
  • the processed starch substituted with 60 g of succinic acid was mixed with 520 g of an aqueous solution to which 1 wt% xanthan gum was added, gelatinized at 80 ° C, and then cooled to 50 ° C.
  • the primary emulsion was further homogenized by two passes of a 250 bar high pressure homogenizer to increase the stability of the composition. After spray drying for 2 hours at 180 °C to powder to prepare a microcapsules (containing 6% by weight of phosphatidylserine) of an average particle diameter of 475 nm.
  • the processed starch substituted with 40 g of succinic acid was mixed with 520 g of sterile water, gelatinized at 80 ° C, and then cooled to 50 ° C.
  • Example 1 Example 2
  • Example 3 Example 4
  • Comparative Example 1 Comparative Example 2 0 days ⁇ ⁇ ⁇ ⁇ ⁇ X 30 days ⁇ ⁇ ⁇ ⁇ ⁇ X X 60 days ⁇ ⁇ ⁇ ⁇ ⁇ X X 90 days ⁇ ⁇ ⁇ ⁇ ⁇ X X
  • the phosphatidylserine-containing microcapsules prepared according to the method of the present invention can be seen that the water dispersibility and stability is very good because it is maintained at 4 °C for more than 3 months without precipitation and layer separation. . It can also be seen that microcapsule formulations in a very stable form are obtained for formulations which have been added with excipients or using additional coating materials other than starch.

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Biochemistry (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Medicinal Preparation (AREA)
  • Manufacturing Of Micro-Capsules (AREA)
PCT/KR2012/003504 2011-05-04 2012-05-04 포스파티딜세린의 마이크로캡슐화 방법 WO2012150839A2 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201280033216.7A CN103635181A (zh) 2011-05-04 2012-05-04 磷脂酰丝氨酸的微胶囊化方法

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Application Number Priority Date Filing Date Title
KR1020110042580A KR101763947B1 (ko) 2011-05-04 2011-05-04 포스파티딜세린의 마이크로캡슐화 방법
KR10-2011-0042580 2011-05-04

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WO2012150839A2 true WO2012150839A2 (ko) 2012-11-08
WO2012150839A3 WO2012150839A3 (ko) 2013-01-03

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CN110583801A (zh) * 2019-10-17 2019-12-20 东北农业大学 一种辛烯基琥珀酸酐改性淀粉与黄原胶复合制备粉末油脂的方法
CN111363767A (zh) * 2020-04-22 2020-07-03 山东惠仕莱生物科技有限公司 一种食品用磷脂酰丝氨酸的制备方法
CN116570018A (zh) * 2023-04-19 2023-08-11 广东萃怪香料有限公司 一种香料缓释纳米粒子及其制备方法和应用

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CN103892281B (zh) * 2014-04-11 2016-04-06 内蒙古伊利实业集团股份有限公司 含磷脂酰丝氨酸的营养组合物及其制备方法与应用
CN109222109A (zh) * 2017-12-15 2019-01-18 理星（天津）生物科技有限公司 一种磷脂酰丝氨酸微丸及其制备方法和应用
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CN110368362B (zh) * 2019-08-01 2022-10-04 聊城大学 一种磷脂酰丝氨酸乳剂的制备方法
CN110692893A (zh) * 2019-11-12 2020-01-17 南通厚元生物科技有限公司 一种含有磷脂酰丝氨酸和ω-3脂肪酸的固体饮料制备方法
CN111418846A (zh) * 2020-04-27 2020-07-17 南通厚元生物科技有限公司 含工业大麻蛋白和磷脂酰丝氨酸的微胶囊粉末及其制备方法

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WO1991011178A1 (de) * 1990-01-26 1991-08-08 Fluntera Ag Einkapselung von wirkstoffen mittels stärke
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110583801A (zh) * 2019-10-17 2019-12-20 东北农业大学 一种辛烯基琥珀酸酐改性淀粉与黄原胶复合制备粉末油脂的方法
CN111363767A (zh) * 2020-04-22 2020-07-03 山东惠仕莱生物科技有限公司 一种食品用磷脂酰丝氨酸的制备方法
CN116570018A (zh) * 2023-04-19 2023-08-11 广东萃怪香料有限公司 一种香料缓释纳米粒子及其制备方法和应用
CN116570018B (zh) * 2023-04-19 2024-01-02 广东萃怪香料有限公司 一种香料缓释纳米粒子及其制备方法和应用

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