WO2024090652A1 - Chardon marie soluble dans l'eau et procédé de préparation de celui-ci - Google Patents

Chardon marie soluble dans l'eau et procédé de préparation de celui-ci Download PDF

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WO2024090652A1
WO2024090652A1 PCT/KR2022/018444 KR2022018444W WO2024090652A1 WO 2024090652 A1 WO2024090652 A1 WO 2024090652A1 KR 2022018444 W KR2022018444 W KR 2022018444W WO 2024090652 A1 WO2024090652 A1 WO 2024090652A1
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milk thistle
water
soluble
soluble milk
silymarin
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PCT/KR2022/018444
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English (en)
Korean (ko)
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김종예
김인호
김한식
남희수
남경수
김다희
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주식회사 보고신약
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Priority claimed from KR1020220155494A external-priority patent/KR20240058726A/ko
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Publication of WO2024090652A1 publication Critical patent/WO2024090652A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives

Definitions

  • the present invention relates to water-soluble milk thistle and a method for producing the same. More specifically, a method for producing water-soluble milk thistle that simplifies the production process and increases the recovery rate to produce a high content of water-soluble milk thistle. , relates to water-soluble milk thistle prepared by the above method.
  • Milk thistle ( Silybum marianum (L.) Gaerth) is a perennial plant belonging to the Asteraceae family and is a type of Western thistle that is mainly native to the Mediterranean, also known as St. Mary's, artichoke, and white thistle. Milk thistle seeds are known to contain a flavonoid called silymarin.
  • Silymarin is a type of polyphenolic flavonoid and consists of the main active ingredient silibin and isomers such as isosilybin, dihydrosilybin, silydianin, and silychristin. It is done.
  • Silimari is a powerful antioxidant, and is known to protect liver cells by preventing destruction of cell membranes by binding to the receptors of toxic substances and silinmarin, and is known to have the benefit of liver regeneration through increased protein synthesis, treating liver diseases such as chronic hepatitis and cirrhosis. It is used as an adjuvant therapy. It is also known to be effective in relieving hangovers by removing gallstones and urinary stones, inhibiting Cytochrome P450, and increasing Phase II, and studies have shown that it can be used to treat and prevent adult diseases, regulate immunity, and treat rheumatoid arthritis.
  • milk thistle has been used as a folk remedy to improve liver, kidney, gall, and bladder problems, and has also been consumed as food.
  • Milk thistle extract is included in the health functional food functional raw material items that help improve the liver notified by the Ministry of Food and Drug Safety, and as it was converted to a notified health functional food raw material in 2012, demand has increased and there are currently about 83 items. It is registered with the Ministry of Food and Drug Safety and is commercially available.
  • silymarin The time for silymarin to reach the highest concentration in the blood is known to be 1.7-2.2 hours, the average remaining time in the body is about 5.5 hours, and the elimination half-life is about 4 hours. Only about 1-2% of silymarin is excreted through urine and the rest through bile. On the other hand, silymarin is a hydrophobic substance that does not dissolve well in water, so it aggregates and forms lumps the moment it comes into contact with water, so it is not suitable for beverage production. After oral administration, the absorption rate in the body is very low, and only about 20-40% is utilized in the body. .
  • Korean Patent Publication No. 10-1655396 Water-soluble milk thistle extract and method for producing the same contains milk thistle dissolved in ethanol with a silymarin content of 30 to 70% (w/w). It is a water-soluble milk thistle extract that is converted to an aqueous solution by mixing 0.5 ⁇ 5.5 : 4.5 ⁇ 9.5 (v:v) of cyclodextrin solution and concentration and removal of ethanol.
  • Patent Document 1 Korean Patent Publication No. 10-1655396
  • Milk thistle has been used in medicine for a long time due to the various effects mentioned above, and its usefulness is expected to increase further as it becomes available as a health functional food.
  • milk thistle is almost insoluble in water and alcohol, and it is known to have a low absorption rate in the body even when administered orally, so it has a very low versatility.
  • the main purpose of the present invention is to simplify the manufacturing process, increase the solubility of milk thistle, and provide a method for producing heat-stable water-soluble milk thistle.
  • Another object of the present invention is to provide water-soluble milk thistle produced using the method for producing water-soluble milk thistle.
  • Another object of the present invention is to provide a health functional food containing the water-soluble milk thistle as an active ingredient.
  • the present invention includes the steps of (a) adding insoluble milk thistle powder to an organic acid solution and dissolving it; (b) recovering the sediment of the organic acid solution in which the milk thistle powder is dissolved; (c) adding and mixing an emulsifier to the recovered sediment and then cooling to emulsify; and (d) adding a dispersing and stabilizing agent to the emulsified precipitate and then stirring.
  • the organic acid may be one or more selected from the group consisting of citric acid, malic acid, tartaric acid, and lactic acid.
  • the concentration of the organic acid solution is 2 to 5% (w/w), and 30 to 40 weight of the milk thistle powder is used based on 100 parts by weight of the organic acid solution. Wealth can be added.
  • the emulsifier may be glycerin.
  • step (c) 1 to 7% (w/w) of an emulsifier is added relative to the recovered sediment, mixed at 300 to 500 rpm for 0.5 to 2 hours, and then 5 to 10 times. It can be emulsified by cooling at °C for 0.5 to 2 hours.
  • the dispersing and stabilizing agent may be one or more selected from the group consisting of soy lecithin, alginic acid, and sodium alginate.
  • step (d) involves adding 1 to 2% (w/w) of a dispersing and stabilizing agent based on the weight of the emulsified sediment, followed by stirring at 400 to 500 rpm for 20 to 40 minutes. can do.
  • step (d) 0.5 to 1% (w/w) of ethanol or fermented alcohol is added to the sampled result of step (d) to produce silymarin produced by a silymarin reaction.
  • a step of checking with an indicator substance may be further included.
  • the present invention provides water-soluble milk thistle prepared by the above method and containing 55 to 80 mg/g of silymarin.
  • the relative bioavailability (F rel ) of silymarin in the milk thistle may be 1.47 to 1.49.
  • the present invention provides a health functional food containing the water-soluble milk thistle.
  • Water-soluble milk thistle produced by the method of the present invention simplifies the manufacturing process, has a content of 2 to 3% by weight, is heat stable, and can increase solubility, so it can be provided as a health functional food.
  • Figure 1 shows a manufacturing process diagram of water-soluble milk thistle according to an embodiment of the present invention.
  • Figure 2 shows the solubilization stability of water-soluble milk thistle according to an embodiment of the present invention.
  • Figure 3 shows the refrigerated stability of water-soluble milk thistle according to an embodiment of the present invention.
  • Figure 4 shows the solubility of water-soluble milk thistle according to an embodiment of the present invention.
  • Figure 5 shows the pH stability of water-soluble milk thistle according to an embodiment of the present invention.
  • Figures 6a to 6c show the thermal stability of water-soluble milk thistle according to an embodiment of the present invention, with Figure 6a showing water-soluble milk thistle according to heating time at 60°C, Figure 6b at 80°C, and Figure 6c at 100°C. This shows the thermal stability of the slurry.
  • Figure 7 shows the UV stability of water-soluble milk thistle according to an embodiment of the present invention.
  • Figure 8 is a test report testing the silymarin content of water-soluble milk thistle according to an embodiment of the present invention.
  • Figure 9 shows the pharmacokinetic profile of water-soluble milk thistle in rats according to an embodiment of the present invention.
  • the first embodiment of the present invention includes the steps of (a) adding insoluble milk thistle powder to an organic acid solution and dissolving it; (b) recovering the sediment of the organic acid solution in which the milk thistle powder is dissolved; (c) adding and mixing an emulsifier to the recovered sediment and then cooling to emulsify; and (d) adding a dispersing and stabilizing agent to the emulsified precipitate and then stirring.
  • the organic acid may be one or more selected from the group consisting of citric acid, malic acid, tartaric acid, and lactic acid.
  • Citric acid is preferred in terms of price, but is not limited thereto.
  • the concentration of the organic acid solution in step (a), may be 2-5% (w/w), preferably 2.5-3% (w/w), but is limited thereto. That is not the case. If the concentration of the organic acid solution is less than 2% (w/w), there is a problem in that the insoluble milk thistle does not dissolve well, and if the concentration of the organic acid solution exceeds 5% (w/w), subsequent fermentation There is a problem in that the amount of organic acid remaining in the silymarin reaction step using alcohol or ethanol affects the pH.
  • the organic acid solution For 100 parts by weight of the organic acid solution, 30 to 40 parts by weight, preferably 33 to 35 parts by weight, of the milk thistle powder may be added, but is not limited thereto.
  • the step (b) is a step of recovering the sediment of the organic acid solution in which the milk thistle powder was dissolved.
  • the sediment can be recovered by removing the water (purified water) that is the upper layer of the organic acid solution in which the milk thistle powder was dissolved. .
  • step (c) it is preferable to use glycerin as the emulsifier, but it is not limited thereto.
  • polysorbate 80 it is not preferable because there is a problem of generating an off-flavor.
  • step (c) 1 to 7% (w/w), preferably 3 to 5% (w/w) of emulsifier is added compared to the recovered sediment, and the mixture is operated at 300 to 500 rpm, preferably 350 to 450 rpm. After mixing for 0.5 to 2 hours, preferably 0.5 to 1 hour, it can be emulsified by cooling at 10°C or lower, preferably 5 to 10°C, for 0.5 to 2 hours, preferably 0.5 to 1 hour.
  • the dispersing and stabilizing agent may be one or more selected from the group consisting of soy lecithin, alginic acid, and sodium alginate, but is not limited thereto.
  • step (d) 1 to 2% (w/w), preferably 1 to 1.5% (w/w) of the dispersing and stabilizing agent is added relative to the weight of the emulsified sediment, and then the mixture is stirred at 300 to 500 rpm for 20 Allow to stir for ⁇ 40 minutes. If it is outside the above range, there is a problem of severe foaming occurring, so care must be taken not to exceed the above range.
  • soy lecithin As the dispersing and stabilizing agent, it is necessary to pre-dissolve it in lukewarm water of 20-30°C. In cold water or hot water outside the above temperature, when soy lecithin is added, moisture absorption begins immediately, making it difficult to dissolve. There is a problem that does not work.
  • step (d) 0.5 to 1% (w/w) of ethanol or fermented alcohol, preferably 0.5 to 1% (w/w), is added to the sampled result of step (d). It may further include the step of adding % (w/w) of fermented alcohol to confirm silymarin produced by the silymarin reaction as an indicator substance.
  • Organic solvents such as hexane and ethyl acetate can be used during the silymarin reaction, but this is undesirable in terms of productivity or economic efficiency because a separate process is required to remove all organic solvents after extraction and compression.
  • fermented alcohol is consumed It has the advantage of being a raw material that can be used.
  • the fermented alcohol may be used at a concentration of 90% (w/w) or more, preferably 95% (w/w) or more, but is not limited thereto.
  • the silymarin reaction is preferably performed at 300 to 500 rpm, preferably 400 rpm, at room temperature of 60°C or less, preferably 20 to 30°C, for 0.5 to 1.5 hours, preferably 1 hour. If it is less than the above range, the silymarin reaction does not occur easily, and if it exceeds the above range, the adsorption reaction phenomenon is accelerated, that is, it has a shape like elastic rubber clay, but when the alcohol and moisture are removed, it hardens like a stone. there is.
  • the second embodiment of the present invention relates to water-soluble milk thistle prepared by the above method.
  • the water-soluble milk thistle has the advantage of being a health functional material that can be provided as an active ingredient in health functional foods because heat stability and pH stability are improved, solubility is increased, and sensory properties such as taste are improved.
  • the water-soluble milk thistle of the present invention may contain 55 to 80 mg/g (5.5 to 8.0%), preferably 65 to 70 mg/g (6.5 to 7.0%) of silymarin, but is not limited thereto.
  • the relative bioavailability (F rel ) of silymarin in the milk thistle of the present invention may be 1.47 to 1.49, preferably 1.48, but is not limited thereto.
  • the third embodiment of the present invention relates to a health functional food containing the water-soluble milk thistle.
  • the “health functional food” refers to food manufactured and processed in the form of tablets, capsules, powders, granules, liquids, and pills using raw materials or ingredients with functional properties useful to the human body.
  • functionality means controlling nutrients for the structure and function of the human body or obtaining useful effects for health purposes, such as physiological effects.
  • the health functional food of the present invention can be manufactured by methods commonly used in the field of technology, and can be manufactured by adding raw materials and components commonly added in the field of technology.
  • the formulation of the health functional food can also be manufactured without limitation as long as it is a formulation recognized as a health functional food.
  • the health functional food composition of the present invention can be manufactured in various dosage forms, and unlike general drugs, it has the advantage of being made from food and having no side effects that may occur during long-term use of the drug.
  • insoluble milk thistle powder 100 g was added to 300 g of citric acid solution at a 2% (w/w) concentration to dissolve the insoluble milk thistle powder. After the citric acid solution in which the milk thistle powder was dissolved was left for 1 hour, the supernatant was removed and the precipitate was recovered.
  • emulsifier As an emulsifier, 4% (w/w) glycerin was added to the recovered sediment, mixed at 400 rpm for 1 hour, and then cooled at 7°C for 1 hour to emulsify. After adding 1.5% (w/w) of soy lecithin based on the weight of the emulsified sediment as a dispersing and stabilizing agent, the mixture was stirred at 400 rpm for 30 minutes to obtain water-soluble milk thistle.
  • the water-soluble milk thistle obtained above was freeze-dried to obtain water-soluble milk thistle powder.
  • insoluble milk thistle powder 100 g was added to 300 g of lactic acid solution at a 3% (w/w) concentration to dissolve the insoluble milk thistle powder. After the lactic acid solution in which the milk thistle powder was dissolved was left for 1 hour, the supernatant was removed and the sediment was recovered.
  • emulsifier As an emulsifier, 2% (w/w) glycerin was added to the recovered sediment, mixed at 400 rpm for 1 hour, and then cooled at 5°C for 1 hour to emulsify. After adding 1% (w/w) of sodium alginate based on the weight of the emulsified precipitate as a dispersing and stabilizing agent, the mixture was stirred at 400 rpm for 30 minutes to obtain water-soluble milk thistle.
  • the water-soluble milk thistle obtained above was freeze-dried to obtain water-soluble milk thistle powder.
  • insoluble milk thistle powder 100 g was added to 300 g of tartaric acid solution at a concentration of 4% (w/w) to dissolve the insoluble milk thistle powder. After the tartaric acid solution in which the milk thistle powder was dissolved was left for 1 hour, the supernatant was removed and the precipitate was recovered.
  • emulsifier As an emulsifier, 5% (w/w) glycerin was added to the recovered sediment, mixed at 400 rpm for 1 hour, and then cooled at 3°C for 1 hour to emulsify. After adding 1.5% (w/w) of alginic acid based on the weight of the emulsified precipitate as a dispersing and stabilizing agent, the mixture was stirred at 400 rpm for 30 minutes to obtain water-soluble milk thistle.
  • the water-soluble milk thistle obtained above was freeze-dried to obtain water-soluble milk thistle powder.
  • insoluble milk thistle powder 100 g was added to 300 g of malic acid solution at a 5% (w/w) concentration to dissolve the insoluble milk thistle powder. After the malic acid solution in which the milk thistle powder was dissolved was left for 1 hour, the supernatant was removed and the precipitate was recovered.
  • emulsifier As an emulsifier, 3% (w/w) glycerin was added to the recovered sediment, mixed at 400 rpm for 1 hour, and then cooled at 5°C for 1 hour to emulsify. After adding 1.5% (w/w) of soy lecithin based on the weight of the emulsified sediment as a dispersing and stabilizing agent, the mixture was stirred at 400 rpm for 30 minutes to obtain water-soluble milk thistle.
  • the water-soluble milk thistle obtained above was freeze-dried to obtain water-soluble milk thistle powder.
  • the water-soluble milk thistle powder was dispersed in distilled water in amounts of 2 mg/mL, 10 mg/mL, and 20 mg/mL, respectively, and then incubated at 100°C for 15 minutes. The solubilized form was confirmed by heating through photographs.
  • the water-soluble milk thistle powder prepared in Example 1 was dispersed in distilled water at amounts of 2 mg/mL, 10 mg/mL, and 20 mg/mL, respectively.
  • the product was heat treated at 100 degrees for 15 minutes using a water bath, left in the refrigerator at 4°C, and refrigeration stability was confirmed through photographs.
  • the water-soluble milk thistle powder prepared in Example 1 was dispersed in distilled water at amounts of 2 mg/mL, 10 mg/mL, 20 mg/mL, and 40 mg/mL, respectively, and then filtered. After heat treatment at 100 degrees for 15 minutes using a water bath, it was cooled at room temperature for 20 minutes and the change in content was analyzed by measuring absorbance at 288 nm.
  • the water-soluble milk thistle powder prepared in Example 1 was dissolved in an amount of 339 mg/mL in 25% glycerin adjusted by pH (3, 5, 7, 9), and then reacted at 37°C for 30 minutes using a water bath. The centrifuged supernatant was diluted in ethanol and absorbance was measured at 288 nm to analyze changes in content.
  • the water-soluble milk thistle powder prepared in Example 1 was dissolved at an amount of 339 mg/mL in 25% glycerin adjusted to pH 7.4, and then washed by temperature (60°C, 80°C, 100°C) and time (30 min) using a water bath. , 60 min, 90 min), the centrifuged supernatant was diluted in methanol and the absorbance was measured at 288 nm to analyze the change in content.
  • Example 2 0.2 g of the water-soluble milk thistle powder prepared in Example 1 was dissolved in 1.8 mL of an aqueous solution of distilled water and glycerin in a 3:1 ratio, and then exposed to UV (365 nm) at different times (1 h, 3 h, 6 h, 12 h). , 24 h). After diluting the UV-exposed water-soluble milk thistle solution in methanol, the absorbance was measured to analyze the change in content.
  • KRIBB-AEC-20309 Eight-week-old male SD rats were used, and the animals were maintained in a temperature-controlled environment with a 12-hour light/12-hour dark cycle. All protocols for animal experiments were approved by the KRIBB Animal Experiment Ethics Committee (KRIBB-AEC-20309).
  • mice were administered intravenously or orally the test compound dissolved in the appropriate vehicle. Blood samples were collected into lithium heparinized tubes via the saphenous vein and at indicated times (i.e., 0.083, 0.167, 0.25, 0.5, 1, 1.5, 2, 4, and 6 hours). Then, plasma samples were obtained by centrifugation.
  • rat plasma samples 50 ⁇ L of rat plasma samples were subjected to protein precipitation with 150 ⁇ L ACN containing internal standard (500 ng/mL 4-MUF). The mixture was vortexed and centrifuged, and the supernatant was collected in a new vial.
  • the final sample was analyzed using an LC-MS/MS system.
  • the bioavailability of silymarin was analyzed after oral administration of silymarin or milk thistle to rats. Plasma concentrations were observed for 6 hours and 1 hour after administration of silymarin and milk thistle, respectively, and bioavailability was calculated.
  • milk thistle contains 6.742% of silymarin.
  • Figure 9 shows a pharmacokinetic graph. Additionally, Table 2 below shows pharmacokinetic parameters.
  • the powder was prepared by mixing the raw materials shown below according to a method commonly performed in the art.
  • 2 g of milk thistle obtained in Examples 1 to 4 2 g of complex probiotic (1 ⁇ 10 9 CFU/g), 5 g of lactose, and 1 g of talc are mixed and filled into an airtight bag to prepare a powder.
  • the tablets were prepared by mixing 250 mg of milk thistle, 150 mg of corn starch, 100 mg of lactose, and 20 mg of magnesium stearate obtained in Examples 1 to 4 according to a method commonly performed in the art, followed by a conventional tablet manufacturing method. Tablets were prepared by compression according to the following.
  • Capsules were prepared by mixing 50 mg of milk thistle, 3 mg of crystalline cellulose, 14.8 mg of lactose, and 0.2 mg of magnesium stearate obtained in Examples 1 to 4 according to a method commonly performed in the art. Capsules were prepared by mixing them and filling them into gelatin capsules.
  • the mixed powder was prepared by using 5 g of milk thistle obtained in Examples 1 to 4 and an appropriate amount of the vitamin mixture (70 ⁇ g of vitamin A acetate, 1.0 mg of vitamin E, 0.13 mg of vitamin B1, vitamin B2) according to a method commonly performed in the art.
  • vitamin B6 0.5 mg, vitamin B12 0.2 ⁇ g, vitamin C 10 mg, biotin 10 ⁇ g), nicotinic acid amide 1.7 mg, folic acid 50 ⁇ g, calcium pantothenate 0.5 mg, mineral mixture (ferrous sulfate 1.75 mg, zinc oxide) 0.82 mg, magnesium carbonate 25.3 mg, potassium phosphate monobasic, 15 mg, calcium phosphate dibasic 55 mg, potassium citrate 90 mg, calcium carbonate 100 mg, magnesium chloride 24.8 mg) were mixed according to the usual health functional food manufacturing method. , a powder was prepared.
  • the beverage was prepared by mixing the raw materials shown below according to a method commonly performed in the art. 522 mg of honey, 5 mg of thioctosanamide, 10 mg of nicotinic acid amide, 3 mg of sodium riboflavin hydrochloride, 2 mg of pyridoxine hydrochloride, 30 mg of inositol, 50 mg of ortic acid, 1 g of milk thistle obtained in Examples 1 to 4, 200 mL of water was mixed using a homogenizer.
  • Raw materials include 1.5% by weight of milk thistle, 0.5% by weight of citric acid, tartaric acid or malic acid, 2% by weight of grain syrup, 20% by weight of glutinous rice paste, 15% by weight of coix radish, 15% by weight of brown rice powder, 43.8% by weight of purified water, and 0.5% by weight of vitamin C. %, and may include 1.5% by weight of polypropylene glycol and 0.2% by weight of gum arabic.
  • the above ring was aged at 3°C for 18 hours to prepare the ring.
  • the above production example was prepared by dosage form according to a conventional method, but it can also be used to produce a health functional food composition.
  • the composition ratio of the above vitamin and mineral mixture is generally a mixture of ingredients suitable for health functional foods in a preferred production example, but the mixing ratio may be modified arbitrarily.

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Abstract

La présente invention concerne un procédé de préparation de chardon Marie soluble dans l'eau, comprenant les étapes consistant à : (a) ajouter et dissoudre une poudre de chardon Marie insoluble dans une solution d'acide organique ; (b) récupérer un sédiment de la solution d'acide organique dans laquelle la poudre de chardon Marie a été dissoute ; (c) ajouter et mélanger un émulsifiant au sédiment récupéré, puis refroidir et émulsifier ; et (d) ajouter un agent dispersant et stabilisant au sédiment émulsifié, puis agiter. Selon la présente invention, il est possible de fabriquer une grande quantité de chardon Marie soluble dans l'eau en simplifiant le processus de préparation tout en augmentant le taux de récupération.
PCT/KR2022/018444 2022-10-25 2022-11-22 Chardon marie soluble dans l'eau et procédé de préparation de celui-ci WO2024090652A1 (fr)

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KR20220138503 2022-10-25
KR10-2022-0138503 2022-10-25
KR10-2022-0155494 2022-11-18
KR1020220155494A KR20240058726A (ko) 2022-10-25 2022-11-18 수용성 밀크씨슬 및 그의 제조방법

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Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20150102539A (ko) * 2014-02-28 2015-09-07 주식회사 바이오랜드 수용성 은행잎 추출물 및 이의 제조방법
KR101655396B1 (ko) * 2013-08-06 2016-09-08 에스케이바이오랜드 주식회사 수용성 밀크씨슬 추출물 및 이의 제조방법
KR20200049948A (ko) * 2018-10-29 2020-05-11 재단법인 유타 인하 디디에스 및 신의료기술개발 공동연구소 난용성 약물 서방출용 미립구의 제조방법
KR102205300B1 (ko) * 2020-09-17 2021-01-22 최승훈 불용성 또는 지용성 물질의 수용성 분산 가능한 하이브리드 현탁액의 제조공정

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101655396B1 (ko) * 2013-08-06 2016-09-08 에스케이바이오랜드 주식회사 수용성 밀크씨슬 추출물 및 이의 제조방법
KR20150102539A (ko) * 2014-02-28 2015-09-07 주식회사 바이오랜드 수용성 은행잎 추출물 및 이의 제조방법
KR20200049948A (ko) * 2018-10-29 2020-05-11 재단법인 유타 인하 디디에스 및 신의료기술개발 공동연구소 난용성 약물 서방출용 미립구의 제조방법
KR102205300B1 (ko) * 2020-09-17 2021-01-22 최승훈 불용성 또는 지용성 물질의 수용성 분산 가능한 하이브리드 현탁액의 제조공정

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHULEEGONE SORNSUVIT: "The Bioavailability and Pharmacokinetics of Silymarin SMEDDS Formulation Study in Healthy Thai Volunteers", EVIDENCE-BASED COMPLEMENTARY AND ALTERNATIVE MEDICINE, OXFORD UNIVERSITY PRESS, US, vol. 2018, 19 July 2018 (2018-07-19), US , pages 1 - 7, XP093162744, ISSN: 1741-427X, DOI: 10.1155/2018/1507834 *

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