WO2019098518A1 - Procédé de préparation d'un extrait de thé vert et extrait de thé vert ainsi préparé - Google Patents
Procédé de préparation d'un extrait de thé vert et extrait de thé vert ainsi préparé Download PDFInfo
- Publication number
- WO2019098518A1 WO2019098518A1 PCT/KR2018/010949 KR2018010949W WO2019098518A1 WO 2019098518 A1 WO2019098518 A1 WO 2019098518A1 KR 2018010949 W KR2018010949 W KR 2018010949W WO 2019098518 A1 WO2019098518 A1 WO 2019098518A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- green tea
- tea extract
- flavonol
- catechin
- weight
- Prior art date
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/10—Preparation or pretreatment of starting material
- A61K2236/19—Preparation or pretreatment of starting material involving fermentation using yeast, bacteria or both; enzymatic treatment
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
Definitions
- the present invention relates to a method for preparing green tea extract and a green tea extract prepared therefrom, and more particularly, to a method for preparing green tea extract having an increased amount of aspartic acid of gallic acid, non-gallate catechin and flavonol, .
- the tea is a sprout or leaf of Camellia sinensis O, Kuntze, which belongs to Camellia (Camellia) and contains 75-80% moisture and 20-25% solids.
- Solid contents include various organic compounds such as catechin, caffeine, amino acid, fiber, and pectin, lipid, resin, essential oil, vitamin, chlorophyll and the like.
- These ingredients form a unique taste and flavor of tea, and particularly have physiological activity effects such as inhibition of cholesterol elevation by catechins, inhibition of blood sugar increase, inhibition of arteriosclerosis, antioxidant activity, antibacterial activity, antiulcer activity and mutation inhibition Scientifically identified, the value of health beverages and functional foods is being reassessed.
- Green tea contains a large amount of antioxidant catechin, which is known to inhibit oxidation of low density lipoproteins in the human body and to inhibit cholesterol biosynthesis.
- Catechin is a generic term for catechins contained in green tea and catechins such as catechin (C), gallocatechin (GC), epicatechin (EC), epigallocatechin (EGC), epicatechin Epicatechallocatechin gallate (EGCG), epigallocatechin gallate is the most abundant, and its physiological activity is also known to be the highest.
- the flavor of the green tea extract is improved by controlling the ratio of non-gallate catechins containing no gallate, and an efficient production technique of green tea extract having a high gallate catechin ratio is known,
- the production method of green tea extract having a high gallate catechin ratio is not known.
- An object of the present invention is to provide a method for preparing green tea extract having an excellent anti-inflammatory effect by increasing the content of asparagine of gallic acid, non-galactic catechin and flavonol.
- the present invention is a.
- the enzyme is a complex enzyme comprising glucanase and arabinase.
- the present invention also provides a green tea extract prepared by the method of the present invention.
- the present invention also provides an anti-inflammatory cosmetic composition comprising the green tea extract of the present invention as an active ingredient.
- the present invention also provides a pharmaceutical composition for antiinflammation comprising the green tea extract of the present invention as an active ingredient.
- the present invention also provides an anti-inflammatory food composition containing the green tea extract of the present invention as an active ingredient.
- the method for preparing green tea extract of the present invention can increase the content of asparaginase of gallic acid, non-galactose catechin, and flavonol in green tea extract, and thus it can exhibit excellent anti-inflammatory effect.
- the green tea extract prepared by the method of the present invention is excellent in anti-inflammatory effect and can be used as an anti-inflammatory food composition, a cosmetic composition and a pharmaceutical composition.
- FIG. 1 is a graph showing the degree of mRNA expression of interleukin-1? (IL-1?) In cells treated with green tea extract prepared in Example 1 and Comparative Example 1.
- FIG. 1 is a graph showing the degree of mRNA expression of interleukin-1? (IL-1?) In cells treated with green tea extract prepared in Example 1 and Comparative Example 1.
- FIG. 2 is a graph showing the degree of mRNA expression of interleukin-6 (IL-6) in cells treated with green tea extract prepared in Example 1 and Comparative Example 1.
- FIG. 1 is a graph showing the degree of mRNA expression of interleukin-6 (IL-6) in cells treated with green tea extract prepared in Example 1 and Comparative Example 1.
- FIG. 1 is a graph showing the degree of mRNA expression of interleukin-6 (IL-6) in cells treated with green tea extract prepared in Example 1 and Comparative Example 1.
- FIG. 3 is a graph showing the degree of mRNA expression of cyclooxygenase-2 (COX-2) in cells treated with green tea extract prepared in Example 1 and Comparative Example 1.
- COX-2 cyclooxygenase-2
- FIG. 4 is a graph showing the content of catechins transferred into cells of the green tea extract prepared in Example 1.
- the present invention relates to a method for preparing an green tea extract having increased amounts of an aspartic acid of gallic acid, non-gallate catechin and flavonol,
- the enzyme is a complex enzyme including glucanase and arabinase.
- Gallic acid is a substance produced by hydrolysis of tannin. It is also used as a natural antioxidant and has been known to have such effects as obesity, antioxidant, hypertension, antibacterial, anti-inflammatory, blood glucose control, dyslipidemia and liver function .
- Non-gallate catechin is known to exhibit an anti-inflammatory effect in catechins, a type of flavonoid, which does not contain gallate.
- the antiserum of flavonol includes myricetin, quercetin and kaempferol.
- the myristate, quercetin and camphorol have excellent physiological activities such as antioxidant and anti-inflammation, and the absorption of catechin , And various applications have been made in various fields.
- the present invention provides a method for preparing green tea extract having an excellent anti-inflammatory effect by increasing the content of galactic acid, non-galactic catechin and an unglycoside of flavonol.
- the step (a) is a step of preparing green tea extract.
- the green tea may be one prepared by a conventional ordinary method, and the green tea may include at least one selected from the group consisting of green tea leaves, green tea leaves and green tea roots, have.
- the green tea extract is prepared using an extraction solvent, and the extraction solvent includes at least one selected from the group consisting of water, an alcohol having 1 to 5 carbon atoms and ethyl acetate, and is preferably composed of water and ethanol And at least one selected from the group consisting of
- the extraction temperature and the extraction time are not particularly limited, but the extraction temperature is preferably room temperature to 80 ° C, and the extraction time is 1 to 5 hours.
- the green tea extract of step (a) can be extracted by various methods using the above-mentioned extraction solvent.
- water of about 10 to 30 times the weight of the green tea is added and subjected to primary extraction at 100 ° C. for 4 hours, followed by secondary extraction for 4 hours in the same manner,
- the combined extracts are filtered, and the filtrate is concentrated with a concentrator.
- the concentrated extract is dried using a spray drying or vacuum freeze-freeze dryer.
- 70% ethanol extract is prepared by adding 70% ethanol of about 10 to 30 times the weight of green tea, extracting the mixture at 50 to 80 ° C for 30 minutes to 3 hours, filtering and concentrating the filtrate with a concentrator do.
- the concentrated extract is dried using a spray drying or vacuum freeze-freeze dryer.
- 95% ethanol extract is prepared by adding 95% ethanol of about 10 to 30 times the weight of green tea, allowing to stand at room temperature for 1 to 3 days (shaking operation is repeated every 6 hours) , And the same procedure is repeated twice to obtain an extract.
- the primary and secondary extracts are combined and filtered, and the filtrate is concentrated with a concentrator.
- the concentrated extract is dried using a spray drying or vacuum freeze-freeze dryer.
- the step (b) is a step of reacting the green tea extract and the enzyme produced in the step (a).
- the enzyme is a complex enzyme, and contains glucanase (enzyme code number 3.2.1.6) derived from a black mold ( Aspergillus niger ) and arabinanase (enzyme code number 3.2.1.99).
- the complex enzyme hydrolyzes the sugar, and by reacting the green tea extract with the complex enzyme, the flavonol glycoside contained in the green tea extract can be hydrolyzed to increase the content of the flavonol sugar.
- the content of non-galactose catechins and gallic acid can be increased by decalizing catechin compounds including gallate among the catechins contained in the green tea extract.
- the complex enzyme is contained in an amount of 3 to 30% by weight, preferably 5 to 15% by weight based on the total weight of the green tea extract prepared in the step (a).
- the complex enzyme comprises glucanase and arabinanase in a weight ratio of 1:10 to 10: 1, preferably in a weight ratio of 1: 5 to 5: 1.
- the sugar of the flavonol glycoside and gallate of the catechin can be simultaneously hydrolyzed by more than a predetermined amount during the enzyme reaction time.
- the green tea extract and the complex enzyme may be reacted at 20 to 60 ° C for 12 to 48 hours, preferably 30 to 50 ° C for 20 to 30 hours.
- the green tea extract and the complex enzyme can hydrolyze the sugar bound to flavonol and hydrolyze the gallate of catechin as the reaction is carried out at 20 to 60 ° C for 12 to 48 hours, And the content of non-galactose catechins can be increased. However, if the temperature range is exceeded, the complex enzyme may not function properly or may be inactivated. Also, the hydrolysis is sufficient within the reaction time to increase the content of flavonol aspartate and non-galactate catechin. However, after the reaction time, the catechins are oxidized to decrease the content of non-galactose catechin can do.
- the present invention may further include the step of inactivating the complex enzyme after reacting the green tea extract and the complex enzyme.
- the deactivation may be performed at 50 to 90 ° C for 10 minutes to 3 hours, preferably at 65 to 80 ° C for 30 minutes to 1 hour.
- the present invention may further include a step of removing sugar from the green tea extract prepared in the step (b).
- the method may further include a step of concentrating the green tea extract prepared in step (b) to prepare a concentrate, and then removing sugar from the concentrate.
- the green tea extract and the complex enzyme are reacted and then filtered to concentrate the filtrate with a concentrator to prepare a concentrate. At this time, it is preferable that the concentrated liquid contains about 10% by weight of solids.
- the method of removing the sugar is not particularly limited, in the present invention, it is preferable to separate and remove sugar using chromatography.
- the concentrate is adsorbed on a column equipped with an adsorption resin, and is washed with water 2 to 5 times the column volume and eluted with 2 to 5 times of the alcohol to obtain a green tea fraction.
- the fraction may be concentrated and lyophilized to prepare a green tea extract.
- the lyophilization method is not particularly limited, and may be performed by a method known in the art.
- the method for preparing green tea extract of the present invention can provide a method for preparing green tea extract having increased content of asparaginase of gallic acid, non-gallate catechin and flavonol. Among them, A manufacturing method can be provided.
- the non-galactose catechins refer to catechins not containing galate among catechins, and the non-gallyate catechins include gallocatechin, epigallocatechin, catechin, and epicatechin.
- the antiserum of flavonol includes prednisine, quercetin and camphorol.
- the green tea extract contains 2 to 10% by weight of gallic acid and 20 to 60% by weight of non-gallate catechin based on the total weight of the green tea extract, and contains 4 to 15 mg / g of irregular body of flavonol.
- non-galactose catechins are included in an amount of 70 to 100% by weight based on the total weight of the catechins.
- the glycans, the non-galactose catechins and the antigens of flavonols have anti-inflammatory effects. Therefore, in the present invention, the anti-inflammatory effect can be exhibited by increasing the content of galactic acid, non-galactose catechin, and flavonol in the green tea extract. In addition, since the irregular body of the flavonol promotes the absorption of catechins, the anti-inflammatory effect can be maximized by increasing the content of the irreversible body of flavonol.
- IL-1 interleukin-6
- COX-2 cyclooxygenase-2
- the present invention also relates to green tea extract prepared by the production method of the present invention.
- the green tea extract of the present invention has higher content of non-saccharides of gallic acid, non-galactic catechin and flavonol than that of the conventional green tea extract. Especially, the content of fly ash is higher than that of the conventional green tea extract.
- it contains 2 to 10% by weight of gallic acid and 20 to 60% by weight of non-gallate catechin based on the total weight of the green tea extract, and contains 4 to 15 mg / g of irregular body of flavonol.
- the green tea extract of the present invention inhibits the expression of at least one selected from the group consisting of interleukin-1? (IL-1?), Interleukin-6 (IL-6) and cyclooxygenase- Activity can be exhibited.
- IL-1? interleukin-1?
- IL-6 Interleukin-6
- cyclooxygenase- Activity can be exhibited.
- the green tea extract of the present invention can exhibit anti-inflammatory effect.
- the present invention also relates to an anti-inflammatory cosmetic composition containing the green tea extract of the present invention as an active ingredient.
- the cosmetic composition for anti-inflammation may be used as an active ingredient of functional cosmetics.
- the content of the green tea extract contained in the functional cosmetics is not particularly limited, and may be, for example, 0.01 to 99.9% by weight.
- the functional cosmetic of the present invention may further comprise cosmetics conventionally used as an active ingredient of the green tea extract.
- glycerol propylene glycol, 1,3-butylene glycol
- a surfactant such as sorbitol, polyethylene glycol, carboxyvinyl polymer, xanthan gum, carboxymethylcellulose, hydroxyethylcellulose, hydroxymethylcellulose, locust bean gum, allantoin, carrageenan, Aluminum stearate, zinc stearate, and witchhazel can be used.
- a surfactant such as sorbitol, polyethylene glycol, carboxyvinyl polymer, xanthan gum, carboxymethylcellulose, hydroxyethylcellulose, hydroxymethylcellulose, locust bean gum, allantoin, carrageenan, Aluminum stearate, zinc stearate, and witchhazel
- the ultraviolet absorber butylmethoxydibenzoylmethane, octylmethoxycinnamate,
- titanium dioxide As the pigment, there can be used titanium dioxide, particulate ditanium dioxide, ka Coloring pigments such as yellow iron oxide, black iron oxide, red iron oxide, ultramarine, chromium oxide and chromium hydroxide can be used as extender pigments such as rhenium, nylon powder, talc, sericite, mica and polymethyl methacrylate, Natural moisturizing substances such as chitin, chitosan, hyaluronic acid, hyaluronic acid, lactic acid, glycolic acid and the like can be used, and as a preservative, paraoxybenzoic acid esters, imida Zoledinyl urea, and the like. In addition, one or more of the above-described components may be blended according to the characteristics of the product.
- ka Coloring pigments such as yellow iron oxide, black iron oxide, red iron oxide, ultramarine, chromium oxide and chromium hydroxide can be used as extender pigments such as rhenium, nylon powder,
- the functional cosmetic composition may be prepared in any form conventionally produced in the art and may be in the form of, for example, a solution, suspension, emulsion, paste, gel, cream, lotion, powder, soap, surfactant- , A powder foundation, an emulsion foundation, a wax foundation, and a spray, but is not limited thereto. More specifically, it can be manufactured in the form of a soft lotion, a nutritional lotion, a nutritional cream, a massage cream, an essence, an eye cream, a cleansing cream, a cleansing foam, a cleansing water, a pack, a spray or a powder.
- the formulation is a paste, cream or gel
- an animal oil a vegetable oil, a wax, a paraffin, a starch, a tracer, a cellulose derivative, polyethylene glycol, silicone, bentonite, silica, talc or zinc oxide
- a carrier component a carrier component that may be used as a carrier component .
- lactose When the formulation is a powder or a spray, lactose, talc, silica, aluminum hydroxide, calcium silicate or polyamide powder may be used as a carrier component.
- talc In the case of a spray, in particular, chlorofluorohydrocarbons, propane / Or propellants such as dimethyl ether.
- a solvent, a solubilizing agent or an emulsifying agent is used as a carrier component, and examples thereof include water, ethanol, isopropanol, ethyl carbonate, ethyl acetate, benzyl alcohol, benzyl benzoate, - butyl glycol oil, glycerol aliphatic ester, polyethylene glycol or fatty acid esters of sorbitan.
- a carrier such as water, a liquid diluent such as ethanol or propylene glycol, a suspension such as ethoxylated isostearyl alcohol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan ester, a microcrystalline cellulose , Aluminum metahydroxide, bentonite, agar or tracant, etc. may be used.
- the carrier component is selected from the group consisting of aliphatic alcohol sulfate, aliphatic alcohol ether sulfate, sulfosuccinic acid monoester, isethionate, imidazolinium derivative, methyl taurate, sarcosinate, fatty acid amide ether sulfate , Alkylamido betaines, aliphatic alcohols, fatty acid glycerides, fatty acid diethanolamides, vegetable oils, lanolin derivatives, or ethoxylated glycerol fatty acid esters.
- the present invention also relates to a pharmaceutical composition for antiinflammation comprising the green tea extract of the present invention as an active ingredient.
- the green tea extract contains 0.1 to 50% by weight based on the total weight of the composition.
- the content is in the above range, it is not only suitable for exhibiting the intended effect of the present invention but also can satisfy both stability and safety of the composition and is preferable from the viewpoint of cost effectiveness.
- the pharmaceutical composition according to the present invention can be orally administered in the form of solid, semi-solid or liquid with addition of a compatible inorganic or organic carrier.
- a compatible inorganic or organic carrier examples include tablets, pills, soft and hard capsules, powders, fine granules, granules, solutions, emulsions, syrups and pellets.
- the pharmaceutical composition can be easily formulated according to a conventional method, and a surfactant, an excipient, a coloring agent, a spice, a preservative, a stabilizer, a buffer, a suspending agent or other commonly used adjuvant can be suitably used.
- the dosage of the active ingredient will vary depending on the age, sex, body weight and the disease or condition to be treated, the route of administration, or the judgment of the prescriber. Dosage determinations based on these factors are within the level of those skilled in the art and may be administered, for example, 100 to 1,000 mg, preferably 300 to 500 mg, in divided doses of 1 to 3 times per day, Are not intended to limit the scope of the present invention.
- the pharmaceutical composition may be administered as an individual therapeutic agent or in combination with another therapeutic agent, and may be administered sequentially or simultaneously with a conventional therapeutic agent. It is important to take into account all of the above factors and to administer the amount in which the maximum effect can be obtained in a minimal amount without adverse effect, and can be easily determined by those skilled in the art.
- the present invention also relates to an anti-inflammatory food composition
- an anti-inflammatory food composition comprising the green tea extract of the present invention as an active ingredient.
- the green tea extract contains 0.1 to 50% by weight based on the total weight of the composition.
- the content is in the above range, it is not only suitable for exhibiting the intended effect of the present invention but also can satisfy both stability and safety of the composition and is preferable from the viewpoint of cost effectiveness.
- the food composition according to the present invention may further comprise, in addition to the above-mentioned components, other ingredients effective for preventing, ameliorating or treating obesity at a level that does not inhibit the efficacy of the green tea extract.
- other ingredients effective for preventing, ameliorating or treating obesity at a level that does not inhibit the efficacy of the green tea extract.
- the food composition according to the present invention may be a health food, a functional food, and a food additive composition.
- the composition can be applied to various formulations such as tablets, pills, capsules, granules, drinks, caramels, diet bars, and tea bags through a conventional method including adding various kinds of excipients or additives.
- the compositions may be formulated without difficulty by those of ordinary skill in the art, in addition to the active ingredients, which are conventionally used in the art, and synergistic effects may occur when combined with other ingredients.
- the complex enzyme in which the green tea extract was mixed with glucanase and Arabinanase at a weight ratio of 1: 1 was added to the green tea extract in an amount of 10% by weight based on the total weight of the green tea extract and reacted at 40 ° C for 24 hours.
- the complex enzyme was deactivated for 1 hour. Thereafter, the filtrate was concentrated by using a filter cloth to remove ethanol, and the concentrate was concentrated to contain only 10% by weight of the solid content.
- the concentrate was adsorbed on a column equipped with an adsorption resin, washed with water 2 to 5 times the column volume, eluted with 2 to 5 times of the alcohol, and concentrated and lyophilized to obtain a green tea extract Respectively.
- Flavonol, myristate, quercetin and camelol were purchased from Sigma.
- the instrument was analyzed by HPLC (Waters Alliance 2695 system, Waters, USA) and the detection wavelengths were 275 nm (catechin) and 365 nm (flavonol).
- the column was analyzed by concentration gradient solvent composition method using 0.1% formic acid (FA) and acetonitrile (ACN) solvent using Agilent Poroshell SB C18 (150 x 4.6 mm, 2.7 ⁇ m) Respectively. All analytical solvents were HPLC grade reagents and data were processed using Waters' Empower 2 program.
- the green tea extract of Example 1 prepared using the complex enzyme exhibited a higher activity than the green tea extract of Comparative Example 1, which was prepared without using the complex enzyme, as compared with the green tea extract of Galactan, non-gallate catechin and flavonol And it was confirmed that the contents were all high.
- the gallic acid was about 98 times
- the non-galactic catechin was about 2.5 times
- the Flavonol anhydride was about 7.5 times.
- the green tea extract of Comparative Example 1 contained more gallate catechins than the non-gallate catechins, but the green tea extract of Example 1 showed that most of the catechins were non-gallate catechins.
- the green tea extract of the present invention prepared using the complex enzyme increases the content of asparagine of gallic acid, non-gallate catechin and flavonol.
- the RAW 264.7 mouse-derived macrophage cell line purchased from the American Type Culture Collection (ATCC) ), Interleukin-6 (IL-6), and cyclooxygenase-2 (COX-2)
- the RAW 264.7 cell line was cultured on a 6 well plate at a density of 1 ⁇ 10 6 / well.
- the green tea extract of Example 1 and Comparative Example 1 was pretreated for 2 hours at a concentration of 10 g / ml, and LPS (Lipopolysaccharide) 6 hrs to induce an inflammatory reaction.
- IL-1 ⁇ IL-1 ⁇
- IL-6 interleukin-6
- COX-2 cyclooxygenase
- FIGS. 1 to 3 show the result of treatment of RAW 264.7 macrophage cell line with unstimulated control, LPS as a positive control, and LPS and green tea extract of Example 1 and Comparative Example 1, respectively, 1 (IL-1?), Interleukin-6 (IL-6) and cyclooxygenase (COX-2).
- the green tea extract prepared in Comparative Example 1 inhibited the production of interleukin-1? (IL-1?), Interleukin-6 (IL-6) and cyclooxygenase (COX-2).
- the Flavonol of the flavonol was fractionated from the green tea extract.
- Flavonol fractions of flavonol were prepared by dissolving each of the green tea extracts of Example 1 in DMSO and methanol mixed solvent (1: 9, v / v) at a concentration of 20%. Thereafter, the filtrate was adsorbed on a column (35x250 mm, 10 mu m, C18), and a fraction of an unglycosylated flavonol obtained by using a concentration gradient of water and acetonitrile was concentrated and lyophilized.
- the green tea extract containing 35% of epicatechin was added to the human colon cancer cell line (HT-29).
- the experimental group was divided into three groups.
- quercetin was added as a positive control and blank fraction of flavonol of Example 1 was added to the test group in an amount of 100 ppm each for 1 hour Lt; / RTI > Then, the cells were washed with PBS, 500 ⁇ L of a mixed solution of 90% methanol and 10% DMSO was added and the cells were disrupted by sonication.
- the impurities were purified using a 0.45 ⁇ m PDVF filter, and the content of intracellular catechin Were measured.
- the green tea extract prepared by the production method of the present invention promotes absorption of intracellular catechin by increasing the content of the irregular body of flavonol.
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Abstract
La présente invention concerne un procédé de préparation d'un extrait de thé vert présentant une teneur accrue en acide gallique, en catéchine non gallate et en une forme aglycone d'un flavonol, et un extrait de thé vert ainsi préparé, ainsi qu'un produit cosmétique, une composition pharmaceutique et une composition alimentaire anti-inflammatoires en contenant.
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- 2017-11-14 KR KR1020170151218A patent/KR102394664B1/ko active IP Right Grant
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- 2018-09-18 WO PCT/KR2018/010949 patent/WO2019098518A1/fr active Application Filing
- 2018-09-18 CN CN201880086051.7A patent/CN111601582A/zh active Pending
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KR20190054542A (ko) | 2019-05-22 |
CN111601582A (zh) | 2020-08-28 |
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