Method for encapsulating and improving stability of active ingredient using micelles

Abstract

The present disclosure provides a micelle composition and a method of preparing the same, the micelle composition comprising: a saccharide surfactant; and a glycoside active ingredient encapsulated in the saccharide surfactant. Specifically, the composition according to the present invention can stably encapsulate a glycoside active ingredient by using a saccharide surfactant, thereby improving the skin absorption rate of the active ingredient. In addition, under the condition that citric acid, tannic acid or tocopherol is added into the composition, the packaging stability of the glycoside active ingredient in the micelle can be further improved.

Description

TECHNICAL FIELD

[0001] The present invention relates to a micelle composition capable of stably encapsulating glycoside active ingredients by containing a saccharide surfactant, and improving skin absorption. BACKGROUND

[0002] The existing method of simply improving the solubility of poorly soluble substances using a surfactant cannot be expected to enhance the pharmacological effects of active materials, and even if micelles are formed, there is a problem that the active materials encapsulated inside can be leaked. Therefore, high molecular block copolymer micelles are more used as carriers of active ingredients. First, high molecular block copolymer micelles exhibit a lower critical micelle concentration than low molecular weight surfactants, thereby having high stability. In addition, since the high molecular chain exhibits a low dissociation rate, it can continuously exert its function. Also, the method of encapsulating poorly soluble substances into micelles is simple, and is easily redispersed when redissolved, and does not require the addition of other additives at the time of administration.

[0003] However, high molecular micelles are prepared using high molecules obtained by synthesis, and thus are not suitable in terms of environmental, social, and corporate governance (ESG; Environmental Social Governance). Active materials of glycoside ingredients are widely present in plant systems, and thus environmentally friendly and safe carriers matching the same are required. In addition, although active materials of glycoside ingredients are poorly soluble in water, since they have a hydrophilic sugar in their structure, they have the disadvantage of having a large particle size when encapsulated into high molecular micelles, etc., which is not suitable for encapsulation into high molecular micelles.

[0004] Therefore, together with a raw material and a method that secure safety and sustainability, there is an urgent need to develop a carrier that encapsulates poorly soluble glycoside ingredients into water.

[0005]

Prior Art Documents

[0006]

Patent Documents

[0007] Korean Patent No. 2072439 SUMMARY

[0008] Technical Problem to be Solved

[0009] In one aspect, the present disclosure aims to provide a micelle composition including: a saccharide surfactant; and a glycoside active ingredient encapsulated in the saccharide surfactant.

[0010] In another aspect, the present disclosure aims to provide a method, which is a method of preparing the micelle composition, the method comprising: a step of hydrating a saccharide surfactant in water; and a step of dissolving a glycoside active ingredient in one or more alcohols selected from the group consisting of C1-C6 alcohols.

[0011] Solution to the problem

[0012] In one aspect, a micelle composition is provided, comprising: a saccharide surfactant; and a glycoside active ingredient encapsulated in the saccharide surfactant.

[0013] In one aspect, the saccharide surfactant can be a glucoside surfactant.

[0014] In one aspect, in the composition, the glucoside surfactant is one or more selected from the group consisting of decyl glucoside, lauryl glucoside, cocoyl glucoside, octyl / decyl glucoside, cetyl stearyl glucoside, arachinyl glucoside, and C12-20 alkyl glucoside.

[0015] In one aspect, the glycoside active ingredient can be a saponin glycoside.

[0016] In one aspect, the saponin glycoside can be one or more glycosides selected from the group consisting of ginsenoside, green tea saponin, red ginseng saponin, legume saponin, and camellia saponin.

[0017] In one aspect, the ginsenoside can include compound K.

[0018] In one aspect, the green tea saponin can include rogchaponin R12.

[0019] In one aspect, the saccharide surfactant can be contained in an amount of 0.001 to 50% by weight, relative to the total weight of the composition.

[0020] In one aspect, the glycoside active ingredient can be contained in an amount of 0.001 to 20% by weight, relative to the total weight of the composition.

[0021] In one aspect, the weight ratio of the saccharide surfactant : glycoside active ingredient can be 1-50:1.

[0022] In one aspect, the composition can further include a non-covalent crosslinker.

[0023] In one aspect, the non-covalent crosslinker can be citric acid or tannic acid.

[0024] In one aspect, the non-covalent cross-linking agent can be contained in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition.

[0025] In one aspect, the weight ratio of the saccharide surfactant : glycoside active ingredient : non-covalent cross-linking agent can be 1-50 : 1 : 0.002-0.2.

[0026] In one aspect, the average particle size of the micelles can be 5 to 200 nm.

[0027] In one aspect, at least 90% of the micelle particles included in the micelle composition can have a particle size of 5 to 200 nm.

[0028] In one aspect, the composition can further include a tocopherol.

[0029] In one aspect, the tocopherol can be contained in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition.

[0030] In one aspect, the weight ratio of the saccharide surfactant : glycoside active ingredient : tocopherol can be 1-50 : 1 : 0.006-0.6.

[0031] In one aspect, the composition can be used as a cosmetic material.

[0032] In another aspect, a method for preparing the micelle composition is provided, wherein the method includes the steps of hydrating a saccharide surfactant in water, and dissolving a glycoside active ingredient in one or more alcohols selected from the group consisting of C1-C6 alcohols.

[0033] In one aspect, the method can further include the step of mixing the solution hydrated in the water and the solution dissolved in the alcohol, and evaporating the alcohol.

[0034] Effects of the Invention

[0035] In one aspect, the composition of the present invention can allow the micelles formed in the composition to maintain a certain and stable size.

[0036] In one aspect, the composition of the present invention can be used as a transparent solubilizer.

[0037] In one aspect, the micelles of the composition of the present invention have excellent stability.

[0038] In one aspect, the composition of the present invention has high applicability as a carrier.

[0039] In one aspect, the composition of the present invention has excellent absorption capacity on the surface of the skin.

[0040] In one aspect, the composition of the present application encapsulates active ingredients of natural sources, and thus is highly safe even when applied to a living body.

[0041] In one aspect, the composition of the present application is environmentally friendly.

[0042] In one aspect, the composition of the present application has high encapsulation efficiency for poorly soluble glycoside active ingredients. BRIEF DESCRIPTION OF DRAWINGS

[0043] Figure 1 is a chemical structural formula of ginsenoside species that can be contained in ginsenoside purified from ginseng.

[0044] Figure 2 is a structural formula of a compound that can be contained in green tea saponin purified from green tea.

[0045] Figure 3 is a preparation result of a micelle composition containing ginsenoside purified from ginseng as an active ingredient according to one embodiment of the present disclosure.

[0046] Figure 4 is a preparation result of a micelle composition containing green tea saponin purified from green tea as an active ingredient according to one embodiment of the present disclosure.

[0047] Figure 5 is a chemical structural formula of curcumin methylene dioxy.

[0048] Figure 6 is a preparation result of a micelle composition of a comparative example containing curcumin methylene dioxy as an active ingredient according to one embodiment of the present disclosure.

[0049] Figure 7 is a compound K release curve measurement result of a micelle composition to which citric acid, tannic acid, or tocopherol is added according to one embodiment of the present disclosure.

[0050] Figure 8 is a skin absorption capacity evaluation result of a micelle composition according to one embodiment of the present disclosure.

[0051] Figure 9 is a result of analyzing the size distribution of nanoparticles in a micelle composition according to one embodiment of the present disclosure.

[0052] Figure 10 is a result of analyzing the morphology and size of particles in a micelle composition according to one embodiment of the present disclosure. DETAILED DESCRIPTION

[0053] The terms used in the present specification are based on the functions in the present application and are chosen as commonly used terms in the art as far as possible, but these terms can be changed according to the intention of those skilled in the art, precedents, or the appearance of new technology, etc. In addition, there are terms arbitrarily selected by the applicant in specific cases, and in this case, the meaning thereof is explained in detail in the description part of the related application. Therefore, the terms used in the present specification are not mere terms, but should be defined according to the meaning thereof and the overall content of the present application.

[0054] Unless otherwise defined, all terms used in the present specification including technical or scientific terms have the same meaning as those generally understood by those skilled in the art to which the present application pertains. The terms generally understood should be interpreted as having the same meaning as the meaning of the related art in the context, and should not be interpreted as an idealized or overly formalized meaning unless explicitly defined in the present application.

[0055] Numerical ranges include the numbers defined in the present application. All maximum numerical limitations given in the present specification are treated as if a lower numerical limitation was explicitly written down, including all lower numerical limitations. All minimum numerical limitations given in the present specification are treated as if a higher numerical limitation was explicitly written down, including all higher numerical limitations. All numerical limitations given in the present specification are treated as if a narrower numerical range was explicitly written down, including all better numerical ranges within the broader numerical range.

[0056] As used in the present specification, the terms "comprise", "have", "contain" are general or open-ended, and do not exclude elements or method steps not further mentioned. The term "or a combination thereof" used in the present specification means all permutations and combinations of the items listed before the term. For example, "A, B, C, or a combination thereof" is intended to include A, B, C, AB, AC, BC, or ABC, as well as at least one of BA, CA, CB, CBA, BCA, ACB, BAC, or CAB, when order is important in a particular context. With this example, combinations such as BB, AAA, MB, BBC, AAABCCCC, CBBAAA, CABABB, and the like are also included, unless otherwise indicated by context. It will be appreciated by persons skilled in the art that, unless otherwise indicated herein, the number of items or terms in a typical arbitrary combination is not limited by the number of items or terms in the example, unless otherwise indicated by context.

[0057] The following detailed description of exemplary implementations of the present disclosure.

[0058] In one aspect, a micelle composition is provided, comprising: a saccharide surfactant; and a glycoside active ingredient encapsulated within the saccharide surfactant.

[0059] In the present specification, "saccharide surfactant" refers to a surfactant having a saccharide in its structure.

[0060] In one embodiment, the saccharide surfactant can be a glucoside surfactant.

[0061] In one embodiment, the glucoside surfactant can be one or more selected from the group consisting of decyl glucoside, lauryl glucoside, cocoyl glucoside, octyl / decyl glucoside, cetyl stearyl glucoside, arachinyl glucoside, and C12-20 alkyl glucoside in the composition.

[0062] In the present specification, "glycoside" refers to a molecule in which a saccharide molecule is combined with another functional group through a glycosidic bond. The glycoside is mainly found in plants.

[0063] In the present specification, "active ingredient" refers to an ingredient that exhibits a target activity alone or in combination with a carrier that is not active by itself.

[0064] In one embodiment, the glycoside active ingredient can be a saponin glycoside.

[0065] In one embodiment, the saponin glycoside can be one or more selected from the group consisting of ginsenoside, green tea saponin, red ginseng saponin, soybean saponin, and camellia saponin.

[0066] In the present specification, "ginseng" refers to a plant of the genus Panax in the family Araliaceae. In the present invention, ginseng can be used without limitation of species and age, and all ginsengs, whether dried or not, can be used. In addition, in the present invention, ginseng can be used without limitation of parts, and specifically, the root of ginseng can be used. For example, the ginseng can include Panax ginseng C.A. Meyer.

[0067] In the present specification, "green tea" refers to green tea of the genus Camellia in the family Theaceae. For example, the green tea can be Camellia sinensis. In addition, for example, the green tea can be Yabukita variety.

[0068] In the present specification, "red ginseng" refers to a processed product of fresh ginseng (Panax ginseng) steamed with steam and dried. In the steaming and drying process as described above, various new physiologically active ingredients that are not included in fresh ginseng and are beneficial to the body can be generated, and specifically, saponin, panacen, nitrogen-containing components, polyacetylenes, flavonoids, etc. can be contained.

[0069] In this specification, "beans" refers to beans of the genus Glycine in the family Fabaceae. For example, they can be black beans (Seoritae, Glycin max MERR), black beans (Seomoktae, Rhynchosia Nolubilis), black soybeans (Black soybean, Glycine max ( L. ) Merr.), blue bean (Glycine max MERR), yellow bean (Glycine max MERR), field bean (Viciafaba), kidney bean (Phaseolus vulgaris), pinto bean (Phaseolus vulgaris L.), small red bean (Vignaangularis), small black bean (Phaseolus angularis WF WIGHT.), sprouting bean (Glycine max (L.) Merr.), or soybean (Glycine max).

[0070] In this specification, the term "camellia" refers to camellia of the genus Camellia in the family Theaceae, and may include, for example, Camellia japonica or Camellia oleifera.

[0071] In one embodiment, the ginseng purified saponins may include saponins obtained from ginseng extract. The green tea purified saponins may include saponins obtained from green tea extract. The red ginseng purified saponins may include saponins obtained from red ginseng extract. The legume purified saponins may include saponins obtained from legume extract. The camellia purified saponins may include saponins obtained from camellia extract.

[0072] In an embodiment, the "extract" refers to all substances obtained by extracting the components of ginseng, green tea, red ginseng, or camellia, regardless of the extraction method, extraction solvent, extracted component, or form of the extract, including substances obtained by the extraction method including a process of treating heat, acid, base, enzyme, etc. during the extraction of the components. In addition, all substances obtained by processing or treating the substances obtained by extracting the components of ginseng, green tea, red ginseng, or camellia after the extraction, are a broad concept. Specifically, the processing or treating can be further fermentation or enzyme treatment of the ginseng, green tea, red ginseng, or camellia extract.

[0073] In an embodiment, the ginseng purified saponin can include compound K. In addition, the compound K can exist in the form of a stereoisomer of compound K, a salt thereof, a hydrate thereof, or a solvate thereof.

[0074] In the present specification, compound K can be represented by the following Chemical Formula 1.

[0075] [Chemical Formula 1]

[0076]

[0077] In an embodiment, the green tea purified saponin can include rogchaponin R12. In addition, the rogchaponin R12 can exist in the form of a stereoisomer of rogchaponin R12, a salt thereof, a hydrate thereof, or a solvate thereof.

[0078] In the present specification, rogchaponin R12 can be represented by the following Chemical Formula 2.

[0079] [Chemical Formula 2]

[0080]

[0081] In an embodiment, the sugar-based surfactant can be present in an amount of 0.001 to 50% by weight relative to the total weight of the composition. For example, the sugar-based surfactant can be present in an amount of 0.001% or more, 0.005% or more, 0.01% or more, 0.02% or more, 0.03% or more, 0.04% or more, 0.05% or more, 0.06% or more, 0.07% or more, 0.08% or more, 0.09% or more, 0.1% or more, 0.2% or more, 0.3% or more, 0.4% or more, 0.5% or more, 0.6% or more, 0.7% or more, 0.8% or more, 0.9% or more, 1.0% or more, 1.1% or more, 1.2% or more, 1.3% or more, 1.4% or more, 1.5% or more, 1.6% or more, 1.7% or more, 1.8% or more, 1.9% or more, 2.0% or more, 2.1% or more, 2.2% or more, 2.3% or more, 2.4% or more, 2.5% or more, 2.6% or more, 2.7% or more, 2.8% or more, 2.9% or more, 3.0% or more, 3.1% or more, 3.2% or more, 3.3% or more, 3.4% or more, 3.5% or more, 3.6% or more, 3.7% or more, 3.8% or more, 3.9% or more, 4.0% or more, 4.1% or more, 4.2% or more, 4.3% or more, 4.4% or more, or 4.5% or more, by weight relative to the total weight of the composition. In addition, the sugar-based surfactant can be present in an amount of 50% or less, 48% or less, 46% or less, 44% or less, 42% or less, 40% or less, 38% or less, 36% or less, 34% or less, 32% or less, 30% or less, 28% or less, 26% or less, 24% or less, 22% or less, 20% or less, 19.0% or less, 18.0% or less, 17.0% or less, 16.0% or less, 15.0% or less, 14.0% or less, 13.0% or less, 12.0% or less, 11.0% or less, 10.0% or less, 9.5% or less, 9.0% or less, 8.5% or less, 8.0% or less, 7.5% or less, 7.0% or less, 6.5% or less, 6.0% or less, or 5.5% or less, by weight relative to the total weight of the composition.

[0082] In one embodiment, the glycoside active ingredient can comprise 0.001 to 20% by weight relative to the total weight of the composition. For example, the glycoside active ingredient can comprise 0.001 or more, 0.005 or more, 0.01 or more, 0.05 or more, 0.1 or more, 0.15 or more, 0.2 or more, 0.25 or more, 0.30 or more, 0.35 or more, 0.40 or more, 0.45 or more, 0.50 or more, 0.51 or more, 0.52 or more, 0.53 or more, 0.54 or more, 0.55 or more, 0.56 or more, 0.57 or more, 0.58 or more, 0.59 or more, 0.60 or more, 0.61 or more, 0.62 or more, 0.63 or more, 0.64 or more, 0.65 or more, 0.66 or more, 0.67 or more, 0.68 or more, 0.69 or more, 0.70 or more, 0.71 or more, 0.72 or more, 0.73 or more, 0.74 or more, 0.75 or more, 0.76 or more, 0.77 or more, 0.78 or more, 0.79 or more, 0.80 or more, 0.81 or more, 0.82 or more, 0.83 or more, 0.84 or more, 0.85 or more, 0.86 or more, 0.87 or more, 0.88 or more, 0.89 or more, 0.90 or more, 0.91 or more, 0.92 or more, 0.93 or more, 0.94 or more, 0.95 or more, 0.96 or more, 0.97 or more, 0.98 or more, or 0.99 or more, by weight relative to the total weight of the composition. In addition, the glycoside active ingredient can comprise 20 or less, 19 or less, 18 or less, 17 or less, 16 or less, 15 or less, 14 or less, 13 or less, 12 or less, 11 or less, 10 or less, 9 or less, 8 or less, 7 or less, 6 or less, 5 or less, 4.9 or less, 4.8 or less, 4.7 or less, 4.6 or less, 4.5 or less, 4.4 or less, 4.3 or less, 4.2 or less, 4.1 or less, 4.0 or less, 3.9 or less, 3.8 or less, 3.7 or less, 3.6 or less, 3.5 or less, 3.4 or less, 3.3 or less, 3.2 or less, 3.1 or less, 3.0 or less, 2.9 or less, 2.8 or less, 2.7 or less, 2.6 or less, 2.5 or less, 2.4 or less, 2.3 or less, 2.2 or less, or 2.1 or less, by weight relative to the total weight of the composition.

[0083] In one embodiment, the weight ratio of the saccharide surfactant: glycoside active ingredient can be 1-50: 1. For example, the weight ratio of the saccharide surfactant: glycoside active ingredient can be 1-50: 1, 1-49: 1, 1-48: 1, 1-47: 1, 1-46: 1, 1-45: 1, 1-44: 1, 1-43: 1, 1-42: 1, 1-41: 1, 1-40: 1, 1-39: 1, 1-38: 1, 1-37: 1, 1-36: 1, 1-35: 1, 1-34: 1, 1-33: 1, 1-32: 1, 1-31: 1, 1-30: 1, 1-29: 1, 1-28: 1, 1-27: 1, 1-26: 1, 1-25: 1, 1-24: 1, 1-23: 1, 1-22: 1, 1-21: 1, 1-20: 1, 1-19: 1, 1-18: 1, 1-17: 1, 1-16: 1, 1-15: 1, 1-14: 1, 1-13: 1, 1-12: 1, 1-11: 1, 1-10: 1, 1-9: 1, 1-8: 1, 1-7: 1, 1-6: 1, 2-10: 1, 2-9: 1, 2-8: 1, 2-7: 1, 2-6: 1, 3-10: 1, 3-9: 1, 3-8: 1, 3-7: 1, 3-6: 1, 4-10: 1, 4-9: 1, 4-8: 1, 4-7: 1, 4-6: 1, 1-10: 2, 1-9: 2, 1-8: 2, 1-7: 2, 1-6: 2, 2-10: 2, 2-9: 2, 2-8: 2, 2-7: 2, 2-6: 2, 3-10: 2, 3-9: 2, 3-8: 2, 3-7: 2, 3-6: 2, 4-10: 2, 4-9: 2, 4-8: 2, 4-7: 2, or 4-6: 2.

[0084] In one embodiment, the composition can further include a non-covalent crosslinker. The non-covalent crosslinker refers to a crosslinker that enhances the intramicellar interaction through electrostatic interaction and hydrogen bonding. The composition of the present application can enhance the shell of the micelle, further improving the stability, by including the non-covalent crosslinker.

[0085] In one embodiment, the non-covalent crosslinker can be citric acid or tannic acid.

[0086] In an embodiment, the non-covalent crosslinking agent can be present in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition. For example, the non-covalent crosslinking agent can be present in an amount of 0.0001% or more, 0.0005% or more, 0.001% or more, 0.0015% or more, 0.002% or more, 0.0025% or more, 0.003% or more, 0.0035% or more, 0.004% or more, 0.0045% or more, 0.005% or more, 0.0055% or more, 0.006% or more, 0.0065% or more, 0.007% or more, 0.0075% or more, 0.008% or more, 0.0085% or more, 0.009% or more, 0.0095% or more, 0.01% or more, 0.0105% or more, 0.011% or more, 0.0115% or more, 0.012% or more, 0.0125% or more, 0.013% or more, 0.0135% or more, 0.014% or more, 0.0145% or more, 0.015% or more, 0.0155% or more, 0.016% or more, 0.0165% or more, 0.017% or more, 0.0175% or more, 0.018% or more, 0.0185% or more, 0.019% or more, 0.0195% or more, 0.02% or more, 0.025% or more, 0.03% or more, 0.035% or more, 0.04% or more, 0.045% or more, 0.05% or more, 0.055% or more, 0.06% or more, 0.065% or more, 0.07% or more, 0.075% or more, 0.08% or more, 0.085% or more, 0.09% or more, 0.095% or more, 0.1% or more, 0.5% or more, 1% or more, 1.5% or more, 2% or more, 2.5% or more, 3% or more, 3.5% or more, 4% or more, 4.5% or more, or 5% or more, by weight, relative to the total weight of the composition. Alternatively, the non-covalent crosslinking agent can be present in an amount of 5% or less, 4.5% or less, 4% or less, 3.5% or less, 3% or less, 2.5% or less, 2% or less, 1.5% or less, 1% or less, 0.95% or less, 0.9% or less, 0.85% or less, 0.8% or less, 0.75% or less, 0.7% or less, 0.65% or less, 0.6% or less, 0.55% or less, 0.5% or less, 0.45% or less, 0.4% or less, 0.35% or less, 0.3% or less, 0.25% or less, 0.2% or less, 0.15% or less, 0.1% or less, 0.095% or less, 0.09% or less, 0.085% or less, 0.08% or less, 0.075% or less, 0.07% or less, 0.065% or less, 0.06% or less, 0.055% or less, 0.05% or less, 0.045% or less, 0.04% or less, 0.035% or less, 0.03% or less, or 0.025% or less, by weight, relative to the total weight of the composition.

[0087] In an embodiment, the saccharide surfactant: glycoside active ingredient: non-covalent crosslinking agent weight ratio can be 1-50: 1: 0.002-0.2. For example, the saccharide surfactant: glycoside active ingredient: non-covalent crosslinking agent weight ratio can be 1-50: 1: 0.002-0.2, 1-45: 1: 0.002-0.2, 1-40: 1: 0.002-0.2, 1-35: 1: 0.002-0.2, 1-30: 1: 0.002-0.2, 1-25: 1: 0.002-0.2, 1-20: 1: 0.002-0.2, 1-15: 1: 0.002-0.2, 1-10: 1: 0.002-0.2, 1-9: 1: 0.002-0.2, 1-8: 1: 0.002-0.2, 1-7: 1: 0.002-0.2, 1-6: 1: 0.002-0.2, 1-5: 1: 0.002-0.2, 1-4: 1: 0.002-0.2, 1-3: 1: 0.002-0.2, 2-3: 1: 0.002-0.2, 2-3: 1: 0.004-0.15, 2-3: 1: 0.008-0.1, 2-3: 1: 0.012-0.05, 2-3: 1: 0.016-0.03.

[0088] In an embodiment, the average particle size of the micelles can be 5 to 200 nm. For example, the average particle size of the micelles can be 5 to 200, 6 to 190, 7 to 180, 8 to 170, 9 to 160, 10 to 150, 11 to 140, 12 to 130, 13 to 120, 14 to 110, 15 to 100, 16 to 90, 17 to 80, 18 to 70, 19 to 60, 20 to 50, 21 to 48, 22 to 46, 23 to 44, 24 to 42, 25 to 40, 25.5 to 39, 26 to 38, 26.5 to 37, 27 to 36, 27.5 to 35, 28 to 34, 28.5 to 33, 29 to 32, or 29.5 to 31 nm.

[0089] In an embodiment, at least 90% of the micelle particles included in the micelle composition can have a particle size of 5 to 200 nm. For example, at least 90% of the micelle particles included in the micelle composition can have a particle size of 5 to 200, 6 to 190, 7 to 180, 8 to 170, 9 to 160, 10 to 150, 11 to 140, 12 to 130, 13 to 120, 14 to 110, 15 to 100, 16 to 90, 17 to 80, 18 to 70, 19 to 60, 20 to 50, 21 to 48, 22 to 46, 23 to 44, 24 to 42, 25 to 40, 25.5 to 39, 26 to 38, 26.5 to 37, 27 to 36, 27.5 to 35, 28 to 34, 28.5 to 33, 29 to 32, or 29.5 to 31 nm.

[0090] In an embodiment, the composition can further include tocopherol. By including tocopherol, the compositions of the present application can enhance the core inside the shell of the micelles, further improving stability.

[0091] In an embodiment, the tocopherol can be included in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition. For example, the tocopherol can be included in an amount of 0.001 to 5.0, 0.003 to 4.75, 0.005 to 4.5, 0.007 to 4.25, 0.009 to 4.0, 0.011 to 3.75, 0.013 to 3.5, 0.015 to 3.25, 0.017 to 3.0, 0.019 to 2.75, 0.021 to 2.5, 0.023 to 2.25, 0.025 to 2.0, 0.027 to 1.75, 0.029 to 1.5, 0.031 to 1.25, 0.033 to 1.0, 0.035 to 0.9, 0.037 to 0.8, 0.039 to 0.7, 0.041 to 0.6, 0.043 to 0.5, 0.045 to 0.4, 0.047 to 0.3, 0.049 to 0.2, 0.051 to 0.1, 0.053 to 0.09, 0.055 to 0.08, or 0.057 to 0.07% by weight, relative to the total weight of the composition.

[0092] In an embodiment, the weight ratio of the sugar-based surfactant: glycoside active ingredient: tocopherol can be 1-50: 1: 0.006-0.6. For example, the weight ratio of the sugar-based surfactant: glycoside active ingredient: tocopherol can be 1-50: 1: 0.006-0.6, 1-45: 1: 0.006-0.6, 1-40: 1: 0.006-0.6, 1-35: 1: 0.006-0.6, 1-30: 1: 0.006-0.6, 1-25: 1: 0.006-0.6, 1-20: 1: 0.006-0.6, 1-15: 1: 0.006-0.6, 1-10: 1: 0.006-0.6, 1-9: 1: 0.006-0.6, 1-8: 1: 0.006-0.6, 1-7: 1: 0.006-0.6, 1-6: 1: 0.006-0.6, 1-5: 1: 0.006-0.6, 1-4: 1: 0.006-0.6, 1-3: 1: 0.006-0.6, 2-3: 1: 0.006-0.6, 2-3: 1: 0.01-0.5, 2-3: 1: 0.0015-0.45, 2-3: 1: 0.018-0.425, 2-3: 1: 0.02-0.04.

[0093] In an embodiment, the composition can be characterized as a cosmetic composition.

[0094] In an exemplary embodiment, the cosmetic composition can further include, on the basis of the ingredients, other ingredients capable of providing a beneficial effect different from the main effect, within a range not impairing the main effect. As to the other ingredients other than the effective ingredients of the present application, one skilled in the art can easily and appropriately select and formulate them according to the dosage form or purpose of use of the other cosmetic composition. In addition, as an embodiment, the cosmetic composition of the present application can further include, on the basis of the ingredients, other ingredients conventionally formulated in cosmetic compositions, as needed. For example, moisturizers, emollients, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, bactericides, antioxidants, plant extracts, pH adjustors, alcohols, pigments, fragrances, blood circulation promoters, cooling agents, antiperspirants, purified water, etc. can be mentioned. The other formulation ingredients that can be included in the cosmetic composition of the present application are not limited thereto, and the formulation amounts of the ingredients can be adjusted within a range not impairing the objects and effects of the present application.

[0095] In an exemplary embodiment, the cosmetic composition can be in one or more dosage forms selected from the group consisting of massage creams, oils, body products, packs, films, eye creams, lotions, creams, and makeup cosmetic compositions, but is not limited thereto. In addition, the compositions of these respective dosage forms can contain appropriate additives required in the formulation of the dosage forms thereof.

[0096] In an exemplary embodiment, the cosmetic composition can further include functional additives and ingredients included in general cosmetic compositions, in addition to the added effective ingredients. As the functional additives, ingredients selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, high-molecular peptides, high-molecular polysaccharides, sphingolipids, and seaweed concentrates can be included. In addition, ingredients included in general cosmetic compositions can be formulated as needed, in addition to the functional additives. As the ingredients that can be included in addition thereto, oil components, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, bactericides, antioxidants, plant extracts, pH adjustors, alcohols, pigments, fragrances, blood circulation promoters, cooling agents, antiperspirants, purified water, etc. can be mentioned.

[0097] On the other hand, a method for preparing the micellar composition of the present application is provided, the method including the steps of hydrating a saccharide surfactant in water; and dissolving a glycoside effective ingredient in one or more alcohols selected from the group consisting of C1-C6 alcohols. The micellar composition, the saccharide surfactant, and the glycoside effective ingredient are as described above.

[0098] In an embodiment, the order of the hydrating step and the dissolving step is not particularly limited.

[0099] In one embodiment, the step of hydrating in the water can be a method of hydrating a saccharide surfactant in water as a conventional method in the art without limitation.

[0100] In one embodiment, the step of dissolving in the alcohol can be a method of dissolving a glycoside active ingredient in an alcohol as a conventional method in the art without limitation.

[0101] In one embodiment, the method can further include the step of mixing the solution hydrated in the water and the solution dissolved in the alcohol, and evaporating the alcohol.

[0102] In one embodiment, the one or more alcohols selected from the group consisting of the C1-C6 alcohol can be ethanol or methanol.

[0103] In one embodiment, the step of evaporating can be a method of evaporating an alcohol used as a solvent in a solution as a conventional method in the art without limitation.

[0104] The present application can provide the following embodiments as one embodiment.

[0105] The first embodiment can provide a micelle composition including: a saccharide surfactant; and a glycoside active ingredient encapsulated in the saccharide surfactant.

[0106] The second embodiment can provide a composition according to the first embodiment, wherein the saccharide surfactant is a glucoside surfactant.

[0107] The third embodiment can provide a composition according to the second embodiment, wherein the glucoside surfactant is one or more selected from the group consisting of decyl glucoside, lauryl glucoside, cocoyl glucoside, octyl / decyl glucoside, cetearyl glucoside, arachidyl glucoside, and C12-20 alkyl glucoside.

[0108] The fourth embodiment can provide a composition according to any one of the first to third embodiments, wherein the glycoside active ingredient is a saponin glycoside.

[0109] The fifth embodiment can provide a composition according to the fourth embodiment, wherein the saponin glycoside is one or more selected from the group consisting of ginsenoside, green tea saponin, red ginseng saponin, soybean saponin, and camellia saponin.

[0110] The sixth embodiment can provide a composition according to the fifth embodiment, wherein the ginsenoside includes compound K.

[0111] The seventh embodiment can provide a composition according to the fifth embodiment, wherein the green tea refined saponin includes rogchaponin R12.

[0112] The eighth embodiment can provide a composition according to any one of the first through seventh embodiments, wherein the saccharide surfactant is contained in an amount of 0.001 to 50% by weight, relative to the total weight of the composition.

[0113] The ninth embodiment can provide a composition according to any one of the first through eighth embodiments, wherein the glycoside effective ingredient is contained in an amount of 0.001 to 20% by weight, relative to the total weight of the composition.

[0114] The tenth embodiment can provide a composition according to any one of the first through ninth embodiments, wherein the weight ratio of the saccharide surfactant : glycoside effective ingredient is 1-50:1.

[0115] The eleventh embodiment can provide a composition according to any one of the first through tenth embodiments, wherein the composition further includes a non-covalent crosslinker.

[0116] The twelfth embodiment can provide a composition according to the eleventh embodiment, wherein the non-covalent crosslinker is citric acid or tannic acid.

[0117] The thirteenth embodiment can provide a composition according to the eleventh or twelfth embodiment, wherein the non-covalent crosslinker is contained in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition.

[0118] The fourteenth embodiment can provide a composition according to any one of the eleventh through thirteenth embodiments, wherein the weight ratio of the saccharide surfactant : glycoside effective ingredient : non-covalent crosslinker is 1-50:1:0.002-0.2.

[0119] The fifteenth embodiment can provide a composition according to any one of the first through fourteenth embodiments, wherein the average particle diameter of the micelles is 5 to 200 nm.

[0120] The sixteenth embodiment can provide a composition according to any one of the first through fifteenth embodiments, wherein at least 90% of the micelle particles included in the micelle composition have a particle diameter of 5 to 200 nm.

[0121] The seventeenth embodiment can provide a composition according to any one of the first through sixteenth embodiments, wherein the composition further includes a tocopherol.

[0122] The eighteenth embodiment can provide a composition according to the seventeenth embodiment, wherein the tocopherol comprises 0.0001 to 5% by weight, relative to the total weight of the composition.

[0123] The nineteenth embodiment can provide a composition according to any one of the first to eighteenth embodiments, wherein the weight ratio of the sugar surfactant: glycoside active ingredient: tocopherol is 1-50: 1: 0.006-0.6.

[0124] The twentieth embodiment can provide a use of the micellar composition according to any one of the first to nineteenth embodiments for preparing a cosmetic composition.

[0125] The twenty-first embodiment can provide a method for preparing the micellar composition according to any one of the first to twentieth embodiments, wherein the method comprises the steps of hydrating the sugar surfactant in water; and dissolving the glycoside active ingredient in one or more alcohols selected from the group consisting of C1-C6 alcohols.

[0126] The twenty-second embodiment can provide a method according to the twenty-first embodiment, wherein the method further comprises the steps of mixing the solution hydrated in the water and the solution dissolved in the alcohol, and evaporating the alcohol.

[0127] The present application is further concretely explained by way of examples and the like. It should be construed that the examples are only for illustrating the present application, and the scope of the present application is not limited to the examples, which will be apparent to those having ordinary knowledge in the art.

[0128] Examples

[0129] 1. Preparation of purified saponin from natural sources

[0130] As ginseng, the roots of Panax ginseng C. A. Meyer with 4 years or more of root were prepared. As green tea, the roots of Camellia sinensis var. Yabukita with 30 years or more of root were prepared (purchased at Osulloc Farm).

[0131] After reflux extraction of 2 kg of ginseng or green tea with 4 L of water, aqueous methanol, or methanol 3 times, the residue was separated from the filtrate by filtration with a filter cloth and centrifugal separation, and the separated filtrate was concentrated under reduced pressure. The concentrated juice obtained was suspended in water, and then extracted 5 times with 1 L of diethyl ether to remove pigments, and the water layer was extracted 3 times with 50 ml of 1-butanol. After the total 1-butanol layer thus obtained was treated with 5% KOH, it was washed with distilled water, and then concentrated under reduced pressure to obtain 1-butanol concentrated juice, which was dissolved in a small amount of methanol, and then a large amount of ethyl acetate was added. The precipitate thus formed was dried to obtain 40-80 g of a purified saponin extract of natural origin.

[0132] 2. Preparation and evaluation of micellar compositions containing glycoside active ingredients

[0133] First, ginseng purified saponin and green tea purified saponin as glycosides were dissolved in ethanol or an ethanol aqueous solution ( Figure 1 and Figure 2 ) in preparation for the purpose of fully hydrating each sugar surfactant in water in preparation. At this time, the ginseng purified saponin includes Compound K as a main substance (Heliyon, Volume 9, Issue 4, 2023, e14803), and the green tea purified saponin includes Rogchaponin R12 as a main substance (Planta Med 2011; 77: 2029-2036).

[0134] Each component is shown in Table 1 and Table 2. The ethanol portion was put into the water portion and mixed, and all the ethanol was evaporated using an evaporator (Hei-VAP Advantage ML / G3; Heidolph, Germany) to prepare micelles, and then it was evaluated by the naked eye whether or not it was encapsulated.

[0135] Based on the fact that the preparation was observed with the naked eye to remain transparent, it was evaluated whether or not the micelles were encapsulated.

[0136] [Table 1]

[0137]

[0138] [Table 2]

[0139]

[0140] From the experimental results, it can be confirmed that the examples were solubilized to be transparent, and thus the active ingredients were stably encapsulated in the micelles. On the contrary, in the case of the comparative examples, precipitation occurred, and thus the active ingredients were not stably encapsulated in the micelles ( Figure 3 and Figure 4 ).

[0141] 3. Preparation and evaluation of micelle composition containing non-glycoside active ingredient

[0142] First, kojyl methylenedioxycinnamate (ACT Co., LTD., Korea) as a non-glycoside active ingredient was dissolved in THF or THF aqueous solution in preparation, and each sugar surfactant was fully hydrated in water in preparation. Each component is shown in Table 3. The THF portion was put into the water portion and mixed, and all THF was evaporated using an evaporator, and micelles were prepared, and then it was evaluated by the naked eye whether it was encapsulated.

[0143] The kojyl methylenedioxycinnamate has Figure 5 the chemical formula shown.

[0144] Based on the fact that it was observed with the naked eye after preparation that it remained transparent, it was evaluated whether the micelles were encapsulated.

[0145] [Table 3]

[0146]

[0147] From the experimental results, it can be confirmed that in the examples containing glycoside active ingredients, solubilization to transparency Figure 3 , and in non-glycoside active ingredients (Comparative Examples 6 to 8), precipitation Figure 6 occurred after preparation.

[0148] 4. Confirmation of the effect of improving the stability of the micelle composition by adding citric acid or tannic acid

[0149] In order to confirm the effect of improving the stability of the micelle composition by adding citric acid (sigma-aldrich, USA), tannic acid (sigma-aldrich, USA), and tocopherol (TAMA BIOCHEMICAL CO., LTD., Japan), the composition was prepared as shown in Table 4.

[0150] The ethanol portion was put into the water portion and mixed, and all ethanol was evaporated using an evaporator, and micelles were prepared. Then, the micelle composition was loaded into a dialysis bag (dialysis bag; Spectra / Por, Spectrum Laboratories, Inc., USA), and the release profile of compound K was confirmed over time in distilled water (DW). At this time, compound K was quantified by high performance liquid chromatography (HPLC; Waters, USA).

[0151] [Table 4]

[0152]

[0153] The experimental results are Figure 7 As shown, it can be confirmed that the release of compound K in Examples 6 and 7 is reduced compared to Example 5. This confirms that the stability of the micelle composition is further improved when citric acid or tannic acid is added.

[0154] Furthermore, it was confirmed that the addition of tocopherol in Example 8 also further improved the stability of the micelle composition.

[0155] 5. Confirmation of the micellar composition's enhanced skin absorption effect

[0156] To confirm the skin permeability-enhancing effect of the micelle composition, a composition was prepared as shown in Table 5. The micelle composition was then loaded into the donor chamber of a Franz diffusion cell (Hanson Research, USA), and absorption was confirmed over time.

[0157] At this time, the receptor chamber was filled with a PBS:ethanol mixture (9:1, v / v), and human skin (Biohead, South Korea) was fixed between the donor and receptor chambers.

[0158] [Table 5]

[0159]

[0160] The experimental results are Figure 8 As shown. It was confirmed that the absorption of compound K increased when the micelle composition of the present invention (Examples 5 and 6) was used compared to Comparative Examples 1 and 2. In addition, it was confirmed that Example 6 had a tendency to decrease compared to Example 5, but there was no significant difference.

[0161] 6. Preparation of Micellar Compositions and Confirmation of Mass-Based Encapsulation Efficacy

[0162] To confirm the preparation of micelle compositions and the encapsulation effect based on mass, a composition was prepared as shown in Table 6. The ethanol portion was added to the water portion and mixed, and all the ethanol was evaporated using an evaporator to prepare micelles. The encapsulation was then visually evaluated.

[0163] [Table 6]

[0164]

[0165] As in Example 11, although complete precipitation did not occur, a slight precipitation was observed during the storage after preparation when the mass ratio was close to 1:1.

[0166] The micellar composition of the present application is prepared according to the combination selected based on the structural simulation, and is achieved through experiments. Since the form of mixed micelles is adopted, stability is maintained despite the high encapsulation amount compared to other micelles.

[0167] 7. Measurement of particle size and observation of morphology of the micellar composition

[0168] In order to measure the particle size and observe the morphology of the micellar composition, the composition of Example 8 was used to confirm the preparation and mass-based encapsulation effect.

[0169] The particle size was measured using DLS (Zetasizer, Malvern Instruments Ltd., UK), and the results are shown in Table 1. Figure 9 The particle morphology was measured using CryoTEM (Tecnai G2 Spirit TWIN FEI microscope, USA), and the approximate size of the micelles is shown in Table 2. Figure 10 Table 2

Claims

1. A micellar composition comprising: a saccharide surfactant; and a glycoside active ingredient encapsulated in the saccharide surfactant.

2. The composition according to claim 1, wherein the saccharide surfactant is a glucoside surfactant.

3. The composition according to claim 2, wherein the glucoside surfactant is one or more selected from the group consisting of decyl glucoside, lauryl glucoside, cocoyl glucoside, octyl / decyl glucoside, cetyl stearyl glucoside, arachinyl glucoside, and C12-20 alkyl glucoside.

4. The composition according to claim 1, wherein the glycoside active ingredient is a saponin glycoside.

5. The composition according to claim 4, wherein the saponin glycoside is one or more selected from the group consisting of ginsenoside, green tea saponin, red ginseng saponin, soybean saponin, and camellia saponin.

6. The composition according to claim 5, wherein the ginsenoside includes Compound K.

7. The composition according to claim 5, wherein the green tea saponin includes rogchaponin R12.

8. The composition according to claim 1, wherein the saccharide surfactant is contained in an amount of 0.001 to 50% by weight, relative to the total weight of the composition.

9. The composition according to claim 1, wherein the glycoside active ingredient is contained in an amount of 0.001 to 20% by weight, relative to the total weight of the composition.

10. The composition according to claim 1, wherein the weight ratio of the saccharide surfactant: glycoside active ingredient is 1-50:

1.

11. The composition according to claim 1, wherein the composition further comprises a non-covalent cross-linking agent.

12. The composition according to claim 11, wherein the non-covalent cross-linking agent is citric acid or tannic acid.

13. The composition according to claim 11, wherein the non-covalent cross-linking agent is contained in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition.

14. The composition according to claim 11, wherein the weight ratio of the saccharide surfactant: glycoside active ingredient: non-covalent cross-linking agent is 1-50:1:0.002-0.

2.

15. The composition according to claim 1, wherein the average particle size of the micelles is 5 to 200 nm.

16. The composition according to claim 1, wherein at least 90% of the micelle particles included in the micellar composition have a particle size of 5 to 200 nm.

17. The composition according to claim 1, wherein the composition further comprises a tocopherol.

18. The composition according to claim 17, wherein the tocopherol is contained in an amount of 0.0001 to 5% by weight, relative to the total weight of the composition.

19. The composition according to claim 17, wherein the weight ratio of the saccharide surfactant: glycoside active ingredient: tocopherol is 1-50:1:0.006-0.

6.

20. The composition according to claim 1, wherein the composition is a cosmetic composition. the method comprising:

21. A method of preparing the micellar composition of any one of claims 1 to 19, wherein, ​ a step of hydrating a saccharide surfactant in water; and a step of dissolving a glycoside active ingredient in one or more alcohols selected from the group consisting of C1-C6 alcohols.

22. The method of claim 21, wherein, the method further comprises: a step of mixing the solution hydrated in the water and the solution dissolved into the alcohol, and evaporating the alcohol.

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