KR102009339B1 - Composition for skin cell regeneration, anti-wrinkle, antioxidant, anti-imflamation, and skin whitening - Google Patents
Composition for skin cell regeneration, anti-wrinkle, antioxidant, anti-imflamation, and skin whitening Download PDFInfo
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/4375—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
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- A23L29/00—Foods or foodstuffs containing additives; Preparation or treatment thereof
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4906—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom
- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
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- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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Abstract
The present invention relates to a composition for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening. The imperialline according to the present invention promotes collagen synthesis of fibroblasts of the skin, thereby regenerating the skin, improving wrinkles, inhibiting free radical production, inhibiting antioxidant effects, NO production, inhibiting anti-inflammatory effects and melanin synthesis, and whitening effects. By showing it can be used as a pharmaceutical composition, external skin preparations, cosmetic composition or health food.
Description
The present invention relates to a composition for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening.
Collagen is a major substrate protein produced by skin fibroblasts and is present in extracellular epilepsy.Its important functions include mechanical firmness of skin, resistance of connective tissue and tissue binding, support of cell adhesion, cell division and differentiation. Induction of growth or wound healing) is known. This collagen is reduced by age and light aging by ultraviolet irradiation, which is known to be closely related to the wrinkle formation of the skin. In addition, in recent years, extensive research on aging of the skin has been developed an important function of collagen in the skin.
Active ingredients are known that promote collagen synthesis and exhibit wrinkle improvement. For example, retinoic acid, transforming growth factor (TGF) [non-patent document 1], protein derived from animal placenta [patent document 1], betulinic acid (betulinic acid) [patent document 2], chlorella extract [ Patent Documents 3 and 4 are known as collagen synthesis promoting substances. However, the active ingredients are limited in the amount of use due to safety problems such as irritation and redness when applying the skin, or there is a problem in that the effect of improving the skin function is not expected by substantially promoting collagen synthesis of the skin.
On the other hand, free radicals introduced from outside the living body or generated in the living body cause many problems such as promoting aging of the living body or generating cancer. Therefore, many researches and developments on antioxidants that inhibit oxidation by active oxygen have been made. Antioxidants are widely distributed in copper and plant systems, and many phenolic compounds, flavonoids, tocopherols, vitamin C, and selenium are known in fruits and vegetables. However, the antioxidants present in nature are not expected to have a substantial enough effect on skin application. Therefore, many synthetic antioxidants having excellent antioxidant power and low cost are used, but their use is limited due to safety concerns such as human side effects.
In addition, inflammation is an immune response of the human body in response to a wound or disease, and oxidative stress such as ultraviolet rays, free radicals, and free radicals activates inflammatory factors to cause various diseases and aging of the skin. Vascular activating polypeptides such as kinin, plasmin, and complement act on vasodilation, contraction and chemotaxis, and other lymphokines such as interleukin-6 (IL-6). Phosphorus and arachidonic acid are responsible for the inflammatory response. Arachidonic acid is metabolized to prostaglandin and leukotriene, which are inflammatory mediators, through two pathways, cyclooxygenase or lipooxygenase, to mediate various inflammatory reactions.
On the other hand, the anti-inflammatory agent that acts to remove the inflammatory source, reduce the biological response and symptoms to eliminate inflammation. Materials used for anti-inflammatory purposes so far are nonsteroidal flufenamic acid, ibuprofen, benzydamine, indomethacin, and indonethacin, and prednisolone as a steroid system. , Dexamethasone, and the like. In addition, allantoin, azene, hydrocortisone, etc. are known to be effective in anti-inflammatory, but these substances have a limited amount of use as a matter of safety to the skin, or a problem that can not be expected to substantially reduce the effect of the inflammation. There is this.
Also, to have white and fair skin is everyone's constant desire. It is genetically determined by the concentration and distribution of melanin in human skin, but is also influenced by environmental or physiological conditions such as sun ultraviolet rays, fatigue and stress. Melanin is a type of amino acid tyrosine (tyrosine) acts as an enzyme called tyrosinase (tyrosinase) is converted into dopa (DOPA), dopaquinone (dopaquinone) is produced through a non-enzymatic oxidation reaction. The pathway by which melanin is produced is known, but the mechanisms that induce melanin synthesis, the previous stages of tyrosinase action, are still unknown.
Meanwhile, as a general known whitening component, substances that inhibit tyrosinase enzyme activity such as kojic acid and arbutin, hydroquinone, vitamin-C (L-Ascorbic acid) and derivatives thereof and various There is a plant extract. By inhibiting the synthesis of melanin pigments, they not only brighten the skin tone to realize skin whitening, but also improve skin hyperpigmentation such as blemishes and freckles due to ultraviolet rays, hormones or heredity. However, when the skin is applied, there are limitations on the amount of use due to safety problems such as irritation and redness, or there is a problem in that a substantial effect cannot be expected due to a slight effect.
Therefore, it is safe for the living body, the active ingredient is stable, and above all, the skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and whitening activity is superior to the existing skin rejuvenation, wrinkle improvement, antioxidant, anti-inflammatory and whitening substances. There is an urgent need for the development of these components.
[Prior literature]
[Patent Documents]
Japanese Patent Laid-Open No. 8-231370
Japanese Patent Laid-Open No. 8-208424
Japanese Patent Laid-Open No. 9-40523
Japanese Patent Laid-Open No. 10-36283
[Non-Patent Documents]
Cardinale G. et al, Adv. Enzymol., 41, p. 425, 1974
Therefore, the present inventors have imperialline to promote the collagen synthesis of fibroblasts of the skin and inhibit collagenase activity to promote the regeneration of the skin, improve wrinkles, eliminate free radicals to produce antioxidant effect, NO production It was confirmed that the anti-inflammatory effect and inhibiting melanin synthesis to exhibit a whitening effect and completed the present invention.
Accordingly, an object of the present invention to provide a composition for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening comprising a compound represented by the following formula (1) as an active ingredient:
[Formula 1]
As a means for solving the above problems, the present invention
It provides a pharmaceutical composition for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening comprising a compound represented by the formula (1) as an active ingredient.
[Formula 1]
As another means for solving the above problems, the present invention
It provides a skin external preparation for skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and skin whitening comprising a compound represented by the following formula (1) as an active ingredient.
[Formula 1]
As another means for solving the above problems, the present invention
It provides a cosmetic composition for skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and skin whitening comprising a compound represented by the formula (1) as an active ingredient.
[Formula 1]
As another means for solving the above problems, the present invention
It provides a health food for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening comprising a compound represented by the formula (1) as an active ingredient.
[Formula 1]
The imperialline according to the present invention promotes skin regeneration by promoting collagen synthesis of skin fibroblasts and inhibiting collagenase activity, exhibits antioxidant effects by eliminating free radicals, and inhibits NO production involved in the inflammatory response. It is excellent in anti-inflammatory effect, it can be used in medicine, cosmetics or health food by suppressing melanin synthesis and showing whitening effect.
EMBODIMENT OF THE INVENTION Hereinafter, the structure of this invention is demonstrated concretely.
Skin regeneration, wrinkle improvement, anti-oxidation, anti-inflammatory and whitening ingredients show excellent skin regeneration, wrinkle improvement, anti-oxidation, anti-inflammatory and whitening activity at low concentrations. Excellent absorption ability, low volatility for long time stay sufficient for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and whitening effect, stable active ingredient on composition or skin, It is desirable that the formulation be easy and safe for the skin. However, among the known components, components that satisfy all of the above properties are rare. For example, some skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and whitening ingredients have excellent skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and whitening activity at low concentrations in vitro, but have the ability to penetrate and absorb skin. It is difficult to apply to real skin apart. Other active ingredients are less hydrophilic and difficult to formulate in medicine or cosmetics. In addition, some skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and whitening ingredients may decompose or transform into other compounds that are already lost when applied to the skin when exposed to heat, light or oxygen. .
As can be seen in the following examples, imperialline shows excellent collagen synthesis promoting effect, antioxidant effect, anti-inflammatory effect and whitening effect at low concentrations, so that the drug for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening Can be used as an active ingredient in cosmetics, health foods and the like.
Therefore, the present invention therefore provides a pharmaceutical composition for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening comprising the compound represented by the following formula (1) as an active ingredient.
[Formula 1]
The compound name of the compound of Formula 1 is (5α, 17β) -3β, 20-Dihydroxycevan-6-one; (5α, 17β) -3β, 20β-Dihydroxycevane-6-one; (3-beta, 5-alpha, 17 -beta) -3,20-dihydroxycevan-6-one; 3,20-dihydroxy-, (3-beta, 5-alpha, 17-beta) -cevan-6-on, also called imperialine do.
The compound of Formula 1 may be used by separating or synthesizing from a plant extract or using a commercially available compound.
The pharmaceutical composition for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin whitening of the present invention may include the compound of Formula 1 in the form of a glycoside, non-glycoside or a pharmaceutically acceptable salt of the compound of Formula 1.
The pharmaceutically acceptable salt of the compound of Formula 1 may be an acid addition salt formed using an organic acid or an inorganic acid, and the organic acid may be, for example, formic acid, acetic acid, propionic acid, lactic acid, butyric acid, isobutyric acid or trifluoroacetic acid. , Malic acid, maleic acid, malonic acid, fumaric acid, succinic acid, succinic acid monoamide, glutamic acid, tartaric acid, oxalic acid, citric acid, glycolic acid, glucuronic acid, ascorbic acid, benzoic acid, phthalic acid, salicylic acid, anthranilic acid, dichloroacetic acid, aminooxyacetic acid And benzenesulfonic acid, p-toluenesulfonic acid and methanesulfonic acid salts and inorganic acids include, for example, hydrochloric acid, bromic acid, sulfuric acid, phosphoric acid, nitric acid, carbonic acid and boric acid salts. It may preferably be in the form of hydrochloride or acetate, more preferably in the form of hydrochloride.
The above-mentioned acid addition salts may be a) directly mixing the compound of formula 1 and an acid, b) dissolving and mixing one of them in a solvent or a hydrous solvent, or c) solvent or submerging the compound of formula 1 It is prepared by a general salt preparation method which is placed in an acid in a solvent and mixed with them.
In addition to the above, salts that can be additionally salted are Gabar salt, Gabapentin salt, Pregabalin salt, Nicotinate, Adipate salt, Hemimalonate, Cysteine salt, Acetylcysteine salt, Methionine salt, Arginine salt, Lysine salt, Ornithine salt, Aspartate.
In addition, when using the compound of Formula 1 of the present invention as a medicine, it may further contain one or more active ingredients exhibiting the same or similar functions. For example, it may include known skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin lightening ingredients. The inclusion of additional skin rejuvenation, wrinkle improvement, antioxidant, anti-inflammatory and skin lightening ingredients will further enhance the skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and skin lightening effects of the compositions of the present invention. When the ingredient is added, skin safety, ease of formulation, and stability of the active ingredients may be considered. In one embodiment of the invention, the composition is a skin regeneration component known in the art, retinoic acid, TGF, protein from animal placenta, betulinic acid and chlorella extract, as antioxidant ingredients known in the art, tocopherol, selenium , Vitamin C and phenolic compounds, as whitening ingredients known in the art, substances that inhibit tyrosinase enzyme activity such as kojic acid, arbutin, hydroquinone, vitamin-C (L- Ascorbic acid) and derivatives thereof and various plant extracts may further comprise one or two or more components selected from the group consisting of. Additional ingredients may be included from 0.0001% to 10% by weight relative to the total composition weight, and the content range may be adjusted according to requirements such as skin safety, ease of formulating the compound of Formula 1, and the like. .
In addition, the pharmaceutical composition for skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and skin whitening of the present invention may further comprise a pharmaceutically acceptable carrier.
Pharmaceutically acceptable carriers may contain various components such as buffers, sterile water for injection, general saline or phosphate buffered saline, sucrose, histidine, salts, polysorbates and the like.
The pharmaceutical composition of the present invention may be administered orally or parenterally, and may be administered in the form of a general pharmaceutical preparation, for example, in various dosage forms, orally and parenterally, during clinical administration. , Diluents or excipients such as extenders, binders, wetting agents, disintegrants, surfactants and the like.
Solid preparations for oral administration include tablets, pills, powders, granules, capsules, and the like, and such solid preparations include at least one excipient in the pharmaceutical composition of the present invention, for example, starch, calcium carbonate, It may be prepared by mixing sucrose or lactose, gelatin and the like.
In addition to simple excipients, lubricants such as magnesium styrate talc are also used. Liquid preparations for oral use include suspensions, solutions, emulsions, syrups, and the like, and various excipients such as wetting agents, sweeteners, fragrances, and preservatives, in addition to water and liquid paraffin, which are commonly used simple diluents.
Formulations for parenteral administration include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, lyophilized preparations, suppositories. As the non-aqueous solvent and the suspension solvent, propylene glycol, polyethylene glycol, vegetable oil such as olive oil, injectable ester such as ethyl oleate, and the like can be used. As the base of the suppository, witepsol, macrogol, tween 61, cacao butter, laurin butter, glycerogelatin and the like can be used.
In the present invention, the 'skin regeneration effect' refers to the recovery of skin tissue against damage caused by external and internal causes. The damage caused by the external causes may include ultraviolet rays, external pollutants, wounds, traumas, and the like, and the damage caused by the internal causes may include stress.
In the present invention, the 'wrinkle improvement effect' refers to inhibiting or inhibiting the generation of wrinkles on the skin, or alleviating wrinkles already generated.
In the present invention, the term 'antioxidative effect' refers to a cell caused by free radicals or reactiveVIe oxygen species (ROS) which are highly reactive due to oxidative stress caused by intracellular metabolism or ultraviolet light. Refers to the inhibition of oxidation, including the removal of free radicals or reactive oxygen species, thereby reducing damage to cells.
In the present invention, the "anti-inflammatory effect" refers to inhibiting inflammation, which is one of the defense responses of biological tissues to a certain stimulus, which involves three kinds of tissue degeneration, circulatory disorder and exudation, and tissue proliferation. Refers to complex lesions. More specifically, inflammation is part of innate immunity and, as in other animals, human innate immunity recognizes patterns of cell surfaces that are specific to pathogens. Phagocytes recognize cells with such surfaces as nonmagnetic devices and attack pathogens. If the pathogen breaks through the body's physical barrier, an inflammatory reaction occurs. Inflammatory reactions are nonspecific defenses that create a hostile environment against invading microbes. In inflammatory reactions, when wounded or an external infectious agent enters the body, white blood cells in the early stages of immune response rush to express cytokines. Therefore, the expression level of cytokines in cells is an indicator of inflammatory response activation. Examples of skin diseases related to inflammation include atopic dermatitis, psoriasis, radiation, chemicals, burns, etc., erythematous disease, acid burns, bullous skin disease, mammary gland-type diseases, allergic itching, seborrheic eczema, rose acne, Vulgaris, polymorphic exudative erythema, nodular erythema, glansitis, vulvitis, inflammatory hair loss such as alopecia areata, cutaneous T-cell lymphoma, and the like.
In the present invention, the term "whitening effect" means not only brightening skin tone by inhibiting the synthesis of melanin pigments, but also improving skin hyperpigmentation such as blemishes and freckles due to ultraviolet rays, hormones or heredity.
The pharmaceutical composition of the present invention may provide a desirable skin regeneration effect, wrinkle improvement effect, antioxidant effect, anti-inflammatory effect and whitening effect when an effective amount of the compound of Formula 1 is included. In the present invention, the term 'effective amount' means an amount of a compound capable of promoting regeneration of damaged skin, improving wrinkles, inhibiting or alleviating oxidation of cells, inhibiting inflammation, or exhibiting a whitening effect. . The effective amount of the compound of formula 1 included in the composition of the present invention will vary depending on the form in which the composition is commercialized, how the compound is applied to the skin, the time it stays on the skin, and the like. For example, when the composition is manufactured as a medicine, it may include the compound of Formula 1 in a higher concentration than when manufactured as a cosmetic that is routinely applied to the skin. Therefore, the daily dosage is 0.1 to 100 mg / kg, preferably 30 to 80 mg / kg, more preferably 50 to 60 mg / kg, 1 to 1 day, based on the amount of the compound of Formula 1 It may be administered six times.
The pharmaceutical compositions of the present invention may be used alone or in combination with other methods for achieving the use.
The present invention can also be provided in the formulation of the skin external preparation for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and whitening comprising the compound of Formula 1 as an active ingredient.
When the compound of Formula 1 is used as an external preparation for skin, it is further added to fatty substances, organic solvents, solubilizers, thickening and gelling agents, emollients, antioxidants, suspending agents, stabilizers, foaming agents, fragrances, surfactants. Common in water, ionic or nonionic emulsifiers, fillers, metal ion sequestrants and chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or external preparations for the skin It may contain adjuvants commonly used in the field of dermatology, such as any other ingredients used as. The ingredients may also be introduced in amounts generally used in the field of dermatology.
When the compound of Formula 1 is provided as an external preparation for skin, it is not limited thereto, and may have a formulation such as an ointment, a patch, a gel, a cream, or a spray.
The present invention can also be provided in the formulation of a cosmetic for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and whitening comprising the compound of Formula 1 as an active ingredient.
When the compound of Formula 1 is used as a cosmetic, the cosmetic prepared by containing the compound of Formula 1 as an active ingredient may be prepared in the form of a general emulsion formulation and solubilized formulation. For example, lotions such as flexible lotions or nourishing lotions, emulsions such as facial lotions, body lotions, creams such as nourishing creams, moisture creams, eye creams, essences, cosmetic ointments, sprays, gels, packs, sunscreens, makeup bases, liquids Formulations such as foundations, powders, cleansing creams, cleansing lotions, makeup removers such as cleansing oils, cleansing foams, soaps, body washes and the like.
In addition, the cosmetics are in addition to the compound of Formula 1, fatty substances, organic solvents, solubilizers, thickening and gelling agents, emollients, antioxidants, suspending agents, stabilizers, foaming agents, fragrances, surfactants, water Commonly used in ionic or nonionic emulsifiers, fillers, metal ion sequestrants and chelating agents, preservatives, vitamins, blockers, wetting agents, essential oils, dyes, pigments, hydrophilic or lipophilic active agents, lipid vesicles or cosmetics It may contain adjuvants conventionally used in the cosmetic field, such as any other ingredient.
The compound of Formula 1 may be a relatively high concentration of the compound of Formula 1 in the case of a wash-off type cosmetic such as a make-up remover, a detergent, etc., in which the active ingredient stays on the skin within a short time when it is commercialized. It may include. On the other hand, in the case of a leave-on type cosmetic such as a lotion, an emulsion, a cream, an essence, etc., in which the active ingredient stays on the skin for a long time, the compound of Chemical Formula 1 is lower than the wash-off type cosmetic. It may be included. Although not limited thereto, in one embodiment of the present invention, the composition may include the compound of Formula 1 in an amount of 0.0001% to 10% by weight (preferably 0.0001% to 1% by weight) based on the total weight of the composition. Can be. When the composition of the present invention contains less than 0.0001% by weight of the compound of Formula 1, sufficient skin regeneration, anti-wrinkle, antioxidant, anti-inflammatory and whitening effects cannot be expected, and when it contains more than 10% by weight, allergy This is to prevent unwanted reactions or skin safety problems may occur.
The present invention also relates to a health food for skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and whitening comprising the compound of Formula 1.
In the present specification, "health food" is a food prepared by adding the compound of Formula 1 to food materials, such as beverages, teas, spices, gums, confectionery, encapsulated, powdered, suspensions, etc. It means to bring a certain effect, but unlike the general medicine has the advantage that there are no side effects that can occur when taking a long-term use of the drug as a raw material.
Since the health food of the present invention thus obtained can be consumed on a daily basis, high skin regeneration, wrinkle improvement, antioxidant, anti-inflammatory and whitening effects can be expected and are very useful.
When the compound of Formula 1 is used as a food additive, the compound of Formula 1 may be added as it is or used with other foods or food ingredients, and may be appropriately used according to a conventional method. The mixed amount of the active ingredient can be suitably determined according to the purpose of use (prevention, health or therapeutic treatment). Generally, in the preparation of food or beverages, the composition of the present invention is added in an amount of up to 15 parts by weight, preferably up to 10 parts by weight based on the raw materials. However, in the case of long-term intake for health and hygiene or health control, the amount may be below the above range, and the active ingredient may be used in an amount above the above range because there is no problem in terms of safety. .
There is no particular limitation on the kind of food. Examples of the food to which the substance may be added include meat, sausages, bread, chocolate, candy, snacks, confectionery, pizza, ramen, other noodles, gums, dairy products including ice cream, various soups, beverages, teas, drinks, Alcoholic beverages and vitamin complexes, and the like and include all of the health foods in the conventional sense.
The health beverage composition of the present invention may contain various flavors or natural carbohydrates, etc. as additional components, as in the general beverage. The above-mentioned natural carbohydrates are glucose, monosaccharides such as fructose, disaccharides such as maltose and sucrose, and polysaccharides such as dextrin and cyclodextrin, sugar alcohols such as xylitol, sorbitol and erythritol. As the sweetening agent, natural sweetening agents such as tautin and stevia extract, synthetic sweetening agents such as saccharin and aspartame, and the like can be used. The proportion of said natural carbohydrate is generally about 0.01 to 0.04 g, preferably about 0.02 to 0.03 g per 100 mL of the composition of the present invention.
In addition to the above, the health food of the present invention includes various nutrients, vitamins, electrolytes, flavors, coloring agents, pectic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloid thickeners, pH adjusting agents, stabilizers, preservatives, glycerin, alcohols. And carbonation agents used in carbonated beverages. In addition, the health food of the present invention may contain a flesh for preparing natural fruit juice, fruit juice drink and vegetable drink. These components can be used independently or in combination. The proportion of such additives is not critical but is generally selected in the range of 0.01 to 0.1 parts by weight per 100 parts by weight of the composition of the present invention.
Hereinafter, the present invention will be described in detail by way of examples. However, the following examples are merely to illustrate the invention, but the content of the present invention is not limited to the following examples.
Reference Example One: Imperiallin ( imperialine Material information
[Formula 1]
IMPERIALINE; SIPEIMINE; kashmirine; RADDEAMINE; Raddeamine, Sipeimine
CAS No .: 61825-98-7
Where to buy: Tauto Biotech Co., Ltd.
Plant of origin: Fritillaria pallidiflora Schreb; F.roylei Hook.
Example 1: collagen synthesis effect
The substances shown in Table 1 below were added to the culture solution of human-derived fibroblasts to test collagen synthesis promoting effects at the cellular level.
The synthesis of collagen was quantified using a PICP EIA kit (Procollagen Type I C-Peptide Enzyme ImmunoAssay KIT). Evaluation of cytotoxicity at concentrations of 10 ppm, 1 ppm, 0.1 ppm, 0.01 ppm, and 0.001 ppm in human-derived fibroblasts before the experiment (method of culturing fibroblasts and performing MTT test [Reference: Mossman T. (1983) Rapid Colorimetric Assay for Cellular Growth & SurvVIal: application to proliferation & cytotoxicity assays.Journal of Immunological Methods 65, 55-63].
In the experiments, the final concentrations of imperialline were 1 ppm and 10 ppm, and each sample was added to the culture medium of human fibroblasts, incubated for 1 day, and then the culture medium was taken and the degree of collagen synthesis at each concentration was measured using a PICP EIA kit. It was measured at 450 nm using a spectrophotometer. For comparison of the effects, the degree of collagen synthesis was measured by the same method for the culture medium (control) of the fibroblasts to which nothing was added and the sample to which the vitamin C was added at a final concentration of 52.8 μg / ml. Collagen production was measured as UV absorbance, the collagen production increase rate was calculated as the ratio of collagen production relative to the control, the results are summarized in Table 1 below.
1 ppm
10 ppm
(No addition)
52.8 μg / ml
As can be seen from the results of Table 1, imperialline generally exhibited better collagen synthesis effect at a lower concentration than when vitamin C was known to have collagen synthesis ability.
Example 2: Collagenase Active inhibitory effect
It was confirmed as follows the collagenase activity inhibitory effect on the material of Table 2.
Evaluation of cytotoxicity at concentrations of 10 ppm, 1 ppm, 0.1 ppm, 0.01 ppm, and 0.001 ppm in human-derived fibroblasts before the experiment (method of culturing fibroblasts for MTT test [Reference: Mossman T. (1983) Rapid Colorimetric Assay for Cellular Growth & SurvVIal: application to proliferation & cytotoxicity assays.Journal of Immunological Methods 65, 55-63].
Fibroblasts, which are human normal skin cells, were seeded in a 24-well microplate at 2.5 × 10 4 cells per well, incubated for 24 hours at 10% serum DMEM medium and 37 ° C., and then 10% serum DMEM medium was removed. After washing once with phosphate buffer solution, it was further incubated for 30 minutes in serum-free DMEM medium without imperialline and serum-free DMEM medium without imperialline as a control.
Thirty minutes after stimulation with TNF-α (tumor necrosis factor-alpha) 50ng / ml, a substance known to produce MMP-1 after 30 minutes of sample treatment. In this case, the TNF-α untreated group and the treated group were treated with the TNF-α-treated group and the TNF-α-treated group among the controls not containing imperialline.
The supernatant of each well was collected to measure the amount (ng / ml) of newly synthesized MMP-1 using an MMP-1 assay kit (Amersham, USA), and the collagenase activity inhibition rate was determined according to Equation 1 below. -1 generation inhibition rate (%) was calculated, the results are shown in Table 2 below.
The amount of MMP-1 in the control group means the amount of MMP-1 in the TNF treatment group, and the amount of MMP-1 in the experimental group refers to the group to which the substance is added at each concentration.
[Equation 1]
Example 3: whitening effect - confirm melanin production inhibitory effect
The compound of formula 1 was added to the culture solution of mouse melanoma cells (B-16 mouse melanoma cells) to test the whitening effect at the cellular level. (Lotan R., Lotan D. Cancer Res. 40: 3345-3350, 1980).
Before the experiment, rat melanoma cells were assessed for toxicity, and non-toxic concentrations were selected for whitening evaluation.
The compound of formula 1 was tested in a final concentration of 5ug / ml, 10ug / ml, 20ug / ml in the culture medium, Arbutin control was added to the medium to 200ug / ml treated with B-16 melanoma cells, respectively Incubated for 3 days.
Then, cells were trypsin-treated (trypsin) was removed from the culture vessel and centrifuged to extract melanin. The detached cells were added with 1 ml of sodium hydroxide solution (1 N concentration), boiled for 10 minutes to dissolve the melanin, and the absorbance was measured at 400 nanometers (nm) using a spectrophotometer to measure the amount of melanin produced.
The melanin amount was measured by the absorbance of the unit cell count (10 6 cells). The relative melanin production relative to the control group was calculated as the inhibition rate (%) and the results are summarized in Table 3. In addition, the experiment was repeated three times.
As can be seen from the results of Table 3, the compound of Formula 1 has a superior melanin production inhibitory ability against the cultured mouse melanoma cells compared with the known whitening material Arbutin (Arbutin).
Example 4: antioxidant effect Free radical Erasure rate
Free radical scavenging activity was measured to confirm the antioxidant activity of imperialline. Free radical scavenging activity was measured using DPPH. DPPH was purchased from Sigma Co., Ltd, USA. First, a 1.5 mM (0.06 mg / ml) standard DPPH ethanol solution was made. Then, ethanol was added to the ascorbic acid, an antioxidant, as a compound of Formula 1 and a reference material, respectively, to prepare samples at concentrations of 50 µg / ml, 25 µg / ml, 12.5 µg / ml, 6.25 µg / ml, and 3.125 µg / ml. . Then, the sample and the standard DPPH solution were added in the same ratio, stirred well, and then reacted at 37 ° C. for 30 minutes, and the absorbance was measured at 520 nm. At this time, ethanol was added instead of the sample as a control. The free radical scavenging ability was obtained from IC 50 , which is a half maximal inhibitory concentration, and the results are shown in Table 4 below. IC 50 is a general method of expressing free radical scavenging ability as a concentration of ascorbic acid and a compound of formula (1) required to remove 50% of free radicals from an additive-free control group.
As can be seen in Table 4, the compound of Formula 1 has a lower activity than that of ascorbic acid (Vitamin C), which is a representative strong antioxidant, but exhibits an excellent level of antioxidant effect as a natural substance and is stable and has an antioxidant efficacy. It can be seen that it is suitable for use as.
Example 5: anti-inflammatory effect NO Generation suppression effect
In order to confirm the anti-inflammatory effect and skin trouble alleviating effect of the compound of the formula (1), nitric oxide (NO) formation inhibitory experiment was conducted by GRIESS method using RAW264.7 cell line (ATCC number: CRL-2278).
Specifically, RAW264.7 cells, which are macrophages of mice, were passaged several times, placed in a 24-well plate to enter 3 × 10 5 cells in one well, and then cultured for 24 hours. Subsequently, the compound of formula 1 was diluted with the concentration shown in Table 5 and replaced with the cell medium containing. The concentration refers to the concentration of the compound dissolved in the medium used for the evaluation, 1% = 10 mg / ml, 0.1% = 1 mg / ml, 0.01 = 0.1 mg / ml, 0.001 = 0.01 mg / ml . Meanwhile, L-NMMA (L-NG-Monomethylarginine), a NO-producing inhibitor, was treated as a positive control and incubated for 30 minutes, and cultured for 24 hours by treating 1 μg of LPS (Lipopolysaccharide) as a stimulus. 100 μl of the supernatant was taken and transferred to a 96-well plate, 100 μl of the GRIESS solution was added thereto, reacted at room temperature for 10 minutes, and the absorbance at 540 nm was measured. Determining the NO inhibitory effect of the compound of formula 1 compared to the negative control treated with only LPS and no inhibitor, the results are shown in Table 5 below.
As can be seen in Table 5, the compound of Formula 1 has a lower activity compared to NMMA, which is a representative anti-inflammatory substance, but shows excellent activity as a natural substance, so the anti-inflammatory effect acts as a secondary role in whitening and wrinkle improvement. A synergistic effect can be expected.
Formulation example 1: Preparation of Pharmaceutical Formulations
1. Preparation of powder
0.001 g of compound of Formula 1
1g lactose
The above ingredients were mixed and filled in airtight cloth to prepare a powder.
2. Preparation of Tablets
0.2 mg of compound of Formula 1
Corn Starch 100mg
Lactose 100mg
Stearic acid Magnesium 2mg
After mixing the above components, tablets were prepared by tableting according to a conventional method for producing tablets.
3. Preparation of Capsule
0.2 mg of compound of Formula 1
Corn Starch 100mg
Lactose 100mg
Stearic acid Magnesium 2mg
After mixing the above components, the capsule was prepared by filling in gelatin capsules according to the conventional method for producing a capsule.
4. Manufacture of rings
0.003 g of compound of Formula 1
Lactose 1.5 g
1 g of glycerin
Xylitol 0.5 g
After mixing the above components, it was prepared to be 4 g per ring according to a conventional method.
5. Preparation of Granules
2 mg of compound of formula 1
Soybean Extract 50mg
Glucose 200 mg
Starch 600 mg
After mixing the above components, 100 mg of 30% ethanol was added and dried at 60 ° C. to form granules, and then filled in fabric.
Formulation example 2: manufacture of cosmetics
1. Preparation of Soft Cosmetics (Skin Lotion)
Like the following composition, a flexible longevity containing the compound of formula 1 as an active ingredient was prepared according to a conventional method.
0.1 wt% of a compound of Formula 1
Beta-1,3-Glucan 1.0 wt%
Butylene Glycol 2.0 wt%
Propylene Glycol 2.0 wt%
Carboxy vinyl polymer 0.1 wt%
Fiji-12 nonylphenyl ether 0.2% by weight
Polysorbate 80 0.4 wt%
Ethanol 10.0 wt%
0.1% by weight of triethanolamine
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
2. Preparation of Nutrients (Milk Lotion)
As shown in the following composition, nutrient longevity containing the compound of Formula 1 as an active ingredient was prepared according to a conventional method.
0.1 wt% of a compound of Formula 1
Beta-1,3-Glucan 1.0 wt%
Beeswax 4.0 wt%
Polysorbate60 1.5 wt%
Sorbanthesquioleate 1.5 wt%
0.5% by weight of liquid paraffin
Caprylic / Capric Triglycerides 5.0 wt%
Glycerin 3.0 wt%
Butylene Glycol 3.0 wt%
Propylene Glycol 3.0 wt%
Carboxy vinyl polymer 0.1 wt%
0.2% by weight of triethanolamine
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
3. Preparation of nutrition cream
As in the following composition, a nourishing cream containing the compound of formula 1 as an active ingredient was prepared according to a conventional method.
0.2 wt% of a compound of Formula 1
Beta-1,3-Glucan 5.0 wt%
Beeswax 10.0 wt%
Polysorbate60 1.5 wt%
Sebum 60 Cured Castor Oil 2.0 wt%
0.5 wt% sorbitan sesquioleate
10.0% by weight of liquid paraffin
Squalane 5.0 wt%
Caprylic / Capric Triglycerides 5.0 wt%
Glycerin 5.0 wt%
Butylene Glycol 3.0 wt%
Propylene Glycol 3.0 wt%
0.2% by weight of triethanolamine
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
4. Preparation of Massage Cream
As in the following composition, a massage cream containing a compound of Formula 1 as an active ingredient was prepared according to a conventional method.
0.1 wt% of a compound of Formula 1
Beta-1,3-Glucan 3.0 wt%
Beeswax 10.0 wt%
Polysorbate60 1.5 wt%
Sebum 60 Cured Castor Oil 2.0 wt%
Sorbanthesquioleate 0.8 wt%
40.0% by weight of liquid paraffin
Squalane 5.0 wt%
Caprylic / Capric Triglyceride 4.0 wt%
Glycerin 5.0 wt%
Butylene Glycol 3.0 wt%
Propylene Glycol 3.0 wt%
0.2% by weight of triethanolamine
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
5. Manufacture of pack
As in the following composition, a pack containing the compound of formula 1 as an active ingredient was prepared according to a conventional method.
0.2 wt% of a compound of Formula 1
Beta-1,3-Glucan 1.0 wt%
Polyvinyl Alcohol 13.0 wt%
Sodium Carboxymethyl Cellulose 0.2% by weight
Glycerin 5.0 wt%
Allantoin 0.1 wt%
Ethanol 6.0 wt%
0.3% by weight of sebum-12 nonylphenyl ether
Polysorbate 60 0.3 wt%
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
Formulation example 3: External skin preparations Produce
1. Preparation of Gel
As in the following composition, a gel containing the compound of formula 1 as an active ingredient was prepared according to a conventional method.
0.1 wt% of a compound of Formula 1
Beta-1,3-Glucan 0.1 wt%
0.05% by weight of ethylenediamine sodium acetate
Glycerin 5.0 wt%
Carboxy vinyl polymer 0.3 wt%
Ethanol 5.0 wt%
Fiji-60 Cured Castor Oil 0.5 wt%
0.3% by weight of triethanolamine
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
2. Manufacture of ointments
As in the following composition, an ointment containing the compound of formula 1 as an active ingredient was prepared according to a conventional method.
0.5% by weight of compound of formula 1
Beta-1,3-Glucan 10.0 wt%
Beeswax 10.0 wt%
Polysorbate 60 5.0 wt%
Sebum 60 Cured Castor Oil 2.0 wt%
Sorbanthesquioleate 0.5 wt%
Vaseline 5.0 wt%
10.0% by weight of liquid paraffin
Squalane 5.0 wt%
Shea Butter 3.0 wt%
Caprylic / Capric Triglycerides 5.0 wt%
Glycerin 10.0 wt%
Propylene Glycol 10.2 wt%
0.2% by weight of triethanolamine
0.05 wt% preservative
0.05% by weight of pigment
0.05% by weight fragrance
Purified water to 100% by weight
3. Preparation of Topical Drug (Gel Ointment)
As the following composition, a gel ointment comprising the compound of formula 1 as an active ingredient was prepared according to a conventional method.
0.5% by weight of compound of formula 1
Beta-1,3-Glucan 10.0 wt%
1.5% by weight of polyacrylic acid (Carbopol 940)
Isopropanol 5.0 wt%
Hexylene glycol 25.0 wt%
Triethanolamine 1.7 wt%
Deionized water to 100% by weight
4. Preparation of medicament (patch) for topical administration
As in the following composition, a patch containing the compound of Formula 1 as an active ingredient was prepared according to a conventional method.
0.5% by weight of compound of formula 1
Beta-1,3-Glucan 3.0 wt%
Hexylene glycol 20.0 wt%
Diethylamine 0.7 wt%
1.0% by weight of polyacrylic acid (Carbopol 934P)
Sodium sulfite 0.1 wt%
1.0 weight% of polyoxyethylene lauryl ether (E.O = 9)
1.0% by weight of polyhydroxyethylene cetyl stearyl ether (Cetomacrogol 1000)
Viscous paraffin oil 2.5% by weight
Caprylic acid ester / capric acid ester (Cetiol LC) 2.5% by weight
Polyethylene glycol 400 3.0 wt%
Deionized water to 100% by weight
Formulation example 4: manufacture of food
Food containing the compound of formula 1 of the present invention was prepared as follows.
1. Preparation of flour food
0.05 to 1.0 parts by weight of the compound of Formula 1 was added to the flour, and using the mixture to prepare bread, cake, cookies, crackers and noodles to prepare a health food.
2. Manufacturing of Dairy Products
0.2 parts by weight of the compound of Formula 1 was added to milk, and various dairy products such as butter and ice cream were prepared using the milk.
3. Manufacture of wire
Brown rice, barley, glutinous rice, and yulmu were alphad by a known method, and then dried and roasted to prepare a powder having a particle size of 60 mesh. Black beans, black sesame seeds, and perilla were also steamed and dried by a known method, and then ground to a powder having a particle size of 60 mesh. The compound of Chemical Formula 1 was concentrated under reduced pressure in a vacuum concentrator, and the dried product obtained by drying with a spray and a hot air dryer was pulverized with a particle size of 60 mesh to obtain a dry powder.
The dry powder of the grains, seeds and the compound of Formula 1 prepared in the above was prepared by blending in the following ratio with respect to 100 parts by weight of the mixed powder.
Cereals (30 parts by weight brown rice, 15 parts by weight brittle, 20 parts by weight of barley),
Seeds (7 parts by weight perilla, 8 parts by weight black beans, 7 parts by weight black sesame seeds),
Compound of formula 1 (0.1 parts by weight),
Ganoderma lucidum (0.5 parts by weight),
Foxglove (0.5
Parts by weight
)
Formulation example 5: manufacture of beverages
1. Manufacture of health drinks
0.1 mg of compound of Formula 1
Citric acid 1000 mg
100 g oligosaccharides
Plum concentrate 2 g
1 g of taurine
Purified water By adding a full 900 mL
After mixing the above components according to the conventional healthy beverage production method, and stirred and heated at 85 ℃ for about 1 hour, the resulting solution is filtered and obtained by sterilization in a sterilized 2L-container, sealed sterilization and then stored in the refrigerator It was used to prepare a healthy beverage composition of the invention.
Although the composition ratio is a composition suitable for a preferred beverage in a preferred embodiment, the composition ratio may be arbitrarily modified according to regional and ethnic preferences such as demand hierarchy, demand country, and intended use.
2. Preparation of Vegetable Juice
1 g of the compound of Chemical Formula 1 of the present invention was added to 1,000 mL of tomato or carrot juice to prepare vegetable juice for health promotion.
3. Preparation of Fruit Juice
1 g of the compound of Formula 1 was added to 1,000 mL of apple or grape juice to prepare fruit juice for health promotion.
Claims (24)
[Formula 1]
[Formula 1]
The external preparation is an external preparation for skin in the form of an ointment, patch, gel, cream or spray.
[Formula 1]
Cosmetic composition in the form of a lotion, essence, lotion, cream, pack, gel, powder, foundation or detergent.
[Formula 1]
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