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WO2020111540A1 - Composition pharmaceutique pour la prévention ou le traitement du vieillissement ou de maladies associées au vieillissement, comprenant un complexe d'anthocyanine-polysaccharide en tant que principe actif - Google Patents

Composition pharmaceutique pour la prévention ou le traitement du vieillissement ou de maladies associées au vieillissement, comprenant un complexe d'anthocyanine-polysaccharide en tant que principe actif Download PDF

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Publication number
WO2020111540A1
WO2020111540A1 PCT/KR2019/014662 KR2019014662W WO2020111540A1 WO 2020111540 A1 WO2020111540 A1 WO 2020111540A1 KR 2019014662 W KR2019014662 W KR 2019014662W WO 2020111540 A1 WO2020111540 A1 WO 2020111540A1
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Prior art keywords
aging
anthocyanin
alginic acid
composition
complex
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English (en)
Korean (ko)
Inventor
장익순
조은비
이제호
장봉근
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Korea Basic Science Institute KBSI
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Korea Basic Science Institute KBSI
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/56—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule
    • A61K47/61—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic macromolecular compound, e.g. an oligomeric, polymeric or dendrimeric molecule the organic macromolecular compound being a polysaccharide or a derivative thereof
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105—Plant extracts, their artificial duplicates or their derivatives
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
    • A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
    • A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline 
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18—Magnoliophyta (angiosperms)
    • A61K36/185—Magnoliopsida (dicotyledons)
    • A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/541—Organic ions forming an ion pair complex with the pharmacologically or therapeutically active agent
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
    • A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • 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
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/73—Polysaccharides
    • A61K8/733—Alginic acid; Salts thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/18—Antioxidants, e.g. antiradicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P39/00—General protective or antinoxious agents
    • A61P39/06—Free radical scavengers or antioxidants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • A61Q19/08—Anti-ageing preparations
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2200/00—Function of food ingredients
    • A23V2200/30—Foods, ingredients or supplements having a functional effect on health
    • A23V2200/302—Foods, ingredients or supplements having a functional effect on health having a modulating effect on age
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/20—Natural extracts
    • A23V2250/21—Plant extracts
    • A23V2250/2104—Anthocyanins
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
    • A23V2250/00—Food ingredients
    • A23V2250/50—Polysaccharides, gums
    • A23V2250/502—Gums
    • A23V2250/5026—Alginate
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/57—Compounds covalently linked to a(n inert) carrier molecule, e.g. conjugates, pro-fragrances

Definitions

  • the present invention relates to a pharmaceutical composition for preventing or treating aging or aging-related diseases, including anthocyanin-polysaccharide complex, and more specifically, for preventing or treating aging or aging-related diseases, including anthocyanin-alginate complex It relates to a pharmaceutical composition.
  • Aging refers to the process of being born, growing, and getting old as a natural phenomenon over time. As time progresses, aging occurs, resulting in disease, and the likelihood of death gradually increases, leading to a condition where continuous life is impossible. Although the aging process is not necessarily associated with senile disease, it is true that the incidence of disease increases with the degree of aging. Although the exact biological mechanism for the aging process is still unknown, it has been confirmed that the aging phenomenon is a multifactorial phenomenon involving internal or external factors of life.
  • PPKO Phenyl-2-PyridiylKetoxime
  • ECM extracellular matrix
  • HDF human dermal fibroblast
  • the present invention has been devised to solve the above problems, and the present inventors have tried to find a source of antioxidants effective for the prevention, improvement or treatment of aging or aging-related diseases, resulting from Aronia extract (ABF) It was experimentally confirmed that anthocyanin is effective in preventing, improving or treating aging or aging-related diseases, and when anthocyanin forms a complex with alginic acid, it is found that it has a significant effect on improving the absorption rate of the anthocyanin in the body, and based on this The present invention has been completed.
  • an object of the present invention is to provide a composition for preventing, improving or treating aging or aging-related diseases, comprising the anthocyanin-alginic acid complex as an active ingredient.
  • Another object of the present invention is to provide an anthocyanin-alginic acid complex production method for enhancing the efficacy of anthocyanins, comprising the step of mixing aronia extract (ABF) with an alginate solution.
  • ABSF aronia extract
  • compositions for preventing or treating aging or aging-related diseases comprising anthocyanin-alginic acid complex as an active ingredient.
  • the alginic acid can be ionic bonded to anthocyanin, thereby improving stability and solubility, and enhancing the absorption of anthocyanin into the body.
  • the composition may inhibit reactive oxygen species (ROS).
  • ROS reactive oxygen species
  • the free radicals or nitric oxide may be induced by PPKO (Phenyl-2-PyridiylKetoxime).
  • the present invention provides a composition for enhancing anthocyanin efficacy, comprising anthocyanin and alginic acid.
  • the efficacy may be stabilization, solubility and absorption in the body of anthocyanins.
  • the present invention provides a method for preparing anthocyanin-alginate complex for enhancing the efficacy of anthocyanin, which comprises mixing aronia extract (ABF) in an alginate solution.
  • ABSF aronia extract
  • the present invention provides an anthocyanin-alginic acid complex as an active ingredient, a food or health functional food composition for preventing or improving aging or aging-related diseases.
  • the present invention provides an anthocyanin-alginate complex as an active ingredient, a cosmetic composition for improving aging or aging-related diseases.
  • the present inventors not only significantly increased the anthocyanin-alginic acid complex body absorption rate of anthocyanin, but also inhibited the generation of free radicals (ROS) and nitrogen monoxide (NO) in human skin fibroblasts, or induced a decrease in free radicals that have already occurred. It has been experimentally confirmed that the complex can be used for the prevention, improvement or treatment of aging or aging-related diseases, and the above substances can be usefully used in related development fields such as pharmaceuticals, food, and cosmetics. There will be.
  • ROS free radicals
  • NO nitrogen monoxide
  • Figure 1 shows the results confirming the effect of the anthocyanin-alginic acid complex (Ciaplex-A) according to the present invention on the survival of cells.
  • Figure 5a shows the results confirming the effect of the anthocyanin-alginic acid complex (Ciaplex-A) according to the present invention on the reduction in the amount of free radicals (ROS).
  • Figure 5b shows the results confirming the effect of the representative antioxidant ascorbic acid (AA) on the reduction of the amount of free radicals (ROS).
  • Figure 5c shows the results confirming the effect of the representative antioxidant N- acetylcysteine (NAC) on the reduction of the amount of free radicals (ROS).
  • Figure 6a shows the results confirming the effect of the anthocyanin-alginic acid complex (Ciaplex-A) according to the present invention on the reduction of the already occurring free radicals (ROS).
  • Figure 6c shows the results confirming the effect of the representative antioxidant, N-acetyl cysteine (NAC) on the reduction of free radicals (ROS) has already occurred.
  • the present inventors not only significantly increases the anthocyanin-alginic acid complex absorption rate in the body, but also inhibits the generation of free radicals (ROS) and nitrogen monoxide (NO) in human skin fibroblasts or induces a decrease in free radicals that have already occurred. It was confirmed experimentally, and it was found that the complex can be used for preventing, improving or treating aging or diseases related to aging. Based on this, the present invention was completed.
  • ROS free radicals
  • NO nitrogen monoxide
  • the present invention provides an anthocyanin-alginate complex as an active ingredient, a pharmaceutical composition for preventing or treating aging or aging-related diseases.
  • prevention refers to all actions that inhibit or delay the onset or aging-related diseases by administration of the pharmaceutical composition according to the present invention.
  • treatment refers to all actions in which symptoms of aging or age-related diseases are improved or beneficially altered by administration of a pharmaceutical composition according to the present invention.
  • anthocyanin is a group of flavonoid-based pigments, sugar (glucose, galactose, xylose, rhamnose or arabinose) and acid (malic acid, p-hydroxy benzoic acid, succinic) on one or both of hydroxyl groups of aglycone.
  • acid, p-coumaric acid, coffeic acid and ferulic acid refers to a pigment glycoside bound to a glycoside.
  • anthocyanins are known to lower the rate of apoptosis in leaves by preventing the verbs of plants from extreme cold.
  • anthocyanins have antioxidant properties in vitro, but in vivo, anthocyanins are conserved to less than 5%, and most of the absorbed anthocyanins are rapidly chemically modified to exist as metabolites.
  • aging or aging-related disease refers to a disease that occurs in the process of being born, growing, and getting old as a natural phenomenon over time.
  • the aging-related disease may be selected from the group consisting of skin wrinkles, photoaging, blackening, skin pigmentation, skin burns, skin inflammation, and skin cancer, but is not limited thereto.
  • the alginate anion according to the present invention has biocompatibility and can form a complex by forming ionic bonds with anthocyanin cations derived from Aaronia extract, thereby improving structural stability, solubility and absorption in the body.
  • PPKO Phenyl 2-pyridyl ketoxime
  • the cell viability in the group (1, 5, 10 ⁇ g/mL) in which the complex was applied at low concentration This increase was observed to confirm that the complex promotes cell differentiation (see Example 3).
  • DPPH radical scavenging ability of the anthocyanin-alginic acid complex (Ciaplex-A)
  • DPPH radical scavenging ability of representative antioxidants ascorbic acid and N-acetylcysteine It was confirmed that the value and the DPPH radical scavenging ability value of the complex were almost the same at all concentrations, and in particular, at the concentration of 100 ⁇ g/ml, they had the same DPPH radical scavenging ability value (see Example 4).
  • the anthocyanin-alginic acid complex according to the present invention affects cell differentiation to increase cell viability and participates in radical scavenging and reduction of free radical generation, thereby having excellent antioxidant capacity.
  • the complex may be usefully used for the prevention, improvement or treatment of aging or aging-related diseases, preferably pharmaceutical, food, health functional food for prevention, improvement or treatment of aging or aging-related diseases Or it may be used for cosmetic compositions, but is not limited thereto.
  • the pharmaceutical composition according to the present invention includes an anthocyanin-alginic acid complex as an active ingredient, and may also include a pharmaceutically acceptable carrier.
  • the pharmaceutically acceptable carrier is commonly used in formulation, and includes, but is not limited to, saline, sterile water, Ringer's solution, buffered saline, cyclodextrin, dextrose solution, maltodextrin solution, glycerol, ethanol or liposomes, etc. If not necessary, it may further contain other conventional additives such as antioxidants or buffers.
  • diluents, dispersants, surfactants, binders, or lubricants may be additionally added to formulate into injectable formulations such as aqueous solutions, suspensions or emulsions, pills, capsules, granules, or tablets.
  • injectable formulations such as aqueous solutions, suspensions or emulsions, pills, capsules, granules, or tablets.
  • suitable pharmaceutically acceptable carriers and formulations the formulations described in Remington's literature can be used to formulate according to each component.
  • the pharmaceutical composition of the present invention is not particularly limited in the formulation, but may be formulated as an injection, an inhalant, an external preparation for skin, or an oral intake.
  • the pharmaceutical composition of the present invention may be administered orally or parenterally (eg, applied intravenously, subcutaneously, skin, nasal cavity, or airways) according to a desired method, and the dosage is the patient's condition and weight, disease Depending on the degree, drug type, route of administration and time, it can be appropriately selected by those skilled in the art.
  • composition according to the invention is administered in a pharmaceutically effective amount.
  • a pharmaceutically effective amount means an amount sufficient to treat a disease at a reasonable benefit/risk ratio applicable to medical treatment, and the effective dose level is the type of patient's disease, severity, and activity of the drug , Sensitivity to drug, time of administration, route of administration and rate of excretion, duration of treatment, factors including co-drugs and other factors well known in the medical field.
  • the composition according to the present invention may be administered as an individual therapeutic agent or in combination with other therapeutic agents, and may be administered sequentially or simultaneously with a conventional therapeutic agent, and may be administered single or multiple. Considering all of the above factors, it is important to administer an amount that can achieve the maximum effect in a minimal amount without side effects, which can be easily determined by those skilled in the art.
  • the effective amount of the composition according to the present invention may vary depending on the patient's age, sex, and body weight, and in general, 0.001 to 150 mg per 1 kg of body weight, preferably 0.01 to 100 mg, administered daily or every other day, or 1 to 1 day It can be divided into three doses. However, since the dosage may be increased or decreased depending on the route of administration, the severity of neurodegenerative diseases, sex, weight, age, etc., the dosage does not limit the scope of the present invention in any way.
  • the present invention provides an anthocyanin-alginic acid complex as an active ingredient, a food or health functional food composition for preventing or improving aging or aging-related diseases.
  • the term "improvement” refers to any action that at least reduces the severity of parameters associated with the condition being treated, such as symptoms.
  • the food or dietary supplement composition may be used simultaneously or separately with a medicament for treatment before or after the onset stage of the disease in order to prevent, ameliorate, or treat aging or aging-related diseases.
  • the food or dietary supplement composition according to the present invention is formulated as one selected from the group consisting of tablets, pills, powders, granules, powders, capsules and liquid formulations, including one or more of carriers, diluents, excipients and additives It is characterized by.
  • Examples of the above-mentioned natural carbohydrate include monosaccharides, for example, disaccharides such as glucose and fructose, such as maltose, sucrose, etc.; And polysaccharides, for example, conventional sugars such as dextrin, cyclodextrin, and sugar alcohols such as xylitol, sorbitol, and erythritol.
  • As the flavoring agent natural flavoring agents (taumatine, stevia extract (for example, rebaudioside A, glycyrrhizine, etc.) and synthetic flavoring agents (saccharin, aspartame, etc.) can be advantageously used.
  • composition according to the invention includes various nutrients, vitamins, minerals (electrolytes), flavoring agents such as synthetic flavoring agents and natural flavoring agents, coloring agents and neutralizing agents, pactic acid and salts thereof, alginic acid and salts thereof, organic acids, protective colloidal thickeners , pH adjusting agents, stabilizers, preservatives, glycerin, carbonic acid used in alcohol or carbonated beverages, etc.
  • Other compositions in the present invention may contain flesh for the preparation of natural fruit juices and vegetable drinks.
  • carrier excipients, diluents, and additives
  • lactose dextrose, sucrose, sorbitol, mannitol, erythritol, starch, and acacia Rubber
  • calcium phosphate alginate, gelatin, calcium phosphate, calcium silicate, microcrystalline cellulose, polyvinylkyrrolidone, cellulose, polyvinylpyrrolidone, methylcellulose, water, sugar syrup, methyl hydroxy benzoate, propylhydroxy It is preferred that at least one selected from the group consisting of benzoate, talc, magnesium stearate and mineral oil is used.
  • the present invention provides an anthocyanin-alginate complex as an active ingredient, a cosmetic composition for improving aging or aging-related diseases.
  • the cosmetic composition according to the present invention may include anthocyanin-alginic acid complex, as well as ingredients commonly used in cosmetic compositions, for example, conventional adjuvants such as antioxidants, stabilizers, solubilizers, vitamins, pigments, and fragrances , And a carrier.
  • the composition of the present invention may be used in addition to the anthocyanin-alginic acid complex, in addition to the anthocyanin-alginic acid complex, organic sunscreens that have been conventionally used to the extent that they do not impair the skin protective effect by reacting with the anthocyanin-alginate complex.
  • organic sunscreen examples include glyceryl baba, drometrizolitrisiloxane, drometrizole, digaloyl trioleate, disodium phenyldibenzimidazole tetrasulfonate, diethylhexylbutamidotriazone, diethylamino Hydroxybenzoylhexylbenzoate, die-methoxycinnamate, mixture of Lawson and dihydroxyacetone, methylenebis-benzotriazolyltetramethylbutylphenol, 4-methylbenzylidene camphor, menthyl anthranylate, benzophenone -3 (oxybenzone), benzophenone-4, benzophenone-8 (dioxyphenbenzone), butylmethoxydibenzoylmethane, bisethylhexyloxyphenolmethoxyphenyltriazine, cynoxate, ethyldihydroxypropylparva, Octoc
  • cosmetics and cleansing agents such as convergent makeup, softening makeup, nutrient makeup, various creams, essences, packs, foundations, cleansing agents, soaps, treatments, and cosmetics And so on.
  • Specific formulations of the cosmetic composition of the present invention include skin lotion, skin softener, skin toner, astringent, lotion, milk lotion, moisture lotion, nutrition lotion, massage cream, nutrition cream, moisture cream, hand cream, essence, nutrition essence, pack, Contains formulations such as soap, shampoo, cleansing foam, cleansing lotion, cleansing cream, body lotion, body cleanser, emulsion, lipstick, makeup base, foundation, press powder, rust powder, and eye shadow.
  • the present invention provides a composition for enhancing anthocyanin efficacy, comprising anthocyanin and alginic acid.
  • efficacy may be, but is not limited to, stabilization, solubility and absorption in the body of anthocyanins.
  • the present invention provides a method for preparing anthocyanin-alginate complex for enhancing the efficacy of anthocyanin, which comprises mixing aronia extract (ABF) in an alginate solution.
  • the concentration ratio of the concentration of anthocyanin and alginic acid may be 1 to 4 to 1 to 12, preferably 1 to 8, but is not limited thereto.
  • the present invention provides a method of preventing, improving or treating aging or diseases related to aging, comprising administering the pharmaceutical composition to an individual.
  • “individual” means a subject in need of a method for preventing, improving or treating a disease, and more specifically, a human or non-human primate, mouse, rat, dog, cat Means mammals, such as horses and cows.
  • Dulbecco's modified Eagle's medium (DMEM), 3-(4,5-dimethylthiazolyl)-2,5-diphenyltetrazolium bromide (3-(4,5-dimethylthiazoleyl)-2,5-diphenyltetrazolium bromide, MTT), N-acetylcysteine (NAC), 5-bromo-4-chloro-3-indolyl- ⁇ - D -galactopyranoside (5-bromo-4-chloro-3-indolyl- ⁇ - D -galactopyranoside, X-gal, L-NG-nitroargininemethylester (L-NAME), propidiumiodide, fetal bovine serum (FBS), Penicillin, streptomycin and other reagents used in cell culture were purchased from Life Technologies (Grand Island, NY, USA). L-NG-monomethylarginine (L-NMMA) was purchased from Calbiochem (LaJolla, CA, USA
  • DMEM fetal bovine serum
  • PPKO phenyl-2-pyridylketoxime
  • the DDPH radical scavenging ability is a method of measuring the antioxidant capacity of any substance, and the DDPH radical scavenging ability is purple, and the DDPH radical scavenging ability of the antioxidant using the principle that the radical turns pale yellow when reacted with an antioxidant ( Antioxidant capacity).
  • the wavelength of 517 nm which measures absorbance, detects purple, but does not detect yellow, so a sample with good antioxidant ability has small absorbance, and a sample with poor antioxidant ability has large absorbance.
  • 2,2-diphenyl-1-picrylhydrazyl (2.2-Diphenyl-1-picrylhydrazyl, DPPH) was dissolved in 80% of ethanol to prepare a final concentration of 0.2 mM.
  • Anthocyanin-alginic acid complex (Ciaplex-A), ascorbic acid (AA) and N-acetylcysteine (NAC) were made into solutions with concentrations of 0, 25, 50, 100, 200, 500 and 1000 ⁇ g/ml, respectively.
  • 100 ⁇ l of the solution was applied to each experimental group of a 96-well plate. Thereafter, 100 ⁇ l of 0.2 mM DPPH reagent was added to the experimental group, and reacted in an incubator at 37° C. for 30 minutes, followed by an ELISER reader (Multiskan EX; Thermo Lab system, Boverly, MA, USA) at a wavelength of 517 nm. The ability to scavenge DDPH radicals was measured.
  • MTT assay is an experimental method to measure cell viability, and the yellow tetrazolium of the MTT reagent loses the ring structure by reductase from the mitochondria of living cells and loses the ring structure.
  • mitochondrial activity is reduced compared to the case where all the cells are alive, and accordingly, the action of dehydrogenase decreases, so only a small amount of yellow MTT reagent turns purple. . Therefore, the darker the purple color, the more cells survived, and the higher the cell viability was measured.
  • Cells were seeded in a 96 well-plate at 2 X 10 4 cell/well, and this experiment was performed when the cell density was 80-90%.
  • the wells were washed twice using 100 ⁇ l of 1 X PBS, and the anthocyanin-alginic acid complex (Ciaplex-A), ascorbic acid (AA), and N-acetylcysteine (NAC) were respectively 0 and 1 based on the DPPH assay results. , 5, 10, 50, 100 and 200 ⁇ g / ml concentration was applied to each experimental group. After culturing for 24 hours and 48 hours in an incubator at 37° C.
  • Cells are seeded in a 96 well-plate at 4.75 X 10 5 cells/well and expression of beta-galactosidase using senescence ß-galactosidase staining kit (Cell signaling technology co.) was confirmed.
  • cell viability was measured by treating the cell counting assay kit-8 (CCK-8).
  • the Aaronia extract (ABF) 20 mg was dissolved in 20 ml of a pH 3 aqueous solution of Phosphate buffer so that the precipitate was not visible, and 160 mg of alginic acid was dissolved in 20 ml of distilled water so that the precipitate was not visible.
  • ABF ABF solution was added and stirred at room temperature for 72 hours to prepare anthocyanin-alginic acid complex.
  • the ratio of aronia extract and alginic acid is shown in Table 1 below.
  • anthocyanin-alginic acid complex (Ciaplex-A) is treated on cells. After applying the complex to the cells and 24 hours and 48 hours respectively, the cell viability was measured.
  • the cell viability measured 48 hours after applying the anthocyanin-alginic acid complex was significantly reduced in the high-concentration treatment group (100, 200 ⁇ g/ml) of the complex, and the low-concentration group (1 , 5, 10 ⁇ g / ml) was confirmed to increase.
  • anthocyanins are involved in cell proliferation (results for cell growth and division) to maximize the effect of cell differentiation, thereby maintaining high cell viability when anthocyanins are applied at low concentrations.
  • Ascorbic acid (AA) and N-acetylcysteine (NAC) are representative substances known to have antioxidant properties.
  • Example 1-3 the DPPH assay of Example 1-3 was performed to confirm the antioxidant activity of the anthocyanin-alginic acid complex (Ciaplex-A), and ascorb, a representative antioxidant, to increase the reliability of the experiment results. Comparative experiments for acid (AA) and N-acetylcysteine (NAC) were added.
  • AA anthocyanin-alginic acid complex
  • NAC N-acetylcysteine
  • the anthocyanin-alginic acid complex (Ciaplex-A) has the same value of DPPH radical scavenging ability at all concentrations as the representative antioxidants, and the same DPPH radical at a concentration of 100 ⁇ g/ml. It was confirmed that it has an erasing ability value.
  • Beta-galactosidase (ß-galactosidase) is an enzyme that hydrolyzes the glycosidic bond of lactose into glucose and galactose, and is also called ⁇ -gal. It is a representative biomarker for confirming aging of cells together with p16 ink4A .
  • Example 1-5 the SA-ß-gal staining experiment of Example 1-5 was performed to confirm whether aging of human skin fibroblasts progressed.
  • beta-galactosidase a marker of aging
  • Nitrogen monoxide is involved in aging by inhibiting mitochondrial respiration or DNA synthesis, and free radicals (ROS) generate DNA by-products and resulting DNA by-products and lipid peroxide. It is known to be involved in cytotoxicity by producing back.
  • PPKO is a small compound of the extracellular matrix (ECM) that surrounds old fibroblasts. It increases the free radicals (ROS) and induces the production of other free radical species, nitrogen monoxide (NO), which promotes cell aging. It was identified through research.
  • ECM extracellular matrix
  • ROS free radicals
  • NO nitrogen monoxide
  • anthocyanin-alginic acid complex (Cyiaplex-A), ascorbic acid (AA), and N-acetylcysteine (NAC) are applied to cells, respectively, to produce the active oxygen and nitrogen monoxide generated by PPKO.
  • the alginate anion has biocompatibility and is capable of significantly improving the structural stability, solubility, and absorption in the body of the anthocyanin in the body by forming a complex by forming an complex with the anthocyanin cation derived from the Aronia extract. , It was confirmed that it inhibits the generation of free radicals (ROS) and nitrogen monoxide (NO) in human skin fibroblasts, or induces the reduction of free radicals that have already occurred. It is expected to be useful in related development fields such as cosmetics and cosmetics.
  • ROS free radicals
  • NO nitrogen monoxide

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Abstract

La présente invention concerne une composition pharmaceutique pour la prévention ou le traitement du vieillissement ou de maladies associées au vieillissement, comprenant un complexe d'anthocyanine-polysaccharide et, plus particulièrement, une composition pharmaceutique pour la prévention ou le traitement du vieillissement ou de maladies associées au vieillissement comprenant un complexe d'anthocyanine-acide alginique. Les présents inventeurs ont confirmé par l'expérimentation que le complexe d'anthocyanine-acide alginique non seulement augmente significativement le taux d'absorption d'anthocyanine dans le corps, mais inhibe également la génération d'espèces réactives de l'oxygène (reactive oxygen species - ROS) et de monoxyde d'azote (NO) dans les fibroblastes de la peau humaine ou induit une diminution des espèces réactives de l'oxygène qui ont déjà été générées. Les présents inventeurs ont établi que le complexe peut être utilisé pour prévenir, améliorer ou traiter le vieillissement ou des maladies associées au vieillissement. Par conséquent, les substances ci-dessus peuvent être efficacement utilisées dans des domaines de développement apparentés tels que des produits pharmaceutiques, des aliments et des produits cosmétiques.
PCT/KR2019/014662 2018-11-30 2019-11-01 Composition pharmaceutique pour la prévention ou le traitement du vieillissement ou de maladies associées au vieillissement, comprenant un complexe d'anthocyanine-polysaccharide en tant que principe actif Ceased WO2020111540A1 (fr)

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KR10-2018-0152469 2018-11-30

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FR3124391A1 (fr) * 2021-06-29 2022-12-30 L'oreal Composition cosmétique parfumée comprenant au moins un sucre, un colorant anthocyani(di)ne et une matière parfumante, et procédé de traitement de matière kératinique et/ou de vêtement mettant en œuvre la composition

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3124391A1 (fr) * 2021-06-29 2022-12-30 L'oreal Composition cosmétique parfumée comprenant au moins un sucre, un colorant anthocyani(di)ne et une matière parfumante, et procédé de traitement de matière kératinique et/ou de vêtement mettant en œuvre la composition

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