WO2017057919A1 - Composition antibactérienne comprenant de l'acide saccharique et un flavonoïde - Google Patents

Composition antibactérienne comprenant de l'acide saccharique et un flavonoïde Download PDF

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Publication number
WO2017057919A1
WO2017057919A1 PCT/KR2016/010910 KR2016010910W WO2017057919A1 WO 2017057919 A1 WO2017057919 A1 WO 2017057919A1 KR 2016010910 W KR2016010910 W KR 2016010910W WO 2017057919 A1 WO2017057919 A1 WO 2017057919A1
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WIPO (PCT)
Prior art keywords
acid
composition
antimicrobial
sugar
less
Prior art date
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PCT/KR2016/010910
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English (en)
Korean (ko)
Inventor
김소희
윤유나
홍용덕
안수선
이존환
Original Assignee
(주)아모레퍼시픽
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Publication of WO2017057919A1 publication Critical patent/WO2017057919A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • 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
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7012—Compounds having a free or esterified carboxyl group attached, directly or through a carbon chain, to a carbon atom of the saccharide radical, e.g. glucuronic acid, neuraminic acid
    • 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
    • A61K8/60—Sugars; Derivatives thereof
    • 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

Definitions

  • an antimicrobial composition including a sugar acid and a flavonoid as an active ingredient is disclosed.
  • penicillin has been a turning point for major changes in the suppression of antibiotic-induced pathogens, health and longevity by disease suppression.
  • an object of the present invention is to provide a composition comprising a sugar acid, the antimicrobial activity is increased.
  • an object of the present invention is to increase the antimicrobial activity of both by utilizing the synergistic effect of flavonoids and sugar acids.
  • an object of the present invention is to obtain an antimicrobial effect with lower concentrations of flavonoids and sugar acids.
  • the present invention sugar acid (sugar acid) as an active ingredient; And a flavonoid, an isomer thereof, a pharmaceutically acceptable salt thereof, a prodrug thereof, a hydrate thereof, or a solvate thereof.
  • the antimicrobial composition may produce an antimicrobial composition having improved antimicrobial activity by synergistic effect between the sugar acid and the flavonoids as an active ingredient.
  • an antimicrobial composition which is an aspect of the present invention, is useful because it can inhibit the growth of various microorganisms including bacteria or kill microorganisms even with a low concentration of active ingredients while reducing the harmfulness to humans and the environment.
  • 1 is a diagram measuring the antimicrobial activity of three sugar acids (mucoacid, glucuronic acid, galacturonic acid) and a quercetin combination (negative control: medium without bacteria, positive control: medium with bacteria ).
  • Figure 2 is a diagram measuring the antimicrobial synergistic effect of the combination of quercetin and galacturonic acid (negative control: media without bacteria, positive control: media added bacteria).
  • FIG. 3 is a diagram briefly showing a method of a test board test.
  • Figure 4 is a diagram confirming the antimicrobial effect against other bacteria of the quercetin and galacturonic acid combination.
  • the present invention as an active ingredient, sugar acid (sugar acid); And a flavonoid, an isomer thereof, a pharmaceutically acceptable salt thereof, a prodrug thereof, a hydrate thereof, or a solvate thereof.
  • antimicrobial may mean inhibiting the growth of microorganisms or killing microorganisms.
  • the sugar acid may mean a saccharide including a carboxyl group.
  • the sugars included in the sugar acid may be monosaccharides.
  • the sugar acid may include aldonic acid, ulosonic acids, aldaric acid, and uronic acid.
  • aldonic acid may mean an acid obtained by oxidizing an aldehyde group of aldose
  • uronic acid may mean that a primary hydroxyl group of 2-ketose is oxidized
  • uronic acid is a terminal hydroxyl group of aldose or ketose. It may mean that is oxidized
  • Aldar acid may mean that both ends of the aldose is oxidized.
  • the aldonic acid may include glycerin acid, xylonic acid, gluconic acid, and ascorbic acid
  • the uronic acid may include neuramic acid and ketodeoxy oxtuloconic acid
  • the uronic acid may include glucuronic acid, galacturonic acid and iduronic acid
  • the aldar acid may include tartaric acid, mucus acid and sugar acid (Saccharic acid).
  • the sugar acid may be aldaric acid or uronic acid.
  • the sugar acid may be one or more of glucuronic acid (mucuric acid), mucic acid (galcic acid) and galacturonic acid (galacturonic acid), but is not limited thereto.
  • the mucous acid is also called meso-galactaric acid.
  • isomers in particular are not only optical isomers (eg, essentially pure enantiomers, essentially pure diastereomers or mixtures thereof), but also form isomers ( conformation isomers (ie, isomers that differ only by their angles of one or more chemical bonds), position isomers (especially tautomers) or geometric isomers (eg, cis-trans isomers) do.
  • essentially pure means, when used in connection with, for example, an enantiomer or diastereomer, about 90% or more, specifically about 95% or more, of specific compounds, for example enantiomers or diastereomers, More specifically at least about 97% or at least about 98%, even more specifically at least about 99%, even more specifically at least about 99.5% (w / w).
  • pharmaceutically acceptable means the approval of a government or equivalent regulatory body to use in animals, more specifically in humans, by avoiding significant toxic effects when used in conventional medicinal dosages. Received, approved, or listed in a pharmacopoeia or recognized as another general pharmacopeia.
  • salts means salts according to one aspect of the invention that are pharmaceutically acceptable and have the desired pharmacological activity of the parent compound.
  • the salt is formed from (1) an inorganic acid such as hydrochloric acid, hydrobromic acid, sulfuric acid, nitric acid, phosphoric acid, or the like; Or acetic acid, propionic acid, hexanoic acid, cyclopentanepropionic acid, glycolic acid, pyruvic acid, lactic acid, malonic acid, succinic acid, malic acid, maleic acid, fumaric acid, tartaric acid, citric acid, benzoic acid, 3- (4-hydroxybenzoyl) Benzoic acid, cinnamic acid, mandelic acid, methanesulfonic acid, ethanesulfonic acid, 1,2-ethane-disulfonic acid, 2-hydroxyethanesulfonic acid, benzenesulfonic acid, 4-chlorobenzenes
  • prodrug refers to a drug that modulates physical and chemical properties by chemically changing a drug, which itself does not exhibit physiological activity, but is originally produced by the action of a chemical or enzyme in the body after administration. The drug can be turned into a drug.
  • hydrate refers to a compound to which water is bound, and is a broad concept including an inclusion compound having no chemical bonding force between water and the compound.
  • solvate means a higher order compound produced between molecules or ions of a solute and molecules or ions of a solvent.
  • the flavonoid may be flavonol.
  • the flavonol may be quercetin (quercetin).
  • the composition may include galacturonic acid and quercetin as active ingredients.
  • the sugar acid may be included in 0.0001 to 10.0% by weight, based on the total weight of the composition.
  • At least 0.4 wt% at least 0.5 wt%, at least 0.6 wt%, at least 0.7 wt%, at least 0.8 wt%, at least 0.9 wt%, at least 1.0 wt%, at least 3 wt%, at least 5 wt%, at least 7 wt% Or more, 9 wt% or more, 10 wt% or less, 9 wt% or less, 8 wt% or less, 6 wt% or less, 4 w
  • one or more of the flavonoids, isomers thereof, pharmaceutically acceptable salts thereof, prodrugs thereof, hydrates thereof, or solvates thereof may be included at least 0.00001% by weight, based on the total weight of the composition.
  • 0.00001% by weight, 0.0001% by weight, 0.005% by weight, 0.01% by weight, 0.5% by weight, 1% by weight, 3% by weight, 5% by weight, 7% by weight, 9% by weight It may be at least 10 wt%, up to 9 wt%, up to 8 wt%, up to 6 wt%, up to 4 wt%, up to 2 wt%, up to 1.0 wt%, up to 0.9 wt%, up to 0.8 wt%, 0.7 wt% or less, 0.6 wt% or less, 0.5 wt% or less, 0.4 wt% or less, 0.3 wt% or less, 0.2 wt% or less, 0.1 wt%, up
  • At least one of the sugar acid, flavonoids, isomers thereof, pharmaceutically acceptable salts thereof, prodrugs thereof, hydrates thereof or solvates thereof may be included in a weight ratio of 10 to 30: 1. .
  • 10: 1, 13: 1, 15: 1, 17: 1, 19: 1, 20: 1, 23: 1, 25: 1, 27: 1, 29: 1, or 30: 1 May be, but is not limited thereto.
  • the bacteria may be Staphylococcus aureus . That is, there is an antimicrobial synergistic effect against staphylococci.
  • Staphylococcus aureus is a bacterium that causes purulent diseases such as atopic dermatitis, food poisoning, purulent, otitis media and cystitis.
  • the antimicrobial composition may be a pharmaceutical composition, a food composition or a cosmetic composition.
  • the present invention is directed to an individual in need of preventing, ameliorating, or treating a disease caused by a microorganism; And preventing, ameliorating diseases caused by a microorganism comprising administering an antimicrobial composition comprising at least one of a flavonoid, an isomer thereof, a pharmaceutically acceptable salt thereof, a prodrug thereof, a hydrate thereof, or a solvate thereof. Or to a method of treatment.
  • the administration of the method may be carried out according to the administration method and administration dose described herein.
  • the present invention a sugar acid for preparing an antimicrobial food composition
  • flavonoids, isomers thereof, food acceptable salts thereof, prodrugs thereof, hydrates thereof, or solvates thereof are also useful as a sugar acid for preparing an antimicrobial food composition.
  • a sugar acid for preparing an antimicrobial cosmetic composition for preparing an antimicrobial cosmetic composition
  • flavonoids, isomers thereof, cosmetically acceptable salts thereof, prodrugs thereof, hydrates thereof, or solvates thereof for preparing an antimicrobial cosmetic composition
  • the present invention in another aspect, a sugar acid; And a combination comprising at least one of flavonoids, isomers thereof, pharmaceutically acceptable salts thereof, prodrugs thereof, hydrates thereof or solvates thereof.
  • the pharmaceutical composition may further comprise suitable carriers, excipients and diluents commonly used in the manufacture of pharmaceutical compositions.
  • the pharmaceutical composition comprising the composition according to the present invention may be used in any form suitable for pharmaceutical preparations, including external preparations such as ointments, gels, creams, patches, or sprays according to conventional methods. .
  • the dosage of the preparation is different depending on the subject's age, sex, weight, symptoms, and method of administration, but it is preferable to apply it at 1.0 to 3.0 ml per day and apply it 1 to 5 times a day for more than one month.
  • the food composition may be a health functional food composition, it may be a fermented food composition that requires fermentation, such as tea (tea), dairy products, kimchi, brewed foods.
  • the formulation of the food composition according to one aspect of the present invention is not particularly limited, but may be, for example, formulated as a tablet, granule, powder, liquid such as drink, caramel, gel, bar, and the like.
  • the food composition of each formulation may be suitably selected by a person skilled in the art according to the formulation or purpose of use in addition to the active ingredient, and may be synergistic when applied simultaneously with other raw materials.
  • Cosmetic compositions include cosmetics such as various creams, lotions, various creams, lotions, skins, and the like, cleansing agents, face washes, soaps, and essences.
  • the cosmetic added with the composition containing the composition of the present invention may take the form of a solution, an emulsion, a viscous mixture, or the like.
  • the cosmetic of the present invention is not particularly limited in the formulation, for example, latex, cream, lotion, essence, pack, gel, powder, makeup base, foundation, lotion, ointment, patch, beauty liquid, cleansing foam, cleansing Formulations such as creams, cleansing water, body lotions, body creams, body oils, body essences, shampoos, rinses, body cleansers, soaps, hair dyes, sprays and the like.
  • the cosmetic of the present invention may include a composition selected from the group consisting of water-soluble vitamins, oil-soluble vitamins, polymer peptides, polymer polysaccharides, sphingolipids and seaweed extract.
  • Other components that may be added include fats and oils, moisturizers, emollients, surfactants, organic and inorganic pigments, organic powders, ultraviolet absorbers, preservatives, fungicides, antioxidants, plant extracts, pH adjusters, alcohols, pigments, flavorings, Blood circulation accelerators, cooling agents, restriction agents, purified water and the like.
  • the compounding component which may be added other than this is not limited to this, Moreover, any of the above components can be mix
  • the checkboard test confirmed the antimicrobial effects of biochanin A (biochanin A) and sugar acids (mucoacid, glucuronic acid, galacturonic acid).
  • the initial concentration of the substance was all confirmed to be 1% and diluted twice.
  • Commercially available resazurin was added to measure the antimicrobial activity.
  • Rezazurin has the property of changing from blue to pink at pH 4 or so. That is, if the germs survive, pink, and if the germs are killed, the color becomes blue. However, even if the bacteria are killed, if the pH of the substance itself is low, pink can be obtained.
  • biocanin A had no synergistic effect on all three kinds of sugar acids and antibacterial activity (FIG. 1).
  • Example 1-2 S. aureus Confirmation of synergistic effect of quercetin and galacturonic acid on bacteria
  • S. aureus was diluted twice with 0.5% quercetin and 0.5% galacturonic acid, respectively, using a checkboard test. The antimicrobial activity against the bacteria was measured. Experimental method was the same as in Example 1-1 except for the initial concentration.

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Epidemiology (AREA)
  • Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Medicinal Chemistry (AREA)
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  • Polymers & Plastics (AREA)
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  • Engineering & Computer Science (AREA)
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  • Dermatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

La présente invention concerne une composition antibactérienne comprenant comme principes actifs de l'acide saccharique et un flavonoïde. Selon un aspect de la présente invention, il est possible de produire une composition antibactérienne qui présente une activité antibactérienne améliorée grâce à un effet synergique entre l'acide saccharique et un flavonoïde, qui en sont les principes actifs. L'utilisation de la composition antibactérienne de la présente invention est utile car cette dernière peut inhiber la prolifération de divers micro-organismes, y compris des bactéries, et détruire ces micro-organismes avec une faible concentration des principes actifs tout en diminuant la nocivité sur les êtres humains et l'environnement.
PCT/KR2016/010910 2015-09-30 2016-09-29 Composition antibactérienne comprenant de l'acide saccharique et un flavonoïde WO2017057919A1 (fr)

Applications Claiming Priority (2)

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KR10-2015-0137240 2015-09-30
KR1020150137240A KR20170038214A (ko) 2015-09-30 2015-09-30 당산 및 플라보노이드를 포함하는 항균용 조성물

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11684597B2 (en) 2019-01-28 2023-06-27 The United States Of America As Represented By The Secretary Of The Army Administration of tailored feedstock to increase nitro-containing amphenicol antibiotic susceptibility

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050202064A1 (en) * 1996-03-15 2005-09-15 Nobuto Koyama Product of heat treatment of uronic acid, food, drink or drug including the product
KR100700912B1 (ko) * 2005-12-30 2007-03-28 고려대학교 산학협력단 녹차 잎에서 분리된 산성 다당류를 함유하는 피부 여드름간균과 아토피 황색 포도상 구균의 인체 세포결합 저해활성조성물
WO2009039324A1 (fr) * 2007-09-21 2009-03-26 Forest Laboratories Holdings Limited Formes de dosage soluble contenant des dérivés de céphème convenant pour une administration parentérale
CN101797266A (zh) * 2010-04-21 2010-08-11 张登科 一种含有槲皮苷的药物组合物及用途

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050202064A1 (en) * 1996-03-15 2005-09-15 Nobuto Koyama Product of heat treatment of uronic acid, food, drink or drug including the product
KR100700912B1 (ko) * 2005-12-30 2007-03-28 고려대학교 산학협력단 녹차 잎에서 분리된 산성 다당류를 함유하는 피부 여드름간균과 아토피 황색 포도상 구균의 인체 세포결합 저해활성조성물
WO2009039324A1 (fr) * 2007-09-21 2009-03-26 Forest Laboratories Holdings Limited Formes de dosage soluble contenant des dérivés de céphème convenant pour une administration parentérale
CN101797266A (zh) * 2010-04-21 2010-08-11 张登科 一种含有槲皮苷的药物组合物及用途

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
AMIN, M. U. ET AL.: "Antiblotic Additive and Nynergistic Action ot Rutin. Morin and Quercetin against Methicillin Resistant Staphylococcus Aureas", BMC COMPLEMENTARY AND ALTERNATIVE MEDICINE, vol. 15, no. 59, 12 March 2015 (2015-03-12), XP021219392 *
BETTS, J. W. ET AL.: "In Vitro Activity of Epigallocatechin Gallate and Quercetin Alone and in Combination Versus Clinical Isolates of Methicillin-resistant Staphylococcus Aureus", JOURNAL OF NATURAL PRODUCTS, vol. 78, no. 8, pages 2145 - 2148, XP055385473 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11684597B2 (en) 2019-01-28 2023-06-27 The United States Of America As Represented By The Secretary Of The Army Administration of tailored feedstock to increase nitro-containing amphenicol antibiotic susceptibility

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