WO2020059828A1 - バイオフィルム形成抑制剤 - Google Patents

バイオフィルム形成抑制剤 Download PDF

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Publication number
WO2020059828A1
WO2020059828A1 PCT/JP2019/036851 JP2019036851W WO2020059828A1 WO 2020059828 A1 WO2020059828 A1 WO 2020059828A1 JP 2019036851 W JP2019036851 W JP 2019036851W WO 2020059828 A1 WO2020059828 A1 WO 2020059828A1
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Prior art keywords
echinacea
biofilm formation
item
streptococcus
formation inhibitor
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PCT/JP2019/036851
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English (en)
French (fr)
Japanese (ja)
Inventor
亨 石原
行哲 薮田
礼訓 八巻
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株式会社山田養蜂場本社
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Priority to JP2020549092A priority Critical patent/JP7368858B2/ja
Publication of WO2020059828A1 publication Critical patent/WO2020059828A1/ja

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    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23FCOFFEE; TEA; THEIR SUBSTITUTES; MANUFACTURE, PREPARATION, OR INFUSION THEREOF
    • A23F3/00Tea; Tea substitutes; Preparations thereof
    • A23F3/16Tea extraction; Tea extracts; Treating tea extract; Making instant tea
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G3/00Sweetmeats; Confectionery; Marzipan; Coated or filled products
    • A23G3/34Sweetmeats, confectionery or marzipan; Processes for the preparation thereof
    • A23G3/36Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds
    • A23G3/48Sweetmeats, confectionery or marzipan; Processes for the preparation thereof characterised by the composition containing organic or inorganic compounds containing plants or parts thereof, e.g. fruits, seeds, extracts
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23GCOCOA; COCOA PRODUCTS, e.g. CHOCOLATE; SUBSTITUTES FOR COCOA OR COCOA PRODUCTS; CONFECTIONERY; CHEWING GUM; ICE-CREAM; PREPARATION THEREOF
    • A23G4/00Chewing gum
    • A23G4/06Chewing gum characterised by the composition containing organic or inorganic compounds
    • AHUMAN NECESSITIES
    • A23FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23LFOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A23L33/105Plant extracts, their artificial duplicates or their derivatives
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K36/00Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
    • A61K36/18Magnoliophyta (angiosperms)
    • A61K36/185Magnoliopsida (dicotyledons)
    • A61K36/28Asteraceae or Compositae (Aster or Sunflower family), e.g. chamomile, feverfew, yarrow or echinacea
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/96Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
    • A61K8/97Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
    • A61K8/9783Angiosperms [Magnoliophyta]
    • A61K8/9789Magnoliopsida [dicotyledons]
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/06Ointments; Bases therefor; Other semi-solid forms, e.g. creams, sticks, gels
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00Medicinal preparations characterised by special physical form
    • A61K9/08Solutions
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/02Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04Antibacterial agents
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q11/00Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses

Definitions

  • the present invention relates to a biofilm formation inhibitor.
  • Biofilms are diverse populations of bacteria protected by polysaccharides. Bacteria attached to the surface of the substance produce polysaccharides such as water-insoluble glucan to form microcolonies, and various bacterial groups propagate in the microcolonies to form biofilms. Representative examples of biofilms include slime generated around water in kitchens, bathrooms, washrooms, and the like, and plaque formed in the oral cavity by periodontal disease-related bacteria.
  • Glucan sucrose (glucansucrase) is produced by a strain of the genus Streptococcus sp. It has been found to form biofilms. Among them, Streptococcus mutans and Streptococcus downey of the genus Streptococcus are causative bacteria of caries.
  • Streptococcus mutans bacteria survive in the human oral cavity and proliferate using nutrients such as sugars consumed in meals.
  • insoluble glucan is generated from sugar by the enzyme glucan sucrose (GTF) of Streptococcus mutans bacteria, and a biofilm (plaque) is formed on the tooth surface.
  • GTF glucan sucrose
  • plat a biofilm
  • Various bacteria, including Streptococcus mutans bacteria adhere to this biofilm and generate acids. This acid demineralizes tooth enamel and causes tooth decay. Therefore, suppression of biofilm formation by Streptococcus mutans bacteria leads to prevention of caries.
  • Patent Documents 1 to 3 Non-Patent Document 1
  • Patent Document 1 reports that legume 7S globulin, a legume storage protein, has a biofilm formation inhibitory effect on Streptococcus mutans.
  • Patent Document 2 reports that serotonin and a serotonin derivative have an effect of inhibiting the biofilm formation of Streptococcus mutans in addition to inhibiting glucan sucrose activity.
  • Patent Document 3 reports that an extract of Assam tea can suppress biofilm formation of bacteria.
  • Non-Patent Document 1 As a result of examining the effect of green tea and black tea extracts on glucan synthesis catalyzed by glucosyltransferase derived from Streptococcus mutans, it was reported that the extract significantly inhibited the synthesis of insoluble glucan. .
  • Assam tea, green tea and black tea contain caffeine, which causes yellowing of leaves and promotes vasoconstriction, so that people who do not want to take it, and pregnant women There is a problem that there are people who can not take such.
  • An object of the present invention is to provide a biofilm formation inhibitor for Streptococcus spp., Which is highly safe and has an excellent biofilm formation inhibitory action.
  • Echinacea which is not known to have a biofilm formation inhibitory effect by Streptococcus mutans bacteria, similar to Echinacea
  • green tea showed growth ability against Streptococcus mutans bacteria
  • hot water extract of Echinacea showed growth inhibition.
  • echinacea does not contain caffeine and thus does not have the above-mentioned problems.
  • the present invention has been completed based on these findings and further studied, and provides the following biofilm formation inhibitor of Streptococcus sp.
  • Item 1 A biofilm formation inhibitor for Streptococcus spp., Comprising a hot water extract of Echinacea as an active ingredient.
  • Item 2. Item 4. The biofilm formation inhibitor according to Item 1, comprising only a hot water extract of echinacea as an active ingredient.
  • Item 3. Item 3.
  • Item 4. Item 4.
  • Item 5. Item 5.
  • Item 6. The biofilm formation inhibitor according to any one of Items 1 to 5, which is for human use.
  • Item 7. A method for suppressing the formation of a biofilm of Streptococcus sp., Comprising the step of administering an effective amount of a hot water extract of Echinacea to a mammal.
  • Item 9. Item 9.
  • Item 7 or 8 wherein the Streptococcus bacterium is Streptococcus mutans.
  • Item 10. The method according to any one of Items 7 to 9, wherein the hot water extract of Echinacea is administered in the form of a gum, mouthwash, dentifrice, candy, or tea beverage.
  • Item 11. The method according to any one of Items 7 to 10, wherein the mammal is a human.
  • Item 12. Use of a hot water extract of Echinacea in the production of a biofilm formation inhibitor of Streptococcus.
  • Item 13 Item 13. The use according to item 12, wherein echinacea leaves are used.
  • Item 14. Item 14.
  • Item 12 or 13 wherein the Streptococcus bacterium is Streptococcus mutans.
  • Item 15. The use according to any one of Items 12 to 14, wherein the biofilm formation inhibitor is a gum, a mouthwash, a dentifrice, a candy, or a tea beverage.
  • Item 16. The use according to any one of Items 12 to 15, wherein the biofilm formation inhibitor is for human use.
  • Item 17. A composition for suppressing the formation of a biofilm of Streptococcus, comprising a hot water extract of Echinacea as an active ingredient.
  • Item 18. Item 18.
  • Item 19. Item 19.
  • Item 20. The composition according to any one of Items 17 to 19, which is a gum, a mouthwash, a dentifrice, a candy, or a tea beverage.
  • Item 21. The composition according to any one of Items 17 to 20, which is for human use.
  • the hot water extract of Echinacea has excellent biofilm formation inhibitory activity, glucan sucrose inhibitory activity, and growth inhibitory activity against Streptococcus spp., Thus being useful as an active ingredient of a Streptococcus spp. It is.
  • Echinacea is a safe material, with its aerial parts and roots including flowers being widely used as supplements, mainly in North America and Europe. Echinacea does not contain caffeine, which is useful for people who do not want to take caffeine and who cannot.
  • the biofilm formation inhibitor of Streptococcus bacterium of the present invention contains a hot water extract of Echinacea as an active ingredient, and preferably contains only a hot water extract of Echinacea as an active ingredient.
  • Echinacea purpurea (Echinacea purpurrea) is a perennial plant native to the United States, which belongs to the Asteraceae family. Echinacea is a type of herb and is thought to have a protective effect against colds, flu, etc. by increasing immunity.
  • a partial or whole extract of echinacea can be used.
  • a part of echinacea include leaves, bark, stems, stems, fruits, seeds, flowers, roots, and the like. These can be used alone or in combination of a plurality of sites, and are preferably leaves.
  • Echinacea can be used in any state, such as a raw product, a dried product, a cut or crushed product.
  • the extraction temperature for producing the hot water extract of Echinacea can be appropriately set and is usually 40 to 100 ° C, preferably 70 to 100 ° C.
  • the extraction time can be appropriately set and is usually 5 minutes to 5 days, preferably 10 minutes to 24 hours.
  • the number of extractions is usually 1 to 5 times, preferably 1 to 3 times.
  • Water used when producing the hot water extract of echinacea is not particularly limited, and includes, for example, tap water, groundwater, mineral water, ion-exchanged water, distilled water, pure water, and the like.
  • the recovered hot water extract can be used as it is. If necessary, filters, ultrafiltration, molecular sieve chromatography (gel filtration), adsorption chromatography, ion exchange chromatography, affinity chromatography, high-performance liquid Purification by chromatography (HPLC), dialysis, combinations thereof, and the like can be performed.
  • the hot water extract of the above echinacea As the hot water extract of the above echinacea, the recovered extract (including those further purified as necessary), a concentrated solution obtained by concentrating the extract, freeze-drying, spray drying, etc. And the like from which solids have been removed.
  • the concentration, freeze-drying and spray-drying of the extract can be performed according to a conventional method.
  • the biofilm formation inhibitor of the present invention may contain additional components as long as the effects of the present invention are not hindered.
  • the ratio of the hot water extract of echinacea in the biofilm formation inhibitor is 0.001 to 99.9% by mass, preferably 0.01 to 80% by mass, more preferably 0.1 to 70% by mass, and Preferably, 1 to 50% by mass can be exemplified.
  • the biofilm formation inhibitor of the present invention is not particularly limited in its form, and may have a formulation such as a powder, a granule, a tablet, a capsule, a liquid, a suspension, and an emulsion.
  • biofilm formation inhibitor of the present invention can be suitably used as a component of cosmetics, food compositions, quasi-drugs, and pharmaceuticals.
  • Biofilm formation inhibitor of the present invention cosmetics, food compositions (particularly health, health maintenance, food compositions for the purpose of promotion, such as health foods, functional foods, nutritional composition (nutritional composition), Nutritional supplements, supplements, foods for health use, foods for specified health use, nutritional functional foods, or functionally labeled foods)), quasi-drugs, and pharmaceuticals are also included.
  • the biofilm formation inhibitor of the present invention also includes the meaning of an additive that imparts a biofilm formation inhibitory effect on Streptococcus spp.
  • components commonly used in cosmetics for example, bactericides, preservatives, surfactants, alcohols, aqueous components, water, coloring agents, pH adjusters, dissolving agents Auxiliaries, abrasives, foaming agents, humectants, enzymes, flavoring agents, chelating agents, thickeners, cleaning agents (lactic acid bacteria), and the like can be appropriately compounded as necessary.
  • cosmetics are also arbitrary, and examples include (paste or liquid) dentifrice, mouthwash and the like.
  • excipients if necessary, excipients, brighteners, minerals, vitamins, flavonoids, quinones, polyphenols, amino acids, nucleic acids, essential fatty acids, cooling agents, binders, sweeteners , A disintegrant, a lubricant, a colorant, a fragrance, a stabilizer, a preservative, a sustained release regulator, a surfactant, a dissolving agent, a wetting agent, and the like.
  • Food compositions include all foods and drinks that can be consumed by animals (including humans).
  • the type of food and drink is not particularly limited, for example, beverages (soft drinks such as coffee, juice, tea drinks, milk drinks, lactic acid drinks, yogurt drinks, carbonated drinks, sake such as sake, Western liquor, fruit wine Spreads (such as custard cream); Pastes (such as fruit paste); Western confectionery (chocolate, donut, pie, cream puff, gum, jelly, candy, cookie, cake, pudding, etc.); Japanese confectionery (Dafuku, mochi) , Buns, castella, anmitsu, yokan, etc.); frozen desserts (ice cream, popsicles, sherbet, etc.); (Dressing, sprinkling, umami seasoning, soup base, etc.).
  • beverages soft drinks such as coffee, juice, tea drinks, milk drinks, lactic acid drinks, yogurt drinks, carbonated drinks, sake such as sake, Western liquor, fruit wine Spreads (such as custard cream); Pastes (such as fruit
  • the dosage unit form when used as a supplement is not particularly limited and can be appropriately selected and includes, for example, tablets, capsules, granules, solutions, powders and the like.
  • the amount of the food composition to be taken can be appropriately set according to various conditions such as the weight, age, sex, and symptoms of the user.
  • Echinacea Only the hot water extract of Echinacea can be used for the above-mentioned medicines, or it can be used by mixing with other medicine ingredients described in the Japanese Pharmacopoeia such as vitamins and crude drugs.
  • composition of the present invention is prepared as a medicament, a hot water extract of Echinacea, together with a non-toxic carrier, diluent or excipient acceptable in a medicament, tablets (uncoated tablets, sugar-coated tablets, effervescent tablets, films) Coated tablets, chewable tablets, troches, etc.), capsules, pills, powders (powder), fine granules, granules, liquids, suspensions, emulsions, syrups, pastes, etc.
  • oral and oral preparations can be obtained.
  • the dose of the drug can be appropriately determined according to various conditions such as the weight, age, sex, and symptoms of the patient.
  • the pharmaceuticals and cosmetics of the present invention also include quasi-drugs.
  • the biofilm formation inhibitor of the present invention described above is applied to mammals including humans (preferably humans).
  • the biofilm formation inhibitor of the present invention is basically used for oral use or in the oral cavity.
  • the hot water extract of Echinacea has an excellent biofilm formation inhibitory action, a glucan sucrose inhibitory activity, and a growth inhibitory action against Streptococcus spp., So that Streptococcus spp. It is useful as an active ingredient of a biofilm formation inhibitor of Streptococcus mutans.
  • the hot water extract of Echinacea has an effect of suppressing the biofilm formation of Streptococcus spp., And thus is expected to have a preventive effect on caries (caries), gingivitis, periodontal disease, bad breath, and the like.
  • Echinacea is still highly safe, with the aerial parts and roots including flowers being widely used as supplements mainly in North America and Europe. Echinacea does not contain caffeine, which is useful for people who do not want to take caffeine and who cannot.
  • Test example 1 Glucan sucrose has been confirmed to be produced by bacteria of the genus Streptococcus, Lactococcus, Leuconostoc, Weissera, or Lactobacillus of the order Lactobacillus to form a biofilm.
  • Streptococcus mutans and Streptococcus dawnei belonging to the genus Streptococcus are causative bacteria of caries.
  • the test was carried out focusing on the glucan sucrose activity by Streptococcus mutans, which is generally known as a causative bacteria of caries, and biofilm formation.
  • ⁇ Method> Dissolve 0.5 g of dried echinacea or green tea with 25 mL of water, extract with hot water for 10 minutes, filter through qualitative filter paper No. 2 (ADVATEC), dry with centrifugal evaporator Genevac EZ-2, and distill The test was carried out after adjusting to a predetermined concentration with water.
  • the glucan sucrose inhibitory activity, the antibacterial activity against Streptococcus mutans bacteria, and the biofilm formation inhibitory effect of Streptococcus mutans bacteria were evaluated.
  • the glucan sucrose inhibitory activity was evaluated by measuring the amount of glucose produced by the enzyme reaction using Glucose CII-Test Wako (Fujifilm Wako Pure Chemical Industries, Ltd.).
  • Antibacterial activity was determined by incubating Streptococcus mutans bacteria in a brain heart infusion medium at 37 ° C. for 0, 4, 8, 20, and 24 hours, and the growth of the bacteria was evaluated by turbidity (600 nm).
  • Biofilm formation inhibitory effect by Streptococcus mutans bacteria was incubated in brain heart infusion medium at 37 ° C for 48 hours, and Streptococcus mutans attached to microtiter plate was stained with crystal violet and extracted with ethanol. was measured at 595 nm.
  • glucan sucrose inhibitory activity (IC 50 ) of the hot water extract of Echinacea leaves is 4.03 mg / mL, and Hattori M 1) has reported that biofilm formation by Streptococcus mutans bacteria has been suppressed by green tea (IC 50). : 3.48 mg / ml).
  • FIG. 1 shows the test results of the antibacterial activity against Streptococcus mutans bacteria.
  • Streptococcus mutans significantly increased after 20 hours and 24 hours at concentrations of 1.25, 2.50, and 5.00 mg / ml.
  • concentrations of 1.25, 2.50, and 5.00 mg / ml 1.25, 2.50, and 5.00 mg / ml.
  • an increase in Streptococcus mutans bacteria was not confirmed at any concentration at the same time.
  • Table 2 shows the test results of the biofilm formation inhibitory effect of Streptococcus mutans bacteria.
  • the biofilm formation amount when cultured in a brain heart infusion medium was defined as 100%.
  • the bifilm formation inhibitory effect of Streptococcus mutans bacteria was confirmed to be 49.1% and 71.8%, respectively, when the amount of biofilm formation when the hot water extract of Echinacea leaves and green tea was exposed to 2.5 mg / ml was confirmed. It was confirmed that the leaf hot water extract had a stronger biofilm formation inhibitory effect than the green tea hot water extract.
  • Echinacea is a novel material whose biofilm formation inhibitory effect by Streptococcus mutans is not known, and as compared with Echinacea, the activity of green tea is higher than that of green tea used in beverages. It was found that they exhibited a formation inhibitory effect and a glucan sucrose inhibitory activity of the same degree. Green tea showed growth ability against Streptococcus mutans bacteria, while Echinacea showed growth inhibition.
  • Test example 2 1.0 g of the dried echinacea leaf was extracted with 20 mL of distilled water using hot water for 60 minutes, and filtered through qualitative filter paper No. 2 (ADVATEC). Hot water extraction was further performed twice using the filtration residue. In addition, 1.0 g of dried echinacea leaves was extracted by shaking with 20 mL of 95% ethanol for 10 minutes, and filtered through qualitative filter paper No. 2 (ADVATEC). Shaking extraction was further performed twice using the filtration residue. The obtained filtrate was dried with a centrifugal evaporator miVAC and a freeze dryer FREEZE DRYER FD-5N, and the extraction efficiency was calculated from the obtained extract powder weight. Table 3 shows the results. As a result, the extraction efficiency with hot water was 8 times that of ethanol extraction with 4%, and the extraction efficiency was 32%.

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PCT/JP2019/036851 2018-09-21 2019-09-19 バイオフィルム形成抑制剤 WO2020059828A1 (ja)

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Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004532831A (ja) * 2001-03-27 2004-10-28 シー.エス. バイオサイエンス、 インコーポレイテッド 歯科用調剤
JP2005068014A (ja) * 2003-08-21 2005-03-17 Nonogawa Shoji Kk 抗菌剤
JP2005511584A (ja) * 2001-11-06 2005-04-28 ペルフェッティ ヴァン メッレ ソシエタ ペル アチオニ 固形口腔用組成物
JP2005512992A (ja) * 2001-11-06 2005-05-12 ペルフェッティ ヴァン メッレ ソシエタ ペル アチオニ 抗歯石および抗歯垢固形口腔組成物従来技術
JP2007001961A (ja) * 2005-06-27 2007-01-11 Forestry & Forest Products Research Institute 抗菌剤及びそれを含む口腔用組成物並びに飲食品
CN108245552A (zh) * 2018-01-24 2018-07-06 弘美制药(中国)有限公司 一种用于口腔的组合物及其应用

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004532831A (ja) * 2001-03-27 2004-10-28 シー.エス. バイオサイエンス、 インコーポレイテッド 歯科用調剤
JP2005511584A (ja) * 2001-11-06 2005-04-28 ペルフェッティ ヴァン メッレ ソシエタ ペル アチオニ 固形口腔用組成物
JP2005512992A (ja) * 2001-11-06 2005-05-12 ペルフェッティ ヴァン メッレ ソシエタ ペル アチオニ 抗歯石および抗歯垢固形口腔組成物従来技術
JP2005068014A (ja) * 2003-08-21 2005-03-17 Nonogawa Shoji Kk 抗菌剤
JP2007001961A (ja) * 2005-06-27 2007-01-11 Forestry & Forest Products Research Institute 抗菌剤及びそれを含む口腔用組成物並びに飲食品
CN108245552A (zh) * 2018-01-24 2018-07-06 弘美制药(中国)有限公司 一种用于口腔的组合物及其应用

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