KR20150145332A - Anti-periodontitis composition comprising flavone compounds or Kaempferia parviflora extract - Google Patents

Abstract

The present invention relates to a composition for preventing, alleviating, or treating periodontitis containing kaempferia parviflora extracts or fractions thereof as an active ingredient, and a composition for preventing, alleviating, or treating periodontitis containing at least one flavone compounds selected from a group comprising compounds expressed as chemical formula 1 to 3 or pharmaceutically acceptable salts thereof as an active ingredient. The active ingredients can be effectively used for managing oral and periodontal diseases by suppressing generation of collagen-degrading enzymes and bone resorption enzymes.

Description

The present invention relates to a periodontitis composition comprising flavone compounds or camphoria parviflora extract,

The present invention relates to a process for the production of < RTI ID = 0.0 > Kaempferia & parviflora extract or fraction thereof, or a flavone compound isolated therefrom as an active ingredient. The present invention also relates to a composition for preventing, ameliorating or treating periodontal disease.

The periodontal disease is the most common oral disease with tooth decay (Narang R. et al., Bangladesh Journal of Medical Science, 2013, 12, 244-249). Clinically, periodontal inflammation and bleeding, gingivitis (Preshaw PM et al., Diabetologia, 2012, 55, 21-31). In the present study, it was reported that the tooth loss was caused by the reduction of the tooth surface. Periodontal disease is a series of processes consisting of colonization of bacteria, infiltration of periodontal tissue by bacteria, and destruction of periodontal tissue.

First, the saliva protein present in the saliva in the oral cavity is adsorbed on the tooth surface to form a film. Plaque is formed by growing Gram-positive bacteria such as Streptococcus on the surface of this coating (Taubman MA et al., Nature Reviews Immunology, 2006, 6, 555-563). Over time, as the plaque moves in the apical direction, anaerobic gram-negative bacteria such as Porphyromonas and Actinobacillus grow, and these bacteria, bacterial components, and bacterial products are released into the gingival epithelium (Wolf HF et al., Periodontology, Stuttgart, New York: Thieme, 2006). Ultimately, lipopolysaccharide, a cell wall component of germs, secretes cytokines such as active oxygen, prostaglandin, leukotrien, histamine, and interleukin secreted by stimulating the immune system cytokine causes inflammation of the gums, and collagen, which is a matrix of periodontal tissue, is degraded by enzymes such as collagenase, resulting in retraction of the gums. This process continues with the destruction of the entire periodontal tissue, including loss of the alveolar bone (Madianos PN et al., J Clin Periodontol 2005, 32, 57-71; Mayank H. et al. Journal of Oral Science, 2011, 53, 263-271).

Antimicrobial agents such as chlorhexidine, sanguinarine and triclosan and antiinflammatory agents such as hydrogen peroxide have been applied to oral products such as toothpaste and toothpaste to kill periodontal disease bacteria by treatment of periodontal disease, (Leszczyʼnska A. et al., Advances in Medical Sciences, 2011, 56, 123-131). Because periodontal disease is a complex complication of inflammation caused by stimulation of microorganisms, reduction of collagen by matrix metalloproteinase (MMP), and loss of bone, periodontal disease is a common complication of periodontal disease (Craig SM et al., Biomark Med., 2010, 4, 171-189).

MMP-8, a collagenase, is known to degrade collagen type 1, collagen type 3, and extracellular substances, which are major components of periodontal tissue (Gursoy UK et al. J Clin Periodontol., 2010, 37, 487-493; Adina BB, et al., Annals of RSCB, 2012, 17, 251-257). Unlike other collagen degrading enzymes, MMP-8 is overexpressed in inflammatory periodontal tissue, and the amount of MMP-8 found in saliva can confirm the onset and extent of periodontal disease and periodontal disease (Gursoy Killi M. et al., J Clin Periodontol. 2002, 2002, 38, 306-321; < RTI ID = 0.0 > , 29, 224-232).

Tartrate-resistant acid phosphatase (TRAP), a type of osteoclastic enzyme, is known to occur specifically when osteoclast precursor cells differentiate into osteoclasts Baul'huin M. et al., Cell Mol Life Sci. ≪ RTI ID = 0.0 > et al., ≪ / RTI > , 2007, 64, 2334-2350). TRAP is involved in the absorption and degradation of bone matrix and collagen, and is known to affect osteoclast differentiation, polynucleation, maturation and activation (Wei W., Wan Y., PPAR Res., 2011, Nat Rev Drug Discov., 2011, 11, 401-419; Wang X. et al., ≪ RTI ID = 0.0 > Curr Opin Biotechnol., 2012, 23, 570-578).

(Tewtrakul S. et al., Food Chem., 2009, 115, 534-538), antiallergic effects (Tewtrakul S. et al., J. Ethnopharmacol. 2008, 109, 535-538), antibacterial effects (Kummee S. et al., Songklanakarin J Sc Technol., 2008, 30, 463-466) There is no known about.

Therefore, the present inventors have newly confirmed that the extract of camphorafibiflora or the flavone-based compounds isolated therefrom is effective for preventing, improving and treating periodontal disease by inhibiting the production of collagenolytic enzymes and bone resorption enzymes, .

It is an object of the present invention to provide a pharmaceutical composition for preventing or treating periodontal disease and a method for treating periodontal disease using the same.

Another object of the present invention is to provide a food composition for preventing or improving periodontal disease.

It is another object of the present invention to provide a composition for oral care.

It is still another object of the present invention to provide a composition for inhibiting the production of collagenolytic enzymes and bone resorption enzymes, which can be used for the treatment of periodontal disease by inhibiting the production of collagenolytic enzymes and bone resorption enzymes, and a method for suppressing them.

In one aspect of the present invention, there is provided a composition for preventing, ameliorating or treating periodontal disease, comprising a camphoria parviflora extract or a fraction thereof as an active ingredient.

According to another aspect of the present invention, there is provided a pharmaceutical composition for preventing, ameliorating or treating periodontal disease comprising at least one flavone-based compound selected from the group consisting of compounds represented by the following formulas (1) to (3) or a pharmaceutically acceptable salt thereof as an active ingredient A composition is provided:

[Chemical Formula 1]

,

,

(2)

, 및

, And

(3)

.

.

Hereinafter, the present invention will be described in detail.

The present invention relates to a process for the production of < RTI ID = 0.0 > Kaempferia & parviflora extract or fractions thereof as an active ingredient. The present invention also provides a composition for prevention, improvement and treatment of periodontal disease.

Since the composition of the present invention inhibits the production of collagenolytic enzymes and bone resorption enzymes, it can be usefully used for prevention, improvement and treatment of periodontal disease.

The term "prevention" in the present invention means any action that inhibits periodontal disease or delays the onset of the periodontal disease by administration of the composition.

The term "improvement" in the present invention means any action that improves or improves the symptoms of periodontal disease by the administration of the composition.

In the present invention, the term "treatment" means any action that improves or alters the symptoms caused by periodontal disease by the administration of the composition.

Periodontal disease is often referred to as style, and it is divided into gingivitis and periodontitis depending on the severity of the disease. It is relatively light and has a rapid recovery period. Gingivitis is a type of periodontal disease that is limited to soft tissues. Gingivitis and gingivitis around the bone is a case of progression. In the present invention, periodontal disease includes all diseases or symptoms such as gingivitis, gingival bleeding, gingival retraction, periodontal pocket formation, and alveolar bone destruction.

Kaempferia parviflora ) is a kind of ginger and plant, often called black ginger, black ginger, black ginger and so on. Its shape is similar to that of ordinary ginger, but its genus is black. Its origin is native to the tropical primeval forests of Southeast Asia, Thailand and Laos, and is currently grown in Thailand and Laos. Leaves tend to bend up straight from the center of the lump, and the bottom is reddish green, with new leaves emerging from late May to early June. Black ginger spreads its leaves broadly in early June and then blooms with a white, purple flower, usually hidden under the leaf.

In the present invention, commercially available commercially available camphorafibiflora may be purchased, used, or cultivated or cultivated in nature.

There is no particular limitation on the method for producing the camphorafibiblofera extract, and conventional extraction methods in the art such as ultrasonic extraction, filtration and reflux extraction can be used. Preferably, the camphorafibrate dried product obtained by pulverizing rootstocks, stems or leaves of the camphorafibiflora with foreign substances removed by washing and drying is dissolved in water, C ₁ -C ₆ organic solvent, subcritical fluid and supercritical fluid And more preferably one or more solvents selected from the group consisting of C ₁ -C ₆ alcohols, acetone, ether, benzene, chloroform, ethyl acetate, methylene chloride, hexane, cyclohexane and petroleum ether And C ₁ -C ₆ organic solvent extracts selected from the group consisting of ethanol extracts, and most preferably ethanol extracts. At this time, the extraction solvent is preferably 2 to 20 times the dry weight of the camphorafibiblo flora. For example, the dried product of Camphorafibioflora is pulverized and placed in an extraction container, followed by adding ethanol, stirring at 50 ° C for 60 minutes, and filtering to obtain an ethanol extract. In addition, the camphoria faviflora extract of the present invention can be obtained by extracting and purifying the dried camphorafabi flora by using an ultra-high pressure extraction apparatus, or by separating and purifying from the oil obtained by directly pressing the camphoria faviflora plant . If necessary, it may further comprise a step of filtration, concentration or lyophilization, according to methods known to those skilled in the art. In addition, using known techniques such as solvent fractionation, silica gel chromatography, prep-HPLC, etc., specific fractions enriched in active material can be prepared.

In the present invention, a camphorafibiflora extract such as an ethanol extract, a hot water extract, a methanol extract, a hexane extract, an ethyl acetate extract, and a chloroform extract was prepared using a dry powder of camphorafabi flora (Example 1).

On the other hand, in the present invention, the fraction of camphorafibiflora can be obtained by fractionation from the camphorafabiflora extract. For example, a fraction can be obtained by loading a methanol extract of camphoria fibrilola into a column, fractionating it with a mixed organic solvent, fractionating some of the fraction into alcohol again, and further fractionating the mixture with a mixed organic solvent 2).

The present invention also provides a composition for the prevention, improvement and treatment of periodontal disease comprising at least one flavone-based compound selected from the group consisting of compounds represented by the following formulas (1) to (3) or a pharmaceutically acceptable salt thereof as an active ingredient do:

[Chemical Formula 1]

,

,

(2)

, 및

, And

(3)

.

.

In the composition of the present invention, the flavone-based compounds represented by the above general formulas (1) to (3) are representative active ingredients present in camphorafibiflora and can be isolated from the extracts of camphorafibiflora. However, it can be isolated and isolated from plants such as Caesalpinia pulcherrima, Boesenbergia pandurata, Helichysum nitens, etc., as well as Camperia faviflora (Srinivas et al, Phytochemistry, 63 (7): 789-793, 2003; Tharworn et al., Phytochemistry, 22 (2): 625-626, 1983; Francisco et al., Phytochemistry, 27 (3): 753-755, 1988).

The separation and purification of the flavonoid compounds represented by the above formulas (1) to (3) of the present invention can be carried out by column chromatography and high performance liquid chromatography (HPLC), which are packed with various synthetic resins such as silica gel and activated alumina May be used alone or in combination, but the extraction and separation purification method is not necessarily limited to the above method.

As an example, a method for separating the compound represented by the above Chemical Formulas 1 to 3 according to the present invention from a camphorafabi flora can be carried out as follows.

The compound of formula (1) (5,7- Dimethoxy flavone )

The methanol extract of camphorafabi flora was loaded on a column packed with silica gel and separated into a solvent mixture of ethyl acetate and methanol in a ratio of 10: 0.5 (v / v) The third fraction of the five fractions was further separated by 70% methanol using Rp-18 column chromatography, followed by separation into two fractions in total, and the second fraction of the two fractions was again purified by silica gel After loading onto a packed column, the mixture was separated into a solvent mixed with ethyl acetate and methanol at a ratio of 10: 0.4 (v / v) and separated into two fractions in a total of two fractions. The first fraction (See Example 2-1).

The compound of formula (2) (5,7,4'- Trimethoxy flavone )

The methanol extract of camphorafabi flora was loaded on a column packed with silica gel and separated into a solvent mixture of ethyl acetate and methanol in a ratio of 10: 0.5 (v / v) The fourth fraction of the five fractions was further separated by 70% methanol using Rp-18 column chromatography, followed by separation into two fractions in total, and the second fraction of the two fractions was concentrated to dryness (See Example 2-2).

The compound of formula (3) (3,5,7,3 ', 4'- Pentamethoxy flavone )

The methanol extract of camphorafabi flora was loaded on a column packed with silica gel and separated into a solvent mixture of ethyl acetate and methanol in a ratio of 10: 0.5 (v / v) The third fraction of the five fractions was further separated by 70% methanol using Rp-18 column chromatography and divided into two fractions according to the separation procedure, and the first fraction of the two fractions was concentrated to dryness (See Examples 2-3).

In addition, the compounds represented by Formulas 1 to 3 of the present invention can be used in the form of pharmaceutically acceptable salts. &Quot; Pharmaceutically acceptable, " as used herein, are physiologically tolerated and when administered to humans, do not normally produce an allergic reaction or a similar reaction. As salts, acid addition salts formed by pharmaceutically acceptable free acids are useful. Acid addition salts include those derived from inorganic acids such as hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, hydrobromic acid, hydroiodic acid, nitrous acid or phosphorous acid, and aliphatic mono- and dicarboxylates, phenyl-substituted alkanoates, hydroxyalkanoates, Dioleate, aromatic acid, aliphatic and aromatic sulfonic acids. Such pharmaceutically innocuous salts include, but are not limited to, sulfate, pyrosulfate, bisulfate, sulfite, bisulfite, nitrate, phosphate, monohydrogenphosphate, dihydrogenphosphate, metaphosphate, pyrophosphate chloride, bromide, Butyrate, caprate, heptanoate, propiolate, oxalate, malonate, succinate, succinate, maleic anhydride, maleic anhydride, , Sebacate, fumarate, maleate, butyne-1,4-dioate, hexane-1,6-dioate, benzoate, chlorobenzoate, methylbenzoate, dinitrobenzoate, hydroxybenzoate, Methoxybenzoate, phthalate, terephthalate, benzene sulfonate, toluene sulfonate, chlorobenzene sulfide Propyl sulphonate, naphthalene-1-yne, xylenesulfonate, phenylsulfate, phenylbutyrate, citrate, lactate,? -Hydroxybutyrate, glycolate, maleate, Sulfonate, naphthalene-2-sulfonate or mandelate.

The acid addition salt according to the present invention can be prepared by dissolving the acid addition salt in a conventional manner, for example, by dissolving the above formula 1, 2 or 3 in an excess amount of an aqueous acid solution, ≪ / RTI >

In addition, the compounds represented by the general formulas (1) to (3) of the present invention can be formulated with a pharmaceutically acceptable metal salt using a base. The alkali metal or alkaline earth metal salt is obtained, for example, by dissolving the compound in an excess amount of an alkali metal hydroxide or alkaline earth metal hydroxide solution, filtering the insoluble compound salt, and evaporating and drying the filtrate. At this time, it is preferable for the metal salt to produce sodium, potassium or calcium salt. The corresponding silver salt is also obtained by reacting an alkali metal or alkaline earth metal salt with a suitable silver salt (for example, silver nitrate).

Meanwhile, the composition of the present invention may be a pharmaceutical composition. When the composition of the present invention is a pharmaceutical composition, the composition may contain, alone or in combination with one or more pharmaceutically acceptable carriers, excipients or diluents, the flavone-based compound of the present invention or the camphorafabi flora extract containing the same ≪ / RTI > The pharmaceutically acceptable carrier includes, for example, a carrier for oral administration or a carrier for parenteral administration. Carriers for oral administration may include lactose, starch, cellulose derivatives, magnesium stearate, stearic acid, and the like. The carrier for parenteral administration may also contain water, suitable oils, saline, aqueous glucose and glycols, and may further contain a stabilizer and a preservative. Suitable stabilizers include antioxidants such as sodium hydrogen sulfite, sodium sulfite or ascorbic acid. Suitable preservatives include benzalkonium chloride, methyl- or propyl-paraben and chlorobutanol. Other pharmaceutically acceptable carriers can be found in Remington's Pharmaceutical Sciences, 19th ed., Mack Publishing Company, Easton, Pa., 1995).

The pharmaceutical composition of the present invention can be administered to mammals including humans by any method. For example, it can be administered orally or parenterally. Parenteral administration methods include, but are not limited to, intravenous, intramuscular, intraarterial, intramedullary, intrathecal, intracardiac, transdermal, subcutaneous, intraperitoneal, intranasal, enteral, topical, sublingual or rectal administration Lt; / RTI >

The pharmaceutical composition of the present invention may be formulated into oral preparations or parenteral administration preparations according to the route of administration as described above. In the case of a preparation for oral administration, the composition of the present invention may be formulated into a powder, a granule, a tablet, a pill, a sugar, a tablet, a liquid, a gel, a syrup, a slurry, . For example, an oral preparation can be obtained by combining the active ingredient with a solid excipient, then milling it, adding suitable auxiliaries, and then processing the mixture into a granular mixture. Examples of suitable excipients include sugars including lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol and maltitol, and starches including corn starch, wheat starch, rice starch and potato starch, Cellulose such as methylcellulose, sodium carboxymethylcellulose and hydroxypropylmethyl-cellulose and the like, fillers such as gelatin, polyvinylpyrrolidone and the like. In addition, crosslinked polyvinylpyrrolidone, agar, alginic acid, or sodium alginate may optionally be added as a disintegrant.

Furthermore, the pharmaceutical composition of the present invention may further comprise an anti-coagulant, a lubricant, a wetting agent, a flavoring agent, an emulsifying agent or an antiseptic agent. The preparation for parenteral administration may be formulated by a method known in the art in the form of injections, creams, lotions, external ointments, oil agents, moisturizers, gels, aerosols and nasal inhalers. These formulations are described in Remington's Pharmaceutical Science, 15th edition, 1975. Mack Publishing Company, Easton, Pennsylvania 18042, Chapter 87: Blaug, Seymour, a commonly known formulary for all pharmaceutical chemistries.

The total effective amount of the pharmaceutical composition of the present invention may be administered to a patient in a single dose and may be administered by a fractionated treatment protocol administered over a prolonged period of time in multiple doses. In the case of parenteral administration, it is preferably administered in an amount of 0.01 to 50 mg, more preferably 0.1 to 30 mg per kg of body weight per day on the basis of the flavone-based compound of the present invention or camphorafabi flora extract containing the same. When administered orally, it is preferable to administer the pharmaceutical composition of the present invention in an amount of preferably 0.01 to 100 mg, more preferably 0.1 to 50 mg per kg of body weight per day on the basis of the flavone-based compound of the present invention or camphorafabi flora extract containing the same And the like. However, the dose of the flavone-based compound of the present invention or the camphorafabi flora extract containing the same is not limited to the administration route and the number of treatments of the pharmaceutical composition, but also various factors such as age, body weight, health status, sex, severity of disease, Those skilled in the art will appreciate that effective doses of the inventive flavone-based compounds or camphorafabi flora extracts containing the same, as well as effective dosages for the patient, . ≪ / RTI > The pharmaceutical composition according to the present invention is not particularly limited to the formulation, administration route and administration method as long as the effect of the present invention is exhibited.

Meanwhile, the present invention provides a method for treating periodontal disease, comprising administering to a subject having a periodontal disease incidence or onset a pharmaceutically effective amount of the composition for preventing, improving and treating periodontal disease. The periodontal disease includes all diseases or symptoms such as gingivitis, gingival bleeding, gingival recession, periodontal disease formation, and alveolar bone destruction.

The term "individual" as used herein refers to all animals, including humans, who have already developed or can develop periodontal disease, and by administering to a subject a composition comprising the extract, fraction or compound of the present invention, Prevention, improvement and treatment. For example, a composition of the present invention can treat a human suffering from a variety of periodontal diseases. The composition of the present invention can be administered in combination with a conventional therapeutic agent for periodontal disease.

The route of administration of the composition may be administered via any conventional route so long as it can reach the target tissue. The composition of the present invention may be administered intraperitoneally, intravenously, intramuscularly, subcutaneously, intradermally, orally, intranasally, intrapulmonarily, or rectally, though it is not intended to be limited thereto. The composition may also be administered by any device capable of transferring the active agent to the target cell.

In addition, the present invention relates to a pharmaceutical composition for the prevention and / or treatment of periodontal disease, comprising as an active ingredient at least one flavonoid compound selected from the group consisting of camphorafibiflora extract or a fraction thereof, or a compound represented by any one of formulas 1 to 3 or a pharmaceutically acceptable salt thereof Prevention or amelioration of the symptoms of the disease.

The food composition of the present invention includes all forms of conventional foods, nutritional supplements, health function foods, food additives and feeds, Animals are targeted for eating. Food compositions of this type may be prepared in a variety of forms according to conventional methods known in the art.

For example, common foods include but are not limited to beverages (including alcoholic beverages), fruits and processed foods (e.g., canned fruits, jars, jam, maare marlade), fish, meats and their processed foods (Eg, ham, sausage, cornbee, etc.), breads and noodles (eg udon, buckwheat noodles, ramen noodles, spaghetti, macaroni, etc.), juice, various drinks, cookies, The flavone-based compound of the present invention or the camphorafabi flora extract containing the same can be added to plant preservatives, margarine, vegetable proteins, retort foods, frozen foods, various kinds of seasonings such as soybean paste, soy sauce, sauce and the like. The nutritional supplement may be prepared by adding the flavonoid compound of the present invention or a camphorafibiflora extract containing the same to capsules, tablets, rings and the like. The health functional foods include, but are not limited to, for example, lubrication, granulation, or the like so that the flavone-based compound of the present invention or the camphorafabi flora extract itself containing the same can be manufactured in the form of tea, juice, , Encapsulated and powdered. In addition, in order to use the flavone-based compound of the present invention or the camphorafabi flora extract containing the flavone-based compound as a food additive, it may be used in the form of a powder or a concentrated liquid. In addition, the flavone-based compound of the present invention or a camphorafabi flora extract containing the same can be mixed with known active ingredients known to have periodontal disease-improving effects and can be prepared in the form of a composition.

The at least one flavone-based compound selected from the group consisting of the camphorafib boom extract of the present invention or a fraction thereof or the compound represented by the formulas (1) to (3) may be contained as an active ingredient in a food composition for preventing and improving periodontal disease, The amount is effective to achieve the periodontal disease improving action, and is not particularly limited, but is preferably 0.01 to 100% by weight based on the total weight of the total composition. The food composition of the present invention can be prepared by mixing together with the flavone-based compound of the present invention or camphorafabi flora extract containing it, with other periodontal disease improving active ingredients known to have periodontal disease improving effect.

In addition, the flavone-based compound of the present invention or camphorafabi flora extract containing the same can be provided in the form of a composition for oral administration. The oral care product comprising the oral care composition of the present invention includes all forms such as toothpaste, toothpaste, mouth spray, dietary film, and the like, and includes products intended for humans or animals including livestock. These types of oral care products can be prepared in a variety of forms according to conventional methods known in the art.

Compositions comprising, as an active ingredient, at least one flavone-based compound selected from the group consisting of the camphorafib boom extract of the present invention or the compounds represented by formulas 1 to 3 isolated therefrom, or a pharmaceutically acceptable salt thereof, Collagenase, and bone resorption enzyme, it can be very useful for prevention, improvement and treatment of periodontal disease and oral care.

FIG. 1 shows the results of measurement of the decrease in the amount of MMP-8 (matrix metalloprotease-8) mRNA expressed by the camphoraflaviflora ethanol extract in the gingival cell HGF.
FIG. 2 shows the results of measurement of the decrease in the expression level of MMP-8 mRNA by the hydrothermal extract of Campia faviflora in the gingival cell, HGF.
FIG. 3 shows the expression of MMP-8 mRNA by five kinds of camphorafibiflora extracts (1. methanol extract, 2. ethanol extract, 3. nucleic acid extract, 4. ethyl acetate extract, and 5. chloroform extract) The results are shown in Fig.
FIG. 4 shows the results of measurement of the decrease in the amount of MMP-8 mRNA expression by 5,7-dimethoxy flavone in gingival cell HGF.
FIG. 5 is a graph showing a decrease in the expression level of MMP-8 mRNA by 5,7,4'-trimethoxy flavone and 3,5,7,3 ', 4'-pentamethoxy flavone in HGF, a gingival cell The results are shown.
FIG. 6 shows the results of measurement of the decrease in the amount of MMP-8 protein expressed by the camphorafibioflora ethanol extract in gingival cell HGF.
FIG. 7 shows the results of measurement of the decrease in the amount of MMP-8 protein expressed by 5,7-dimethoxy flavone in gingival cell HGF.
FIG. 8 shows the results of measurement of the decrease in the amount of TRAP (tartrate-resistant acid phosphatase) mRNA expressed by the camphorafibioflora ethanol extract in Raw 264.7 cells after osteoclast differentiation.
FIG. 9 shows the results of measurement of the decrease in TRAP mRNA expression by 5,7-dimethoxy flavone in Raw 264.7 cells after osteoclast differentiation.

Hereinafter, the present invention will be described in more detail with reference to Examples and Experimental Examples. However, the following examples are illustrative of the present invention, and the present invention is not limited to the following examples.

Example  One: Camperia Fabio Flora  Preparation of extract

Example  1-1: Camperia Fabio Flora  Preparation of ethanol extract

The dried camphorafabi flora rootstock was pulverized with a mixer, and 100 g of the pulverized camphorafibibphora sample was added to 1 L of ethanol and extracted with stirring at 50 ° C for 60 minutes. The extracted sample was filtered with filter paper of Whatman No. 2, and the filtered extract was concentrated with a vacuum rotary condenser to remove the solvent component to obtain a camphorafibrate ethanol extract.

Example  1-2: Camperia Fabio Flora Heat number  Preparation of extract

The dried camphorafabi flora rootstock was pulverized with a mixer, and 100 g of the pulverized camphorafibiblofer sample was added to 1 L of water and extracted with stirring at 100 ° C for 4 hours. The extracted sample was filtered with Wattmann filter paper No. 2, and the filtered extract was concentrated with a vacuum rotary condenser to remove the solvent component to obtain a Camphoraflavi hot water extract.

Example  1-3: Camperia Fabio Flora  Preparation of methanol extract

The dried camphoria faviflora rootstock was pulverized with a mixer, and 100 g of the pulverized camphorafibiblofera sample was added to 1 L of methanol and extracted with stirring at 50 ° C for 60 minutes. The extracted sample was filtered with Wattman No. 2 filter paper, and the filtered extract was concentrated with a vacuum rotary condenser to remove solvent components to obtain a methanol extract of camphorafibrate.

Example  1-4: Camperia Fabio Flora Hexane  Preparation of extract

The dried camphoria faviflora rootstock was pulverized with a mixer, and then 100 g of the pulverized camphorafabi flora sample was added to 1 L of nucleic acid and extracted with stirring at 50 ° C for 60 minutes. The extracted sample was filtered through Wattman No. 2 filter paper, and the filtered extract was concentrated with a vacuum rotary condenser to remove the solvent components to obtain a camphorafibrate hexane extract.

Example  1-5: Camperia Fabio Flora  Preparation of ethyl acetate extract

The dried camphoria faviflora rootstock was pulverized with a mixer, and 100 g of the pulverized camphorafabi flora sample was added to 1 L of ethyl acetate and extracted with stirring at 50 DEG C for 60 minutes. The extracted sample was filtered with Wattman No. 2 filter paper, and the filtered extract was concentrated with a vacuum rotary condenser to remove the solvent component to obtain camphorafibatri-ethyl acetate extract.

Example  1-6: Camperia Fabio Flora  Preparation of chloroform extract

The dried root of camphorafabi flora was pulverized with a mixer, and 100 g of the pulverized camphorafibibphira sample was added to 1 L of chloroform and extracted with stirring at 50 ° C for 60 minutes. The extracted sample was filtered with Wattmann filter paper No. 2, and the filtered extract was concentrated with a vacuum rotary condenser to remove solvent components to obtain a camphorafibiblochloroform extract.

Example  2: Camperia Fabio Flora  Separation of flavonoid compounds from ethanol extracts

Example  2-1: 5,7- Dimethoxy flavone  Separation and structure determination

The concentrated camphorafiboflora ethanol extract obtained in Example 1-1 was loaded on a column packed with silica gel (6 x 15 cm), and a solvent system in which ethyl acetate and methanol were mixed at a ratio of 10: 0.5 (v / v) . The fractions were divided into five fractions according to the above sorting order, and the respective fractions were concentrated and dried. Three fractions ("Fraction 3") of the five fractions were collected by developing solvent 70% methanol using Rp-18 column chromatography (Lichroprep RP-18 25-40 um, Merck & Co., USA). The fractions were divided into two fractions according to the above sorting order and concentrated and dried. The fraction 2 of the two fractions ("fraction 3-2") was loaded on a column packed with silica gel at 6 × 15 cm and mixed with a solvent system of ethyl acetate and methanol at a ratio of 10: 0.4 (v / v) And finally fraction 1 of the two fractions ("fraction 3-2-1") was concentrated and dried to isolate the ultraviolet screening substance.

¹ H-NMR spectrum and ¹³ C-NMR spectrum were measured at 500 MHz and 125 MHz (solvent: CDCl ₃ ), respectively, in order to determine the structure of the single active substance separated from the above. This compound was found to have a molecular weight of 282 with [M] observed at m / z 282 in EI / MS. (Sutthanut K. et al., J. Chromatogr., 1143: 227-233, 2007) were compared with the results of ¹ H-NMR, ¹³ C-NMR and EI / As a result, it was confirmed that the single substance isolated from the above was 5,7-dimethoxy flavone represented by the following formula (1).

[Chemical Formula 1]

Example  2-2: 5,7,4'- Of trimethoxy flavone  Separation and structure determination

The concentrated methanol extract of camphorafibrate obtained in Example 1-1 was loaded on a column packed with silica gel (6 x 15 cm), and a solvent system in which ethyl acetate and methanol were mixed at a ratio of 10: 0.5 (v / v) . The fractions were divided into five fractions according to the above sorting order, and the respective fractions were concentrated and dried. Four fractions ("Fraction 4") of the five fractions were collected by developing solvent 70% methanol using Rp-18 column chromatography (Lichroprep RP-18 25-40 um, Merck & Co., USA). The fractions were divided into two fractions according to the above sorting order and concentrated and dried. Finally, the fraction No. 2 ("fraction 4-2") was concentrated and dried to isolate the ultraviolet screening substance.

¹ H-NMR spectrum and ¹³ C-NMR spectrum were measured at 500 MHz and 125 MHz (solvent: CDCl ₃ ), respectively, in order to determine the structure of the single active substance separated from the above. This compound was found to have a molecular weight of 312 with [M] observed at m / z 312 in EI / MS. (Sutthanut K. et al., J. Chromatogr., 1143: 227-233, 2007) were compared with the results of ¹ H-NMR, ¹³ C-NMR and EI / As a result, it was confirmed that the single substance isolated from the above was 5,7,4'-trimethoxy flavone represented by the following formula (2).

(2)

Example  2-3: 3,5,7,3 ', 4'- Pentamethoxy flavone  Separation and structure determination

The concentrated methanol extract of camphorafibrate obtained in Example 1-1 was loaded on a column packed with silica gel (6 x 15 cm), and a solvent system in which ethyl acetate and methanol were mixed at a ratio of 10: 0.5 (v / v) . The fractions were divided into five fractions according to the above sorting order, and the respective fractions were concentrated and dried. Three fractions ("Fraction 3") of the five fractions were collected by developing solvent 70% methanol using Rp-18 column chromatography (Lichroprep RP-18 25-40 um, Merck & Co., USA). The fractions were divided into two fractions according to the above sorting order and concentrated and dried. Finally, the No. 1 fraction ("fraction 3-1") was concentrated and dried to isolate the ultraviolet screening substance.

¹ H-NMR spectrum and ¹³ C-NMR spectrum were measured at 500 MHz and 125 MHz (solvent: CDCl ₃ ), respectively, in order to determine the structure of the single active substance separated from the above. This compound was found to have a molecular weight of 372 with [M] observed at m / z 372 in EI / MS. (Sutthanut K. et al., J. Chromatogr., 1143: 227-233, 2007) were compared with the results of ¹ H-NMR, ¹³ C-NMR and EI / As a result, it was confirmed that the single substance isolated from the above was 3,5,7,3 ', 4'-pentamethoxy flavone represented by the following formula (3).

(3)

Experimental Example  One: Camperia Fabio Flora  Inhibition of Collagenase Production by Ethanol Extract

HGF gingival cells (ATCC; Manassas, Va., USA) were cultured in DMEM (Dulbecco's Modified Eagle's Media) medium containing 10% calf serum and then transferred to a 6-well microtiter plate Cells / well. After growing up to 90%, the cells were treated for 1 day in a culture medium containing lipopolysaccharide at a concentration of 1 μg / ml. The gingival cells were treated with 1 μg / ml and 10 μg / ml of the camphorafiboflora ethanol extract of Example 1-1 dissolved in the culture solution. After 1 day, the expression pattern of collagenase, MMP-8, was measured by reverse transcriptase-polymerase chain reaction. GAPDH showed that the amount of mRNA was constant.

As a result, as shown in Fig. 1, it was confirmed that the ethanol extract of camphorafiboflora significantly inhibited the production of MMP-8 mRNA in HGF gingival cells.

Experimental Example  2: Camperia Fabio Flora Heat number  Inhibition of collagenase production by extract

The gingival cells were treated with 10 μg / ml of the hot-water extract of Campia faviflora in Example 1-2 in the same manner as in Experimental Example 1.

As a result, as shown in Fig. 2, it was confirmed that the hydrolyzate of camphorafibioflora significantly inhibited the production of MMP-8 mRNA in HGF gingival cells.

Experimental Example  3: Camperia Fabio Flora  Inhibition of Collagenase Production by Solvent Extract

The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. The results are shown in Table 1. Acetate extract and 10 μg / ml of camphorafibiblochloroform extract of Example 1-6 were each treated in the same manner as in Experimental Example 1.

As a result, as shown in FIG. 3, it was confirmed that the methanol extract of camphorafibioflora, the nucleic acid extract of ethanol extract, the ethyl acetate extract and the chloroform extract greatly inhibited the production of MMP-8 mRNA in HGF gingival cells.

Experimental Example  4: 5,7- Dimethoxy flavone  Inhibition of collagenase production

The 5, 7-dimethoxy flavone of Example 2-1 was treated at a concentration of 1 [mu] M and 10 [mu] M in the same manner as in Experimental Example 1.

As a result, it was confirmed that 5,7-dimethoxy flavone significantly inhibited the production of MMP-8 mRNA in HGF gingival cells as shown in Fig.

Experimental Example  5: 5,7- Dimethoxy flavone  Inhibition of collagenase production

The 5,7,4'-trimethoxy flavone obtained in Example 2-2 and the 3,5,7,3 ', 4'-pentamethoxy flavone obtained in Example 2-3 were mixed at a concentration of 10 μM in the above experiment The gingival cells were treated in the same manner as in Example 1.

As a result, as shown in FIG. 5, both 5,7,4'-trimethoxy flavone and 3,5,7,3 ', 4'-pentamethoxy flavone showed MMP-8 mRNA production in HGF gingival cells It can be confirmed that there is an effect of suppressing it greatly.

Experimental Example  6: Camperia Fabio Flora  Inhibition of Collagenase Production by Ethanol Extract

HGF gingival cells were cultured in DMEM medium containing 10% calf serum, and then placed in a 6-well plate incubator at 1,00,000 cells / well. After growing up to 90%, the cells were treated for 1 day in a culture medium containing lipopolysaccharide at a concentration of 1 μg / ml. The gingival cells were treated with 1 μg / ml and 10 μg / ml of the camphorafiboflora ethanol extract of Example 1-1 dissolved in the culture solution. After 24 hours, the HGF gingival cells were lysed with NP40 buffer solution containing a proteinase inhibitor cocktail. The amount of protein extracted from HGF gingival cells was quantitated using the Bradford method. After the sample was boiled for 5 minutes, the same amount of protein (20 g) was separated by electrophoresis using 10% SDS-PAGE. After electrophoresis, the separated proteins were transferred to the nitrocellulose membrane and western blotting was performed. The cells were washed three times for 10 minutes with TBST (Tris-buffer Saline Tween 20). The type and dilution ratio of the primary antibody used in the present invention were 1: 1000. In the secondary antibody reaction, a secondary antibody (anti-goat horseradish) was added to the membrane subjected to the primary antibody reaction, followed by reaction at room temperature for 2 hours. At this time, the dilution ratio of the secondary antibody was 1: 5000. Protein bands were developed using ECL western blotting detection reagents. The protein expression of the collagenase MMP-8 was confirmed, and α-tubulin showed a constant protein loading.

As a result, as shown in FIG. 6, it was confirmed that the expression of MMP-8 protein was decreased in HGF gingival cells by treatment with camphorafib boom ethanol extract. As a result of the above experiment, it can be seen that the camphorafibrate ethanol extract has excellent inhibitory effect on collagenolytic enzyme production in gingival cells.

Experimental Example  7: 5,7- Dimethoxy flavone  Inhibition of collagenase production

The 5, 7-dimethoxy flavone of Example 2-1 was treated at a concentration of 1 [mu] M and 10 [mu] M in the same manner as in Experimental Example 6, respectively.

As a result, it was confirmed that 5,7-dimethoxy flavone significantly inhibited the production of MMP-8 protein in HGF gingival cells as shown in Fig.

Experimental Example  8: Camperia Fabio Flora  Extract Bone resorption enzyme  Production inhibition measurement

Raw 264.7 cells (ATCC; Manassas, Va., USA) were cultured in DMEM medium containing 10% calf serum and then placed in a 6-well plate incubator at 160,000 cells / well. After growing to 90%, the cells were treated for 4 days in a culture medium containing 100 ng / ml of a nucleic acid factor-κB ligand receptor promoter (NF-κB ligand). The Raw 264.7 cells were treated with 1 μg / ml and 10 μg / ml of the camphorafiboflora ethanol extract of Example 1-1 dissolved in the culture solution. After 1 day, the expression pattern of TRAP, a bone resorption enzyme, was measured by reverse transcription polymerase chain reaction. The amount of mRNA was shown to be constant by β-Actin.

As a result, as shown in FIG. 8, it was confirmed that the camphorafiboflore extract significantly inhibited the expression of bone resorption enzyme TRAP mRNA in Raw 264.7 cells that had undergone osteoclast differentiation.

Experimental Example  9: 5,7- Dimethoxy flavone Bone resorption enzyme  Production inhibition measurement

The 5,7-dimethoxy flavone of Example 2-1 was treated with Raw 264.7 cells at the concentrations of 1 μM and 10 μM, respectively, in the same manner as in Experimental Example 8.

As a result, it was confirmed that 5,7-dimethoxy flavone significantly inhibited TRAP mRNA expression in Raw 264.7 cells that had undergone osteoclast differentiation, as shown in FIG.

Manufacturing example  1: Food manufacturing

Manufacturing example  1-1: Health food

Vitamin E acetate 1.0 mg, vitamin B1 0.13 mg, vitamin B2 0.15 mg, vitamin B6 0.5 mg, vitamin B12 0.2 g, vitamin C 10 mg, 10 mg of biotin, 1.7 mg of nicotinic acid amide, 50 mg of folic acid, 0.5 mg of calcium pantothenate, 1.75 mg of ferrous sulfate, 0.82 mg of zinc oxide, 25.3 mg of magnesium carbonate, 15 mg of potassium phosphate monohydrate, 55 mg of calcium phosphate, 100 mg of calcium, and 24.8 mg of magnesium chloride were mixed, and the above components were mixed according to a conventional method for producing health food, and granules were formed to prepare a health food. In the above, the compounding ratio may be arbitrarily modified.

Manufacturing example  1-2: Health drink

(Total 900 ml) was added to 1000 mg of the methanol extract of camphorafiboflora prepared in Example 1-1, 1000 mg of citric acid, 100 g of oligosaccharide, 2 g of plum concentrate and 1 g of taurine, and the above components were added After mixing, the mixture was stirred and heated at 85 DEG C for about 1 hour, and the resulting solution was filtered to obtain a sterilized 2L container, sealed sterilized, and refrigerated to prepare a health drink. In the above, the compounding ratio may be arbitrarily modified.

Manufacturing example  1-3: Chewing gum

Chewing gum was prepared by combining 20% by weight of a gum base, 76.9% by weight of sugar, 1% by weight of a flavor and 2% by weight of water and 0.1% by weight of camphorafiboflora ethanol extract prepared in Example 1-1 .

Manufacturing example  1-4: Candy

Candies were prepared in a conventional manner by mixing 60% by weight of sugar, 39.8% by weight of starch syrup, 0.1% by weight of flavor and 0.1% by weight of camphorafiboflora ethanol extract prepared in Example 1-1.

Manufacturing example  1-5: Biscuit

A mixture of 0.75% by weight of sodium chloride, 0.78% by weight of glucose, 11.78% by weight of palm shortening, 1.54% by weight of ammonium, 0.17% by weight of sodium bicarbonate and 0.16% by weight of sodium bisulfite, 25.59% by weight of Grade I, 22.22% 1.45 wt% of rice flour, 0.0001 wt% of vitamin B, 0.04 wt% of milk fractions, 20.6998 wt% of water, 1.16 wt% of whole milk powder, 0.29 wt% of replacement milk powder, 0.03 wt% of calcium phosphate, 0.29 wt% 7.27% by weight of sprayed milk and 1.0% by weight of camphorafiboflora ethanol extract prepared in Example 1-1 were blended to prepare biscuits by a conventional method.

Manufacturing example  2: Medicines

Manufacturing example  2-1: Powder

The ethanol extract of camphorafabi flora prepared in Examples 1 to 2, 5,7-dimethoxy flavone, 5,7,4'-trimethoxy flavone, and 3,5,7,3 ' 50 mg each of pentamethoxy flavone and 2 g of crystalline cellulose were mixed and filled in an airtight cell according to a conventional acid production method to prepare a powder.

Manufacturing example  2-2: Tablets

The ethanol extract of camphorafabi flora prepared in Examples 1 to 2, 5,7-dimethoxy flavone, 5,7,4'-trimethoxy flavone, and 3,5,7,3 ' 50 mg of each of pentamethoxy flavone, 400 mg of crystalline cellulose, and 5 mg of magnesium stearate were mixed and tableted according to a conventional tablet preparation method.

Manufacturing example  2-3: Capsule

The ethanol extract of camphorafabi flora prepared in Examples 1 to 2, 5,7-dimethoxy flavone, 5,7,4'-trimethoxy flavone, and 3,5,7,3 ' 30 mg of pentamethoxy flavone, 100 mg of whey protein, 400 mg of crystalline cellulose, and 6 mg of magnesium stearate were mixed and filled in gelatin capsules according to a conventional capsule preparation method to prepare capsules.

Manufacturing example  2-4: Injection

The active ingredient was dissolved in distilled water for injection and adjusted to a pH of about 7.5 according to the usual injection preparation method. Then, the ethanol extract of camphorafabi flora prepared in Examples 1 to 2, 5,7-dimethoxy flavone , 5,7,4'-trimethoxy flavone, and 3,5,7,3'4'-pentamethoxy flavone were mixed with distilled water for injection and a pH adjusting agent, respectively, and the mixture was filled in a 2 ml volume ampoule and sterilized An injection was prepared.

Manufacturing example  3: Oral care products

Manufacturing example  3-1: Toothpaste

As shown in the following Table 1, a toothpaste containing the camphoraflavifolia ethanol extract prepared in Example 1-1 and the flavone compound of Example 2 was prepared.

division Ingredients Manufacturing example 3-1-1 3-1-2 3-1-3 3-1-4 Active ingredient Camphoria Fabioflora Ethanol Extract 0.1 - - - 5,7-dimethoxy flavone - 0.05 - - 5,7,4'-trimethoxy flavone - - 0.05 - 3,5,7,3'4'-Penta-methoxy flavone - - - 0.05 abrasive Calcium carbonate 40.0 40.0 40.0 40.0 Wetting agent Sorbitol solution 25.0 25.0 25.0 25.0 Fluorine Sodium fluorophosphate 0.1 0.1 0.1 0.1 Foaming agent Sodium lauryl sulfate 2.0 2.0 2.0 2.0 Binder Carboxymethylcellulose 1.0 1.0 1.0 1.0 Sweetener Sodium saccharin 0.2 0.2 0.2 0.2 antiseptic Methyl paraben 0.1 0.1 0.1 0.1 Spices Combination fragrance 1.0 1.0 1.0 1.0 menstruum Purified water Remainder Remainder Remainder Remainder

Manufacturing example  3-2: Toothpaste

As shown in the following Table 2, a tooth follicular fluid containing the camphoraflavifolia ethanol extract prepared in Example 1-1 and the flavone compound of Example 2 was prepared.

Ingredients Manufacturing example 3-2-1 3-2-2 3-2-3 3-2-4 Camphoria Fabioflora Ethanol Extract 0.1 - - - 5,7-dimethoxy flavone - 0.05 - - 5,7,4'-trimethoxy flavone - - 0.05 - 3,5,7,3'4'-Penta-methoxy flavone - - - 0.05 glycerin 5.0 5.0 5.0 5.0 Pollock Sommer 1.0 1.0 1.0 1.0 Sodium fluoride 0.1 0.1 0.1 0.1 Sodium citrate 0.2 0.2 0.2 0.2 Sodium saccharin 0.01 0.01 0.01 0.01 Combination fragrance 0.15 0.15 0.15 0.15 ethanol 6.0 6.0 6.0 6.0 Purified water Remainder Remainder Remainder Remainder

Manufacturing example  3-3: Mouse Spray

As shown in the following Table 3, mouse sprays containing the methanol extract of camphorafib boccia prepared in Example 1-1 and the flavone compounds of Example 2 were prepared.

Ingredients Manufacturing example 3-3-1 3-3-2 3-3-3 3-3-4 Camphoria Fabioflora Ethanol Extract 0.1 - - - 5,7-dimethoxy flavone - 0.05 - - 5,7,4'-trimethoxy flavone - - 0.05 - 3,5,7,3'4'-Penta-methoxy flavone - - - 0.05 glycerin 7.0 7.0 7.0 7.0 Sodium citrate 0.4 0.4 0.4 0.4 Sodium fluoride 0.02 0.02 0.02 0.02 Sodium saccharin 0.011 0.011 0.011 0.011 Pollock Sommer 1.0 1.0 1.0 1.0 Methyl paraben 0.1 0.1 0.1 0.1 Propylparaben 0.05 0.05 0.05 0.05 Combination fragrance 0.12 0.12 0.12 0.12 ethanol 60.0 60.0 60.0 60.0 Purified water Remainder Remainder Remainder Remainder

Manufacturing example  3-4: Dietary Film

As shown in the following Table 4, a dietary film containing the camphoraflavifolia ethanol extract prepared in Example 1-1 and the flavone compound of Example 2 was prepared.

Raw material name Manufacturing example 3-4-1 3-4-2 3-4-3 3-4-4 Camphoria Fabioflora Ethanol Extract 0.1 - - - 5,7-dimethoxy flavone - 0.05 - - 5,7,4'-trimethoxy flavone - - 0.05 - 3,5,7,3'4'-Penta-methoxy flavone - - - 0.05 Pullulan 20.0 20.0 20.0 20.0 Twin 80 0.1 0.1 0.1 0.1 Carrageenan 0.1 0.1 0.1 0.1 Lokostin 0.1 0.1 0.1 0.1 Xanthan gum 1.0 1.0 1.0 1.0 incense 1.0 1.0 1.0 1.0 Purified water Remainder Remainder Remainder Remainder

The camphorafabi flora extract or its fractions and the flavone compounds represented by formulas (1) to (3) inhibit the production of collagenolytic enzymes and the production of bone resorption enzymes, thereby providing excellent preventive, remedial and therapeutic effects of periodontal disease. Accordingly, the present invention provides a pharmaceutical composition, a food composition, a composition for oral administration, or a medicament, a food, and an oral care product containing such a composition by using a camphorafabi flora extract or a flavone compound represented by Chemical Formulas 1 to 3 as an active ingredient It is very likely to be used industrially.

Claims (11)

Kaempferia The present invention relates to a pharmaceutical composition for preventing or treating periodontal disease. The method according to claim 1, wherein the extract is an extract from at least one solvent selected from the group consisting of water, a C ₁ -C ₆ organic solvent, a subcritical fluid and a supercritical fluid. Pharmaceutical composition. The method of claim 2, wherein the C ₁ -C ₆ organic solvent is selected from the group consisting of C ₁ -C ₆ alcohols, acetone, ether, benzene, chloroform, ethyl acetate, methylene chloride, hexane, cyclohexane, Wherein the pharmaceutical composition is for preventing or treating periodontal disease. The pharmaceutical composition for preventing or treating periodontal disease according to claim 3, wherein the C ₁ -C ₆ organic solvent is ethanol. 5. A method according to any one of claims 1 to 4, wherein the periodontal disease is selected from the group consisting of gingivitis, gingival bleeding, gingival retraction, periodontal pocket formation or alveolar bone destruction Wherein the pharmaceutical composition is a pharmaceutical composition for preventing or treating periodontal disease. Kaempferia parviflora extract as an active ingredient for preventing or ameliorating periodontal disease. Kaempferia parviflora extract as an active ingredient. A pharmaceutical composition for the prevention or treatment of periodontal disease comprising, as an active ingredient, at least one flavone-based compound selected from the group consisting of compounds represented by the following formulas (1) to (3) or a pharmaceutically acceptable salt thereof:
[Chemical Formula 1]

,
(2)

, And
(3)

. The method according to claim 8, wherein the periodontal disease is gingivitis, gingival bleeding, gingival retraction, periodontal pocket formation, or alveolar bone destruction. Or a pharmaceutical composition for therapeutic use. 1. A functional food composition for preventing or ameliorating periodontal disease comprising, as an active ingredient, at least one flavone-based compound selected from the group consisting of compounds represented by the following formulas (1) to (3) or a pharmaceutically acceptable salt thereof:
[Chemical Formula 1]

,
(2)

, And
(3)

. 1. A composition for oral care comprising as an active ingredient at least one flavone-based compound selected from the group consisting of compounds represented by the following formulas (1) to (3) or a pharmaceutically acceptable salt thereof:
[Chemical Formula 1]

,
(2)

, And
(3)

.

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