KR101780836B1 - 3,5-dihydroxy-2-menthenyl stilbene, plant extract containing same, method for collecting same, and application for same - Google Patents

Abstract

3,5-dihydroxy-2-mandenyl stilbene, a plant extract containing the same, an antimicrobial agent, a method of harvesting the same, and an application thereof. 3,5-dihydroxy-2-menthaneylstilbene represented by the following structural formula (1), ginger extract containing 1% by mass or more thereof, application of an antimicrobial agent containing it as an active ingredient, Of the active ingredient. A mixture of the substance of the formula (1) and 3,5-dihydroxystilbene of the following formula (2), a ginger extract containing 1% by mass or more thereof, and an application of an odorant inhibitor containing it as an active ingredient.

Description

3,5-DIHYDROXY-2-MENTHENYL STILBENE, PLANT EXTRACT CONTAINING SAME, METHOD FOR COLLECTING SAME, AND METHOD FOR COLLECTING SAME, AND APPLICATION FOR SAME}

The present invention provides a novel 3,5-dihydroxy-2-menthane stilbene, a plant extract containing it, an application of an antimicrobial agent, and a method of collecting an effective ingredient of a genus lindera plant . The present invention also relates to a mixture comprising 3,5-dihydroxy-2-menthaneylstilbene and 3,5-dihydroxystilbene, a malodorous production inhibitor containing the same, and the like.

The proliferation of microorganisms such as bacteria causes an undesirable situation in living bodies and environments, such as causing diseases and increasing contamination, and antimicrobial agents and bactericides have been used for various purposes in various fields. In recent years, substances derived from natural materials have been attracting attention due to problems such as load on the environment, but in the current state, it is almost no better than synthetic fungicide in terms of efficacy. Because of this, development of an antimicrobial agent that is highly effective from natural products has been desired.

It is known that camphor trees and plants to which ginger is belong include many essential oils, and cinnamon, laurel water and the like contain essential oils having antibacterial properties. Since ginger contains a lot of essential oils rich in direction, it is used as essential oils in cosmetics and soaps, and toothpick branches and so on. Further, as a technique for compounding in an oral composition, an oral composition containing an organic solvent extract of a plant including a promoted tree (Patent Document 1), an oral wetting agent comprising an essential oil extracted from a dried tree 2) has been proposed.

That is, in Patent Document 1, it is described that the promoted wood extract inhibits the formation of plaque by inhibiting glucosyltransferase of Streptococcus mutans. In Patent Document 2, , And denture candidiasis are improved. As described above, the antimicrobial and antifungal activity of the ginger tree has been known in the past. In addition, anti-Helicobacter pylori agent (Patent Document 3) and anti-influenza virus agent (Patent Document 4) are listed as a technique describing the antimicrobial action of ganoderma lucidum.

In addition to the antimicrobial activity, a cosmetic for preventing acne, rough skin and dandruff (patent document 5), a skin external preparation for inhibiting melanin production (patent document 6), an ultraviolet absorber (patent document 7), a protease inhibitor ), Etc., various functions of the tree have been started.

The extraction method of these promoted wood components can be generally divided into a technique of concentrating under reduced pressure after extracting an organic solvent (Patent Documents 1 and 3 to 8) and a technique using an essential oil component obtained by steam distillation (Patent Document 2).

However, the organic solvent extract usually exhibits a dark brown color, and when blended with a preparation or the like, there is a problem that not only coloration but also discoloration occurs with time. It is also conceivable to fractionate components by chromatography or the like to fractionate an excellent fraction in color discoloration, but a detailed fractionation method has not yet been proposed.

There are reports of flavonoids, chalcones, and alkaloids (Non-Patent Documents 1 to 3) as components in the artificial trees, but their functions are not fully understood at present.

Patent Document 1: Japanese Patent Application Laid-Open No. 57-58610 Patent Document 2: Japanese Patent Application Laid-Open No. 2008-036343 Patent Document 3: Japanese Patent Application Laid-Open No. 11-1429 Patent Document 4: JP-A-2004-59463 Patent Document 5: Japanese Patent Application Laid-Open No. 62-238207 Patent Document 6: Japanese Patent Application Laid-Open No. 7-277941 Patent Document 7: JP-A-7-285841 Patent Document 8: Japanese Patent Application Laid-Open No. 2001-122728

Non-Patent Document 1: Chem. Pharm. Bull 37 (4) 944-947 (1989) Non-Patent Document 2: Phytochemistry 27 (12) 3937-3939 (1988) Non-Patent Document 3: Pharmaceutical Magazine 89 (5) 737-740 (1969)

DISCLOSURE OF THE INVENTION The present inventors have intensively studied in order to achieve the above object. As a result, the present inventors have found that by extracting and purifying an extract extracted from a bark of a ginger wood (Lindenia MBELLATA) with a hydrophilic solvent, it has high antimicrobial activity and odor- Dihydroxy-2-mentenylstilbene represented by the following structural formula (1) and its active structural unit represented by the following structural formula (2) are obtained by further performing fractionation and purification, Dihydroxystilbene represented by the following formula (1). Further, it has been confirmed that by increasing the content of these active substances, that is, by removing impurities, it is possible to provide an extract of ginger plants excellent in storage stability.

The 3,5-dihydroxy-2-mandenylstilbene according to the present invention is a novel compound which has not been reported so far, which has a high antibacterial activity against a wide variety of bacterial species, It has become. In addition, 3,5-dihydroxystilbene inhibits the production of malodorous substances such as volatile fatty acids, methyl mercaptan, and hydrogen sulfide by inhibiting the branched amino acid aminotransferase and methionine? Lase, which are metabolic enzymes of bacteria Was made by the inventors of the present invention, and its effect was remarkably improved by using 3,5-dihydroxy-2-menthane stilbene in combination. Therefore, it has been confirmed that these active ingredients are effective as an active ingredient of an antimicrobial agent and a malodor growth inhibitor.

These compounds are components which are hardly contained in the essential oil component obtained by distillation of water vapor of the above-mentioned plant, which is conventionally known, and they are extracted by a hydrophilic organic solvent such as an organic solvent or a hydrous organic solvent, . In addition, the ginseng extract obtained by extracting only the hydrophilic solvent does not have a sufficient content to express the activity of these compounds, and when a sufficient amount of ginseng extract is added to the preparation to express the activity, It is also clear that there is a possibility that the problem of stability of the preparation such as the release agent may occur. The present inventors have further studied for the purpose of solving these problems. As a result, the present inventors have found that by further fractionating and purifying by extractive extraction with a solvent or by combining various chromatographies, the active ingredient 3,5- Dihydroxy-2-menthane stilbene and 3,5-dihydroxystilbene, thereby achieving a sufficient effect and obtaining an extract of ginger which is excellent in formulation stability.

Therefore, the present invention provides the following matters.

Claim 1: 3,5-Dihydroxy-2-mandenylstilbene represented by the following structural formula (1).

Claim 2: LINDERA UMBELLATA or a subspecies thereof, wherein the content of 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) is 1% Species).

[Claim 3] An antimicrobial agent comprising 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) as an active ingredient.

[Claim 4] An extract of Lindenia subcellularum or a subspecies thereof of a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% Lt; / RTI >

[Claim 5] An oral composition containing 3,5-dihydroxy-2-menthaneylstilbene represented by the following structural formula (1).

[Claim 6] An extract from Lindenia buccalata or a subspecies thereof of a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% ≪ / RTI >

[Claim 7] A cosmetic for skin or hair containing 3,5-dihydroxy-2-menthaneylstilbene represented by the following structural formula (1).

Claim 8: An extract from LINDERA UMBELLATA or a subspecies thereof which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of at least 1% Or a cosmetic for hair or hair.

9: A cleaning composition containing 3,5-dihydroxy-2-menthaneylstilbene represented by the following structural formula (1).

Claim 10: An extract from LINDERA UMBELLATA or a subspecies thereof of a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% . ≪ / RTI >

Claim 11: A food or drink containing 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1).

Claim 12: An extract from LINDERA UMBELLATA or a subspecies of ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% by mass or more of the solid content ≪ / RTI >

13. A mixture comprising 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) and 3,5-dihydroxystilbene represented by the following structural formula (2).

14. A process for producing 3,5-dihydroxy-2-menthane stilbene represented by the following structural formula (1), which comprises not less than 1% by mass of the solid content of 3,5-dihydroxy- Extract from LINDERA UMBELLATA or its subspecies of ginger which contains hydroxystilbene in an amount of at least 1% by mass of solids.

(15) An extract from Lindenia buccalata or a subspecies thereof of a ginger which contains 3,5-dihydroxystilbene represented by the following structural formula (2) in an amount of 1% by mass or more of the solid content.

[16] A malodor growth inhibitor comprising the mixture according to claim 13 as an active ingredient.

[17] A malodor growth inhibitor comprising an extract according to claim 14 or 15.

18. An oral composition comprising a mixture according to claim 13.

19. An oral composition containing an extract according to claim 14 or 15.

20. A cosmetic for skin or hair containing the mixture according to claim 13.

[Claim 21] A cosmetic for skin or hair containing the extract according to claim 14 or 15.

22. A cleaning composition comprising a mixture according to claim 13.

23. A cleaning composition comprising an extract according to claim 14 or 15.

[Claim 24] A food or drink containing a mixture according to claim 13.

[Claim 25] A food or drink containing an extract according to claim 14 or 15.

26. A method for producing a porous structure, comprising the steps of: extracting a gingival plant with an aqueous solution of 40 to 100 mass% ethanol, concentrating the extract at a reduced pressure at 50 ° C. or lower, and adjusting the alcohol concentration to 10 to 30% , Followed by elution with an aqueous solution of 40 to 70 mass% ethanol and / or elution with an aqueous alkaline solution of 40 to 70 mass%, followed by removal of the fraction eluted with an aqueous solution of ethanol in an amount of less than 40 mass% Or eluting with an aqueous solution of more than 70% (by mass) to 100% by mass of ethanol, collecting 3,5-dihydroxystilbene from an eluate with an aqueous solution of 40 to 70% by mass of ethanol and / And extracting 3,5-dihydroxy-2-menthaneylstilbene from the eluate with an aqueous solution of more than 100 mass% ethanol.

[27] A method for producing a concentrate according to any one of [27] to [27], wherein the eluate by 40 to 70% by mass ethanol aqueous solution is concentrated under reduced pressure at 50 [deg.] C or lower, and the concentrate is immersed in a total porous spherical or crushed silica gel The method of claim 26, wherein the adsorbent is adsorbed on a body and eluted with a 50 to 80 mass% aqueous methanol solution to obtain 3,5-dihydroxystilbene.

28. The method according to claim 1, wherein the eluate from 70 to 100 mass% ethanol aqueous solution is developed by silica gel chromatography, and the ratio of the elution fraction by n-hexane / acetone mixing ratio (V / V) 18: , And elution fraction between the elution fractions obtained by fractionation of the eluted fractions to obtain 3,5-dihydroxy-2-menthaneylstilbene.

29. The method according to claim 29, wherein the ginger is extracted with an aqueous solution of 40 to 100 mass% ethanol, the extract is further extracted with an aqueous 20 to 40 mass% ethanol solution, the insoluble portion is sampled, Dihydroxy-2-mentenylstilbene and 3,5-dihydroxy stilbene, and recovering the soluble fraction.

30. A method for producing a polymer electrolyte membrane, comprising the steps of: subjecting the soluble part to a concentration of less than 50 ° C under reduced pressure, and adjusting the alcohol concentration to 10 to 30% (V / V) by adsorption treatment with a spherical crosslinked polymer having a porous structure; By weight or more of an aqueous solution of ethanol or ethanol, and collecting the eluted solution.

31. The method according to claim 1, wherein the ginger is extracted with a mixture of carbon dioxide in a supercritical state and an aqueous solution of ethanol in an amount of 2 to 10% by mass, and the soluble fraction is sampled to obtain 3,5-dihydroxy- - < / RTI > menthol stilbene and / or 3,5-dihydroxystilbene.

32. A method of extracting ginger from 40 to 100 mass% ethanol aqueous solution, extracting the extract using a mixture of carbon dioxide in a supercritical state and an aqueous 2 to 10 mass% ethanol solution, extracting the extract, , 3,5-dihydroxy-2-menthaneylstilbene and / or 3,5-dihydroxystilbene.

According to the antimicrobial agent and the malodor production inhibitor of the present invention, it is possible to prevent various infectious diseases caused by microorganisms and to suppress the production of malodor originating from microorganisms. That is, as a means for preventing and treating dental caries and periodontal disease in the oral cavity region, it can be used as a preventive / therapeutic means for a purulent disease or the like in the skin area, However, preservative effect can be expected by mixing with various products. In addition, it is possible to provide means effective for odor generation, such as suppressing body odor, washing clothes, suppressing the damp smell of garments, suppressing odor of food waste, and the like, which are caused by microorganisms.

The antimicrobial agent and the malodor growth inhibitor of the present invention are derived from a ginger which exists in nature and do not put a load on the human body, animal or environment, and therefore they are applied to various foods, beverages, medicines, quasi drugs, cosmetics and miscellaneous goods It can be expected that it can contribute not only to the improvement of the health of the people but also to the pleasant life.

According to the method of manufacturing or collecting the present invention, ginger extracts which can be mixed with the above-mentioned formulations and compositions can be industrially advantageously obtained.

BRIEF DESCRIPTION OF THE DRAWINGS FIG. 1 is a flow chart of a method for fractionating and purifying a dried tree extract. FIG.
2 is a diagram showing ¹ H-NMR (500 MHz, heavy methanol) spectrum of Preparation Example 7;
3 is a diagram showing ¹³ C-NMR (125 MHz, heavy methanol) spectrum of Preparation Example 7;
4 is a view showing the ESIMS (neg) spectrum of Preparation Example 7. Fig.
5 is a diagram showing an EIMS (pos, TMS derivative) spectrum of Preparation Example 7;
6 is a view showing the UV spectrum of Preparation Example 7;
7 is a diagram showing the IR spectrum of Preparation Example 7. Fig.
8 is a diagram showing ¹ H-NMR (500 MHz, middle methanol) spectrum of Preparation Example 6;
9 is a diagram showing ¹³ C-NMR (125 MHz, heavy methanol) spectrum of Preparation Example 6;
10 is a view showing the ESIMS (neg) spectrum of Preparation Example 6;
11 is a view showing the EIMS (pos, TMS derivative) spectrum of Preparation Example 6;
12 is a diagram showing a UV spectrum of Preparation Example 6. Fig.
13 is a diagram showing the IR spectrum of Preparation Example 6;
14 is a flowchart for extracting a promoted wood extract from a promoted tree.
FIG. 15 is a flowchart for supercritical extraction of a promoted wood extract from a promoted tree. FIG.

Hereinafter, the present invention will be described in more detail.

The 3,5-dihydroxy-2-menthane stilbene of the present invention is a novel substance and is represented by the following structural formula (1). The antimicrobial agent of the present invention is 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) as an active ingredient. Also, the malodor growth inhibitor of the present invention comprises 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) and 3,5-dihydroxystyrene represented by the following structural formula (2) Ben is the active ingredient. These active ingredients are active ingredients obtainable by solvent extraction from ginger, especially LINDERA UMBELLATA or subspecies thereof. As the active ingredient, the active ingredient may be used as it is, or an extract of the ginger ingredient containing the active ingredient at a high concentration may be used. As the extract of ginger, which contains the active ingredient at a high concentration, it is particularly preferable to use 3,5-dihydroxy-2-mentenylstilbene of the formula (1) or 3,5-dihydro 2-menthane stilbene and the 3,5-dihydroxystilbene of the formula (2) in an amount of not less than 1% by mass, particularly not less than 3% by mass, of the solid content are preferable, .

In the present invention, ginger is extracted with an aqueous solution of ethanol in an amount of 40 to 100% by mass, preferably 60 to 90% by mass, the extract is concentrated under reduced pressure at 50 占 폚 or lower and the alcohol concentration is adjusted to 10 to 30% ) Is adsorbed onto a spherical cross-linked polymer having a porous structure, for example, a styrene divinylbenzene-based synthetic resin, specifically, Diaion HP-20 (manufactured by Mitsubishi Chemical Corporation) , Preferably less than 30% by mass of ethanol aqueous solution, followed by elution with 40 to 70% by mass, preferably 50 to 70% by mass ethanol aqueous solution, and / %, Preferably more than 70 to 90% by mass ethanol aqueous solution, and elution with an aqueous solution of ethanol in an amount of 40 to 70% by mass, preferably 50 to 70% by mass, is performed to obtain 3,5-dihydroxystilbene To take , And / or by extracting 3,5-dihydroxy-2-mentenylstilbene from an eluate of more than 70 to 100 mass%, preferably more than 70 to 90 mass% ethanol aqueous solution, Can be collected.

In this case, the eluate with an aqueous solution of ethanol in an amount of 40 to 70 mass%, preferably 50 to 70 mass%, is concentrated under reduced pressure at 50 DEG C or lower, and the concentrated extract is subjected to chemical conversion of octadecyl group The mixture is adsorbed to a bound carrier, for example Cosmosil 75C18-OPN made by Nacalai Tesque, and eluted with 50 to 80 mass% aqueous methanol solution to develop into three fractions, - dihydroxystilbene. ≪ / RTI >

In this case, the eluate with an aqueous solution of ethanol in an amount of more than 70% by mass to 100% by mass, preferably in an amount of more than 70% by mass to 90% by mass is developed by silica gel chromatography, and a mixture ratio of n-hexane and acetone (V / V) To elute fractions between the elution fractions by the final 8: 1 volume ratio and the elution fractions by the final 8: 1 volume ratio are preferably obtained to obtain 3,5-dihydroxy-2-menthaneylstilbene.

In the present invention, the ginger is extracted with an aqueous solution of ethanol in an amount of 40 to 100% by mass, preferably 60 to 90% by mass, and the extracted solution is further extracted with an aqueous 20 to 40% by mass ethanol solution, , Followed by extraction with an aqueous solution of ethanol in an amount of more than 40 to 100 mass%, preferably more than 40 to 60 mass%, and collecting the soluble portion, 3,5-dihydroxy-2-mentenylstilbene and 3,5- Dihydroxystilbene. ≪ / RTI >

In this case, the soluble portion was concentrated under reduced pressure at 50 DEG C or lower and the alcohol concentration was adjusted to 10 to 30% (V / V) by adsorption treatment with a spherical cross-linked polymer having a porous structure, By weight or more, preferably 90% by weight or more of ethanol aqueous solution or ethanol, and collecting the eluting solution. As the spherical cross-linked polymer having a porous structure, the same materials as those described above can be used.

Here, the ginger can be a whole plant as a raw material, but a part of it (branches, stems, roots, buds, leaves, flowers, (Fruit), etc.) may be used. Particularly, it is preferable to use branches, stems and roots in view of the yield of the objective compound. In addition, the origin of plants belonging to the ginger family is good. Species include Lindera communis var. Okinawensis, Lindera erythrocarpa, Lindera glauca, Lindera obtusiloba, Lindera obtusiloba f. Villosa, , Lindera sericea, Lindera sericea var. Glabrata, Linda strychnifolia, Lindera umbellata, KIMINOOVA (黄) Lindera umbellata var. Aurantiaca, Linda umbellata var. Lancea, Linda umbellata var. Membranacea, Lindae citriodora, Lindera praecox, Hosoba paraben oin praecox f. Angustifolium, Lindae praecox var. Pubescens, Lindera triloba, , Paraben oin trilobum f. Integrum, Paraben oin trilobum f. Pilo (Paraben oin trilobum f. (Lindera umbellata var. aurantiaca), which is a subspecies of Lindera umbellata and its subspecies, Hime (姬) ghkdtldfLindera umbellata var. Lancea, and uva laver (Lindera umbellata var. Membranacea) can be used more appropriately.

The promoted tree species as these raw materials are preferably in a dry state, but may be used in a wet state.

Extraction from ginger can be carried out by using a low alcohol, a polyhydric alcohol such as glycerin or propylene glycol, a saturated hydrocarbon such as pendan, hexane or heptane, an ethyl acetate, an acetone, a petroleum ether, an acidic solution or an alkaline solution May be used alone or in combination of two or more kinds. Among them, it can be efficiently extracted with an organic solvent, and in particular, a hydrophilic organic solvent is excellent in terms of extraction efficiency. Particularly, lower alcohols having 1 to 4 carbon atoms, that is, methanol, ethanol, propanol, isopropanol, n-butanol, isobutanol, t-butanol or a mixture thereof can be more preferably used. These water-soluble organic solvents are more preferably water-soluble organic solvents, and most preferred are water-soluble alcohols having a concentration of 30 to 95 mass%, because the objective components can be extracted more efficiently.

These extraction solvents are preferably used in a mass ratio of about 1 to 50 times, and particularly preferably 2 to 20 times, to the extraction raw materials.

The extract can be subjected to filtration, centrifugation or the like to remove the solid matter, and after concentration, a crude extracted fraction can be obtained. Since this crude extract fraction also contains 3,5-dihydroxy-2-menthaneylstilbene and 3,5-dihydroxystilbene as active ingredients, such a crude extract fraction may be directly added to the composition , And further fractionated and purified from the viewpoint of securing the stability of the composition.

In this case, fractionation and purification can be performed by a combination of solvent extraction and various chromatography. Considering the molecular weight and physicochemical properties of the target substance, the conditions for the carrier and the eluting solvent can be appropriately selected according to various chromatographic methods.

In order to change the amount ratio (amount ratio) of the antimicrobial agent and the malodor production inhibitor in the extract in response to the purpose of use, the two active ingredients 3,5-dihydroxy-2-mentenylstilbene and 3,5- The method of fractionating dihydroxystilbene can be carried out, for example, in accordance with the following method.

That is, as a first method, there is a method including an adsorption process with an adsorbent and an elution process, that is, a method in which the bark of the ground pulverized tree is extracted with a hydrophilic organic solvent such as ethanol or the like, the solid material is removed with a glass filter, The concentrated crude extract was subjected to an adsorption column chromatography using a spherical crosslinked polymer having a porous structure such as activated carbon or Diaion HP-20 (Mitsubishi Chemical Co., Ltd.) as a carrier. After adsorbing the objective component, water , Ethanol, ethanol, and the like, and then fractionated by successively eluting them. In this case, 3,5-dihydroxystilbene is largely eluted with a highly polar solvent, for example, about 30 to 60 mass% ethanol (hereinafter referred to as eluted portion A), 3,5 (Hereinafter referred to as eluted portion (B)) by a solvent having a lower polarity, for example, about 60 to 90 mass% of ethanol, the dihydroxy-2- The active substance of the species can be isolated. After the separation, it can be decolorized with acidic clay, diatomaceous earth or the like.

By such a process, 3,5-dihydroxy-2-menthaneyl stilbene and 3,5-dihydroxy stilbene are contained in an amount of 1% by mass or more, particularly 5% by mass or more, 7% by mass or more and 20% by mass or less can be prepared, and this can be used as an extract of ginger plants containing the active ingredient of the formula (1) and / or the formula (2) at a high concentration.

The eluted portion A and the eluted portion B are subjected to reverse phase chromatography using an ODS carrier (a carrier obtained by chemically bonding an octadecylsilyl group) to a normal phase chromatography using a silica gel carrier The target component can be purified.

As a second method, a supercritical extraction method by bringing into contact with carbon dioxide in a supercritical state, in addition to a production method including an adsorption step and an elution step by the adsorbent described as the first method, And from the viewpoint of stability, it can be suitably used as a method for obtaining a preferable ginger extract. In this case, the desired components can be extracted by supercritical extraction of the ground water of the ginger with an organic solvent such as ethanol. The extract prepared by the adsorption process and the elution process can be re- In this case, the extract may be dispersed and adsorbed onto a cellulose powder or the like for the purpose of discoloration before supercritical extraction.

That is, in the present invention, the ginger is extracted by using a mixture of carbon dioxide in a supercritical state and an aqueous solution of ethanol in an amount of 2 to 10 mass%, and the soluble portion thereof is sampled to obtain an effective component of ginger , 3,5-dihydroxy-2-menthane stilbene and / or 3,5-dihydroxy stilbene.

Further, the ginger is extracted with an aqueous solution of ethanol in an amount of 40 to 100 mass%, preferably 60 to 90 mass%, and the extract is subjected to extraction using a mixture of carbon dioxide in a supercritical state and an aqueous 2 to 10 mass% Dihydroxy-2-menthane stilbene and / or 3,5-dihydroxy stilbene can be obtained by extracting the extract from the ginger and extracting the active ingredient of the ginger plant .

The conditions of the supercritical extraction are not particularly limited, but it is preferable to perform extraction under the conditions of a temperature of 40 to 80 DEG C, a pressure of 15 to 45 MPa, and an extraction time of 1 to 6 hours.

By carrying out the supercritical extraction process as described above, a mixture of 3,5-dihydroxy-2-menthaneylstilbene and 3,5-dihydroxystilbene can usually be obtained. By adjusting, 3,5-dihydroxy-2-mentenylstilbene or 3,5-dihydroxy stilbene alone can be obtained. Further, if necessary, 3,5-dihydroxy-2-mentenylstilbene or 3,5-dihydroxystilbene may be isolated from the obtained mixture. In this case, 3,5-dihydroxy-2-menthaneylstilbene, 3,5-dihydroxystilbene, as a mixture thereof, or alone, is present in an amount of not less than 1% by mass, particularly not less than 3% Or more and 20 mass% or less can be prepared, and it can be used as a ginger extract containing the active ingredient of the formula (1) and / or the formula (2) at a high concentration.

The extracts of 3,5-dihydroxy-2-mentenylstilbene represented by the above formula (1) or the ginger extract containing the extract at a high concentration thereof have an extremely high antimicrobial activity And can be effectively used as an antimicrobial agent. The extracts of 3,5-dihydroxystilbene represented by the above formula (2) or the ginger extracts containing the same at a high concentration thereof have an odor-inhibiting activity, and they are used in combination It becomes clear that the activity of inhibiting the offensive odor is remarkably increased, and it can be effectively used as an offensive odor inhibitor.

The antimicrobial active agent and the malodor growth inhibitor of the present invention can be formulated for the above-mentioned purposes in oral compositions, skin, cosmetic for hair, cleaning composition, and food and drink.

When the antimicrobial agent and the malodor growth inhibitor according to the present invention are incorporated into the composition, the amount of the antimicrobial agent and the malodor production inhibitor is preferably in the range of 3,5-dihydroxy-2-mentenylstilbene and 3,5-dihydroxy- ).

When an antimicrobial effect is expected, it is preferable that 0.00001 to 3 mass%, particularly 0.0005 to 1 mass% in terms of 3,5-dihydroxy-2-mentenylstilbene content, And from the viewpoint of ensuring usability and usability of the composition. When the blending amount is less than 0.00001 mass%, sufficient antimicrobial activity is not exhibited. When the blending amount exceeds 3 mass%, there arises a problem in feeling of use and usability of the composition, and a feeling of discomfort such as taste, smell, May occur.

In addition, when the odor-inhibiting effect is expected, the total amount of the composition is preferably from 0.0001 to 3 mass% in terms of the total amount of 3,5-dihydroxy-2-menthane stilbene and 3,5-dihydroxy stilbene %, Particularly 0.0005 to 1% by mass, particularly 0.001 to 0.8% by mass, is preferably added from the viewpoints of effect development and securing usability and usability of the composition. When the total amount of the 3,5-dihydroxy-2-menthane stilbene content and the 3,5-dihydroxystilbene content is less than 0.0001 mass%, sufficient malodor growth inhibiting activity is not exhibited and more than 3 mass% , There arises a problem in feeling of use and usability of the composition, and there may be a feeling of discomfort such as taste, odor, and defective dissolution.

The amount of 3,5-dihydroxystilbene is preferably 0.0001 to 2 mass%, particularly 0.001 to 1 mass%, based on the entire composition.

In the case of using the ginseng extract obtained by fractionation purification as the active ingredients of the above formulas (1) and (2), when the composition is formulated at a high concentration in the composition, the coloring, There may be a problem of In this case, the blending amount of the extract is preferably from the viewpoint that less than 10% by mass of the whole composition prevents discoloration, and the lower limit is preferably 0.001% by mass or more, particularly 0.01% by mass or more.

In addition to the antimicrobial agent and the malodor production inhibitor, the composition of the present invention may be formulated into other components such as an oral composition, cosmetic for skin or hair, a cleaning composition, And a known component used for food, drink, food and the like.

The antimicrobial agent and the malodor growth inhibitor of the present invention can be used in various formulations and can be used in human or animal products such as external preparations for skin, skin or hair cosmetics, or oral compositions. Specifically, examples of the external preparation for skin or cosmetics for skin include creams, hand creams, emulsions, lotions, lotions, soaps, hand soaps, body soaps, antiperspirants, athlete's foot preparations, acne remedies, disinfectants, , Adhesives, packs, eyedrops and the like. Hair cosmetics can be incorporated into shampoos, rinses, treatments, tonics, hair restorers, hair gels, hair waxes, hair creams, hair foams, hair sprays, hair waters and the like. Oral compositions may be formulated into a dentifrice, a mouthwash, a gum massage cream, and the like.

The antimicrobial agent and the malodor growth inhibitor of the present invention can also be used in cleaning compositions such as medical compositions, kitchen compositions, and residential compositions. For example, the cleaning composition for medical use can be incorporated in a detergent for clothes, a detergent for pretreating clothes, a detergent for running shoes, a softener, a bleaching agent, a rinsing agent, a water repellent agent, an antistatic agent and the like. As the cleaning composition for kitchen, it can be mixed with detergent for dishware, laundry detergent, detergent for range, detergent for automatic dishwasher, and the like. As the composition for cleaning for residential use, it can be mixed with a detergent for bathroom, a detergent for bathroom bath, a detergent for window, a detergent for furniture, flooring, a room, a deodorant in the room, and a cleaning deodorant for air conditioner.

In addition, the antimicrobial agent and the malodor production inhibitor of the present invention can be used for various functional foods including various food compositions, for example, specific health foods, nutritional functional foods, and the like.

These compositions according to the present invention can be prepared by appropriately selecting and blending known compounding ingredients that satisfy the intended use, kind, formulation, and the like of the composition, and can be prepared by a routine method. For example, surfactants, oils, alcohols, moisturizers, thickeners, chelating agents, pH adjusters, perfumes, pigments, ultraviolet absorptive / scattering agents, vitamins, water and the like can be appropriately compounded as needed. The optional components are not limited to these, and may be compounded in such a range as not to hinder the effect of the present invention.

The oral composition of the present invention may be in the form of a solid, a solid, a liquid, a liquid, a gel, a paste, a chewing gum or the like and may be in the form of a skirt, a liquid skirt, a liquid skirt, Gum massage cream, oral paste, mouth washer, trochie, chewing gum, and the like. The manufacturing method may also be a routine method depending on the formulation.

In the composition for oral cavity, other optional ingredients may be appropriately added in addition to the essential ingredients described above in response to the purpose, the formulation of the composition, etc. For example, in the case of a continuous skirt, a known abrasive, , A sweetening agent, an antiseptic, an effective ingredient, a coloring matter, a perfume, and the like may be blended if necessary, and these components may be mixed with water.

Concretely, in the case of a skirt type, one or two or more kinds of abrasives such as calcium hydrogenphosphate, anhydride and dihydrate, calcium carbonate, aluminum hydroxide, alumina, silicic anhydride and other synthetic resins may be blended (The blending amount is usually from 5 to 60 mass%, and from 10 to 55 mass% in the case of continuous skirt).

In the case of a paste-like composition such as a continuous skirt, as a binder, alginic acid derivatives such as carrageenan, carboxymethylcellulose sodium and hydroxyethylcellulose, gums such as xanthan gum, synthetic binders such as polyvinyl alcohol, , And the like. (The blending amount is usually 0.3 to 10 mass%).

As the viscosifier, one or more of polyhydric alcohols such as glycerin and propylene glycol, and sugar alcohols such as sorbitol, xylitol, maltitol and erythritol may be blended (the blending amount is usually 5 to 70 mass%).

As the surfactant, conventionally known nonionic surfactants, anionic surfactants, amphoteric surfactants, and cationic surfactants, which are usually blended, may be blended.

The blending amount of the surfactant is appropriately selected depending on the form of the composition, the intended use, and the like. For example, 0 to 10 mass%, particularly 0.1 to 5 mass%, and 0 to 5 mass% of the liquid skirt and the cleaning agent may be blended into the continuous skirt.

As the sweetening agent, saccharin sodium and the like can be blended.

The perfume can be at least one selected from natural perfumes such as peppermint oil and spearmint oil and flavors obtained by processing (current part, wake cut, identification, liquid extraction, essence, powder flavor etc.) of these natural perfumes, , Carbohydrate and anethole, and flavorings such as strawberry flavor, apple flavor, banana flavor, pineapple flavor, grapeflavor, mango flavor, butter flavor, milk flavor, fruit mix flavor and tropical fruit flavor , A composition for oral cavity, and the flavor of the examples is not limited.

The blending amount is not particularly limited, but it is preferable that the above-mentioned perfume material is used in an amount of 0.000001 to 1 mass% in the formulation. It is preferable that the flavorings for inhalation using the perfume materials are used in an amount of 0.001 to 2.0 mass% in the formulation.

The oral composition of the present invention may contain, in addition to the compounds of the above formulas (1) and (2), one or more known active ingredients such as enzymes, fluorides, vitamins and derivatives thereof, Two or more species can be blended. The blending amount may be an effective amount within the range not hindering the effect of the present invention (blending amount is usually from 0.0001 to 5.0 mass%).

The oral composition of the present invention can be used by putting it in a predetermined container such as an aluminum tube, a laminate tube made of plastic or the like on both sides of the aluminum foil, a plastic tube, a bottle-shaped container or an aerosol container.

The skin or hair cosmetic composition of the present invention can be formulated into various formulations such as an aqueous solution, a solubilization system, an emulsion system, an emulsion system, a gel system, a paste system, an ointment system, an aerosol system, a water- . For example, a skin or hair external preparation such as a cosmetic can be used as a body soap, a lotion, a lotion, a shampoo, a rinse, a hair conditioner, a hair tonic, a milky lotion, a cream, a gel, a pack, a mask, a mist, A pressure-sensitive adhesive, a dispersing agent, an aerosol spray, a stick type, and the like, and the manufacturing method thereof can employ a routine method depending on the formulation.

In this case, the skin or hair cosmetic composition may be blended with other known optional components as needed, in addition to the above-mentioned components in response to the purpose, formulation of the composition, and the like. For example, inorganic particles having a deodorizing function, a limiting agent, a chelating agent and the like can be appropriately compounded to enhance the deodorizing or deodorizing effect.

Here, examples of the inorganic particles having a deodorizing function include silicic acid, silicic anhydride, zinc oxide, aluminum oxide and the like and complexes thereof; Talc, and the like. These can be used singly or as a mixture of two or more kinds (the blending amount is usually 0.01 to 60 mass%).

The shape of the inorganic particles is not particularly limited, such as a spherical shape, a plate shape, a granular shape, a needle shape and the like, but a spherical shape is preferable from the feeling when applied to the skin. The particle diameter of the particles is preferably 0.1 to 50 占 퐉, more preferably 0.3 to 20 占 퐉, from the viewpoint of use feeling.

Examples of the limiting (antiperspirant) component include single salts having a converging action such as aluminum chloride, glycol complexes and amino acid complexes containing single salts thereof, and they may be used alone or in combination of two or more (Blending amount is usually 1.0 to 50.0 mass%).

Examples of the chelating agent include citric acid, tartaric acid, and sodium salts and potassium salts thereof, and they can be used alone or as a mixture of two or more kinds (the amount is usually 0.01 to 5% by mass).

The skin or hair cosmetic composition may further contain at least one selected from the group consisting of oils and fats such as liquid fats and solid fats, waxes, hydrocarbon oils, higher fatty acids, higher alcohols, synthetic ester oils, silicones, various surfactants, A pharmaceutical composition such as a thickener, a vitamin, a hormone and the like, a flavor, a pigment, an emulsifying stabilizer, a pH adjusting agent, an astringent, a refreshing agent and the like may be added and a desired composition may be prepared.

These optional components are not limited and the compounding amount may be a conventional amount within a range not hindering the effect of the present invention.

As the surfactant, conventionally known nonionic surfactants generally used in these formulations can be blended, and there is no particular limitation, and they can be appropriately selected in accordance with the purpose.

The blending amount of the surfactant is preferably in the range of usually 0 to 20 mass%.

In addition, these compositions may be prepared as an aerosol composition. In this case, the aerosol container containing the composition and the jetting agent may be filled, and aerosol compositions such as aerosol compositions containing antiperspirant di .

The blowing agent is not particularly limited and may be appropriately selected in accordance with the purpose. Examples thereof include ethane, propane, ethylene, isobutane, normalbutane, propylene, isopentane, neopentane, normal pentane, cyclopentane, Dimethylbutane, dimethyl ether, compressed gas (carbon dioxide, nitrogen, air or a mixture thereof), and one or more of them may be used (the blending amount is usually 80 to 99 mass% ).

The aerosol container is not particularly limited and can be appropriately selected in accordance with the purpose. Examples of the aerosol container include a container body, a valve fixed to the opening of the container body, and a dispensing button.

In this case, examples of the material of the container body include metals such as aluminum and stainless steel, resins such as polyethylene terephthalate, and pressure-resistant glass.

Further, the aerosol composition containing the limited diodanthurt agent is filled in the aerosol container by a known method, and examples of the filling method include a cooling filling method, a pressure filling method, and an under cup filling method.

In addition, in the case of the cleaning composition according to the present invention, conventionally known additives and the like may be used. Concretely, a perfume, a pH adjuster, other known water-soluble polymers, a stabilizer, a natural extract, a coloring matter and the like can be arbitrarily mixed with a surfactant, a solvent and, if necessary,

Depending on the purpose such as washing or bubbling, a surfactant can be appropriately compounded.

As the surfactant, those generally used such as anionic surfactant, amphoteric surfactant, and nonionic surfactant can be used (the blending amount is usually 5 to 70 mass%).

In addition, depending on the purpose of dissolving the components or the like, a solvent can be appropriately compounded. Specific examples of the solvent include, in addition to water, lower monohydric alcohols such as methanol and ethanol, and polyhydric alcohols such as ethylene glycol and propylene glycol. The content of the solvent is preferably from 5 to 60 mass%, more preferably from 10 to 30 mass%. The solvent may be used alone or in combination of two or more.

In addition, fragrances can be appropriately blended for purposes such as perfume. The perfume ingredient is not particularly limited, and a known perfume can be blended. Specific examples thereof include synthetic fragrances such as hydrocarbons such as aliphatic hydrocarbons, alcohols such as aliphatic alcohols, oxides, aldehydes, ketones, acids, lactones, esters, nitrogen compounds and the like and natural flavors from plants . The perfume ingredients may be used singly or in combination of two or more kinds, and plural ones are usually used.

The pH adjuster that can be appropriately added for the purpose of pH adjustment and the like is not particularly limited, but specific examples thereof include sodium hydroxide, potassium hydroxide, citric acid and salts thereof, benzoic acid and salts thereof, malic acid and salts thereof, And salts thereof, phosphoric acid and salts thereof, and the like.

Examples of the food and drink according to the present invention include candy, candy, gum, gummy jelly, jelly and the like. To these food and drink, conventionally added components may be added. Specifically, a saccharide, an organic acid, a protein, a fat, a flavor, an amino acid, a vitamin and the like may be arbitrarily blended if necessary.

Example

Hereinafter, the formulation examples, the experimental examples, the examples, the comparative examples and the prescription examples are shown and the present invention will be described in detail, but the present invention is not limited to the following examples. Also,

The percentages shown in the following examples are all% by mass. Me is a methyl group, and Et is an ethyl group.

[Preparation Example]

<Preparation of antimicrobial fractions>

The active ingredient present in the ginseng extract is fractionated from the dried branches of the ginseng tree by the method shown below to carry out in accordance with the flowchart of Fig. 1, and the obtained compound is identified, Respectively.

500 g of the dried eggplant tree was extracted with 2.5 L of 70% ethanol heated to 50 캜. After cooling, the solid matter was removed by filtration, the filtrate was concentrated under reduced pressure at 50 캜 or lower, To obtain about 26 g (Comparative Preparation Example 1). This was adsorbed on Diaion HP-20, eluted with 100 ml of 30% ethanol, followed by elution with 100 ml of 60% ethanol, and finally elution with 100 ml of 80% ethanol. 10 g (Comparative Preparation Example 2), 6 g (Preparation Example 1) and 8 g (Preparation Example 2) were obtained as extracts, respectively, by concentration under reduced pressure. The antimicrobial activity and the enzyme inhibitory activity were measured by the method described later, and it was found that the antimicrobial activity was present in the fraction of Preparation Example 2 and that the enzyme inhibitory activity was present in the fraction of Preparation Example 1. Therefore, Was further purified, and the components thereof were specified.

That is, 2 g of the extract of Preparation Example 1 was applied to a liquid column chromatography (Cosmosil 75C18-OPN (Nacalai Tesque)) and fractionated into three fractions by 50% methanol (Comparative Preparation Example 3, Preparation Example 3, Comparative Example 4). Among them, the main peak of the fraction having the highest enzyme inhibitory activity (Preparation Example 3) was aliquoted by HPLC, and 600 mg of a purified product having a purity of 100% was obtained (Preparation Example 6).

Separately, the fractions of Preparation Example 2 were applied to silica gel chromatography and sequentially eluted at a volume ratio of n-hexane: acetone mixture of 20: 1, 15: 1, 10: 1, 7: (Comparative Preparation Example 5, Preparation Example 4, Preparation Example 5, Comparative Preparation Example 6, and Comparative Preparation Example 7). The main peak fraction was fractionated with 50% acetonitrile using Cosmosil 75C18-OPN in the ratio of the fraction eluted with n-hexane: acetone having the highest activity to 10: 1 with the fraction eluted with 15: 1 To obtain 650 mg of a purified product having a purity of 98% (Preparation Example 7).

¹ H-NMR (500 MHz, heavy methanol), ¹³ C-NMR (125 MHz, heavy methanol), ESIMS (neg), EIMS pos, TMS derivative), UV and IR spectra were measured. The results are as follows. The spectra and the chemical structural analysis results of Preparation Example 7 are shown in Figs. 2 to 7. As a result, Preparation Example 7 was identified as 3,5-dihydroxy-2-mandenylstilbene. The spectra and the chemical structure analysis results of Preparation Example 6 are shown in Figs. 8 to 13. As a result, Preparation Example 6 was identified as pinosylvin (3,5-dihydroxystilbene).

Preparation Example 6:

¹ H-NMR (500MHz, methanol): δ = 6.15-6.25 (1H, t), 6.45-6.55 (2H, d), 6.9-7.1 (2H, dd), 7.15-7.25 (1H, t), 7.3 -7.4 (2H, t), 7.45-7.55 (2H, d)

¹³ C-NMR (125 MHz, heavy methanol):? = 103.0-103.5, 105.8-106.4, 127.3-127.6, 128.4-128.6, 129.4-129.6, 129.5-129.8, 129.8-130.1, 138.7-138.9, 140.6-140.9, 159.6 -159.9

ESIMS (neg): m / z = 211.0820 [MH] - (Calcd for C 14 H 11 O 2 211.0759.), M / z = 225.0439 [MH + CH 2] -,

EMS (pos, TMS derivative): m / z = 356.1616 [M + 2 (C ₃ H ₈ Si)] ⁺ ( ^Calcd . For C ₂₀ H ₂₈ O ₂ Si ₂ 356.1628)

m / z = 341.1391 [M + 2 (C 3 H 8 Si) -CH 3] +,

UV:? _Max (MeOH) 306 nm (log? 4.44)

IR (KBr) v _Max 3350 cm ^-1 (OH), 1650 cm ^-1 , 1450 cm ^-1 , 830 cm ^-1 (C = C)

Preparation Example 7:

¹ H-NMR (500MHz, in methanol): δ = 0.6-0.75 (3H, d), 0.75-0.8 (3H, d), 1.35-1.65 (2H), 1.7-1.85 (5H), 2.0-2.3 (3H ), 5.3-5.4 (IH, s), 6.2-6.3 (IH, s), 6.5-6.6 (IH, s), 6.7-6.8 (IH, d), 7.1-7.25 , &lt; / RTI &gt; d), 7.35-7.45 (2H, d), 7.65-7.85

¹³ C-NMR (125 MHz, heavy methanol):? = 16.7-17.3, 21.7-22.3, 23.6-24.0, 24.0-24.5, 28.8-30.3, 32.2-32.6, 37.6-38.3, 102.6-103.1, 105.4-105.9, 122.1 -122.6, 127.0-127.5, 128.0-128.4, 128.4-128.7, 129.2-129.5, 129.5-129.8, 129.9-130.2, 133.2-133.8, 139.3-139.8, 139.8-140.3, 156.6-157.0, 157.8-158.2

ESIMS (neg): m / z = 347.2000 [MH] - (. Calcd for C 24 H 27 O 2 347.2011), m / z = 333.1841 [M-CH 3] -,

m / z = 361.1790 [M- H + CH 2] -,

EMS (pos, TMS derivative): m / z = 492.2836 [M + 2 (C ₃ H ₈ Si)] ⁺ ( ^Calcd . For C ₃₀ H ₄₄ O ₂ Si ₂ 492.2880)

m / z = 422.2025 [M + 2 (C 3 H 8 Si) -C 5 H 10] +,

UV:? _Max (MeOH) 306 nm (log? 4.31)

_{IR: (KBr) ν Max 3350㎝} -1 (OH), 1650㎝ -1, 1450㎝ -1, 830㎝ -1 (C = C)

<Preparation of extract tree extract>

Using the dry branches of the callus tree, components were extracted and fractionated according to the following extraction method according to the flowchart shown in Fig.

5 kg of a dried egg branch of Chinese gourd tree was heated and extracted twice with 25 L of 80% ethanol heated to 50 DEG C. After cooling, the solid matter was removed by filtration and the filtrate was dried under the condition of 50 DEG C or lower The mixture was concentrated under reduced pressure to obtain about 300 g of a ginger extract (moisture content 25%: Comparative Preparation Example 8).

1,000 g of 30% ethanol was added to 300 g of the obtained gypsum tree extract, stirred for 1 hour while being warmed to 50 DEG C, and then allowed to stand for one week to discard the 30% ethanol-soluble portion (Comparative Preparation Example 9) -2-menthane stilbene (8.0%) and 3,5-dihydroxy stilbene (7.3%) (Preparation Example 8).

1,500 ml of 50% ethanol was added to 300 g of the bottle-like extract thus obtained, and stirring and extraction for 1 hour were repeated twice. The insoluble portion (Comparative Preparation Example 10) was discarded and the soluble portion was diluted with 50% , And eluted with 1,500 ml of 99.5% ethanol. The adsorbent was again washed with 1,000 ml of 99.5% ethanol, and the filtrate was combined with the above elution portion and concentrated under reduced pressure at 50 DEG C or lower to obtain 9.56% of 3,5-dihydroxy-2-menthane stilbene, 180 g of a soft extract containing 15.19% of hydroxystilbene was obtained (Preparation Example 9). Further, by treating the extracted yeast extract with acidic clay and diatomaceous earth, a yeast extract containing 14.1% of 3,5-dihydroxy-2-menthaneyl stilbene and 16.6% of 3,5-dihydroxy stilbene (Preparation Example 10).

&Lt; Preparations of the extract of the promoted wood by supercritical extraction-1 >

Using the dry branches of the dried persimmon tree, the components were extracted and fractionated by the supercritical extraction method shown below according to the flowchart shown in Fig.

1 kg of the dried product (chip shape) of Chinese goose bushes was placed in an extractor, supernatant extraction was carried out for 2 hours under the conditions of 40 DEG C and 45 MPa, and 100% by volume of carbon dioxide was added with 5% Respectively. Ethanol was distilled off from the obtained gristle wood extract to obtain a brown yeast extract 37.2 containing 7.5% of 3,5-dihydroxy-2-menthane stilbene and 5.3% of 3,5-hydroxystilbene. g.

1,000 ml of 70% ethanol (EtOH) was added to the extract, and the mixture was heated and refluxed for 1 hour, followed by leaving for one week to insolubilize.

The oily substance was removed by filtration to obtain 30.1 g of a brown extract containing 9.6% of 3,5-dihydroxy-2-mandenylstilbene and 6.7% of 3,5-hydroxystilbene ( Preparation example 11).

&Lt; Preparations of ginseng extract by supercritical extraction-2 >

Similarly to the above, 1 kg of the dried Chinese ginseng extract was extracted with 10 L of 70% ethanol heated to 40 DEG C, and then concentrated under reduced pressure to obtain 70 g of a ginger extract. For the purpose of discoloration, 5% ethanol was added to 100 times the amount of carbon dioxide and supercritical extraction was carried out for 2 hours under the conditions of 40 DEG C and 45 MPa, while being homogeneously dispersed and adsorbed on 700 g of cellulose powder. When the ethanol was distilled off under reduced pressure from the obtained gristle wood extract, 42 g of a brown soft extract containing 3,5-dihydroxy-2-menthane stilbene (10.6%) and 3,5-hydroxystilbene (3.0% Example 12).

[Experimental Example]

The fractions (Preparation Examples 1 to 12 and Comparative Preparation Examples 1 to 10) obtained by the fractionation methods shown in Figs. 1, 14 and 15 were evaluated for antibacterial activity, lower fatty acid production inhibition evaluation, volatile sulfur compound production inhibition evaluation , And used for formulation stability evaluation to evaluate its activity. In addition, a part of these fractions were compounded in a tooth wear composition to evaluate the preparation stability. The results are shown in Tables 1 and 2.

&Lt; Evaluation of antibacterial activity &

The microorganism used in the test was purchased from the American Type Culture Collection (ATCC), and the pre-culture was performed by the following method.

Actinomyces viscosus ATCC 43146, Fusobacterium nucleatum ATCC 10953, Porphyromonas gingivalis ATCC 333277, Prevotella intermedia ATCC 25611 and Streptomyces spp. Streptococcus mutans ATCC 25175 was cultured in Todd-Hewitt-broth (Becton and Dickinson) culture medium containing 5 mg / l of hemin (Sigma) and 1 mg / l of vitamin K (manufactured by Wako Pure Chemical Industries) [THBHM]. The cultivation was carried out at 37 캜 under anaerobic conditions (80 vol% nitrogen, 10 vol% carbon dioxide, 10 vol% hydrogen) for 24 hours.

Escherichia coli ATCC 8739, Pseudomonas aeruginosa ATCC 9027, Staphylococcus aureus ATCC 6538, Bacillus subtilis ATCC 6633, Candida albicans (Candida albicans) albicans ATCC 10231 and Aspergillus niger ATCC 16404 were cultured under aerobic conditions at 37 캜 for 24 hours using Mueller Hinton II liquid medium (manufactured by Becton and Dickinson) .

An ethanol solution of the test sample was prepared and 1/100 amount was added to 4 ml of the liquid medium described above so as to have the concentrations shown in Tables 1 and 2 and stirred well. The above-mentioned target microorganisms were inoculated at 10 ⁵ to 10 ⁶ cfu (Colony forming unit) and cultured for 24 to 48 hours under the same conditions as the pre-culture, and the absorbance at 550 nm was measured by optical microscope observation The presence of microbial growth was determined and the minimum growth inhibitory concentration (MIC) was determined.

<Evaluation of inhibition of low fatty acid production>

Preparation of bacterial enzyme solution:

Porphyromonas gingivalis ATCC33277, and Prevotella intermedia ATCC25611 were likewise cultured in a THBHM liquid medium to steady state. After centrifugation at 8,000 rpm for 10 minutes, the bacterial solution was suspended in phosphate buffered saline (PBS) to have a turbidity at 550 nm of 2.0, and the protease inhibitor cocktail set 2 (Calbiochem) And the cells were disrupted by ultrasonic waves for 3 minutes while ice-cooled (ice-cooled). The cell lysate was centrifuged at 14,000 rpm for 20 minutes at 4 DEG C, and the supernatant was collected to give a crude enzyme solution.

Inhibition of isovaleric acid production by bacterial enzyme inhibition:

To 1 ml of the crude enzyme solution, a PBS solution of L-leucine (Wako Pure Chemical Industries, Ltd.) and α-keto glutaric acid (Wako Pure Chemical Industries, Ltd.), which serves as a substrate for isovaleric acid, Concentration of 2.5 mM, the test sample was added to give a final concentration of 500 μg / ml, and the mixture was reacted at 37 ° C. for 6 hours in a 2 ml reaction system.

1 ml of the reaction solution was extracted with 2 ml of ethyl acetate under acidic conditions of sulfuric acid, and then 1 μl of the ethyl acetate layer was analyzed by gas chromatography under the following conditions, and the inhibition rate (%) of isovaleric acid production for the control was calculated. In the table, VFA production inhibition rate is described. The control is the amount of isovaleric acid production in the absence of the addition of the test sample.

Gas Chromatography Conditions:

Column: FFAP + H ₃ PO ₄ column (Shin Kizzu Kogyo Co., Ltd.)

Column temperature: Increase from 130 캜 to 210 캜

Detector: FID, 230 占 폚 (Shimadzu Corporation)

Carrier gas: nitrogen (50 ml / min)

<Evaluation of inhibition of volatile sulfur compound production>

L-cysteine and L-methionine were added to 1 ml of the crude enzyme solution of Porphyromonas jinx valis, respectively, and the test sample was added to a predetermined concentration, and the total volume was adjusted to 3 ml with PBS. This was placed in a 33 ml sterilized test tube, tightly closed with a silicone stopper, and allowed to react at 37 占 폚 for 1 hour. After the reaction, 5 ml of the gaseous phase in the test tube was analyzed by gas chromatography under the following conditions to calculate methylmercaptan and hydrogen sulfide production inhibition rate (%) for the control. In the table, VSC inhibitory rate is described. The control is the VSC production amount in the absence of the addition of the test sample.

Gas Chromatography Conditions:

Filler: DNP 20% Chromosorb WAW DMCS (GL Science)

Column temperature: 70 ° C

Detector: FPD, 130 占 폚 (Shimadzu Corporation)

Carrier gas: nitrogen (50 ml / min)

&Lt; Evaluation of formulation stability &

A toothbrushing composition containing 0.1% of a moss wood extract as a model skirt composition shown below was prepared by a routine method and stored at -5 ° C and 60 ° C for 1 month and then extruded onto paper and visually observed at -5 ° C The skirt composition stored for 1 month in a thermostatic chamber was used as a control article, and the discoloration of the skirt composition stored at 60 占 폚 for 1 month was evaluated according to the following criteria.

Criteria for discoloration:

?: No change in color was observed compared with the control product.

∘: Almost no change in color was observed compared with the control product.

?: A slight change in color was recognized compared with the control product.

X: Change in color is recognized compared with the control product.

Composition of model skirt composition:

Carboxymethylcellulose sodium 1.4

Propylene glycol 3.0

Sodium lauryl sulfate 1.8

Saccharin sodium 0.15

Methyl paraben 0.1

Butyl paraben 0.01

Silicic anhydride 25.0

70% sorbitol solution 35.0

Spice 1.0

Tables 1 and 2 show the promoted tree extract 0.1

Purified water                                            balance

Total 100.0%

*: As to the stability of the preparation, measurement was conducted for Preparation Examples 1, 2, 8 to 12.

*: The stability of the preparation was measured for Comparative Preparation Examples 1, 2, 8 to 10. [

As shown in Tables 1 and 2, some antimicrobial activity and odor-inhibiting activity were observed in the extract of Guanxi wood (Comparative Preparative Examples 1 and 8) which had not been subjected to fractionation and purification, but the discoloration This is remarkable, so practical use was difficult. On the other hand, it was recognized that the fractions of the present invention were fractionated and purified (Preparation Examples 1 to 12) by the fractionation method of the present invention, whereby not only these activities were enhanced but also the stability in the preparation was remarkably improved.

[Examples, Comparative Examples]

(i) Evaluation of the composition of cucurbita extract

14 was prepared in a conventional manner by blending the obtained extract extracts into a cedar composition having a composition as shown in Tables 3 to 5. [ Evaluation of inhibition of malodorous growth of the oral bacteria shown below and evaluation of inhibition of proliferation were carried out by the following methods. At the same time, the sensation of use and preparation stability of the curing agent composition were evaluated. The results are shown in Tables 3 to 5.

&Lt; Evaluation of odor suppressing effect and proliferation inhibiting effect of oral bacteria &

Porphyromonas gingivalis ATCC33277 Pole, Prevotella intermedia ATCC25611 was anaerobically cultured to the steady state in the THBHM medium used for the above-mentioned evaluation of the antimicrobial activity, and then 9,000 g, Collected by centrifugation for 10 minutes, and resuspended in 2x THBHM medium so that the absorbance at 550 nm was 0.5. An equal volume of this bacterial solution (mixed bacterial solution) was used in the experiment.

1.5 ml of the mixed bacterial suspension and 1.5 ml of the fresh juice (cedar) composition having the composition shown in Tables 3 to 5 were added to a glass-sterilized test tube of 33 ml, and a silicon plug (manufactured by Hiratsawa ANX-3 Co., Ltd.) And then cultured at 37 占 폚 for 18 hours. The odor in the test tube after culturing was collected in a syringe and sensory evaluation was carried out by three professional panelists based on the following evaluation criteria. In addition, sterilized distilled water was added instead of the fresh solution to control. In the table, it is described as the odor suppression effect.

On the other hand, the proliferation inhibitory effect on these two oral bacteria was evaluated by the following method. That is, the inoculum in the test tube after 18-hour incubation was diluted 10-fold with 10-fold dilution with a tryt case soy broth (manufactured by Becton and Dickinson), and the blood agar (Annelopac Anaerobic: Mitsubishi Gas Chemical Co.) for 2 weeks, and the number of grown colonies was counted, and the number of viable cells in the bacterial solution was calculated. Similarly, the number of bacteria added at the start of the experiment was calculated, and the number of bacteria in the bacterial solution after cultivation relative to the number of live bacteria at the start of the experiment was determined based on the following evaluation criteria. In the table, describe the effect of inhibiting proliferation.

Composition of blood agar plates: expressed in mass per liter.

Todd-Hewitt-Bros (manufactured by Becton and Dickinson): 30 g

Agar (manufactured by Becton and Dickinson): 15 g

Hemin (manufactured by Sigma): 5 mg

Vitamin K (manufactured by Wako Pure Chemical Industries, Ltd.): 1 mg

Rabbit deciduous blood (blood) (manufactured by Japan BioTest Laboratories): 100 g

Distilled Water: Rest

(Mass-up was performed so that the total amount was 1 liter.)

Evaluation criteria for sensory evaluation of odor suppression effect:

4 points: It smells very weakly compared with the test tube of the control.

3 points: Compared with the test tube of the control, it smells weakly.

2 points: It smells slightly weaker than the test tube of the control.

1 point: The smell is equal to the test tube of the control.

The average value of three professional panelists was calculated, and the inhibitory effect of odor generation was evaluated by the following evaluation criteria.

Evaluation standard :

◎: 3.5 points or more

○: 3.0 points or more and less than 3.5 points

△: 2.0 points or more and less than 3.0 points

×: 1.0 or more and less than 2.0 points

Evaluation criteria for inhibiting the growth of oral bacteria:

◎: The number of viable bacteria in the bacterial solution is 1/10 or less

○: The number of viable bacteria in the bacterial solution is more than 1/10 and less than 1 times

△: The number of live bacteria in the bacterial solution was more than 1 time and less than 10 times

X: The number of live bacteria in the bacterial solution exceeds 10 times at the start of the experiment

&Lt; Evaluation of formulation stability &

Stability test of preparation

The custody compositions shown in Tables 3 to 5 were stored at -5 캜 and 60 캜 for 1 month, and the stored product at -5 캜 was used as a control, and the discolored state of the stored product at 60 캜 was visually evaluated Respectively. In the table, discoloration is described, and the results are shown.

Evaluation criteria for discoloration:

?: No change in color was observed compared with the control product.

∘: Almost no change in color was observed compared with the control product.

?: A slight change in color was recognized compared with the control product.

X: Change in color is recognized compared with the control product.

<Evaluation of use feeling>

Ten milliliters of the cautery composition shown in Tables 3 to 5 was put into the mouth, and after rubbing for 30 seconds, the four-step evaluation was carried out in comparison with the control product (Comparative Example 1) It was judged by the following evaluation criteria.

Evaluation criteria of feeling:

4: Stimulation is weak compared with the stimulation of the control.

3: There is only an equal stimulation compared to the stimulation of the control.

2: A slight stimulation is recognized compared with the stimulation of the control.

1: Compared with the stimulation of the control, a clear stimulus is recognized.

Evaluation standard :

◎: Average point is 3.5 or more

○: Average point is 3.0 points or more and less than 3.5 points

△: Average point is 2.0 or more and less than 3.0 point

X: Average point is 1.0 or more and less than 2.0 point

(Ii) Evaluation of candy tree extract formulation candy

The candy extracts obtained by the fractionation methods shown in Figs. 14 and 15 were mixed, and the candies having the compositions shown in Table 6 were prepared by a routine method. The effects on the number of black pigment producing bacteria in saliva and the stability of preparation were evaluated by the following methods. The results are shown in Table 6.

<Influence of Candy Tree Extract Mixing Candy on Number of Black Pigment Producing Bacteria in Saliva>

One of the candies (about 2.5 g) having the composition shown in Table 6 was applied to three subjects three times a day for three days without chewing, and the number of bacteria in the mouth was measured.

Before the application of the test candy and after 3 days of application (3 hours after the final application), the solution was rinsed with 3 ml of sterile physiological saline for 10 seconds and diluted 10 times with a tryptic case soy broth (Becton and Dickinson) And plated on kanamycin-containing blood agar plates of the composition shown below using a spiral platter (Gunze Industries, Ltd.) and cultured for 2 weeks under anaerobic conditions (Aneropak Anaerobic: Mitsubishi Gas Chemical) And the number of viable colonies in the physiological saline was calculated by counting the number of grown black colonies. The decrease in the number of viable colonies after application of the test candy compared to the value before the start of the test was judged based on the following evaluation criteria. The results are shown in Table 6 as a decrease in the number of black pigment-producing bacteria. In addition, the test was carried out for a period of cooling off of at least two weeks for each test.

Evaluation standard :

○: The number of growing colonies after the test was 1/100 or less

△: The number of growing colonies after the test exceeds 1/100 and not more than 1/10

X: The number of growing colonies after the test exceeds 1/10 as compared with that before the test

Composition of blood agar flat plate containing kanamycin: expressed in mass per liter.

Todd-Hewitt-Bros (manufactured by Becton and Dickinson): 30 g

Agar (manufactured by Becton and Dickinson): 15 g

Hemin (manufactured by Sigma): 5 mg

Vitamin K (manufactured by Wako Pure Chemical Industries, Ltd.): 1 mg

Rabbit deciduous blood (blood) (manufactured by Japan BioTest Laboratories): 100 g

Kanamycin sulfate (200 mg / ml): 1 ml

Distilled Water: Rest

(Mass-up was performed so that the total amount was 1 liter.)

&Lt; Evaluation of formulation stability &

The test candy was stored at -5 캜 and 60 캜 for 1 month, and the stored product at -5 캜 was used as a control, and the degree of discoloration of the stored product at 60 캜 was judged visually and evaluated. In addition, the determination conformed to the above-mentioned criteria for evaluation of formulation stability evaluation. In the table, discoloration is described, and the results are shown.

From the results shown in the above Table 6, it can be seen that the candy containing the promoted wood extract of the present invention can be obtained by growing a black pigment-producing bacterium such as a bacterium belonging to the genus Porphyromonas in the mouth or a bacterium belonging to the genus Porphyria known to produce volatile sulfur compounds or volatile fatty acids Suppression, or sterilization, it is possible to confirm that the number is reduced, and it is expected that it is possible to prevent bad breath, periodontal disease or dental caries. In addition, it was also confirmed that the purified wood-extracted extract (preparation for preparation) was excellent in stability such as discoloration of the preparation.

(Iii) Assessment of a promoted wood extract formulation tablet

Tablets of the compositions shown in Table 7 were prepared by a conventional method by mixing the obtained promoted wood extracts obtained by the fractionation method shown in Fig. The bad breath suppression effect was evaluated by the following method. The results are shown in Table 7.

<Reduced odor control effect of tablets extract tree extract>

The test was carried out systematically (systemically) using 4 persons who did not have the disease as subjects, and the oral cleaning was stopped 24 hours before the test. On the day of the test, the mouths of the oral cavity after stopping the mouth cleaning and eating after the wake up and closing the mouth for 1 minute were directly analyzed using Proton Transfer Reaction Mass Spectrometry (PTR-MS: Ionicon Analytik) , And a mass peak corresponding to methyl mercaptan and a mass peak corresponding to butyric acid and a peak corresponding to mass of isovaleric acid were measured. Thereafter, the two test tablets (1 g / piece) having the composition shown in Table 7 were dissolved in the oral cavity without chewing, and the ingredients in the mouth were analyzed immediately after, 1 hour and 2 hours later. The data represent the average of four inhibition rates relative to the pre-test readings (ppb) and are listed in the table.

PTR-MS Measurement conditions:

Measured molecular weight M49 (corresponding to methyl mercaptan)

Accumulation time 0.1 second

Speed constant 2 × 10 ^-9

The measurement was repeated six times, and the average value of four cycles except for the first and last cycles was calculated. The relative concentration when the initial value was set to 100 was calculated, and the average of the four users is shown in Table 7.

It is known that bad breath is the highest in the weather during the day, and decreases by oral cleaning and eating. In addition, most of the causes are microorganisms in the oral cavity, so that halitosis occurs by restricting oral cleaning. The physiological bad breath of the health practitioner was measured by the restriction of the food from the time of stopping the oral cleaning for the present time, the time of the weather to the end of the test. In the placebo tablet (Comparative Example 3), the bad breath immediately after ingestion was reduced to about 0.2 by secretion of saliva and the like, and then returned to the level before the test in about 1 to 2 hours thereafter. On the other hand, the promoted wood extract tablet (Examples 27 to 29) was found to inhibit the amount of methylmercapacite in the balloon more than immediately after ingestion depending on the concentration of the compound, and it was recognized that it is useful for prevention of bad breath.

(Iv) Evaluation of makeup extract

The cosmetic compositions having the compositions shown in Table 8 were formulated according to the routine method by blending the grated wood extract obtained by the fractionation methods shown in Figs. 14 and 15. Body odor inhibitory effect was evaluated by the following method. The results are shown in Table 8.

&Lt; Body odor inhibiting effect &

A cosmetic composition having the composition shown in Table 8 was applied under the armpit of 10 subjects, and a gauze previously wiped was stitched on both side portions. Body odor attached to the gauze after 8 hours of wearing was evaluated by a professional panelist according to the following evaluation criteria. In addition, the subjects were prohibited from using other diodanctum preparations three days before the test, and a body-free fragrance body soap was used on the day before the test.

Evaluation criteria of sensory evaluation:

4 points: It does not smell at all compared to unadorned.

3 points: It does not smell more than unadorned.

2 points: It does not smell more than unadorned.

1 point: It has an odor equivalent to unidentified parts.

With respect to the results of 10 subjects, odor inhibitory effect was evaluated by the following evaluation criteria.

Evaluation standard :

&Amp; cir &amp;: The number of persons having three or more points was 8 to 10.

&Amp; cir &amp;: The number of persons having three or more points was 6 to 7.

?: 3 or more persons were 3 or more.

X: The number of persons having three or more points was 0 to 2.

The following cosmetics were used in the following containers and were accommodated in the ratio of the stock solution / liquefied petroleum gas (0.15 MPa / 20 DEG C) in the table.

Container: Aluminum can made by Toyo Seikan Co., Ltd. + Straight Junction Valve made by Purification Company, Japan

(v) Evaluation of dry wood extract and deodorant composition

14 and 15 to prepare a deodorant composition having the composition shown in Table 9 by a routine method. The effect of suppressing the food residue smell and the stability of the preparation were evaluated by the following methods. The results are shown in Table 9.

&Lt; Test for effect of suppressing odor of food residue >

20 g of cabbage cut into about 2 cm square were placed in a 450 ml glass bottle as food residue and allowed to stand in an open system for one night. 1 g of a deodorant composition having the composition shown in Table 9 was sprayed onto glass The whole of the bottle was sprayed to wet. The odor intensity in the bottle was evaluated by three-panelists by the six-stage odor intensity notation method, and the effect of suppressing the odor of the food wastes by the average was evaluated according to one evaluation standard Respectively.

Evaluation criteria for the effect of suppressing odors of food residue:

○: Effective (average value of 6 stage odor intensity: 2 or less)

△: There is a little effect (6th stage average intensity: less than 4 and less than 4)

X: Almost no effect (average of 6 levels of odor intensity: 4 or more)

Step 6 Strength Indication Method:

0: odorless

1: Barely detectable odor

2: Weak odor to know what kind of smell

3: Comfortable sense of smell

4: Strong odor

5: intense smell

&Lt; Evaluation of formulation stability &

Further, the deodorant composition was stored at -5 DEG C and 60 DEG C for 1 month, and the stored product at -5 DEG C was used as a control, and the degree of discoloration was visually determined at 60 DEG C and evaluated. In addition, the determination conformed to the above-mentioned criteria for evaluation of formulation stability evaluation. In the table, discoloration is described, and the results are shown.

(Iv) Evaluation of a liquid detergent composition for extracting wood extract

The liquid detergent compositions having the compositions shown in Table 10 were formulated according to the routine method by blending the dried persimmon extract obtained by the fractionation methods shown in Figs. 14 and 15. The antibacterial effect and the formulation stability were evaluated by the following methods. The results are shown in Table 10.

<Antibacterial activity evaluation of kitchen detergent>

The liquid detergent compositions of various compositions shown in Table 10 were prepared and diluted 5-fold with water, and the disinfection activity of the liquid was evaluated by the following method. That is, 0.6 ml of the test liquid detergent composition was placed in a sterilized test tube, and sterilized distilled water (2.1 ml) was added and mixed. To this was added 0.3 ml of Staphylococcus aureus ATCC 6538 strain suspended in physiological saline to a concentration of 1 × 10 ⁹ cfu / ml, mixed and allowed to stand at 20 ° C. for 20 minutes. Thereafter, stepwise dilution with sterilized physiological saline was performed 10 times, and the mixture was plated on a SCDLP agar medium (manufactured by Nissui Pharmaceutical Co., Ltd.) using a spiral plate (manufactured by Gunze Industries Co., Ltd.) and cultured at 37 ° C for 24 hours , And the number of grown colonies was counted to determine the remaining viable cell count, and the bacteria elimination performance was evaluated based on the following criteria. The results are shown in the table as the bacteria elimination effect.

Evaluation standard :

&Lt; / RTI &gt;: &lt; RTI ID = 0.0 &gt;

?: The number of growing colonies was 1 / 1,000 to 1/10 or less

X: The number of growing colonies exceeds 1/10 as compared with the case of treated with water

&Lt; Evaluation of formulation stability &

The liquid detergent composition was stored at -5 DEG C and 60 DEG C for 1 month, and the stored product at -5 DEG C was used as a control, and the degree of discoloration was visually determined at 60 DEG C and evaluated. In addition, the determination conformed to the above-mentioned criteria for evaluation of formulation stability evaluation. In the table, discoloration is described, and the results are shown.

Hereinafter, a prescription example will be shown. In the prescription examples, the composition of the perfume described as fragrance A to G is as follows.

* Fruits Mix Flavor FM3000 (Combination Spices)

Strawberry Flavor 40%

Apple Fever 15

Melon flavor 17

Banana Flavor 10

Pitch Flavor 5

Orange oil 2.5

Raspberry Fever 2.0

Pineapple Flavor 1.5

Grape Flavor 1.0

Tropical Fruits Flavor 1.5

Milk Flavor 1.0

Grapefruit oil 0.5

Lemon oil 0.5

Rose Oil 0.2

Solvent rest

Total 100.0%

The prescription examples are shown below.

[Prescription Example 1]

Calcium carbonate 40.0%

Propylene glycol 4.0

Glycerin 20.0

Carboxymethylcellulose sodium 1.5

Titanium oxide 0.5

Sodium lauryl sulfate 0.8

Sodium saccharin 0.1

Ethyl paraoxybenzoate 0.1

Prepared Example 9: Promoted Tree Extract 0.05

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0048

(2) 3,5-Dihydroxy stilbene 0.0076)

Perfume A 1.0

Purified water                                             Remainder

Total 100.0%

[Prescription Example 2] Liquid skirt

Glycerin 25.0%

Sorbitol solution (70% aqueous solution) 25.0

Propylene glycol 5.0

Anhydrous silicic acid 0.3

Sodium lauryl sulfate 1.0

Polyoxyethylene (60) hardened castor oil 1.0

Saccharin sodium 0.2

Sodium benzoate 0.3

The promoted wood extract of Preparation Example 11 0.05

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0048

(2) 3,5-Dihydroxy stilbene 0.0034)

Spice B 1.0

Purified water                                             Remainder

Total 100.0%

[Prescription Example 3]

Propylene glycol 4.0%

Glycerin 2.0

Polyoxyethylene (60) hardened castor oil 0.3

Sodium saccharin 0.1

Sodium lauryl sulfate 0.1

Spices E 1.0

The promoted wood extract of Preparation Example 12 0.02

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.00212

(2) 3,5-Dihydroxystilbene 0.0006)

Purified water                                             Remainder

Total 100.0%

[Prescription Example 4] Oral paste

Cetanol 10.0%

Squalane 20.0

Precipitable silica 5.0

Polyoxyethylene (40 moles) Cured castor oil 0.1

Sorbitan monooleate 1.0

Sodium lauryl sulfate 0.2

Saccharin sodium 0.6

Preparative Example 10, Promoted Tree Extract `0.2

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0282

(2) 3,5-dihydroxystilbene 0.0332)

Perfume C 0.6

Purified water                                             Remainder

Total 100.0%

[Prescription Example 5] Oral trockle

Gum arabic 6.0%

Glucose 36.0

Palatinos 36.0

A 10-fold amount of erythritol was used.

                                                  3.0

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0423

(2) 3,5-Dihydroxy stilbene 0.0498)

Fragrance D 1.3

Purified water                                             Remainder

Total 100.0%

[Prescription Example 6]

Sword base 20.0%

Sugar 15.0

Isomaltose 20.0

Palatinos 10.0

Xylitol 10.0

Corn syrup 12.0

The promoted tree extract 0.3 of Preparation Example 8

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.024

(2) 3,5-dihydroxystilbene 0.0219)

Fragrance F 0.6

The syrup

Total 100.0%

[Prescription Example 7] Candy

Sugar 50.0%

Starch syrup 33.0

Organic acid 2.0

Fragrance G 0.2

The promoted tree extract 0.3 of Preparation Example 11

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0288

(2) 3,5-Dihydroxystilbene 0.0201)

Purified water                                             Remainder

Total 100.0%

[Prescription Example 8] Deodorant spray

Fermentation Ethanol 40.0%

Citric acid 0.03

The promoted wood extract 0.2 of Preparation Example 10

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0282

(2) 3,5-dihydroxystilbene 0.0332)

Purified water                                             Remainder

Total 100.0%

[Prescription Example 9]

Iscoline 1.0%

Chlorohydroxy aluminum 20.0

Ethanol 35.0

Hydroxyethylcellulose 0.6

PPG5-CETETH-20 2.0

The promoted tree extract 0.3 of Preparation Example 9

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0287

(2) 3,5-Dihydroxy stilbene 0.0456)

Fragrance 0.5

Purified water                                             Remainder

Total 100.0%

[Prescription Example 10] Acne treatment agent

Liquid paraffin 3.0%

Squalane 10.0

Cetostearyl alcohol 4.0

Wax 2.0

Glycerin monostearate 2.0

Polyoxyethylene (20) sorbitan monolaurate 2.0

Glycolic acid 0.2

Salicylic acid 0.1

Japan Pharmacy Sulfur 5.0

Diglycerin 5.0

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.05

(2) 3,5-Dihydroxy stilbene 0.05

Purified water                                             Remainder

Total 100.0%

[Prescription Example 11] Soap

Sodium fatty acid 80.0%

Parmithic acid 4.0

The promoted tree extract 0.5 of Preparation Example 10

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0705

(2) 3,5-dihydroxystilbene 0.083)

Titanium oxide 0.2

Fragrance 0.8

Purified water                                            Remainder

Total 100.0%

[Prescription Example 12] Hand cream

Liquid paraffin 10.0%

Vegetable squalane 5.0

Jojoba Yu 3.0

Dimethyl Silicon 2.0

Isopropyl myristate 1.5

Decaglycerin monoisostearate 1.0

Decaglycerin triisostearate 0.5

Glycerin monostearate 1.0

Stearic acid 1.5

Polyoxyethylene (20) glyceryl monostearate 0.8

Glycerin 3.0

1,3-butylene glycol 5.0

Triisopropanolamine 0.1

Ethanol 2.0

Carboxyvinyl polymer 0.1

Citric acid 0.1

The promoted tree extract 0.5 of Preparation Example 11

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.048

(2) 3,5-dihydroxystilbene 0.0335)

Fragrance 0.05

Purified water                                             Remainder

Total 100.0%

[Prescription Example 13] Kitchen cleaner

n-hexyl glycoside (average condensation degree of glucose: 1.3 mol) 5.0%

Phosphorus maintenance Dissolve diethanolamide 10.0

Sodium malate 0.5

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.02

(2) 3,5-Dihydroxystilbene 0.01

Purified water                                             Remainder

Total 100.0%

[Prescription Example 14]

Potassium laurate 8.0%

Potassium myristate 4.0

Mono-N-lauryl malic acid amine 1.0

Propylene glycol 10.0

Palm tree fatty acid diethanolamine 5.0

Ethylenediaminetetraacetic acid sodium dihydrate 0.1

Potassium carbonate 3.0

Fragrance 0.1

The promoted tree extract 0.1 of Preparation Example 12

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0106

(2) 3,5-dihydroxystilbene 0.003)

Purified water                                             Remainder

Total 100.0%

[Formulation Example 15] Granular denture cleanser

Mono and potassium hydrogen sulfate 10.0%

And sodium borate 50.0

Sodium tripolyphosphate 20.0

Sodium lauryl sulfate 1.0

Alkaline 0.5

Carboxymethylcellulose sodium 4.0

The Institute 2.0

Spice 1.0

The promoted wood extract of Preparation Example 8 0.1

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.008

(2) 3,5-Dihydroxy stilbene 0.0073)

Sodium sulfate Remainder

Total 100.0%

[Prescription Example 16] Tea drink

Again carriage 89.5%

The promoted tree extract 0.3 of Preparation Example 8

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.024

(2) 3,5-dihydroxystilbene 0.022)

L-cysteine 0.2

plum Extract                                       10.0

Total 100.0%

[Prescription Example 17]

Sodium hydrogen carbonate 53.0%

Citric acid 18.0

Anhydrous sodium sulfate 12.0

Dibasic sodium phosphate 10.0

Polyethylene glycol 3.0

Spice 2.0

Preparative Example 10, Promoted Tree Extract 2.0

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.282

(2) 3,5- Dihydroxystilbene                           0.332)

Total 100.0%

[Prescription Example 18] mouth (mouth)

Ethanol 30.0%

Xylitol 10.0

Spice 2.0

Polyoxyethylene (EO60) hardened castor oil 1.5

The promoted tree extract 0.3 of Preparation Example 9

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0287

(2) 3,5-Dihydroxy stilbene 0.0456)

Purified water                                             Remainder

Total 100.0%

[Prescription Example 19] Drink

Glucose 1.35%

Fructose 1.35

Milk (milk) component 0.1

The promoted tree extract 0.3 of Preparation Example 11

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.0288

(2) 3,5-Dihydroxystilbene 0.0201)

Sodium chloride 0.029

Vitamin C 0.03

Vitamin B1 0.00022

Citric acid 0.01

Malic acid 0.01

Perfume 0.01

Water rest

Total 100.0%

[Prescription Example 20] Gummy

Sugar 40.3%

Syrup 47.2

Gelatin 8.0

Juice 2.0

Citric acid 0.5

Malic acid 0.5

Fragrance 0.5

Preparative Example 10 of Promote Tree Extract 1.0

(Net conversion value:

(1) 3,5-Dihydroxy-2-mandenyl stilbene 0.141

(2) 3,5- Dihydroxystilbene                           0.166)

Total 100.0%

Claims (32)

Dihydroxy-2-mandenyl stilbene characterized by being represented by the following structural formula (1).

Characterized in that the content of 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) is 1% by mass or more based on the solid content of Lindenauella or its subspecies extract.

An antimicrobial agent characterized by comprising 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) as an active ingredient.

Claims: What is claimed is: 1. A composition comprising an extract from Lindenia buccalata or a subspecies thereof of a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% Characterized by an antimicrobial agent.

Dihydroxy-2-mentenylstilbene represented by the following structural formula (1).
[Chemical Formula 5]

Claims: What is claimed is: 1. A process for the production of an extract of Linderera UMBELLATA or a subspecies thereof from a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% &Lt; / RTI &gt;

A cosmetic for skin or hair characterized by containing 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1).

Claims: What is claimed is: 1. A process for the production of an extract of Linderera UMBELLATA or a subspecies thereof from a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% Wherein the cosmetic is a cosmetic for skin or hair.

A cleaning composition comprising 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1).

Claims: What is claimed is: 1. A process for the production of an extract of Linderera UMBELLATA or a subspecies thereof from a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% By weight based on the total weight of the cleaning composition.

Dihydroxy-2-mentenylstilbene represented by the following structural formula (1).

Claims: What is claimed is: 1. A process for the production of an extract of Linderera UMBELLATA or a subspecies thereof from a ginger which contains 3,5-dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% &Lt; / RTI &gt;

Dihydroxy-2-mentenylstilbene represented by the following structural formula (1) and 3,5-dihydroxystilbene represented by the following structural formula (2).

Dihydroxy-2-mentenylstilbene represented by the following structural formula (1) in an amount of 1% by mass or more based on the solid content and a 3,5-dihydroxystyrene represented by the following structural formula (2) And extracting the extract from LINDERA UMBELLATA or a subspecies of ginger which is characterized by containing Ben in an amount of 1% by mass or more of the solid content.

A malodor formation inhibitor characterized by comprising the mixture according to claim 13 as an active ingredient. A malodor formation inhibitor comprising the extract according to claim 14. An oral composition comprising the mixture according to claim 13. An oral composition comprising the extract according to claim 14. A cosmetic for skin or hair characterized by containing the mixture according to claim 13. A cosmetic for skin or hair characterized by containing the extract according to claim 14. A cleaning composition comprising the mixture according to claim 13. A cleaning composition comprising the extract according to claim 14. A food or drink containing the mixture according to claim 13. A food or drink containing the extract according to claim 14. The solution obtained by extracting ginger is extracted with an aqueous solution of 40 to 100 mass% ethanol, the extract is concentrated under reduced pressure at 50 DEG C or lower, and the alcohol concentration is adjusted to 10 to 30% (V / V) The fraction eluted with an aqueous ethanol solution of less than 40% by mass adsorbed on the crosslinking polymer was removed,
(i) eluting treatment with an aqueous solution of 40 to 70% by mass ethanol and elution treatment with an aqueous solution of more than 70 to 100% by mass ethanol,
(ii) eluting with an aqueous solution of ethanol in an amount of more than 70 to 100 mass%, and collecting 3,5-dihydroxy-2-mentenylstilbene from an eluate of more than 70 to 100 mass% Of the active ingredients of ginger. 26. The method of claim 25,
The eluate with an aqueous solution of more than 70 to 100 mass% ethanol was developed by silica gel chromatography, and eluted with an elution fraction of 18: 1 by mixing ratio of n-hexane and acetone (V / V) of 18: To obtain 3,5-dihydroxy-2-mandenyl stilbene. The method according to claim 1, The ginger is extracted with an aqueous solution of 40 to 100 mass% ethanol, the extracted solution is further extracted with an aqueous 20 to 40 mass% ethanol solution, the insoluble portion is sampled, followed by extraction with an aqueous solution of more than 40 to 100 mass% Dihydroxy-2-mentenylstilbene and 3,5-dihydroxystilbene, characterized in that the soluble fraction is collected. 28. The method of claim 27,
A method for producing a polymer electrolyte membrane characterized by comprising the steps of: subjecting a soluble part of claim 27 to a concentration of less than 50 DEG C under reduced pressure and adjusting the alcohol concentration to 10 to 30% (V / V) by adsorption treatment with a spherical crosslinked polymer having a porous structure; Dihydroxy-2-menthane stilbene and 3,5-dihydroxy stilbene, characterized in that the eluting solution is eluted with an aqueous ethanol solution or ethanol of the above formula . The ginger is extracted by using a mixture of carbon dioxide in a supercritical state and an aqueous 2 to 10 mass% ethanol solution, and the soluble fraction is sampled to obtain 3,5-dihydroxy-2-mentenylstilbene Wherein the method comprises the steps of: The ginger is extracted with an aqueous solution of 40 to 100 mass% ethanol, the extract is extracted with a mixture of carbon dioxide in a supercritical state and an aqueous solution of ethanol in an amount of 2 to 10 mass%, the extract is sampled, To obtain 5-dihydroxy-2-menthaneylstilbene. delete delete

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