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WO2018034327A1 - Composition à usage interne contenant un ptérostilbène glucoside - Google Patents

Composition à usage interne contenant un ptérostilbène glucoside Download PDF

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Publication number
WO2018034327A1
WO2018034327A1 PCT/JP2017/029570 JP2017029570W WO2018034327A1 WO 2018034327 A1 WO2018034327 A1 WO 2018034327A1 JP 2017029570 W JP2017029570 W JP 2017029570W WO 2018034327 A1 WO2018034327 A1 WO 2018034327A1
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Prior art keywords
pterostilbene
glycoside
internal composition
composition
internal
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PCT/JP2017/029570
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English (en)
Japanese (ja)
Inventor
博喜 濱田
大介 上杉
恵 下田
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香港友池有限公司
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Publication of WO2018034327A1 publication Critical patent/WO2018034327A1/fr

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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
    • A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
    • A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/16—Emollients or protectives, e.g. against radiation
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Preparation or treatment thereof
    • A23L2/52—Adding ingredients

Definitions

  • the present invention relates to an internal composition containing a pterostilbene glycoside.
  • Patent Document 1 discloses a composition containing carotenoids and pterostilbene as active ingredients. It is described that such a composition has an effect of preventing or improving wrinkles and skin sagging.
  • Patent Document 2 discloses a composition containing protein particles and pterostilbene as active ingredients. It is described that such a composition exhibits a melanin production inhibitory effect and can be used as a whitening agent.
  • the prevention or improvement effect of wrinkles and skin sagging produced by the composition described in Patent Document 1 is a very attractive effect for the market, but there is room for improvement.
  • the whitening effect produced by the composition described in Patent Document 2 has not yet reached a level that the market can satisfy.
  • the object of the present invention is to provide either or both of an internal composition that exhibits an effect of preventing or improving wrinkles and sagging skin, and an internal composition that exhibits a whitening effect.
  • Item 1 An internal composition comprising pterostilbene glycoside as an active ingredient.
  • Item 2 The internal composition according to Item 1, wherein the pterostilbene glycoside is a pterostilbene polysaccharide or a pterostilbene monoglycoside.
  • Item 3 The pterostilbene polysaccharide is represented by the following formula (1): (In the formula, n is an integer of 1 to 9.) Item 3.
  • Item 4 The internal composition according to Item 3, wherein n is 1 or 2.
  • Item 5 The internal composition according to Item 2, wherein the pterostilbene monoglycoside is pterostilbene monoglucoside.
  • Item 6 The pterostilbene monoglucoside is represented by the following formula (2): Item 6.
  • Item 7 The internal composition according to any one of Items 1 to 6, wherein the internal composition does not contain a carotenoid compound.
  • Item 8 The internal composition according to any one of Items 1 to 7, wherein the active ingredient of the internal composition is substantially composed only of pterostilbene glycoside.
  • Item 9 The internal composition according to any one of Items 1 to 8, which is used for promoting the production of type 4 collagen.
  • Item 10 The internal composition according to any one of Items 1 to 9, which is used for at least one of a use for preventing sagging of the skin and a use for imparting skin elasticity.
  • Item 11 The internal composition according to any one of Items 1 to 10, which is used for a purpose of inhibiting tyrosinase activity.
  • Item 12 The composition for internal use according to any one of Items 1 to 11, which is used for whitening.
  • Item 13 The internal composition according to any one of Items 1 to 12, which is a food and drink composition.
  • Item 14 The production of an internal composition according to any one of items 1 to 13, comprising a step of mixing the pterostilbene glycoside with a component that is allowed to be added to the internal composition. Method.
  • Item 15 A cosmetic method comprising a step of internally taking pterostilbene glycosides to a human who seeks at least one effect selected from the group consisting of preventing skin sagging, imparting skin elasticity, and whitening.
  • Item 16 Use of pterostilbene glycoside for the production of an internal composition used for at least one application selected from the group consisting of prevention of sagging skin, imparting skin elasticity, and whitening.
  • composition for internal use of the present invention exhibits the effect of promoting the production of type 4 collagen. Based on such an effect, the composition for internal use of the present invention is useful in one or both of the use for preventing sagging of the skin and the use for giving the skin to the skin.
  • the internal composition of the present invention particularly an internal composition containing pterostilbene monoglycoside as an active ingredient inhibits tyrosinase activity. Based on such an effect, the composition for internal use of the present invention is useful for applications that give a whitening effect.
  • the figure which shows the experimental result which confirmed the expression level of the type 4 collagen gene in a skin cell by the microarray method (Experimental example 1).
  • A shows the result of the negative target experiment
  • B shows the result of adding pterostilbene monoglucoside.
  • the vertical axis of the graph in the figure indicates the relative value of the expression level of the type 4 collagen gene with respect to the expression level of the type 4 collagen gene of A.
  • the figure which shows the experimental result which confirmed the expression level of the type 4 collagen in a three-dimensional skin model by Western blotting (Experimental example 2).
  • the vertical axis of the graph in the figure shows the amount of type 4 collagen in the three-dimensional skin model calculated by densitometry using ⁇ -tubulin as an internal standard.
  • the unit of the horizontal axis in the graph is mM.
  • the figure which shows the tyrosinase inhibition experiment result in vitro (Experimental example 3).
  • A shows pterostilbene
  • B shows pterostilbene monoglycoside
  • C in the figure shows the result when arbutin is added.
  • the vertical axis of the graph in the figure represents the IC 50 value (unit: mM) of tyrosinase.
  • a in the figure shows a chart of results obtained by analyzing a reaction product obtained by reacting pterostilbene monoglycoside with soluble starch in the presence of cyclodextrin glucanotransferase by HPLC.
  • “mono-” means “pterostilbene monosaccharide glycoside”
  • “di-” means “pterostilbene disaccharide glycoside”
  • “Tri-” means “pterostilbene trisaccharide”.
  • tetra- means “pterostilbene tetrasaccharide glycoside”
  • pentasaccharide glycoside
  • hexa- means “pterostilbene six”
  • hepta- means “pterostilbene heptasaccharide glycoside”
  • octa- means “pterostilbene octasaccharide glycoside”.
  • B in the figure is a chart showing that the pterostilbene disaccharide glycoside was isolated based on the retention time of the chart.
  • C in the figure is a chart showing that a pterostilbene trisaccharide glycoside was isolated in the same manner.
  • the photographic image in the figure shows the results of Western blotting.
  • the vertical axis indicates the expression level of type 4 collagen by densitometry analysis using ⁇ -tubulin as an internal standard based on the results of Western blotting.
  • the internal composition of the present invention contains pterostilbene glycoside as an active ingredient.
  • Such a pterostilbene glycoside is not particularly limited as long as it solves the problems of the present invention.
  • a pterostilbene polysaccharide or a pterostilbene monoglycoside can be mentioned.
  • Pterostilbene polysaccharide The above-mentioned pterostilbene polysaccharide is defined as two compounds with respect to the hydroxyl group at the 3-position of pterostilbene (IUPAC name: 4-[(E) -2- (3,5-Dimethylphenyl) ethyl) phenol). It is a glycoside that has been modified with a polysaccharide comprising the above sugars.
  • sugar residue contained in such a pterostilbene polysaccharide is not particularly limited as long as it solves the problems of the present invention.
  • sugar residues derived from monosaccharides represented by glucose, threose, lyxose, allose, psicose, sedoheptulose, boremitol and the like can be mentioned.
  • glucose is preferable.
  • sugar residues described above can all be the same or different from each other within the scope of solving the problems of the present invention. For example, it is preferable that all sugar residues are of the same type.
  • the number of sugar residues contained in the above-mentioned pterostilbene polysaccharide is not particularly limited as long as the problem of the present invention is solved.
  • any of 2 to 10 can be mentioned.
  • the number is preferably 2 or 3, and most preferably 3.
  • the type of glycosidic bond between the monosaccharides constituting the polysaccharide in the above-described pterostilbene polysaccharide is not particularly limited as long as the problem of the present invention is solved.
  • examples thereof include a 1-4 glycoside bond, a 1-3 glycoside bond, and a 1-6 glycoside bond.
  • it is a 1-4 glycosidic bond.
  • it can be an ⁇ -glycoside bond or a ⁇ -glycoside bond.
  • An ⁇ -glycoside bond is preferred.
  • glycosidic bonds when there are a plurality of glycosidic bonds in the above-mentioned polysaccharide, the types of glycosidic bonds can be the same or different. Preferably they are the same type.
  • the steric configuration of the monosaccharide constituting the sugar residue contained in the above-described pterostilbene polysaccharide is not particularly limited as long as the problem of the present invention is solved.
  • it can be a D body or an L body.
  • Preferably it is D form.
  • the compound represented by is most preferable.
  • n means an integer from 1 to 9. Preferably it is 1 to 5, more preferably 1 to 2.
  • the bonding mode between the hydroxyl group at the 3-position of pterostilbene and the sugar is not particularly limited as long as the problem of the present invention is solved.
  • it may be an ⁇ -glycoside bond or a ⁇ -glycoside bond.
  • a ⁇ -glycoside bond is preferable.
  • the above-mentioned pterostilbene polysaccharide is prepared by using pterostilbene and the above monosaccharides as raw materials by chemical synthesis using the Königs-Knoll reaction or the like.
  • Pterostilbene monoglycoside is a monosaccharide with respect to the hydroxyl group at the 3-position of pterostilbene (IUPAC name: 4-[(E) -2- (3,5-Dimethoxyphenyl) ethyl] phenol). Is a modified derivative.
  • the monosaccharide refers to a saccharide that is also called a pure monosaccharide and is not hydrolyzed any more, and is not particularly limited as long as it solves the problems of the present invention. For example, glucose, threose, lyxose, allose, psicose, sedoheptulose, boremitol and the like can be mentioned.
  • glucose is preferable. Therefore, it is preferable that the above-mentioned pterostilbene monoglycoside is pterostilbene monoglucoside.
  • the configuration of the above monosaccharide is not particularly limited as long as it solves the problems of the present invention.
  • it can be a D body or an L body.
  • Preferably it is D form.
  • the bonding mode between the hydroxyl group at the 3-position of pterostilbene and the monosaccharide is not particularly limited as long as the problem of the present invention is solved.
  • it can be an ⁇ -glycoside bond or a ⁇ -glycoside bond.
  • a ⁇ -glycoside bond is preferable.
  • the compound represented by is most preferable.
  • the internal composition of the present invention can include any component other than pterostilbene glycoside.
  • the internal composition of the present invention preferably does not contain a carotenoid compound as an optional component.
  • a carotenoid compound is a derivative of a compound having a chemical structure of the chemical formula C 40 H 56 , and is a compound classified into carotenes formed only of carbon and hydrogen and xanthophylls containing elements other than carbon and hydrogen.
  • Specific carotenes are not particularly limited as long as the problems of the present invention are solved. Examples thereof include compounds such as ⁇ -carotene, ⁇ -carotene, ⁇ -carotene, ⁇ -carotene, and lycopene.
  • Xanthophyll is a derivative of a compound having a chemical structure of the chemical formula C 40 H 56 , and is a compound formed with carbon, hydrogen, and other elements.
  • the specific xanthophyll is not particularly limited as long as it solves the problems of the present invention.
  • astaxanthin for example, astaxanthin, zeaxanthin, lutein, cryptoxanthin, tunaxanthin, salmoxanthine, parasiloxanetin, violaxanthin, anteraxanthin, cucurbitaxanthin, diatoxanthine, alloxanthin, pectenol, pectenolone, mactraxanthine, capsanthin, capsanthin
  • examples thereof include nor, fucoxanthin, fucoxanthinol, peridinin, halocinthiaxanthine, amaranthiaxanthine, canthaxanthin, echinenone, rhodoxanthin, bixin, and norbixin.
  • the xanthophyll includes these monoesters and diesters.
  • the internal composition of the present invention contains substantially only pterostilbene glycoside as an active ingredient.
  • the active ingredient means an ingredient that exhibits one or both of the effect of promoting type 4 collagen production and the effect of inhibiting tyrosinase activity, which will be described later, as the effect exhibited by the internal composition of the present invention.
  • the composition for internal use of the present invention does not contain a component having at least one of a type 4 collagen production promoting action and a tyrosinase activity inhibiting action in addition to the pterostilbene glycoside.
  • the content of the pterostilbene glycoside contained in the internal composition of the present invention is not particularly limited as long as the internal composition of the present invention exhibits the effects of the present invention.
  • the blending amount of the active ingredient with respect to 100% by mass of the internal composition can be usually about 0.001% by mass to 100% by mass.
  • a composition containing a pterostilbene glycoside as an active ingredient exhibits an excellent effect of promoting type 4 collagen production. From this, it is considered that pterostilbene glycosides also exhibit excellent type 4 collagen production promoting effects. Therefore, the composition containing pterostilbene glycoside as an active ingredient is suitably used for the purpose of promoting the production of type 4 collagen.
  • Type 4 collagen also called ceramide transfer protein (CETR)
  • CETR ceramide transfer protein
  • composition for internal use of the present invention is expected to exhibit the effect of suppressing the sagging of the skin and imparting the elasticity by applying it (internal use) to humans.
  • telostilbene glycoside As shown in the following Examples (for example, Experimental Example 3), pterostilbene monoglucoside exhibits excellent tyrosinase inhibitory activity. From this, similarly, other pterostilbene glycosides are expected to exhibit excellent tyrosinase inhibitory activity. Therefore, the composition containing telostilbene glycoside as an active ingredient is suitably used for applications that inhibit tyrosinase activity.
  • Tyrosinase is an enzyme involved in melanin synthesis, and a composition that inhibits this activity is known to have a whitening effect. Therefore, the composition for internal use of this invention can anticipate having a whitening effect by applying this to a human (internal use). That is, it is useful as a whitening agent.
  • the application target of the composition for internal use of the present invention is not particularly limited as long as it is a human who needs the above effects.
  • the amount of the composition for internal use of the present invention is not particularly limited as long as it is within the range where the above effects can be expected.
  • it can be appropriately determined from the amount used in a food / beverage product composition or an oral pharmaceutical composition, which is one form of the internal composition of the present invention described later.
  • the daily intake of a human adult is usually about 1 mg to 10 mg in terms of the amount of pterostilbene glycoside contained in the composition for internal use. Can do.
  • the form of the internal composition of the present invention is not particularly limited as long as it solves the problems of the present invention.
  • a food-drinks composition or an oral pharmaceutical composition can be mentioned.
  • a food / beverage composition is preferable.
  • the internal composition of the present invention can be in the form of a food / beverage composition.
  • the amount of at least one compound selected from the group consisting of a stilbene compound and a glycoside thereof contained in the food and drink composition of the present invention is not particularly limited as long as the effects of the present invention are exhibited.
  • the compounding amount of the active ingredient with respect to 100% by mass of the composition can usually be about 0.001% to 100% by mass.
  • the food / beverage composition of the present invention includes foods for specified health use, functional indication foods, and health functional foods (including beverages) such as functional nutrition foods; nutritional supplements, health supplements, nutritional adjustment foods, etc .; and Any of the general foods (including beverages) can be included.
  • These food and drink compositions need only have the shape of conventional foods and drinks.
  • hair such as hair, eyebrows, eyelashes, and eyelashes
  • It is a food for specified health use or a functional labeling food that can be used as a function of food and drink to exhibit the effect of improving the decline of white hair (such as white hair or hair loss).
  • the food / beverage composition described above can be regarded as a drink made from collagen, whitening collagen to drink, collagen production drink to drink, anti-wrinkle drink to drink, and the like.
  • the shape of the food / beverage product composition described above is not particularly limited.
  • Noodles such as buckwheat, udon, instant noodles and Chinese noodles; fishery and livestock processed foods such as kamaboko, ham and sausage; dairy products such as processed milk and fermented milk; Foods; seasonings such as sauces and sauces; soups, salads, prepared dishes, pickles, breads, cereals and the like.
  • the food / beverage composition of the present invention may be in the form of a preparation generally provided as a supplement, such as a solid preparation such as a powder, granule, capsule, troche or tablet (tablet); a liquid preparation such as a syrup or drink. it can.
  • a preparation generally provided as a supplement such as a solid preparation such as a powder, granule, capsule, troche or tablet (tablet); a liquid preparation such as a syrup or drink. it can.
  • the intake amount of the food / beverage product composition described above can be set as appropriate based on the sex, age, application mode of the food / beverage product composition, desired degree of effect, and the like.
  • the daily intake of a human adult for example, 60 kg body weight
  • compositions for internal use of this invention can be made into the form of an oral pharmaceutical composition.
  • the blending amount of pterostilbene glycoside contained in the pharmaceutical composition is not particularly limited as long as the problem of the present invention is solved.
  • the blending amount of the active ingredient with respect to 100% by mass of the pharmaceutical composition can usually be about 0.001% to 100% by mass.
  • the dosage form of the pharmaceutical composition is not particularly limited as long as it solves the problems of the present invention.
  • the dosage form mainly used internally such as a liquid agent, an extract agent, a suspension agent, an emulsion, an alcoholic beverage agent, a flow extract agent, and a lotion agent, can be mentioned.
  • the dosage of such a pharmaceutical composition is not particularly limited as long as it solves the problems of the present invention. Specifically, it can be set as appropriate based on the gender and age of the person to be applied, the application form of the pharmaceutical composition, the desired degree of effect, and the like. For example, in terms of the amount of pterostilbene glycoside contained in the pharmaceutical composition, it can be generally 1 to 10 mg per day for a human adult.
  • the method for producing an internal composition of the present invention includes a step of mixing a pterostilbene glycoside and a component allowed to be added to the composition for internal use.
  • the pterostilbene glycoside is as described above.
  • the component allowed to be added to the internal composition is not particularly limited as long as it solves the problems of the present invention.
  • it can be set as the component accept
  • the pterostilbene monoglucoside represented by these was obtained from Meister Bio and used for the following experiments.
  • Human skin cells immortalized by introducing the htert gene were prepared and conditioned in Prigrow III (APB) in a predetermined medium. Thereafter, 50 ⁇ M of the above pterostilbene monoglucoside was added to the conditioned medium and cultured in a 5% CO 2 environment at 37 ° C. for 5 days.
  • APB Prigrow III
  • a 3D skin model was prepared according to the protocol of the kit, and this was acclimated using the accessory included in the kit.
  • the above pterostilbene monoglucoside (25 ⁇ M and 100 ⁇ M in final concentration) was added to the conditioned medium and cultured for 7 days.
  • the cultured cells were collected, and the lysate was subjected to Western blotting using an anti-human collagen antibody (COL4A3BP; Abcam) to examine the expression level of type 4 collagen protein.
  • Western blotting using an anti- ⁇ -tubulin antibody as an internal standard was also performed, and the obtained image data was subjected to densitometry analysis.
  • pterostilbene monoglucoside clearly increases the expression level of type 4 collagen in the three-dimensional skin model to a maximum of about 2.5 times compared to the control in an additive concentration-dependent manner. It became. Therefore, a composition containing pterostilbene monoglucoside as an active ingredient may be related to various effects (for example, an effect of giving skin skin due to thickening of the basement membrane) resulting from an increase in type 4 collagen in skin cells. It became clear.
  • pterostilbene monoglucoside (B in the figure) was found to have superior tyrosinase inhibitory activity as compared to pterostilbene (A in the figure) which is an aglycon.
  • pterostilbene monoglucoside exhibited an excellent tyrosinase inhibitory effect nearly 5.5 times. This result shows that pterostilbene monoglucoside exhibits a whitening effect.
  • pterostilbene monoglycoside represented by the above chemical formula (2) was dissolved in 40 mL of distilled water. 4 g of soluble starch (Nacalai Tesque) was added to the lysate thus prepared, and incubated at 60 ° C. for 24 hours in the presence of 0.5 m of cyclodextrin glucanotransferase (Amanoenzyme).
  • This enzyme is an enzyme that catalyzes a reaction of 1-4 glycosidic bonds of other glucose molecules to a compound having glucose molecules.
  • the reaction product thus obtained was subjected to HPLC.
  • the results (HPLC chart) are shown in FIG. 4A.
  • the HPLC conditions are as follows.
  • the above reactants include pterostilbene monosaccharide glycoside, which is a pterostilbene glycoside, and pterostilbene in which about 1 to 7 glucoses are ⁇ (1-4) linked. It was confirmed by HPLC that the polysaccharide was contained. It was suggested that the shorter the retention time, the greater the number of glucose added to pterostilbene.
  • FIG. 4B pterostilbene disaccharide glycoside
  • FIG. 4C pterostilbene trisaccharide glycoside
  • the mass spectrometry data of the isolated pterostilbene disaccharide glycoside and pterostilbene trisaccharide glycoside are as follows. Mass spectrometry was performed using the ESI method.
  • Pterostilbene disaccharide glycoside Found 579.2; Estimated 580.3 Pterostilbene trisaccharide glycoside: found 741.2; estimated 742.3
  • composition containing pterostilbene polysaccharide as an active ingredient may also be related to various effects (for example, an effect of imparting skin elasticity due to thickening of the basement membrane) caused by an increase in type 4 collagen in skin cells. It became clear.
  • ⁇ Used drink> a drink prepared by mixing each material shown in Table 1 below in distilled water so as to be 50 mL in total (target drink) was used.
  • a drink (control drink) was produced in the same manner as the above-mentioned target drink except that pterostilbene monoglucoside was not blended.
  • the period of internal use was 5 days, and a questionnaire survey was conducted on the subject on the 5th day under the supervision of a dermatologist. A similar survey was conducted before the start of the test. Based on the criteria shown in Table 2 below, the questionnaire is evaluated for each panel (gloss, beam, dullness, blotch, sagging, wrinkle (eye), transparency, redness, and foundation). It was done by getting a point. In addition, it was confirmed by the dermatologist based on the report of the meal content from the test subject that each test subject did not ingest a meal that would affect the effect on the skin.
  • all the glycosidic bonds between glucose in the formula are 1-4 bonds, and pterostilbene
  • the bonding mode between the 3-position and glucose and the glycosidic bond between glucose are both ⁇ -bonds) and the following formula (2)

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Abstract

L'invention a pour objet de fournir une composition à usage interne développant des effets de prévention ou d'amélioration concernant les rides, le relâchement de la peau, ou similaire, et/ou une composition à usage interne développant un effet décolorant. Plus précisément, l'invention a pour objet de fournir une composition à usage interne contenant un ptérostilbène glucoside.
PCT/JP2017/029570 2016-08-17 2017-08-17 Composition à usage interne contenant un ptérostilbène glucoside WO2018034327A1 (fr)

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