JP2006257015A - New c-glycoside compound, collagen production promotor, skin cosmetic and beverage and food for beautification - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a new compound having collagen production promoting action, a collagen production promoter containing the new compound as an active ingredient, and a skin cosmetic and beverage and food for beautification in which the collagen production promoters are each formulated. <P>SOLUTION: A new C-glycoside compound is isolated/identified as an active ingredient for collagen production promoter from a leaf part extract of Averrhoa carambola L. The collagen production promoter is formulated into the skin cosmetic or the beverage or the food for beautification. <P>COPYRIGHT: (C)2006,JPO&NCIPI

Description

  The present invention relates to a novel C-glycoside compound, a collagen production promoter containing the C-glycoside compound, and skin cosmetics and cosmetic foods and drinks containing the collagen production promoter.

  The epidermis and dermis of the skin are composed of epidermal cells, fibroblasts, and extracellular matrices such as elastin, hyaluronic acid, and collagen that are outside these cells and support the skin structure. In young skin, the proliferation of fibroblasts is active, and the interaction between skin tissues such as fibroblasts and collagen keeps homeostasis, ensuring moisture retention, flexibility, elasticity, etc. It is maintained in a fresh state with its tension and gloss.

  However, when there is an influence of certain external factors such as irradiation of ultraviolet rays, significant drying of air, excessive skin washing, etc., or when aging progresses, the production amount of collagen, which is a main component of the extracellular matrix, is increased. It causes a decrease in elasticity due to cross-linking. As a result, the skin retains its moisturizing function and elasticity, and the keratin begins to exfoliate abnormally. Therefore, the skin loses its tension and gloss, and exhibits an aging phenomenon such as rough skin and wrinkles. As described above, changes associated with skin aging, that is, wrinkles, dullness, disappearance of texture, decrease in elasticity, and the like are associated with a decrease / denaturation of dermal matrix components such as collagen. Therefore, it is considered that skin aging can be prevented and / or improved by promoting collagen production in dermal fibroblasts.

Conventionally, as a herbal medicine having a collagen production promoting action, a coconut extract (see Patent Document 1) is known. However, a specific compound having a collagen production promoting action contained in the pentagonal extract has not yet been identified.
JP 2002-226323 A

  An object of the present invention is to provide a novel compound having a collagen production-promoting action, a collagen production promoter containing the novel compound as an active ingredient, and a skin cosmetic and a cosmetic food and drink containing the collagen production promoter. And

The present inventors succeeded in isolating and identifying a novel C-glycoside compound having a collagen production-promoting action from a quince leaf extract, and completed the present invention.
That is, the present invention provides the following novel C-glycoside compounds, collagen production promoters, skin cosmetics, and cosmetic foods and drinks.

  (1) A C-glycoside compound represented by the following formula (I).

  (2) A collagen production promoter containing a C-glycoside compound represented by the following formula (I) as an active ingredient.

(3) A skin cosmetic comprising the collagen production promoter according to (2).
(4) A food and drink for cosmetics, which contains the collagen production promoter according to (2).

  According to the present invention, a novel C-glycoside compound having a strong collagen production promoting action can be provided. Since the novel C-glycoside compound represented by the above formula (I) obtained from a quince extract which is a highly safe natural plant has a strong collagen production promoting action, it is used as an active ingredient of a collagen production promoter. By using as the above, it is possible to prevent and / or improve skin aging symptoms such as wrinkles, dullness, disappearance of texture, and decrease in elasticity. In addition, skin cosmetics and beauty foods and drinks formulated with the collagen production promoter promote collagen production and prevent and / or prevent skin aging symptoms such as wrinkles, dullness, loss of texture, reduced elasticity, etc. Can be improved.

Hereinafter, the present invention will be described in detail.
The C-glycoside compound of the present invention is represented by the following formula (I). Hereinafter, the C-glycoside compound represented by the following formula (I) is referred to as “carambola flavone”.

  It has been confirmed in the examples described later that carambola flavones have the structure represented by the above formula (I), and carambola flavones are obtained from an extract of five lion (scientific name: Averrhoa carambola L.). New material released.

  Carambola flavones can be isolated from the quince extract, but other plants, such as bilimbin (scientific name: Oxalidaceae, Averrhoa) Averrhoa bilimbi L.) may also be present. Therefore, the source of isolation of carambola flavones is not limited to pentagons and may be any plant containing carambola flavones.

  Carambola flavones, for example, can be immobilized after subjecting the pentachondria extract to purification operations effective for isolating carambola flavones, such as liquid-liquid partition extraction, various chromatographies, membrane separation, and recrystallization. It can be obtained by performing liquid chromatography using octadecylsilylated silica gel (ODS) or the like as a phase.

Specifically, carambola flavones can be obtained by the following steps (a) to (c).
Step (a)
The step (a) is a step of obtaining a pentagonal extract by subjecting the pentagonal to extraction with water, a hydrophilic organic solvent, or a mixed solvent thereof.

  Goshiko (scientific name: Averrhoa carambola L.) belongs to the genus Carenaceae, and fresh fruits are edible. Goshiko has been described in literature in China since the BC, and its fruit is also called a star fruit because of its star-shaped cross section. Gosho is cultivated in Okinawa, southeastern China, Yunnan and other tropical regions, and can be easily obtained from these regions. There are no particular restrictions on the constituent parts of the quince that can be used as the raw material for extraction, and examples include leaf parts, stem parts, root parts, fruit parts, flower parts, seed parts, or a mixture of these parts. Of these, the leaves are preferably used.

  The pentagonal extract can be obtained by drying an extraction raw material, pulverizing it as it is or using a crusher, and subjecting it to extraction with an extraction solvent. Drying may be performed in the sun or using a commonly used dryer. Moreover, after performing pretreatment, such as degreasing, with a nonpolar solvent such as hexane, it may be used as an extraction raw material. By performing pretreatment such as degreasing, extraction treatment with a polar solvent of a plant can be performed efficiently.

  As the extraction solvent, it is preferable to use a polar solvent, and examples thereof include water and hydrophilic organic solvents. These are used alone or in combination of two or more at room temperature or a temperature below the boiling point of the solvent. It is preferable.

  Examples of water that can be used as the extraction solvent include pure water, tap water, well water, mineral spring water, mineral water, hot spring water, spring water, fresh water, and the like, as well as water that has been subjected to various treatments. Examples of the treatment applied to water include purification, heating, sterilization, filtration, ion exchange, osmotic pressure adjustment, buffering, and the like. Therefore, the water that can be used as the extraction solvent in the present invention includes purified water, hot water, ion-exchanged water, physiological saline, phosphate buffer, phosphate buffered saline, and the like.

  Examples of hydrophilic organic solvents that can be used as extraction solvents include lower aliphatic alcohols having 1 to 5 carbon atoms such as methanol, ethanol, propyl alcohol, and isopropyl alcohol; lower aliphatic ketones such as acetone and methyl ethyl ketone; 1,3-butylene. Examples thereof include polyhydric alcohols having 2 to 5 carbon atoms such as glycol, propylene glycol and glycerin.

  When using the liquid mixture of 2 or more types of polar solvents as an extraction solvent, the mixing ratio can be adjusted suitably. For example, when using a liquid mixture of water and a lower aliphatic alcohol, it is preferable to mix 1 to 90 parts by weight of a lower aliphatic alcohol with respect to 10 parts by weight of water. When using a mixed solution, it is preferable to mix 1 to 40 parts by mass of a lower aliphatic ketone with 10 parts by mass of water, and when using a mixed solution of water and a polyhydric alcohol, water 10 It is preferable to mix 10 to 90 parts by mass of polyhydric alcohol with respect to parts by mass.

  The extraction treatment is not particularly limited as long as the soluble component contained in the extraction raw material can be eluted in the extraction solvent, and can be performed according to a conventional method. For example, the extraction raw material is immersed in an extraction solvent 5 to 15 times (mass ratio) of the extraction raw material, the soluble components are extracted at room temperature or under reflux, and then filtered to remove the extraction residue. A liquid can be obtained. By removing the solvent from the obtained extract and drying, a pentagonal extract can be obtained.

Step (b)
Step (b) is a step of adsorbing the pentagonal extract obtained in step (a) to an adsorbent and then eluting with water, a water-soluble solvent or a mixed solvent thereof. The step (b) is a step of increasing the carambola flavone content of the pentacot extract obtained in the step (a) and purifying for the purpose of decolorization, deodorization, activity improvement and the like.

  The hydrophilic organic solvent that can be contained in the pentacot extract is distilled off as necessary before adsorbing to the adsorbent. The extract obtained by distilling off the hydrophilic organic solvent is dissolved or suspended in, for example, water, a water-soluble solvent or a mixed solvent thereof, and then adsorbed on an adsorbent. After the pentacot extract is adsorbed on the adsorbent, it is eluted with water, a water-soluble solvent or a mixed solvent thereof.

  Examples of the water-soluble solvent that can be used for dissolution, suspension, or elution include the above-described hydrophilic organic solvents. Among the above-described lower alcohols having 1 to 5 carbon atoms, methanol, ethanol, etc., among others, It is preferably used as a turbid solution or an eluate. When a mixed solvent of water and a water-soluble solvent is used, the mixing ratio can be adjusted as appropriate. For example, when using a mixed solvent of water and methanol, the mixing ratio of water and methanol should be 90:10 to 1:99 (volume ratio), preferably 60:40 to 20:80 (volume ratio). Can do.

  The adsorbent is not particularly limited as long as it can adsorb carambola flavone, but known adsorption such as ion exchange resin, synthetic adsorption resin, activated carbon, chelate resin, silica gel, alumina gel type adsorbent, porous glass, etc. The agents can be used alone or in combination. Preferably, a porous synthetic adsorbent such as Diaion HP-20 (manufactured by Mitsubishi Chemical Corporation), which is a porous synthetic adsorbent resin, is used, and pentagram is used for column chromatography using the porous synthetic adsorbent as a filler. Attach the extract and elute with eluent.

Step (c)
Step (c) is a step of subjecting the eluate obtained in step (b) to various chromatography and isolating carambola flavones contained in the eluate.

  Isolation of carambola flavones from the eluate is a combination of various chromatographic processes such as reverse phase column chromatography, normal phase column chromatography, gel permeation chromatography (GPC), and high performance liquid chromatography (HPLC). Can be done. The order of processing of the eluate by various chromatography is not particularly limited.

  As a developing solvent or mobile phase in various chromatography, water, a water-soluble solvent, a low polarity solvent or a mixed solvent thereof, or a nonpolar solvent can be used. As the water-soluble solvent, the above-described hydrophilic organic solvent, acetonitrile, and the like can be used, and it is preferable to use the above-described lower alcohol having 1 to 5 carbon atoms, particularly methanol, ethanol, and the like. In normal phase column chromatography, it is preferable to use a mixed solvent of chloroform, water and methanol, a nonpolar solvent such as n-hexane, etc. as the mobile phase.

  As a filler in various chromatographies, for example, octadecylated silica gel (ODS), silica gel, hydroxypropylated dextran and the like can be used. In reverse phase column chromatography, ODS is preferably used. In normal phase column chromatography, silica gel is preferably used. In gel permeation chromatography (GPC), hydroxypropylated dextran (product) is used. (Name: Sephadex LH-20, manufactured by Amersham Biosciences) is preferably used.

  Since the carambola flavone obtained as described above has a collagen production promoting action, it can be used as an active ingredient of a collagen production promoting agent utilizing the action.

  The collagen production promoter of the present invention may be composed only of carambola flavones or may be formulated with carambola flavones.

  Carambola flavone is formulated into powders, granules, tablets, liquids and other dosage forms according to conventional methods using pharmaceutically acceptable carriers such as dextrin and cyclodextrin and other optional auxiliaries. can do. In this case, as an auxiliary agent, for example, an excipient, a binder, a disintegrant, a lubricant, a stabilizer, a flavoring / flavoring agent, and the like can be used. Examples of the form of collagen production promoter formulated with carambola flavone include tablets, powders, capsules, ointments, liquids for external use, patches and the like.

  In addition, the collagen production promoter of this invention can mix | blend the natural extract etc. which have a collagen production promotion effect | action with a carambola flavone as an active ingredient as needed.

  The collagen production promoter of the present invention can promote collagen production through the collagen production promoting action of carambola flavones. Thereby, the production amount of collagen in the skin tissue increases, and skin aging symptoms such as wrinkles, dullness, disappearance of texture, and decrease in elasticity can be prevented and improved. However, the collagen production promoter of the present invention can be used for all uses other than these uses that are meaningful for exerting a collagen production promoting effect.

  The collagen production promoter of the present invention has a collagen production promotion action and is excellent in the feeling of use and safety when applied to the skin, and therefore is suitable for blending into skin cosmetics. In this case, a collagen production promoter formulated from carambola flavones may be blended, or carambola flavones may be blended as they are. By adding a collagen production promoter or carambola flavone formulated from carambola flavones to the skin cosmetic, it is possible to impart a collagen production promoting action to the skin cosmetic.

  Skin cosmetics that can be blended with the collagen production promoter of the present invention are not particularly limited, for example, ointments, creams, emulsions, lotions, foundations, packs, lips, bathing agents, shampoos, rinses, hair arts, Examples include hair lotion, soap, body shampoo, and the like.

  When the collagen production promoter of the present invention is blended in a skin cosmetic, the blending amount can be appropriately adjusted according to the composition of the collagen production promoter, the dosage form, the type of skin cosmetic into which the collagen production promoter is blended, and the like. In general, however, the concentration of carambola flavone in the skin cosmetic is preferably about 0.0001 to 10% by mass.

  Skin cosmetics, as long as they do not interfere with the collagen production promoting action of carambola flavones, main agents, auxiliaries or other components used in the production of normal skin cosmetics, such as astringents, bactericides / antibacterial agents, whitening agents , UV absorbers, moisturizers, cell activators, anti-inflammatory / anti-allergic agents, antioxidant / active oxygen scavengers, fats and oils, waxes, hydrocarbons, fatty acids, alcohols, esters, surfactants, perfumes Etc. can be used together. By using these auxiliaries and the like in combination, a synergistic effect with other active ingredients used in combination may bring about an excellent effect that is normally expected.

  According to the skin cosmetics of the present invention, the collagen production promoting action of carambola flavone promotes the production of collagen, and prevents and improves skin aging symptoms such as wrinkles, dullness, loss of texture, reduced elasticity, etc. can do.

  The collagen production promoter of the present invention has a collagen production promoting action, and it has been confirmed that carambola flavone as an active ingredient is not digested in the digestive tract. Is also suitable for blending into cosmetic foods and drinks. In this case, a collagen production promoter formulated from carambola flavones may be blended, or carambola flavones may be blended as they are. By blending a collagen production promoter or carambola flavone formulated from carambola flavones into a cosmetic food or drink, the collagen production promoting action can be imparted to the cosmetic food or drink.

  As used herein, “beauty food and drink” refers to foods and drinks intended to beautify the skin, or foods and drinks intended to prevent and improve rough skin, aging of the skin, or various skin diseases associated therewith. Say. In addition, foods and drinks are those that are less likely to harm human health and are taken by oral or gastrointestinal administration in normal social life, such as foods, pharmaceuticals, quasi drugs, etc. It is not limited to this category. Accordingly, the “beauty food and drink” in the present invention includes a wide range of quasi-drugs, pharmaceuticals, etc., in addition to general foods, health foods, insurance functional foods, and the like.

  When the collagen production promoter of the present invention is blended in a cosmetic food or drink, the blending amount can be appropriately changed in consideration of the purpose of use, symptom, sex, etc., but usually 0. It is 01-50 mass%, Preferably it is 0.1-20 mass%. In consideration of the general intake amount of the food and drink to be added, it is preferable that the intake amount of carambola flavone per day for an adult is about 1 to 1000 mg. In addition, when the food or drink to be added is a granular, tablet or capsule food or drink, the addition amount of the collagen production promoter is usually 0.1 to 100% by mass with respect to the food or drink to be added, preferably 5 to 100% by mass.

  The beauty food and drink may be any food or drink that does not interfere with the activity of the carambola flavone, or may be a health and nutritional supplement based on the carambola flavone. .

  When producing a beauty food or drink containing the collagen production promoter of the present invention, for example, glucose, fructose, sucrose, maltose, sorbitol, stevioside, rubusoside, corn syrup, lactose, citric acid, tartaric acid, malic acid , Succinic acid, lactic acid, L-ascorbic acid, DL-α-tocopherol, sodium erythorbate, glycerin, propylene glycol, glycerin fatty acid ester, polyglycerin fatty acid ester, sucrose fatty acid ester, sorbitan fatty acid ester, gum arabic, carrageenan, casein , Gelatin, pectin, agar, vitamin B, nicotinic acid amide, calcium pantothenate, amino acids, calcium salts, pigment, flavoring, preservative, dextrin, starch, gelatin, soy protein, corn tampa It can cellulose, soybean oil, with the addition of any auxiliary agent such as medium-chain triglyceride to any shape of food or beverage.

  The cosmetic food and drink that can be blended with the collagen production promoter of the present invention is not particularly limited. For example, beverages such as soft drinks, carbonated drinks, nutritional drinks, fruit drinks, and lactic acid drinks; ice creams and ice sherbets Frozen confectionery such as oyster ice; buckwheat noodles, udon, harusame, gyoza peel, sushi mai, noodles such as Chinese noodles and instant noodles; rice cake, candy, gum, chocolate, tablet confectionery, snack confectionery, biscuits, jelly, jam, cream , Baked confectionery, bread and other confectionery; crab, salmon, clam, tuna, sardine, shrimp, bonito, mackerel, whale, oyster, saury, squid, red scallop, scallop, abalone, sea urchin, sea bream, tocobushi, etc .; Processed fishery and livestock products such as ham, sausage; dairy products such as processed milk and fermented milk; salad oil, tempura oil, margarine, mayonnaise Fats and processed foods such as shortening, whipped cream, dressing; seasonings such as sauces, sauces; curry, stew, oyakodon, rice bowl, miscellaneous cooking, Chinese rice bowl, bowl, tempura, eel rice, hayashi rice, oden, marbodorf, Retort pouch foods such as beef bowl, meat sauce, egg soup, omelet rice, dumplings, shumai, hamburg, meatballs; various forms of health and nutritional supplements; quasi-drugs such as tablets, capsules, drinks, troches, Examples include pharmaceuticals.

  The collagen production promoter, skin cosmetics and cosmetic foods and beverages of the present invention are suitably applied to humans. However, as long as the respective effects are exerted, they can be applied to animals other than humans. Can also be applied.

  Hereinafter, although a manufacture example, a test example, and a compounding example are shown and this invention is demonstrated concretely, this invention is not restrict | limited to each following example at all.

[Production Example 1] Manufacture of a quince leaf part extract To 100 g of the coarsely crushed material obtained by pulverizing the coconut leaf part, 1000 mL of 50 mass% ethanol was added, and the mixture was gently stirred at 80 ° C for 2 hours. Extraction was performed. Thereafter, the mixture was filtered using a filter paper to obtain an extract. Further, 1000 mL of 50 mass% ethanol was added to the extraction residue, and the same operation was performed to obtain an extract. The obtained extracts were combined and concentrated under reduced pressure at a temperature of 40 ° C., followed by drying with a vacuum dryer to obtain 28.7 g of an extract of pentacot leaves (Sample 1).

[Production Example 2] Production of carambola flavone 100 g of water was added to and suspended in 15 g of the pentacot leaf extract obtained in Production Example 1, and a porous adsorption resin (trade name: Diaion HP-20, Mitsubishi Chemical). (1) 1 L of water, (2) 1 L of 40% by weight methanol, (3) 1 L of 80% by weight methanol, (4) 1 L of methanol in this order, and water fraction 6.60 g, Four fractions were obtained: 1.51 g of 40% by weight methanol fraction, 3.90 g of 80% by weight methanol fraction, and 1.30 g of methanol fraction.

  Subsequently, 3.40 g of 80 mass% methanol fraction was subjected to reverse phase column chromatography (filler; ODS (trade name; Chromatrex ODS, manufactured by Fuji Silysia Chemical Ltd.), developing solvent: acetonitrile: water = 3: 2), Normal phase column chromatography (filler; silica gel (trade name; silica gel 60, manufactured by Merck & Co., Inc.), developing solvent; chloroform: methanol: water = 10: 5: 1) and gel permeation chromatography (filler; hydroxypropylated dextran) (Trade name: Sephadex LH-20, manufactured by Amersham Biosciences), developing solvent: methanol), fractionation / purification, isolation by high performance liquid chromatography under the following conditions, Obtained (sample 2).

<High performance liquid chromatography conditions>
Product name: LC-908 (manufactured by Nippon Analytical Industrial Co., Ltd.)
Stationary phase: JAIGEL-GS310 (manufactured by Nippon Analytical Industrial Co., Ltd.)
Column diameter: 20mm
Column length: 500 mm (two columns with a length of 250 mm are connected)
Mobile phase: Methanol Mobile phase flow rate: 5 mL / min Detector: RI, UV (wavelength: 254 nm)

The obtained purified product was analyzed by ESI-mass spectrum, ¹ H-NMR and ¹³ C-NMR. The results are shown below.

<ESI-mass spectrum>
m / z 563 (M + H) ⁺ , m / z 561 (MH) ^-

< ¹ H-NMR chemical shift δ (assigned hydrogen)>
0.54 (3H, d, J = 5.6Hz, Rha-6-H3), 1.14 (3H, d, J = 6.0Hz, Fuc-6-H3), 2.38 (1H, m, Rha-5-H), 2.92 (1H, br.s, Rha-4-H), 3.17 (1H, overlapped, Rha-3-H), 3.54 (1H, br.s, Fuc-4-H), 3.62 (1H, overlapped, Rha- 2-H), 3.62 (1H, overlapped, Fuc-3-H), 3.72 (1H, br.q, J = 6.0Hz, Fuc-5-H), 4.16 (1H, br.t, J = 8.8Hz , Fuc-2-H), 4.39 (1H, d, J = 9.6Hz, Fuc-1-H), 5.01 (1H, s, Rha-1-H), 6.51 (1H, s, 8-H), 6.74 (1H, s, 3-H), 6.92 (2H, d, J = 8.8Hz, 3'5'-H2), 7.90 (2H, d, J = 8.8Hz, 2'6'-H2)

< ¹³ C-NMR chemical shift δ (assigned carbon)>
16.8 (Fuc-6-C), 17.5 (Rha-6-C), 68.0 (Rha-5-C), 70.3 (Rha-3-C), 70.4 (Rha-2-C), 71.2 (Fuc-1 -C), 71.3 (Rha-4-C), 72.0 (Fuc-4-C), 73.6 (Fuc-2-C), 73.6 (Fuc-5-C), 75.7 (Fuc-3-C), 94.4 (8-C), 100.3 (Rha-1-C), 102.7 (3-C), 103.4 (10-C), 108.8 (6-C), 115.8 (3 ', 5'-C2), 120.9 (1 '-C), 128.1 (2', 6'-C2), 156.3 (9-C), 158.9 (5-C), 160.9 (4'-C), 162.5 (7-C), 163.3 (2-C ), 181.5 (4-C)

  From the above results, it was confirmed that the compound obtained by isolation from the pentacot extract was a C-glycoside compound having a structure represented by the following formula (I).

[Test Example 1] Collagen production promoting action test About the five coconut leaf extract (Sample 1) obtained in Production Example 1 and carambola flavone (Sample 2) obtained in Production Example 2, collagen was obtained as follows. The production promoting effect was tested.

Human normal fibroblasts (Detroit 551) were cultured in a MEM medium containing 10% FBS, 1% NEAA and 1 mmol / L sodium pyruvate, and then cells were collected by trypsin treatment. The collected cells were diluted with the above-mentioned MEM medium to a cell density of 2 × 10 ⁵ cells / mL, then seeded at 100 μL per well in a 96-well microplate, and cultured overnight. After completion of the culture, the medium was removed, and 100 μL of a sample solution (sample concentration: 100 μg / mL, 25 μg / mL) dissolved in 0.5% FBS-containing MEM was added to each well and cultured for 3 days. After the culture, the amount of collagen in the medium of each well was measured by ELISA. In the same manner, the cells were cultured without adding the sample solution, and the amount of collagen was measured. From the obtained measurement results, the collagen production promotion rate (%) was calculated based on the following formula.

Collagen production promotion rate (%) = A / B × 100
In the formula, A represents the amount of collagen when the sample is added, and B represents the amount of collagen when no sample is added.
The results of the above test are shown in Table 1.

  As shown in Table 1, it was confirmed that carambola flavone has a strong collagen production promoting action, similar to the five coconut leaf extract.

[Formulation Example 1]
A cream having the following composition was produced by a conventional method.
Carambola flavone (Production Example 2) 0.001g
Rosemary extract 0.1g
Hamamelis extract 0.1g
3.0g polyglyceryl condensed ricinoleate
Squalane 8.0g
Macadamia nut oil 3.0g
Glyceryl tri-2-ethylhexanoate 5.0 g
4.0 g of methylphenylpolysiloxane
Sodium chloride 0.5g
Preservative (Propyl paraoxybenzoate) 0.1g
Perfume appropriate amount 1,3-butylene glycol 5.0 g
Glycerin 3.0g
Purified water remainder (total amount is 100 g)

[Formulation Example 2]
A serum having the following composition was produced by a conventional method.
Carambola flavone (Production Example 2) 0.002g
Carrot extract 0.1g
Oil soluble licorice extract 0.1g
Royal jelly extract 0.1g
Peach leaf extract 0.1g
Yeast extract 0.1g
Xanthan gum 0.3g
Hydroxyethylcellulose 0.1g
Carboxyvinyl polymer 0.1g
1,3-butylene glycol 4.0 g
Glycerin 2.0g
Potassium hydroxide 0.25g
Fragrance Appropriate amount Preservative (methyl paraoxybenzoate) 0.15g
Ethanol 0.15g
Purified water remainder (total amount is 100 g)

[Composition Example 3]
A pack having the following composition was produced by a conventional method.
Carambola flavone (Production Example 2) 0.001g
0.1g dipotassium glycyrrhizinate
Polyvinyl alcohol 15.0g
Carboxymethylcellulose 5.0g
Glycerin 3.0g
Ethanol 10.0g
Fragrance 0.5g
Preservative (butyl paraoxybenzoate) appropriate amount Antioxidant (tocopherol acetate) appropriate amount Purified water remainder (total amount is 100 g)

[Formulation Example 4]
The following raw materials were uniformly mixed, granulated by a conventional method, and then tableted to produce a tablet-shaped dietary supplement.
Carambola flavone (Production Example 2) 50 parts by weight Powdered sugar (sucrose) 188 parts by weight Glycerin fatty acid ester 12 parts by weight

[Formulation Example 5]
The following ingredients were mixed uniformly and formed into granules by a conventional method to produce a granular dietary supplement.
Carambola flavone (Production Example 2) 34 parts by weight Beet oligosaccharide 1000 parts by weight Vitamin C 167 parts by weight Stevia extract 10 parts by weight

The carambola flavones, collagen production promoters, skin cosmetics and cosmetic foods and beverages of the present invention can greatly contribute to the prevention and improvement of skin aging symptoms such as wrinkle formation, tension loss, and elasticity reduction.

Claims (4)

C-glycoside compound represented by the following formula (I).

A collagen production promoter containing a C-glycoside compound represented by the following formula (I) as an active ingredient.

  A skin cosmetic containing the collagen production promoter according to claim 2. A food and beverage for beauty use, comprising the collagen production promoter according to claim 2.