JP2007223918A - Anti-aging agent and cosmetic for skin - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To provide a naturally occurring substance-derived IV type collagen production promoter, laminin 5 production promoter, anti-aging agent and cosmetic for the skin. <P>SOLUTION: These contain a flavonoid or a flavonoid glucoside expressed by formula (I) as an effective ingredient. In the formula, R<SB>1</SB>and R<SB>2</SB>are each one of (a)-(c). Rha is a rhamnose residue. Glc is a glucose residue. (a): When R<SB>1</SB>is a hydrogen atom, R<SB>2</SB>is a hydrogen atom or an Rha. (b): When R<SB>1</SB>is an Rha, R<SB>2</SB>is a hydrogen atom. (c): When R<SB>1</SB>is an Rha<SP>4</SP>Glc, R<SB>2</SB>is an Rha. <P>COPYRIGHT: (C)2007,JPO&INPIT

Description

  The present invention relates to a type IV collagen production promoter, laminin 5 production promoter, anti-aging agent or skin cosmetic.

  The skin is composed of the stratum corneum, epidermis, basement membrane and dermis. The basement membrane is present at the epidermal dermis boundary, and plays an important role in maintaining skin function as well as connecting the epidermis and dermis (see Non-Patent Document 1). The main skeleton of the basement membrane has a network structure made of type IV collagen. Various glycoproteins mainly composed of laminin 5 exist at the boundary between the basement membrane and the epidermis and connect the basement membrane and the epidermis. In young skin, the basement membrane works to maintain the homeostatic interaction of the epidermis and dermis, ensuring moisture retention, flexibility, elasticity, and the like. Maintained.

  However, when there is an influence of certain external factors such as ultraviolet irradiation, excessive drying of the air, excessive skin washing, etc., or when aging progresses, type IV collagen, which is a main component of the basement membrane, and laminin 5 undergoes degradation and alteration, and the basement membrane structure is destroyed (see Non-Patent Document 2). As a result, the skin's moisturizing function and elasticity are lowered, and the keratin begins to exfoliate abnormally, so the skin loses its tension and gloss, and exhibits aging symptoms such as roughness and wrinkles. As described above, changes accompanying aging of the skin, that is, wrinkles, dullness, disappearance of texture, decrease in elasticity, and the like are associated with a decrease in basement membrane components and a change in basement membrane structure.

  Therefore, it is desired to develop a substance that induces remodeling of the basement membrane structure by enhancing the production of type IV collagen and laminin 5 and improves the skin function. For example, hydrolyzed casein, pre-extract, beech bud extract, erythrina extract, soluble eggshell membrane, cuckoo extract and western kizuta extract (see Patent Document 1), saponin or sapogenol (see Patent Document 2) and the like are known. Moreover, as what has a laminin 5 production promotion effect | action, for example, a cuckoo extract, a licorice extract or its flavonoid fraction, a cypress extract, a cypress extract, a lobster extract, a Koroha extract and a whey extract ( (See Patent Document 3) Onionis extract, Merirot extract, bean extract, azuki bean extract (see Patent Document 4), soybean extract (see Patent Document 5), and the like are known.

Furthermore, it is known that the kaempferol-7-O-α-L-rhamnopyranoside of the present invention has an anti-inflammatory action and a cyclic AMP phosphodiesterase inhibitory action, but production of type IV collagen and laminin 5 It has not been known so far (see Patent Document 6).
JP 2004-18471 A JP 2002-516837 A JP 2003-137767 A JP 2003-137768 A JP 2004-217618 A JP 2004-161678 A Marinkovich MP et al., “J. Cell. Biol.”, 1992, Vol. 199, p.695-703 Lavker et al., “J. Invest. Dermatol.”, 1979, Vol. 73, pp. 59-66.

  The present invention has found that among natural products, it has type IV collagen production promoting action and laminin 5 production promoting action, type IV collagen production promoting agent, laminin 5 production promoting agent, anti-aging agent and the like containing them as active ingredients It aims at providing skin cosmetics.

  In order to achieve the above object, first, the present invention comprises a flavonoid represented by the following formula (I) or a flavonoid glycoside as an active ingredient, a type IV collagen production promoter, laminin 5. Provide production promoter or anti-aging agent.

式中、Ｒ_１及びＲ_２は、下記（ａ）〜（ｃ）のいずれかの組み合わせから選ばれるものである。ただし、Ｒｈａはラムノース残基を表し、Ｇｌｃはグルコース残基を表す。
（ａ）Ｒ_１が水素原子のとき、Ｒ_２は水素原子又はＲｈａ
（ｂ）Ｒ_１がＲｈａであるとき、Ｒ_２はＲｈａ
（ｃ）Ｒ_１がＲｈａ^４Ｇｌｃであるとき、Ｒ_２はＲｈａ

In the formula, R ₁ and R ₂ are selected from any combination of the following (a) to (c). However, Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) when R ₁ is Rha ⁴ Glc, R ₂ is Rha

  2ndly, this invention provides the skin cosmetics characterized by mix | blending the flavonoid or flavonoid glycoside represented by following formula (I).

式中、Ｒ_１及びＲ_２は、下記（ａ）〜（ｃ）のいずれかの組み合わせから選ばれるものである。ただし、Ｒｈａはラムノース残基を表し、Ｇｌｃはグルコース残基を表す。
（ａ）Ｒ_１が水素原子のとき、Ｒ_２は水素原子又はＲｈａ
（ｂ）Ｒ_１がＲｈａであるとき、Ｒ_２はＲｈａ
（ｃ）Ｒ_１がＲｈａ^４Ｇｌｃであるとき、Ｒ_２はＲｈａ

In the formula, R ₁ and R ₂ are selected from any combination of the following (a) to (c). However, Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) when R ₁ is Rha ⁴ Glc, R ₂ is Rha

  According to the present invention, type IV collagen production promoter, laminin 5 production promoter, and anti-aging agent containing flavonoid or flavonoid glycoside having an excellent type IV collagen production promoting effect and laminin 5 production promoting effect as an active ingredient In addition, skin cosmetics containing the substance can be provided.

The present invention will be described in detail below.
[Anti-aging agent, type IV collagen production promoter, laminin 5 production promoter]
The anti-aging agent, type IV collagen production promoter or laminin 5 production promoter of the present invention contains a flavonoid or flavonoid glycoside represented by the following formula (I) as an active ingredient.

式中、Ｒ_１及びＲ_２は、下記（ａ）〜（ｃ）のいずれかの組み合わせから選ばれるものである。ただし、Ｒｈａはラムノース残基を表し、Ｇｌｃはグルコース残基を表す。
（ａ）Ｒ_１が水素原子のとき、Ｒ_２は水素原子又はＲｈａ
（ｂ）Ｒ_１がＲｈａであるとき、Ｒ_２はＲｈａ
（ｃ）Ｒ_１がＲｈａ^４Ｇｌｃであるとき、Ｒ_２はＲｈａ

In the formula, R ₁ and R ₂ are selected from any combination of the following (a) to (c). However, Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) when R ₁ is Rha ⁴ Glc, R ₂ is Rha

  The flavonoid or flavonoid glycoside represented by the general formula (I) can be produced by isolation and purification from a plant extract containing the flavonoid or flavonoid glycoside, or can be produced by synthesis. You can also. In addition, when manufacturing by a synthesis | combination, the synthesis | combining method is not specifically limited, It can synthesize | combine by a well-known method.

  The plant extract containing the flavonoid or flavonoid glycoside can be obtained by an extraction method generally used for plant extraction. Examples of plants containing the above flavonoids or flavonoid glycosides include black-spotted azuki bean (scientific name: Phaseolus atropurureus), geno shouko (scientific name: Geranium thunbergii Siebold et Zuccarini) and the like. Among these, as a raw material for extraction, black-spotted azuki bean is preferable.

  Black-headed azuki bean is a climbing perennial plant belonging to the genus of the leguminous kidney bean distributed in Honshu, Kyushu, Okinawa, etc., and can be easily obtained from these regions. Examples of the part that can be used as the extraction raw material include a trunk, an above-ground part, a root part, and a whole plant, and a trunk part is preferable.

  Genokosho is a perennial plant belonging to the genus Olysium, distributed from Hokkaido to Kyushu, and can be easily obtained from these areas. Examples of the parts that can be used as the extraction raw material include above-ground parts such as leaves, branches, and stems, root parts, flower parts, fruit parts, and the like, and preferably, leaves, branches, stems, and the like. It is the ground part.

  The plant extract containing the flavonoid or flavonoid glycoside can be obtained by drying the raw material for extraction and then pulverizing the raw material 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 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, and those 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. When the solvent is distilled off from the obtained extract, a paste-like concentrate is obtained, and when this concentrate is further dried, a dried product is obtained.

  The method for isolating and purifying the flavonoids or flavonoid glycosides from the extract obtained as described above, the concentrate of the extract or the dried product of the extract is not particularly limited. Can be done by law. For example, the plant extract is concentrated and roughly purified by liquid-liquid partition extraction, ion exchange resin, and column chromatography using a porous resin, and further reverse phase silica gel column chromatography and normal phase silica gel column chromatography. The above flavonoids or flavonoid glycosides can be isolated and purified by subjecting to a graph and crystallization as necessary.

  Since the flavonoids or flavonoid glycosides obtained as described above have a type IV collagen production promoting action and a laminin 5 production promoting action, they are used to produce an anti-aging agent and type IV collagen production. It can be used as an active ingredient of a promoter or a laminin 5 production promoter. The plant extract obtained by the extraction treatment contains the flavonoid or flavonoid glycoside and can be used as an active ingredient of an anti-aging agent, a type IV collagen production promoter or a laminin 5 production promoter as it is. It is preferable to use a purified flavonoid or a flavonoid glycoside with increased purity. An anti-aging agent, a type IV collagen production promoter or a laminin 5 production promoter more excellent in use effect can be obtained by using, as an active ingredient, the above-mentioned flavonoid or flavonoid glycoside having an increased purity. . The plant extract containing the flavonoid or flavonoid glycoside includes an extract obtained by using the plant containing the flavonoid or flavonoid glycoside as an extraction raw material, a diluted or concentrated solution of the extract, and the extract. A dried product obtained by drying, or a crude product or a purified product thereof is included.

  The anti-aging agent, type IV collagen production promoter or laminin 5 production promoter of the present invention may consist of the flavonoid or flavonoid glycoside, or a plant extract containing the flavonoid or flavonoid glycoside. The above flavonoid or flavonoid glycoside, or a plant extract containing the above flavonoid or flavonoid glycoside may be formulated.

  The flavonoid or flavonoid glycoside is an arbitrary agent such as powder, granule, tablet or liquid according to a conventional method using a pharmaceutically acceptable carrier such as dextrin or cyclodextrin and any other auxiliary agent. It can be provided by being formulated into a form, and can be used by being blended with other compositions (for example, skin cosmetics described later), and can be used as an ointment, a liquid for external use, a patch, and the like. In this case, as an auxiliary agent, for example, an excipient, a binder, a disintegrant, a lubricant, a stabilizer, a flavoring agent and the like can be used.

  In addition, the anti-aging agent, type IV collagen production promoter or laminin 5 production promoter of the present invention is, if necessary, other natural extracts having a type IV collagen production promoting action or laminin 5 production promoting action, as described above. It can be blended with a flavonoid or flavonoid glycoside, or a plant extract containing the above flavonoid or flavonoid glycoside and used as an active ingredient.

  The anti-aging agent of the present invention can promote the production of type IV collagen through the action of promoting the production of type IV collagen possessed by the flavonoid or flavonoid glycoside, and the production of laminin 5 possessed by the flavonoid or flavonoid glycoside. Through the promoting action, the production of laminin 5 can be promoted. Thereby, reconstruction of the basement membrane structure can be induced, and skin aging symptoms can be prevented and improved. However, the anti-aging agent of this invention can be used for all the uses meaningful in exhibiting a type IV collagen production promotion effect and / or laminin 5 production promotion effect besides these uses.

  The type IV collagen production promoter of the present invention can promote the production of type IV collagen through the type IV collagen production promoting action of the flavonoid or flavonoid glycoside, thereby reconstructing the basement membrane structure. It can induce and prevent or improve skin aging symptoms. However, the type IV collagen production-promoting agent of the present invention can be used for all purposes that are meaningful for exerting the effect of promoting type IV collagen production in addition to these uses.

  The laminin 5 production promoter of the present invention can promote the production of laminin 5 through the laminin 5 production promoting action of the flavonoid or flavonoid glycoside. Thereby, reconstruction of the basement membrane structure can be induced, and skin aging symptoms can be prevented and improved. However, the laminin 5 production promoter of the present invention can be used for all purposes that are meaningful for exerting a laminin 5 production promoting action in addition to these uses.

[Skin cosmetic]
The skin cosmetic of the present invention is a blend of flavonoids or flavonoid glycosides represented by the following general formula (I).

式中、Ｒ_１及びＲ_２は、下記（ａ）〜（ｃ）のいずれかの組み合わせから選ばれるものである。ただし、Ｒｈａはラムノース残基を表し、Ｇｌｃはグルコース残基を表す。
（ａ）Ｒ_１が水素原子のとき、Ｒ_２は水素原子又はＲｈａ
（ｂ）Ｒ_１がＲｈａであるとき、Ｒ_２はＲｈａ
（ｃ）Ｒ_１がＲｈａ^４Ｇｌｃであるとき、Ｒ_２はＲｈａ

In the formula, R ₁ and R ₂ are selected from any combination of the following (a) to (c). However, Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) when R ₁ is Rha ⁴ Glc, R ₂ is Rha

  The above flavonoids or flavonoid glycosides have a type IV collagen production promoting action and a laminin 5 production promoting action and are excellent in usability and safety when applied to the skin. It is suitable for doing. In this case, the flavonoid or flavonoid glycoside may be blended as it is, or an anti-aging agent, a type IV collagen production promoter or a laminin 5 production promoter formulated from the flavonoid or flavonoid glycoside may be blended. Also good. By incorporating into the skin cosmetics the above flavonoid or flavonoid glycoside, or an anti-aging agent, a type IV collagen production promoter or a laminin 5 production promoter formulated from the above flavonoid or flavonoid glycoside, A type IV collagen production promoting action and a laminin 5 production promoting action can be imparted.

  The skin cosmetics that can be blended with the above flavonoids or flavonoid glycosides are not particularly limited, and examples thereof include ointments, creams, emulsions, lotions, packs, foundations, lip balms, bath preparations, hair arts, hair lotions. , Soap, body shampoo and the like.

  When blending the above flavonoids or flavonoid glycosides in skin cosmetics, the blending amount can be adjusted as appropriate according to the type of skin cosmetic, but the preferred blending rate is converted to a standard extract. About 0.0001 to 10% by mass, and a particularly suitable blending ratio is about 0.005 to 5% by mass in terms of a standard extract.

  The skin cosmetic of the present invention is a main agent, auxiliary agent or other used in the production of normal skin cosmetics as long as it does not interfere with the type IV collagen production promoting action and laminin 5 production promoting action of the flavonoid or flavonoid glycoside. Ingredients such as astringents, bactericides, antibacterial agents, whitening agents, UV absorbers, moisturizers, cell activators, anti-aging agents, anti-inflammatory / anti-allergic agents, antioxidant / active oxygen removers, fats and oils, waxes , Hydrocarbons, fatty acids, alcohols, esters, surfactants, perfumes and the like can be used in combination. When used in combination, it becomes a more general product, and a synergistic effect with other active ingredients used in combination may lead to an excellent effect that is more than normally expected.

  The anti-aging agent, type IV collagen production promoter, laminin 5 production promoter or skin cosmetic of the present invention is preferably applied to humans, as long as the respective effects are exhibited. It can also be applied to animals other than humans.

  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 flavonoids or flavonoid glycosides 525 g of pulverized azuki bean trunk as an extraction raw material was added to 5000 mL of methanol and kept at 80 ° C. for 3 hours with gentle stirring, followed by filtration. Thus, an extract from black-spotted azuki bean was obtained. 5000 mL of methanol was again added to the residue, and the same operation was performed to obtain an extract. The obtained extracts were combined, concentrated under reduced pressure at 40 ° C., and further dried with a vacuum drier to obtain 44.3 g of a black bean extract.

  40.7 g of the resulting black-spotted azuki bean extract was purified by Diaion HP-20 column chromatography. Elution was performed with water, 60% by mass aqueous methanol, and methanol to obtain three fractions each. The 60 mass% aqueous methanol fraction (4.1 g in 4.5 g) obtained second by Diaion HP-20 column chromatography was subjected to normal phase column chromatography, reverse phase column chromatography and high performance liquid chromatography. After fractionation and purification, 1 mg of kaempferol (sample 1) represented by the following formula (II), 45 mg of kaempferol-7-O-α-L-rhamnopyranoside represented by the following formula (III) (sample 2) Kaempferol-3,7-di-O-α-L-rhamnopyranoside 112 mg (sample 3) represented by the following formula (IV), and kaempferol-3-O-β represented by the following formula (V) -D-glucopyranosyl (1 → 4) -α-L-rhamnopyranosyl-7-O-α-L-rhamnopyranoside 15 mg (sample 4) was obtained.

[Test Example 1] Type IV collagen production promotion test The flavonoids or flavonoid glycosides (samples 1 to 4) obtained in Production Example 1 were tested for the type IV collagen production promotion effect as follows.

Human fibroblasts are seeded in a 96-well plate and cultured at 37 ° C. under 5% CO ₂ -95% air in a medium supplemented with sample (samples 1 to 4) (sample concentration: 25 μg / mL) for 72 hours. After that, 100 μL of the supernatant was transferred to an ELISA plate and adsorbed on the plate overnight at 4 ° C., then the solution was discarded, and phosphate physiological buffer (PBS-T) containing 0.05% Tween-20 was used. And washed. Thereafter, a blocking operation was performed with a phosphate physiological buffer containing 1% bovine serum albumin. The solution was discarded, washed with a phosphate physiological buffer solution (PBS-T) containing 0.05% Tween-20, and reacted with an anti-human collagen type IV antibody (rabbit IgG; manufactured by Novotech). Discard the solution, wash with phosphate physiological buffer (PBS-T) containing 0.05% Tween-20, react with HRP-labeled anti-rabbit IgG antibody, and perform the same washing procedure to develop color. Reaction was performed.

  The type IV collagen production promotion rate (%) was calculated by performing the above-mentioned ELISA using a standard product, creating a calibration curve, and setting the amount of type IV collagen production when no sample was added as 100%. Table 2 shows the type IV collagen production promotion rate (%) of each sample.

[Table 2]
Sample IV type collagen production promotion rate (%)
Sample 1 149.3
Sample 2 104.7
Sample 3 127.5
Sample 4 149.9

  As shown in Table 2, it was confirmed that the flavonoids or flavonoid glycosides of Samples 1 to 4 have an excellent type IV collagen production promoting action in fibroblasts.

[Test Example 2] Laminin 5 production promoting action test The flavonoids or flavonoid glycosides (samples 1 to 4) obtained in Production Example 1 were tested for laminin 5 production promoting action as follows.

Normal human epidermal keratinocytes are seeded in a 24-well plate and cultured in a sample-added medium (sample concentration: 50 μg / mL) at 37 ° C. and 5% CO ₂ -95% air for 24 hours. 100 μL of the clean was transferred to an ELISA plate and adsorbed on the plate at 4 ° C. overnight. Thereafter, the solution was discarded and washed with a phosphate physiological buffer solution (PBS-T) containing 0.05% Tween-20. Thereafter, a blocking operation was performed with a phosphate physiological buffer containing 1% bovine serum albumin. The solution was discarded, washed with a phosphate physiological buffer solution (PBS-T) containing 0.05% Tween-20, and reacted with anti-human laminin 5 antibody (mouse IgG, manufactured by Chemicon). The solution was discarded and washed with a phosphate physiological buffer solution (PBS-T) containing 0.05% Tween-20 to react with biotin-labeled anti-mouse IgG (Amersham Bioscience). After discarding the solution, washing with a phosphate buffer solution (PBS-T) containing 0.05% Tween-20 and reacting with a streptavidin-peroxidase complex (Calbiochem), the same washing operation was performed. The color reaction was performed.

  The laminin 5 production promotion rate was calculated as (%), and the absorbance when no sample was added was calculated as 100%. Table 3 shows the laminin 5 production promotion rate (%) of each sample.

[Table 3]
Sample laminin 5 production promotion rate (%)
Sample 1 101.2
Sample 2 137.7
Sample 3 111.2
Sample 4 102.1

  From the results shown in Table 3, it was confirmed that the flavonoids or flavonoid glycosides of Samples 1 to 4 have an excellent laminin 5 production promoting action in keratinocytes.

[Formulation Example 1]
A lotion having the following composition was produced by a conventional method.
Kaempferol (Production Example 1) 0.01 g
Glycerin 3.0g
1,3-butylene glycol 3.0 g
Oleic acid polyoxyethylene sorbitan (20E.O.) 0.5g
Methyl paraoxybenzoate 0.15g
Citric acid 0.1g
Sodium citrate 0.1g
Oil soluble licorice extract 0.1g
Seaweed extract 0.1g
Xylobiose Mixture 0.5g
Kujin extract 0.1g
Fragrance 0.05g
Purified water remainder (total amount is 100 g)

[Formulation Example 2]
A cream having the following composition was produced by a conventional method.
Kaempferol (Production Example 1) 0.05 g
Aloe extract 0.1g
Liquid paraffin 5.0g
Salami beeswax 4.0g
Squalane 10.0g
Cetanol 3.0g
Lanolin 2.0g
Stearic acid 1.0g
Oleic acid polyoxyethylene sorbitan (20E.O.) 1.5g
3.0 g glyceryl monostearate
Oil soluble licorice extract 0.1g
1,3-butylene glycol 6.0 g
1.5 g of methyl paraoxybenzoate
Fragrance 0.1g
Purified water remainder (total amount is 100 g)

[Composition Example 3]
An emulsion having the following composition was produced by a conventional method.
Kaempferol-7-O-α-L-rhamnopyranoside (Production Example 1)
0.01g
Jojoba oil 4.0g
Placenta extract 0.1g
Olive oil 2.0g
Squalane 2.0g
Cetanol 2.0g
Glyceryl monostearate 2.0g
Polyoxyethylene cetyl ether (20E.O.) 2.5g
Oleic acid polyoxyethylene sorbitan (20E.O.) 2.0g
Stearyl glycyrrhetinate 0.1g
1,3-butylene glycol 3.0 g
Hinokitiol 0.15g
Fragrance 0.05g
Purified water remainder (total amount is 100 g)

[Formulation Example 4]
A cream having the following composition was produced by a conventional method.
Kaempferol-3,7-di-O-α-L-rhamnopyranoside (Production Example 1)
0.05g
Aloe extract 0.1g
Liquid paraffin 5.0g
Salami beeswax 4.0g
Squalane 10.0g
Cetanol 3.0g
Lanolin 2.0g
Stearic acid 1.0g
Oleic acid polyoxyethylene sorbitan (20E.O.) 1.5g
3.0 g glyceryl monostearate
Oil soluble licorice extract 0.1g
1,3-butylene glycol 6.0 g
1.5 g of methyl paraoxybenzoate
Fragrance 0.1g
Purified water remainder (total amount is 100 g)

[Formulation Example 5]
A cream having the following composition was produced by a conventional method.
Kaempferol-3-O-β-D-glucopyranosyl (1 → 4) -α-L-rhamnopyranosyl-7-O-α-L-rhamnopyranoside (Production Example 1)
0.05g
Ages extract 0.1g
Polyethylene glycol monostearate 2.0g
Self-emulsifying glyceryl monostearate 5.0 g
Stearic acid 2.0g
Cetanol 2.0g
Squalane 12.0g
Macadamia nut oil 3.0g
0.2g of methylpolysiloxane
Fragrance 0.01g
Preservative (Methyl paraoxybenzoate) 0.15g
Oil soluble licorice extract 0.1g
1,3-butylene glycol 7.0 g
Xanthan gum 0.2g
Purified water remainder (total amount is 100 g)

[Composition Example 6]
A serum having the following composition was produced by a conventional method.
Kaempferol-7-O-α-L-rhamnopyranoside (Production Example 1)
0.01g
Chamomile extract 0.1g
Xanthan gum 0.3g
Hydroxyethylcellulose 0.1g
Carboxyvinyl polymer 0.1g
1,3-butylene glycol 4.0 g
0.1g dipotassium glycyrrhizinate
Glycerin 2.0g
Potassium hydroxide 0.25g
Fragrance 0.01g
Preservative (Methyl paraoxybenzoate) 0.15g
Ethanol 2.0g
Purified water remainder (total amount is 100 g)

[Formulation Example 7]
A serum having the following composition was produced by a conventional method.
Kaempferol-3,7-di-O-α-L-rhamnopyranoside (Production Example 1)
0.05g
Mulberry extract 0.1g
Carboxyvinyl polymer 0.2g
Xanthan gum 0.2g
Sodium hyaluronate 0.1g
Polyethylene glycol 3.0g
Glycerin 6.0g
1,3-butylene glycol 3.0 g
0.1g dipotassium glycyrrhizinate
Preservative (Methyl paraoxybenzoate) 0.15g
L-Arginine 0.15g
Purified water remainder (total amount is 100 g)

[Formulation Example 8]
A pack having the following composition was produced by a conventional method.
Kaempferol-3-O-β-D-glucopyranosyl (1 → 4) -α-L-rhamnopyranosyl-7-O-α-L-rhamnopyranoside (Production Example 1)
0.05g
Yokuinin extract 0.1g
Polyvinyl alcohol 15g
Polyethylene glycol 3g
7g of propylene glycol
Ethanol 10g
0.05 g of methyl paraoxybenzoate
0.1g dipotassium glycyrrhizinate
Fragrance 0.05g
Purified water remainder (total amount is 100 g)

[Formulation Example 9]
A cleaning lotion having the following composition was produced by a conventional method.
Kaempferol-7-O-α-L-rhamnopyranoside (Production Example 1)
0.05g
Lavender extract 0.1g
1,3-butylene glycol 4.0 g
Glycerin 4.0g
Dipropylene glycol 2.0g
Polyoxyethylene polyoxypropylene decyl tetradecyl ether
0.7g
Ethanol 3.0g
0.1g dipotassium glycyrrhizinate
Fragrance 0.001g
Preservative (Methyl paraoxybenzoate) 0.15g
Purified water remainder (total amount is 100 g)

[Composition Example 10]
An emulsion having the following composition was produced by a conventional method.
Kaempferol-3,7-di-O-α-L-rhamnopyranoside (Production Example 1)
0.05g
Rosemary extract 0.1g
1.0 g polyoxyethylene sorbitan monostearate
Tetraoleic acid polyoxyethylene sorbit 1.5g
Lipophilic glyceryl monostearate 1.0g
Stearic acid 0.5g
Behenyl alcohol 1.5g
Cetyl palmitate 0.5g
Squalane 10.0g
Methyl polysiloxane 0.5g
Perfume appropriate amount 1,3-butylene glycol 7.0g
Stearyl glycyrrhetinate 0.1g
Xanthan gum 0.1g
Purified water remainder (total amount is 100 g)

The type IV collagen production promoter, laminin 5 production promoter, anti-aging agent, or skin cosmetic of the present invention induces the reconstruction of the basement membrane structure by promoting the production of the basement membrane component. By inducing the reconstruction of the basement membrane structure, an excellent skin aging prevention effect and skin function improvement effect are exhibited.

Claims (4)

A type IV collagen production promoter comprising a flavonoid represented by the following general formula (I) or a flavonoid glycoside as an active ingredient.

(In the formula, R ₁ and R ₂ are selected from any of the following combinations (a) to (c), where Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) When R ₁ is Rha ⁴ Glc, R ₂ is Rha) The laminin 5 production promoter characterized by containing the flavonoid or flavonoid glycoside represented by the following general formula (I) as an active ingredient.

(In the formula, R ₁ and R ₂ are selected from any of the following combinations (a) to (c), where Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) When R ₁ is Rha ⁴ Glc, R ₂ is Rha) An anti-aging agent comprising a flavonoid represented by the following general formula (I) or a flavonoid glycoside as an active ingredient.

(In the formula, R ₁ and R ₂ are selected from any of the following combinations (a) to (c), where Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) When R ₁ is Rha ⁴ Glc, R ₂ is Rha) A skin cosmetic comprising a flavonoid represented by the following general formula (I) or a flavonoid glycoside.

(In the formula, R ₁ and R ₂ are selected from any of the following combinations (a) to (c), where Rha represents a rhamnose residue and Glc represents a glucose residue.
(A) When R ₁ is a hydrogen atom, R ₂ is a hydrogen atom or Rha
(B) when R ₁ is Rha, R ₂ is Rha
(C) When R ₁ is Rha ⁴ Glc, R ₂ is Rha)