JPS5913707A - Cosmetic composition containing adzuki saponin - Google Patents

Abstract

PURPOSE:To provide a cosmetic containing adzuki saponin extracted from adzuki beans as an active component, and effective to reduce the amount of lipid peroxide on the skin, keep the skin healthy, and prevent and improve the chappy skin, spots and freckles, etc. CONSTITUTION:The objective cosmetic contains 0.01-1% of powdery adzuki saponin (90-98% purity) which is a mixture of the compounds of formula (when R<1> is beta-D-glucopyranosyl (1 2)-beta-D-glucuronopyranosyl, R<2>, R<3>, R<4> and R<6> are methyl and R<5> is OH, etc.) Adzuki saponin has the activity to reduce the amount of lipid peroxide on the skin remarkably, and is expected to have high safety to continuous use. It is used in the cosmetics such as milky lotion, cream, soap, skin powder, etc. Adzuki saponin can be prepared by defatting adzuki beans, extracting with a lower aliphatic alcohol, concentrating the extract, fractionating with water and n-butanol, and separating from the n-butanol layer.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a cosmetic composition containing azukizabonin, and more particularly to a cosmetic composition that reduces the amount of lipid peroxide on the skin surface and maintains the health of the skin.

Maintaining healthy skin is important for preventing rough skin, age spots, and
This is extremely important in the prevention and improvement of skin problems such as ``scratches,'' but in recent years, there has been a noticeable decline in the health of the skin, especially facial skin, especially in women. This is mostly due to changes in dietary habits and irregular lifestyle rhythms, but one factor is thought to be an increase in the amount of lipid peroxide in the skin.

Lipid peroxide is mainly a fatty acid peroxide produced by autoxidation of unsaturated fatty acids, and its production is promoted by internal factors as well as external factors such as ultraviolet rays, radiation, and metal ions. It is also said that it may be a cause of skin disorders due to skin irritation, and it has a significant negative impact on the health of the skin.

In fact, there is a correlation between various facial skin diseases and the amount of lipid peroxide on the skin surface, and it has been proven that an increase in the amount of lipid peroxide causes protein degeneration of epidermal cells and is the main cause of skin inflammation and pigmentation. has been done.

Surprisingly, the present inventors found that azukizabonin extracted from azuki beans significantly lowers the amount of lipid peroxide on the skin surface, and has an extremely deviant effect on maintaining skin health when combined with cosmetics and used continuously. The present invention was completed based on this discovery.

That is, the present invention provides a cosmetic composition containing adzuki sabonin as an active ingredient. Azukizabonin is derived from the azuki bean, which is constantly eaten, and is considered to be highly safe even when used repeatedly.
By repeatedly using the cosmetic composition of the present invention, the health of the skin is maintained, and as a result, "rough skin", "spots", "
Excellent effects can be obtained in the prevention and improvement of conditions such as "Soakakazu".

The azukizabonin used as an active ingredient in the cosmetic composition of the present invention is extracted and separated from the seeds of azuki bean and azuki congener plants such as azuki azuki, azuki azuki, azuki azuki, azuki azuki and a bundu, and purified with a solvent or extracted. It can be obtained by selectively adsorbing saponin from a liquid using a resin adsorbent and purifying it.

For example, azuki seeds are defatted, then extracted with a lower aliphatic alcohol or its water content, the extract is concentrated, the concentrated equine is distributed between water and n-butanol, and the butanol layer is concentrated. The crude saponin component is purified.

The raw material, the azuki seeds, is crushed with the seed coat removed as much as possible. This pulverized material is degreased. In this case, ordinary fat-soluble organic solvents such as ether, hexane, benzene, petroleum ether, reflourin, and ethyl acetate are used.
Ethyl acetate is preferred.

This defatted product is extracted with a lower aliphatic alcohol or a water-containing product thereof. This extraction is carried out by heating the solvent to such an extent that it boils. Examples of lower aliphatic alcohols include methanol, ethanol, prohanol, butanol, etc., with methanol being the most preferred, followed by O~60
Methanol-containing water is preferred. It is preferable to repeat this extraction process several times, and the amount of solvent used in each step is preferably about 2 to 4 times the amount of CΦ/weight relative to the defatted product in step 1.

The extract is then concentrated at as low temperature and pressure as possible. Since a brown precipitate is formed after a certain degree of concentration, it is desirable to separate the precipitate by furnace. The p-liquid is further concentrated and used as eginukichi.

This concentrate (equinu-like) is distributed between water and n-butanol. This distribution process involves (I) shaking the concentrate with a mixture of water and n-butanol in a weight ratio of about 2:1 to about 1=2, preferably in a weight ratio of about 1: )
Either method may be used, such as suspending the concentrate in water and shaking with n-butanol, or (m) dissolving the silk material in water-saturated n-butanol, adding water and shaking. The desired saponin component is transferred to the n-butanol layer. To further explain the case (11) above, the concentrate is suspended in water of the same weight as X, and about 1.0 to 2.0 times @C
Add n-butanol (heavily inhibited) and shake, and repeat this process for 2
By repeating this process ~3 times, the desired adzukizabonin component is transferred to the n-butanol layer. The temperature at this time is room temperature.

The n-butanol layer thus obtained is concentrated at as low temperature and pressure as possible. This concentration is preferably carried out to dryness. This concentrate consists of crude saponin components, which are further subjected to purification treatments.

The first method of this purification treatment is carried out using a combination of an organic solvent that is soluble in the saponin component and an organic solvent that is not soluble in the saponin component. The saponin component is easily soluble in water, methanol, dimethylnulphoxide, pyridine, etc., but insoluble in ethers, hexane, chloroform, acetone, ethyl acetate, etc. These can be combined, but the preferred combination is They are methanol and ethyl ether. That is, the saponin component is purified and precipitated by dissolving the crude saponin component in a soluble organic solvent and adding it to an insoluble solvent or by adding a non-bath dissolvable solvent thereto. At this time, activated carbon treatment is more effective.

As a second purification method, the crude saponin component may be brought into contact with an adsorbent resin to be adsorbed, and then eluted.

The adsorbent resin is preferably a giant reticular, porous, cross-linked polynutylene +11 Its. As a specific example, Selvachrome X A D tie 7'-2
(100 to 200μ, manufactured by Selvachrome), Amberlite XAI')-2 (manufactured by Rohm and Hahne), and the like. As the solvent system used here, water or water containing 30% or less of lower aliphatic alcohol (preferably water containing 1.01 meth, alcohol) is used to dissolve crude saponin, and then lower Fatty alcohol or about 30%
2 lower aliphatic alcohol-containing water (preferably 3
5-99% methanol).

As a third purification method, the crude saponin component was purified by centrifugal liquid chromatography (for example, carrier: KT gel, manufactured by Fuji Gel Sales Co., Ltd.; elution solvent: chloroform/methanol/water = 10/3/1; lower layer rotation speed: 300RPM)
You can also visit and refine it.

Furthermore, following the means of the first or second purification method, the means of the third purification method may be used for purification.

The adzuki saponin thus obtained contains substantially only the zabonin component and can be used as it is as an active ingredient in the present invention.

The obtained azukizabonin was in the form of a white powder that was soluble in water and alcohol, and was subjected to thin layer chromatography on a silica gel plate using chloroform-methanol-water (6:4:1). When a mixture of dicerium and 10% sulfuric acid is sprayed and heated, it gives six reddish-purple spots.

[In the formula, k is β-D-glucopyranosyl (1→2)-β
-D glucuronopyrano/ru group, R,R-R
and k are methyl groups, 艮 is hydroxyl71, I circle, 艮 and R are methyl groups, k is oxy/methyl group, ■(is hydroxyl group;
k and k are a methyl group, k is an oxymethyl group, R is a hydrogen atom, R is a carboxyl group; or K and k are a methyl group, R3 is a notyl group, k is a hydrogen atom, l (is β
-1) -Curcopyranosyl (1→6)-β-D-curcopyranone-oxycarbonyl group, when 艮 is a β-D-glucopyranosyl group, k
and 艮 are methyl groups, 艮 is carboquine groups, k is hydrogen atom, k is β-D-glucopyranosyl (1→6)-β
-D-glucobyranone-oxycarbonyl group, Rka α-■, -rhamnobyranone (1→2)-β-D-
When glucopyranone C1→2)-β-D = glucuronopyranosyl group, R+R and k are methyl groups, k
is an oxy/methyl group, and k5 is a hydroxyl group. Although there are slight differences depending on the azuki beans used as raw materials, it can be obtained with a purity of 90% or more by the purification described in 1.

In the cosmetic composition of the present invention, the powdered azukizabonin or the same is dissolved or dispersed in a solvent such as water or alcohol, and is incorporated as an active ingredient. The amount to be blended can be appropriately selected depending on the desired dosage form, but it is usually preferable to blend adzukizabonin powder in an amount of about 0,000% (assuming a purity of 90 to 98) based on the total amount of the composition.

The cosmetic composition of the present invention can be applied to cosmetic FIs in various dosage forms such as milky lotions, lotions, cream soaps, and soap powders in accordance with conventional methods.
(including medicinal cosmetics as quasi-drugs), other ingredients are not particularly limited, and ingredients normally used in this type of cosmetics, such as liquid paraffin and various surfactants. Agents, beeswax, Nuqualan, cetanol, stearic acid, propylene glycol, preservatives, etc. can be used.

Next, the present invention will be explained in more detail with reference to reference examples and examples.

Reference example 1 (Azugisaboninno production) Red beans (Vign
a angularis (Wild, ) Ohwi
Powder 5 kq of eLOhashi (Hokkaido-produced Dainagon), heat-extract with Hexano 15 A' for 1 hour to degrease, and heat-extract the residue with methanol 15 J. After refluxing for 5 hours, the mixture was filtered to obtain a methanol extract, and the residue was extracted with fresh methanol 151 by heating. The same operation is performed a total of 5 times, and the resulting methanol extracts are combined and concentrated under reduced pressure. During the concentration process of the methanol extract, a brown precipitate is formed, which is separated from each other and precipitated 34.
get g. The furnace liquid was distilled off under reduced pressure and the methanol extract 9
Obtain 6g. Add 961' of this methanol extract to 100' of water.
Suspend in solution and extract with n-butanol (150ml x 3). In the n~butanol transition section, the solvent was distilled off under reduced pressure, and n
- 38 g of butanol extract was obtained, and 46 g of suiko kiss was obtained in the same manner from the water transfer section. 38 g of 11-butanol extract was dissolved in a small amount of methanol and added dropwise to a large amount of ethyl ether with stirring. After collecting 14 g of the resulting precipitate, activated carbon (special Shirasagi, manufactured by Takeda Pharmaceutical Co., Ltd.) - Serai 1-535 (manufactured by Wako Pure Chemical Industries, Ltd.)
Azukizabonin 1 is decolorized and purified using a column as a white powder.
0g? 4. This Azukizabonin has the following properties.

a, [α': 12"4-11.1' (C= 1.0
, methanol) has h or) + C, J reward.

1), infrared absorption spectrum Jl, (1<Rr, CTn
) C3475 (Broad, strong) = 2930 C
Strong), +609 (Broad, Strong), ]100 (Broad, Strong) has a unique absorption thickness.

C. It is a white powder.

d-Solubility is easily soluble in dimethylnulphoxide and pyridine.
Soluble in methanol and water, insoluble in acetone, chloroform, ether and hexane.

e, thin layer chromatography C carrier Nibrecord Noriyoku Gel 60F-254, 0,25 nttn, manufactured by Merck &Co.; developing solvent: chloroform: methanol: water - 6:4:
1) indicates six RE values.

Thin layer chromatogram shows that when a mixture of 1% ceric sulfate and 10% sulfuric acid is sprayed, it shows a reddish-purple color as it heats up.

Example 1 Cleano was produced according to the following recipe according to a conventional method.

Cream formulation ingredients iTi: ;-, 7% nutearic acid 10 nutaryl alcohol 4 butyl stearate
8 Emulsifier
2 Propylene Glycol]
O Glycerin Potassium 4 hydroxide 0.4 Azukizabonin (from Reference Example 1) 0.1 Preservative, flavoring agent
0.2 Purified water
5 g of the remaining cream was placed on a plate, spread flat, and irradiated with ultraviolet rays for 48 hours.

Similarly, a cream was prepared by removing Azukizabonin from the formulation of Example 1 (control cream) and was similarly irradiated with ultraviolet rays. The amounts of these lipid peroxides were measured by the Yagi method (measured values are expressed as TBA (thiobarbic acid) values). Then, 19 women aged 18 to 52 were targeted.
First, the control cream was applied, and after one month, a 24-hour punch test was conducted on the same subject using the cream of Example 1. The results are shown in Table 1.

Table 1 Note: All 'rBA values immediately after manufacture are 8n-rno
As shown in Table 1 of I/7, the cream of Example 1 containing adzukizabonin suppresses skin damage caused by an increase in lipid peroxide.

Example 2 Cosmetic soap was manufactured according to the conventional method using the following formula.

Toilet soap prescription ingredients Yama (Maki soap base 98.60 Azuki sabonin 0.05 Disodium ethylenediaminetetraacetate 0.20 Titanium oxide
0.15 fragrance
1.00 The effect of the obtained cosmetic soap on "rough skin", (-bleeding), and "stains" was tested as usual.

Target 2: 7 boys (C7-51 years old), 15 girls (C23-5)
5 years old). Each subject washed their face with the cosmetic soap using warm water before going to bed and upon waking up. For girls, the condition was that they did not change the proportions [products and makeup methods] they used before and after the test.

Evaluation: According to the criteria shown in Table 2.

Evaluation in Table 2: Improvements from 1 to 2, 1 to 3.2 to 3 were considered valid, and no change or deterioration was considered invalid. In addition, the symptoms were evaluated individually, either alone or accompanied by other symptoms.

Results: As shown in Table 3.

Cosmetics containing Kosaku and Azukizabonin listed in Table 3 and above suppress the effects of lipid peroxide, which is the main cause of skin disorders, and are characterized by extremely effective effects in improving skin symptoms.

Claims (1)

[Claims] (1) A cosmetic composition characterized by containing adzuki bean saponin as an active ingredient.