JP2005220043A - Wrinkle improving agent - Google Patents

Abstract

<P>PROBLEM TO BE SOLVED: To obtain a wrinkle improving agent exhibiting excellent improving effects on wrinkles due to photoaging. <P>SOLUTION: This wrinkle improving agent comprises ergosterol or ergosterol glycoside. <P>COPYRIGHT: (C)2005,JPO&NCIPI

Description

  The present invention is a wrinkle containing ergosterol or an ergosterol glycoside which has an effect of improving wrinkles generated at an exposed site with aging and has an effect of keeping the skin in a dermatological and cosmetically healthy state. It relates to an improving agent.

  Organs of all living organisms including humans are born and grow, then gradually decline with age, eventually stop functioning, and die when a certain part of the function is stopped. The state in which the function gradually declines is called aging. The skin is directly affected by the surrounding environment, and since it has an important function to maintain the environment inside the living body, everything will not stop functioning well, but aging such as wrinkles, spots, dullness, and tarmi This is an organ in which signs are easily manifested, and is particularly prominent in exposed areas exposed to sunlight.

  As skin aging progresses, defense against stimuli such as oxidative stress is weakened, causing the internal environment of the skin to be disturbed and further aging. In particular, since the exposed part is always exposed to strong oxidative stress such as ultraviolet rays, the progress of aging is remarkable. Such skin changes are called photoaging, and no clear mechanism has been proposed, but various factors occur in combination. As a result, wrinkles on the skin surface become deeper and larger, which is not desirable for cosmetic purposes. It becomes a state.

  In the United States, retinoic acid is used as a prescription drug as a substance that has an improvement effect on wrinkles caused by the progress of photoaging, but it has not been approved in Japan because of its side effects and safety issues. (Refer nonpatent literature 1). Therefore, development of a wrinkle improving substance having high safety and sufficient effect is desired.

"FRAGRANCE JOURNAL", April 15, 1998, Volume 26, No. 4, p.75-77

  Accordingly, an object of the present invention is to provide a wrinkle improving agent that is excellent in the effect of improving wrinkles that become noticeable particularly at an exposed site due to aging, and that is excellent in the effect of maintaining cosmetically healthy skin.

  As a result of intensive studies in view of the above circumstances, the present inventors have improved the wrinkle that appears prominently at the exposed site due to aging, and the effect of keeping the skin healthy cosmetically. And it was confirmed that the safety is excellent, and the present invention has been completed. That is, this invention exists in the wrinkle improving agent characterized by mix | blending ergosterol or an ergosterol glycoside.

  INDUSTRIAL APPLICATION This invention is excellent in the improvement effect of the wrinkles which generate | occur | produce especially in an exposure site | part with an aging, and can provide the wrinkle improving agent which maintains skin in a dermatological and cosmetically healthy state.

  Hereinafter, embodiments of the present invention will be described in detail.

Ergosterol used in the present invention is generally known as a functional component contained in mushrooms such as shiitake mushrooms and maitake mushrooms, and is said to have an osteoporosis-preventing effect and the like. Moreover, as a commercial item, it is sold from Wako Pure Chemical Industries, Ltd., Tokyo Chemical Industry, Sigma-Aldrich, etc., and can be obtained easily. The ergosterol glycoside can be synthesized from ergosterol by, for example, the following conventional method.

  Ergosterol and acetobromo-α-D-glucose are reacted with tetramethylurea and silver triflate as a catalyst in a chloroform solvent dried with molecular sieves. After completion of the reaction, washing, concentration, purification by silica gel column chromatography, and isolation are followed by deacetylation to obtain ergosterol glucoside.

  The ergosterol glycoside used in the present invention includes monosaccharides such as galactose, mannose, glucosamine, N-acetylglucosamine, fucose and glucuronic acid, disaccharides such as lactose and maltose, or oligos other than the above-mentioned glucose It can be synthesized using sugar. In addition, the hydroxyl group, amino group, and carboxyl group of these sugars may be substituted, and for example, ergosterol glycoside derivatives described in Japanese Patent No. 3343064 can also be used.

  The ergosterol or ergosterol glycoside used in the present invention can be used singly or in combination of two or more. The blending amount of ergosterol or ergosterol glycoside in the present invention is preferably 0.001 to 10.0% by mass (hereinafter simply referred to as%) based on the total amount of the wrinkle improving agent. If the blending amount is less than this lower limit, the intended effect of the present invention is not sufficient. On the other hand, even if the upper limit is exceeded, the effect commensurate with the increase is not preferred.

The wrinkle improving agent of the present invention can be applied as a skin cosmetic or an external preparation to pharmaceuticals, bathing agents, and the like, and can be, for example, lotions, emulsions, creams, packs and the like.
In addition to the above, a coloring matter, a fragrance, a preservative, a surfactant, a pigment, an antioxidant and the like can be appropriately blended with the wrinkle improving agent of the present invention as long as the object of the present invention is achieved.

  Hereinafter, the present invention will be described in detail based on examples and comparative examples.

Examples 1 and 2 and Comparative Example 1
The following test method examined the wrinkle improvement effect when the sample containing the base alone or ergosterol or ergosterol glycoside was applied to the photoaged skin.

In addition, what was obtained by the following manufacturing methods was used for the ergosterol glycoside in the Example.
-Tetramethylurea (2.6 mL) and silver triflate in a chloroform (100 mL) solvent in which ergosterol (5.7 g) and acetobromo-α-D-glucose (8.9 g) were dried with molecular sieves (5 g) (5.6 g) was added as a catalyst, and the mixture was reacted for 6 hours in the dark and under a nitrogen stream. After completion of the reaction, the reaction solution was filtered, washed and concentrated, and purified and isolated using silica gel column chromatography (elution solvent: ethyl acetate / hexane = 1/4). This was deacetylated to obtain 1.2 g of ergosterol glucoside.

1. Experimental animals One group of 10 hairless mice aged 10 weeks at the start of the test was used.

2. 2. Measurement of wrinkle improvement effect 2-1. Photoaging conditions and measurement method Photoaging was induced by irradiating UVA and UVB once a day, 5 times a week for 8 weeks. Irradiation dose UVA is increased to ^{20J / cm 2, 25J / cm} 2, 30J / cm 2, UVB 20mJ / cm 2, 30mJ / cm 2, 40mJ / cm 2 and per week, 3 weeks after the uppermost A large amount was irradiated.
The wrinkle improvement effect was evaluated by the wrinkle score. The wrinkle score was scored according to the method of Bissett et al. (Photochem Photobiol, 46: 367-378, 1987). That is, the size and depth of the wrinkles are comprehensively evaluated with the naked eye, the highest point is 3 points, “large and deep wrinkles can be confirmed” is 3, “wrinkles can be confirmed” is 2, and “wrinkles cannot be confirmed” "Is 1 and" Normal texture is observed "is 0.

2-2. Sample and Experimental Method Samples were prepared by blending 1% ergosterol or ergosterol glycoside with 50% ethanol aqueous solution (base) (Examples 1 and 2). A sample containing only the base was used as Comparative Example 1.
First, 0.1 mL of these samples were applied to the back skin (approximately 2.5 cm in diameter) of hairless mice at a frequency of once a day and five times a week from the fifth week after the start of UV irradiation to the fourth week after the end of irradiation. Until applied. And after completion | finish of application | coating, the wrinkle score was scored and the base application group was compared as a control.

(Wrinkle score evaluation result)
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Group Wrinkle score value -------------------------------------
Example 1 (ergosterol-containing sample) application group 2.45 ± 0.14
Example 2 (ergosterol glycoside-containing sample) application group 2.60 ± 0.15
Comparative Example 1 (base sample) application group 2.80 ± 0.11
------------------------------------
(Values are mean ± standard error)

  Example 1 showed a significantly lower wrinkle score value compared to Comparative Example 1. Moreover, although Example 2 was inferior to Example 1, the tendency which reduces a wrinkle score was seen compared with the comparative example 1. FIG. From these results, it is shown that ergosterol and ergosterol glycoside are effective against wrinkles induced by photoaging, and it can be seen that they have an effect of improving wrinkles due to photoaging.

Example 3 and Comparative Example 2
In this example and comparative example, a skin lotion having the following composition was prepared according to the following preparation method, and the wrinkle improvement effect was evaluated by using the sample as a sample by the following operation.
Apply skin lotion of Example or Comparative Example to healthy subjects (women, 42-56 years old) who have wrinkles on the corners of each of the five eyes, and with regard to the condition of the skin (wrinkles) in the corners of the eyes by the following method A questionnaire survey was conducted.
Decide each sample on either the left or right side, wrinkles in the corners of the eye corners twice a day for 2 months (60 days) after face washing in the morning and after bathing in the evening (for each sample, focusing on the corners of the eyes) About 0.2 mL each was applied to about 4 cm ² , 2 × 2 cm). Next, after the final application was completed, the questionnaire regarding the condition of the skin (wrinkles) on the left and right eye corners was answered.

Composition of skin lotion Raw material Component Blending amount (%)
A component olive oil 10.0
Isopropyl myristate 1.0
Monolauric acid polyoxyethylene (20) sorbitan 0.5
Propylene glycol 1.0
Glycerin 2.0
B component Methylparaben 0.1
Ethanol 7.0
Purified water Remaining C component with a total amount of 100 Ergosterol 1.0 (Example 3)
0 (Comparative Example 2)

Preparation Method After adding C component ergosterol to B component and dissolving uniformly, add A component, mix and stir and disperse, and then fill the container. In use, the contents are uniformly shaken and dispersed.

  Based on the questionnaire results, the number of respondents who answered that the skin lotion of Example 3 is more effective than Comparative Example 2 for each item related to the skin (wrinkle) state is shown below.

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Item Number of people
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Wrinkles are less noticeable 5
The skin became soft 3
The skin got firmer 5
Shining on the skin 4
My skin became moist 4
-------------------

  From this test result, it can be seen that the skin lotion of Example 3 clearly improved the wrinkles as compared with Comparative Example 2, and further improved the softness and skin firmness deteriorated by photoaging. . Moreover, skin abnormalities such as irritation and itching due to the skin lotion of the present invention were not observed.

Example 4
A skin cream of the following composition was prepared according to the following preparation method, and 20 healthy people (women, 50-56 years old) who listed wrinkles in the corner of the eye as a skin trouble in a preliminary questionnaire were used for more than a week. Went.

Composition of skin cream Raw material Component Blending amount (%)
A component dense wax 2.0
Stearic acid 5.0
Stearyl alcohol 5.0
Reduced lanolin 2.0
Squalene 20.0
Monostearate sorbitan 3.0
Monostearate Polyoxyethylene (20) Sorbitan 3.0
Propylene glycol 5.0
B component Methylparaben 0.2
Purified water Remaining C component with a total amount of 100 Ergosterol 1.0

Preparation Method C component ergosterol was added to component B, and each of components A and B was heated and dissolved at 80 ° C, and then cooled to 30 ° C while mixing and stirring to prepare each skin cream.

  A questionnaire survey was conducted using the skin cream of Example 4. The results are shown below. In addition, the result showed the number of people who answered that they thought after the use compared with before the use in the questionnaire survey of the following items regarding the state of wrinkles.

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Item Number of people
-------------------
Wrinkles are less noticeable 18
Wrinkle size decreased 17
Number of wrinkles decreased 4
Increased wrinkles 0
-------------------

  From this test result, the skin cream of Example 4 is almost all humans who feel that wrinkles are less noticeable than before use, and the factor is that the size of wrinkles is reduced rather than the number of wrinkles. It can be seen that wrinkles due to photoaging were improved. In addition, skin abnormalities such as irritation and itching due to the skin cream of the present invention were not observed.

  It can be applied to skin care cosmetics and external preparations, such as pharmaceuticals and baths, and can be formulated into lotions, emulsions, creams, packs, etc. Very useful.

Claims (1)

A wrinkle improving agent comprising ergosterol or an ergosterol glycoside.