KR100769577B1 - Cosmetic Composition against Aging of the Skin - Google Patents

Abstract

The present invention relates to a cosmetic composition for improving skin wrinkles, and more particularly, franginidine (Prangenidin: 5-Benzofuranacrylic acid, 6,7-dihydroxy-4- (3-methyl-2-butenyl)-, δ-lactone It relates to a cosmetic composition for improving skin wrinkles comprising) as an active ingredient.

The cosmetic composition for improving skin wrinkles of the present invention promotes collagen synthesis of fibroblasts of the skin, and thus has an excellent effect of improving skin elasticity and improving wrinkles.

Frangenidine, Collagen, Skin Wrinkle Improvement, Cosmetics

Description

Cosmetic composition for improving skin wrinkles {Cosmetic Composition against Aging of the Skin}

1 shows the ¹ H-NMR spectrum of franginidine.

2 shows the ¹³ C-NMR spectrum of franginidine.

3 shows the mass spectrum of frangenidine.

[Industrial use]

The present invention relates to a cosmetic composition for improving skin wrinkles, and more particularly, to a skin composition for improving skin wrinkles by promoting collagen synthesis of fibroblasts of the skin to improve skin elasticity and improving skin wrinkles. will be.

[Private Technology]

Collagen, a major component of the extracellular matrix, is present in extracellular epilepsy as a major substrate protein produced in skin fibroblasts. It is also an important protein, accounting for about 30% of the total weight of biological proteins, and has a solid triple helix structure. Collagen forms most of the organic material of the skin, tendons, bones and teeth, especially in bones and skin (dermis). Most other sieve structures exist as fibrous inclusions.

Collagen is a relatively weak immunogen, partly due to the shielding of latent antigenic determinants by the helix structure of collagen, which also makes collagen resistant to proteolysis. The main functions of collagen are known as mechanical firmness of skin, resistance of connective tissue and binding of tissue, support of cell adhesion, induction of cell division and differentiation (in organic growth or wound healing) (Van der Rest et al. 1990). This collagen is reduced by age and photoaging by UV irradiation, which is known to be closely associated with wrinkle formation of the skin (Arthur K. Balin et al., "Aging and the skin", 1989). In recent years, extensive research on skin aging has revealed an important function of collagen in skin.

Conventionally, products using collagen have been released in order to take advantage of collagen's skin moisturizing effect.However, these cosmetics apply collagen to the surface of the skin. It could not be said to be an essential skin function improvement.

In order to solve this problem, interest in collagen synthesis promoting material has been increased, and conventionally known collagen synthesis promoting materials include vitamin C, retinoic acid, and transforming growth factor (TGF) (Cardinale G. et al, Adv. Enzymol., 41, p. 425, 1974), protein from animal placenta (JP8-231370), betulinic acid (JP8-208424), chlorella extract (JP9-40523, JP10- 36283, promoting fibroblast proliferation).

However, these substances have limited use or insignificant effects due to safety problems such as irritation and redness during skin application, and thus, a substantial improvement in skin function cannot be expected. Therefore, there is an urgent need for the development of a new skin wrinkle improvement cosmetic composition that is safer and more effective in vivo than the existing skin wrinkle improvement cosmetic composition.

The present invention is to solve the conventional problems as described above, an object of the present invention to promote the synthesis of collagen to improve the elasticity of the skin, to provide a cosmetic composition for improving skin wrinkles excellent skin wrinkles will be.

In order to achieve the above object, the present invention is Frangenidine (Prangenidin: 5-Benzofuranacrylic acid, 6,7-dihydroxy-4- (3-methyl-2-butenyl)-, δ-lactone) (hereinafter 'frangenidine It provides a collagen synthesis promoter composition comprising a) as an active ingredient.

The present invention also provides a cosmetic composition for improving skin wrinkles comprising the frangenidine as an active ingredient.

EMBODIMENT OF THE INVENTION Hereinafter, this invention is demonstrated in detail.

The inventors of the present invention, while developing a material having an excellent collagen synthesis promoting effect as an active ingredient of the cosmetic composition for improving skin wrinkles, found that the frangenidine has a very strong collagen synthesis promoting effect and completed the present invention. There is no previous study on the collagen synthesis performance and skin wrinkle improvement effect of frangenidine which is an active ingredient of the present invention.

The franginidin is represented by the following formula (1).

Frangenidine in its natural state is a compound mainly found in hawthorn and plant roots. There are many ways to get frangenidine. For example, finely chopped roots (white paper) of hawthorns and plants, added with water, anhydrous or hydrous lower alcohols having 1 to 4 carbon atoms, ethyl acetate, acetone, chloroform or a mixture thereof, and extracted by heating, and solvent fractionation. Obtained by recrystallization.

By preparing a cosmetic composition for improving skin wrinkles containing frangenidine as an active ingredient and applying it to the human body, it is possible to obtain excellent skin elasticity and wrinkle improvement. At this time, the cosmetic composition for improving skin wrinkles may comprise 0.000001% by weight to 10% by weight, and preferably 0.001% by weight to 10% by weight with respect to the total weight of the frangenidine as a collagen production promoter. Preferably from 0.1% to 10% by weight. When the content of frangenidine is less than 0.000001% by weight, no obvious effect can be expected, and when the content is more than 10% by weight, the effect does not increase as compared to the increase in the content.

The cosmetic composition for improving skin wrinkles according to the present invention is an external ointment, cream, foam, lotion, pack, soft water, emulsion, foundation, makeup base, essence, soap, liquid cleanser, bathing agent, sunscreen cream, or sun oil It may be prepared in a dosage form.

In addition, the cosmetic composition of the present invention can be appropriately blended with conventional ingredients, such as oil, water, surfactants, moisturizers, lower alcohols, thickeners, chelating agents, pigments, preservatives, fragrances and the like, which are blended in general skin cosmetics.

Hereinafter, preferred examples are provided to help understanding of the present invention, but the following examples are merely to illustrate the present invention, and the scope of the present invention is not limited to the following examples.

Example 1 Extraction of Frangenidine

1-1: Extraction of Frangenidine Using Methanol

1 kg of dried root of white paper (Angelica dahurica or Angelica dahurica var. Formosana) was placed in 10 liters of methanol, and extracted by heating at 80 ° C. for 3 hours in an extractor equipped with a reflux condenser to obtain 85 g of methanol extract. The hexane fraction was removed from the methanol extract through a solvent fraction, and the obtained fraction was fractionated three times with chloroform to obtain 9 g of chloroform fraction. The obtained chloroform fraction was subjected to silica column chromatography several times to obtain 0.3 g of a fraction containing frangenidine, and the fraction was separated using preparative HPLC (Prep-HPLC) and recrystallization. Got genidine. Frangenidine obtained by the above method was identified by ingredient and content (99.7% by weight) through nuclear magnetic resonance (NMR) and mass spectroscopy. 1 and 2 show ¹ H-NMR spectra and ¹³ C-NMR spectra of the frangenidine, respectively, and the numbers described in the respective peaks correspond to the numbers described in the chemical formulas of FIGS. 1 and 2. 3 shows the mass spectrum of the frangenidine.

1-2: Frangenidine Extraction Using Chloroform

1 kg of dried root of white paper was placed in 10 liters of chloroform, and extracted by heating at 100 ° C. for 3 hours in an extractor equipped with a reflux condenser to obtain 12 g of chloroform extract. The chloroform extract was dissolved in chloroform, and the solvent was fractionated with an alkaline aqueous solution (0.1 M NaOH aqueous solution) to obtain an alkaline aqueous solution soluble part. Frangenidine was obtained using the recrystallization method. Frangenidine obtained by the above method was identified by ingredient and content (99.7% by weight) through nuclear magnetic resonance (NMR) and mass spectroscopy.

Example 2 Collagen Biosynthesis Effect of Frangenidine

Frangenidine was added to the culture solution of human-derived fibroblasts, and the cosmetic effect for skin wrinkle improvement at the cellular level was tested. Biosynthetic collagen was measured using a PICP EIA kit (Procollagen Type I C-Peptide Enzyme ImmunoAssay KIT).

The final concentrations of frangenidine are 0.5 μg / ml, 1 μg / ml, 2 μg / ml, 5 μg / ml, and 10 μg / ml, together with vitamin C and the control group, respectively. Human fibroblast cells) were added to the culture medium and cultured for 1 day, and then the culture medium was taken, and the degree of collagen biosynthesis at each concentration was measured at 450 nm with a PICP EIA Kit using a spectrophotometer. Collagen production amount was measured as UV absorbance, and collagen biosynthesis increase rate was calculated as a percentage value of the synthetic ability relative to the control (no addition), and the results are summarized in Table 1.

[Table 1] Collagen Biosynthesis Effect at Cell Level According to Concentration

Sample added Application concentration (µg / ml) Collagen production amount (Abs) % Increase Control - 1.330 ± 0.083 - Franginidin 0.5 1.537 ± 0.099 115.6 1.0 1.778 ± 0.121 133.7 2.0 1.801 ± 0.135 135.4 5.0 1.813 ± 0.130 136.3 10.0 1.820 ± 0.204 136.8 Vitamin c 52.8 1.739 ± 0.145 130.8

                                                    * Repeat count = 6

As can be seen from the results of Table 1, frangenidine has excellent collagen biosynthesis performance against human-derived fibroblasts, and generally obtains better collagen synthesis effect at a lower concentration than vitamin C, which is known to have collagen synthesis ability. It can be seen that.

Example 3 Franginidin Effect of Wrinkle Improvement

A 6-week-old hairless mouse was used to test the effect of frangidine on the skin wrinkles against skin wrinkles caused by light. The sample was applied by dissolving frangenidine in 1,3-butylene glycol at 5 mg / ml.

Hairless mice were irradiated with 2 MED for 3 days and 10 weeks a day using a solar simulator to form skin wrinkles, and the control treated with 1,3-butylene glycol without addition of the sample and 5 The degree of improvement was qualitatively determined in the group treated with mg / ml of frangenidine solution 0.5 ml / cm ² (2.5 mg / cm ² with frangenidine) twice a day for 6 weeks.

Wrinkle improvement was judged by visual inspection and photographing of the sample treatment area first, and the judgment criteria were judged by three stages of no improvement, slight improvement, and significant improvement compared to the sample treatment group and the control group. Table 2 shows.

[Table 2] Skin wrinkle improvement effect on the mouse

sample No improvement Minor improvements A significant improvement Control 10 0 0 Franginidin One 5 4

                                                    * Population in each group = 10

[Example 4 and Comparative Example 1] cosmetic essence for skin wrinkle improvement

Preparation of cosmetic essence for skin wrinkle improvement

Formulation of the skin wrinkle improvement cosmetic essence comprising a franginidin was prepared in Example 4, except that the cosmetic essence was prepared in the same manner as in Example 4 except that it does not contain a franginidine Example 1 was set. Detailed compositions are shown in Table 3 below.                     

TABLE 3

 Composition water Example 4 (% by weight) Comparative Example 1 (% by weight) Franginidin One - Propylene glycol 10.0 10.0 glycerin 10.0 10.0 Sodium hyaluronate aqueous solution (1%) 5.0 5.0 ethanol 5.0 5.0 Polyoxyethylene Cured Castor Oil 1.0 1.0 Methyl paraoxybenzoate 0.1 0.1 incense 0.05 0.05 Purified water to 100 to 100

 Experimental effect of skin wrinkle improvement through panel test

The skin wrinkle improvement effect of the essence of Example 4 and Comparative Example 1 was tested in healthy 35 to 50 year old women as follows.

Thirty women aged 35 to 50 were divided into two groups of 15 people each, and the first group had an essence of Example 4 containing 1% of frangenidine, and the second group had an essence of Comparative Example 1 on the face for 1 day. It was applied once for 3 months.

After 3 months, the improvement of skin wrinkles was evaluated by subject's questionnaire and image analysis of skin wrinkles. The subject's questionnaire was judged in three stages of improvement of skin wrinkles and elasticity compared with before use, no improvement, slight improvement, and significant improvement. The results are shown in Table 4.

Table 4 Skin Wrinkle Improvement Effect of the Example of the Present Invention

sample No improvement Minor improvements A significant improvement Comparative Example 1 9 5 One Example 4 - 8 7

As can be seen in Table 4, it can be seen that the skin wrinkle improvement effect is excellent when the essence of Example 4 according to the present invention is used.

Wrinkle improvement effect experiment through image analysis                     

Image analysis of wrinkles was performed by collecting replicas under the eyes (Xantopren, Bayer) before the experiment was started, and immediately after the experiment was completed, replicas were taken from the same area under the eyes. The density of skin wrinkles was measured by two-dimensional analysis. The measurement results of skin wrinkle density by image analysis are shown in Table 5 by averaging the decrease rate of skin wrinkle density after use compared to skin wrinkle density before use.

[Table 5] Skin wrinkle improvement effect (image analysis)

sample Skin Wrinkle Density Reduction (%) Comparative Example 1 8 Example 4 42

As can be seen from Table 5, when applying the essence of Example 4 with the addition of the franginidin according to the present invention it can be seen that the density of the skin wrinkles is significantly reduced compared to the cosmetic composition of Comparative Example 1.

In Examples 3 and 4 described above, no skin irritation or side effects by the frangenidine of the present invention were found.

Hereinafter, the preparation examples and comparative examples of the cosmetic composition for improving skin wrinkles containing frangenidine are shown.

[Example 5 and Comparative Example 2] skin external ointment for improving skin wrinkles

Formulation of the skin external ointment for improving skin wrinkles comprising a frangenidine was prepared in Example 5, except that the external topical ointment was prepared in the same manner as in Example 5 except that it does not contain a frangenidine Was made into Comparative Example 2. Detailed compositions are shown in Table 6 below.

TABLE 6

Composition water Example 5 (% by weight) Comparative Example 2 (wt%) Franginidin 2 - Diethyl sebacate 8 8 Prepayment 5 5 Polyoxyethylene Oleyl Ether Phosphate 6 6 Sodium benzoate 0.1 0.1 Waselin to 100 to 100

[Example 6 and Comparative Example 3] cosmetic cream for improving skin wrinkles

Formulation of the cosmetic cream for improving skin wrinkles comprising a frangenidine was prepared in Example 6, and compared to the preparation of the cosmetic cream in the same manner as in Example 6 except that it does not include the frangenidine Example 3 was set. The detailed composition is shown in Table 7 below.

TABLE 7

Composition water Example 6 (% by weight) Comparative Example 3 (wt%) Franginidin 0.5 - Stearic acid 15.0 15.0 Cetanol 1.0 1.0 Potassium hydroxide 0.7 0.7 glycerin 5.0 5.0 Propylene glycol 3.0 3.0 antiseptic 0.05 0.05 incense 0.05 0.05 Purified water to 100 to 100

[Example 7 and Comparative Example 4] supple cosmetics for improving skin wrinkles

Formulation of skin softening for the improvement of wrinkles containing frangenidine was prepared in Example 7, except that the preparation of the softening cosmetics in the same manner as in Example 7 except that it does not include the frangenidine Example 4 was set. The detailed composition is shown in Table 8 below.                     

TABLE 8

Composition water Example 7 (% by weight) Comparative Example 4 (wt%) Franginidin 0.2 - ethanol 10.0 10.0 Polylauric acid polyoxyethylene sorbitan 1.0 1.0 Methyl paraoxybenzoate 0.2 0.2 glycerin 5.0 5.0 1,3-butylene glycol 6.0 6.0 incense 0.05 0.05 Pigment 0.05 0.05 Purified water to 100 to 100

[Example 8 and Comparative Example 5] nourishing cosmetics for improving skin wrinkles

Formulation of nourishing longevity for improving skin wrinkles containing frangenidine was prepared in Example 8, except that the preparation of nutrients in the same manner as in Example 8 except that it does not contain a franginidine Example 5 was set. Detailed compositions are shown in Table 9 below.

TABLE 9

 Composition water Example 8 (% by weight) Comparative Example 5 (wt%) Franginidin 0.1 - Waselin 2.0 2.0 Sesquioleate sorbitan 0.8 0.8 Polyoxyethylene oleylethyl 1.2 1.2 Methyl paraoxybenzoate 0.1 0.1 Propylene glycol 5.0 5.0 ethanol 3.2 3.2 Carboxy Vinyl Polymer 18.0 18.0 Potassium hydroxide 0.1 0.1 Pigment 0.05 0.05 incense 0.05 0.05 Purified water to 100 to 100

[Example 9 and Comparative Example 6] cosmetic pack for improving skin wrinkles

The formulation of the cosmetic pack for improving skin wrinkles containing frangenidine was prepared in Example 9, and compared to the preparation of the cosmetic pack in the same manner as in Example 9 except for not including the frangenidine Example 6 was set. The detailed composition is shown in Table 10 below.

TABLE 10

 Composition water Example 9 (% by weight) Comparative Example 6 (wt%) Franginidin 0.2 - glycerin 5.0 5.0 Propylene glycol 4.0 4.0 Polyvinyl alcohol 15.0 15.0 ethanol 8.0 8.0 Polyoxyethylene oleylethyl 1.0 1.0 Methyl paraoxybenzoate 0.2 0.2 Pigment 0.05 0.05 incense 0.05 0.05 Purified water to 100 to 100

As described above, the cosmetic composition for improving skin wrinkles containing frangenidine as an active ingredient showed a very strong cosmetic effect for improving skin wrinkles against fibroblasts of the skin, and also in the skin wrinkle improvement test using a hairless mouse. Very good skin wrinkle improvement.

The cosmetic composition for improving skin wrinkles of the present invention includes frangenidine as a collagen synthesis promoter to promote collagen synthesis of fibroblasts of the skin, thereby improving skin elasticity and improving skin wrinkles.

Claims (5)

Franginidine (Prangenidin: 5-Benzofuranacrylic acid, 6,7-dihydroxy-4- (3-methyl-2-butenyl)-, δ-lactone) A cosmetic composition comprising as an active ingredient. As a collagen synthesis promoter, a cosmetic composition for improving skin wrinkles comprising frangenidine as an active ingredient. The cosmetic composition for improving skin wrinkles according to claim 2, wherein the cosmetic composition for improving skin wrinkles comprises frangenidine in an amount of 0.000001 wt% to 10 wt% based on the total weight of the composition. The cosmetic composition for improving skin wrinkles according to claim 2, wherein the cosmetic composition for improving skin wrinkles contains 0.1 to 10% by weight of frangenidine based on the total weight of the composition. According to claim 2, wherein the cosmetic composition for improving skin wrinkles ointment, cream, foam, lotion, pack, soft water, latex, foundation, makeup base, essence, soap, liquid cleanser, bath, sunscreen cream, and sun Cosmetic composition for improving skin wrinkles having a formulation selected from the group consisting of oils.

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