JPH10279431A - Composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a composition excellent in an acne-preventing effect, a skin roughness-improving effect and a moisture-retaining effect by including a lignan glycoside and a specific pharmaceutically active ingredient. SOLUTION: This composition comprises (A) a lignan glycoside consisting of a sesaminol glycoside of formula I [R1 , R2 are each a glycosyl group composed from one to four saccharides; the saccharides are glucose, galactose and fructose; (a), (b), (c) are each 1, 2], (B) a pharmaceutically active agent selected from (i) sebum secretion-controlling agents preferably such as pyridoxine (derivative), zinc oxide and a Polygonum bistorta extract and/or (ii) sterilizers preferably such as benzoic acid (derivative), benzalkonium chloride, sulfur, and a ginger extract and, if necessary, (C) an oil agent, a powdery agent, a surfactant, purified water, a colorant, a perfume, etc. The component A preferably contains at least one of sesaminol glycosides of formula II to formula IV (Glc is a glucosyl selected from the residues of glucose, galactose and fructose) as a main ingredient.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition comprising a lignan glycoside and a specific medicinal ingredient, and more particularly to a composition having excellent acne prevention, skin roughness improvement and moisture retention effects.

[0002]

2. Description of the Related Art Conventionally, cosmetics such as milky lotions, creams, lotions, packs, dispersions, and cleaning agents, and quasi-drugs such as ointments, creams, and liquids for external use have been added to these products. A medicinal component is added for the purpose of imparting a predetermined medicinal effect. For example, in addition to suppressing sebum secretion, pharmaceutically active ingredients such as aluminum hydroxychloride, benzalkonium chloride, isopropylmethylphenol, and resorcinol are blended for the purpose of sterilizing acne bacteria and the like.

[0003]

However, in the case of an external preparation containing these medicinal components, the effects of the medicinal components are not sufficient, or the stability is lacking if a sufficient amount is obtained to obtain the medicinal effects. There has been a demand for an improvement, such as impaired usability.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies to improve the effect of a medicinal component, and as a result, when a lignan glycoside is combined with a specific medicinal component, the original medicinal component has the medicinal component. The present inventors have found that the action is sufficiently exerted and completed the present invention.

That is, the present invention relates to the following components (A) and (B): (A) a lignan glycoside represented by the structural formula (I); (B) a medicament selected from sebum secretion regulators and / or fungicides. Agent

Embedded image And lignan glycosides represented by the following structural formulas (II-a) and (II-b):
Or, those containing one or more of the sesaminol glycosides represented by (II-c) as a main component are preferable, and in a preferred embodiment, the lignan glycoside is a sesame seed or a humidified product thereof. It is a hydrated lower alcohol extract of germinated bodies or their defatted products.

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[0006]

BEST MODE FOR CARRYING OUT THE INVENTION The lignan glycoside, which is the component (A) of the present invention, is represented by the above general formula (I). That is, the lignan glycoside according to the present invention comprises 2
The aglycone portion has a methylenedioxyphenyl group and a sugar portion in which one to four sugar residues of glucose, galactose or fructose are bonded to the hydroxyl group.

[0007] The lignan glycoside is preferably glucoside lignan in which the sugar residue in the structural formula (I) is a diglucoside residue and / or a triglucoside residue, and still more preferably the structural formula (II) −
One, two or more of the compounds represented by a), (II-b) or (II-c), or those containing these as main components. Further, the method of preparing the same is not particularly limited.
No. 145066).

[0008] The content of lignan glycosides in the composition of the present invention cannot be uniformly defined by the difference in the content of each component of the lignan glycoside.
In the case of the aqueous lower alcohol extract prepared by the method disclosed in No. 66, the content is 0.05 to 20% by weight (hereinafter simply referred to as “%”), preferably 0.1 to 10%,
0.01 to 10% when blending crude lignan glycoside,
It is preferably 0.05 to 5%, and a highly purified product (of the lignan glycoside represented by the structural formula (I), (II-a), (II-b) or (II-c)) When at least one of them is contained in a total amount of about 60% or more), 0.001 to 5%, preferably 0.01 to 1%.
%.

[0009] On the other hand, the sebum secretion preparation and / or bactericide which is the component (B) of the present invention include the following.

(Sebum secretion preparation agent), namely pyridoxine and its derivatives and salts thereof, biotin, zinc oxide,
Aluminum chloride, sodium chloride, aluminum hydroxychloride, citric acid and its salts, dried seawater,
Aloe extract, Ibukitrano extract, oak extract, watercress extract, Melissa extract, Hamamelis extract, black tea extract, green tea extract, oolong tea extract, horsetail extract, hop extract, rosemary extract, etc. Is mentioned.

Among these sebum secretion preparations, particularly preferred are pyridoxine and its derivatives and salts thereof, zinc oxide, aluminum hydroxychloride, ibukitorano extract, oak extract, watercress extract, melissa extract, Hamamelis extract, black tea extract, green tea extract, oolong tea extract, horsetail extract, hop extract, rosemary extract and the like. The origin of each of these components is not particularly limited, and may be any of animal origin, microorganism origin, and synthetic products. Further, there is no particular limitation on the production method such as the extraction method and the purification treatment method.

(Disinfectant) Disinfectants include benzoic acid and its derivatives and salts thereof, benzalkonium chloride, isopropylmethylphenol, resorcinol, bis (2-pyridylthio-1-oxide) zinc, sulfur, kudin extract, Ginger extract, tea tree extract, eucalyptus extract, and dokudami extract are exemplified.

Among these fungicides, particularly preferred are benzoic acid and its derivatives and salts thereof, benzalkonium chloride, isopropylmethylphenol, resorcinol, bis (2-pyridylthio-1-oxide) zinc, sulfur, Examples include a kujin extract, a ginger extract, a tea tree extract, a eucalyptus extract and a dokudami extract.

In the composition of the present invention, the component (B) can be used alone or in combination of two or more. The amount of the component (B) is not particularly limited. 0.0001 to 10%, more preferably 0.01 to 5%. Within this range, the effects of the present invention are remarkably exhibited. In the case of a bactericide, preferably 0.001 to 3%, more preferably 0.01 to
1%. Within this range, the effects of the present invention are remarkably exhibited.

The composition of the present invention can be prepared by blending the essential components (A) and (B) with various types of bases known as ordinary external preparations according to a conventional method. .

The form of the external preparation is not particularly limited.
For example, skin care cosmetics such as milky lotions, creams, lotions, packs, cleaning agents, makeup cosmetics such as lipsticks and foundations, cosmetics for the scalp and hair, and pharmaceuticals such as ointments, dispersions, creams, and external solutions And so on.

In the composition of the present invention, in addition to the above-mentioned essential components, components to be blended with ordinary external preparations, for example, oils, powders, surfactants, purified water, lower alcohols, polymer compounds, gels An agent, an ultraviolet absorber, an ultraviolet scattering agent, an antioxidant, a dye, a preservative, a fragrance, a cosmetic ingredient, and the like can be appropriately selected and used within a range not to impair the effects of the present invention.

[0018]

EXAMPLES Next, the present invention will be described in more detail with reference to Reference Examples, Test Examples and Examples, but the present invention is not limited thereto.

Reference Example 1 Production of a water-containing methanol extract Preliminarily sterilized quartz sand was spread on a 300 cm ² stainless steel vat, and 10 g of Chinese sesame seeds were sprinkled thereon. And germinated for 2 days in a constant temperature bath. The germination rate was 89% or more. A certain amount of germinated material having a similar germination state was ground with a blender together with 100 ml of hydrated methanol (80% (v / v)). The residue was filtered, and the filtrate was concentrated to dryness to obtain a methanol extract. Then, the extract was washed by extraction with n-hexane to remove fat-soluble substances, thereby obtaining a water-containing methanol extract. The aqueous methanol extract was redissolved in 100 ml of aqueous methanol (80% (v / v)) and subjected to high performance liquid chromatography (HPLC) to analyze the composition.

The HPLC conditions were as follows: A pump (CCPM, manufactured by Tosoh Corporation) was connected to a column (Soken Pak ODS-W5).
μ, 10 mmΦ × 250 mm), UV absorption detector (U
V-8000, manufactured by Tosoh Corporation), elution was performed using a linear gradient of water: methanol starting at 90:10 (v: v) and 60:60 minutes later at 10:90 (v: v). The flow rate was 1 ml / min, and the detection wavelength was 280 nm.

As a result of HPLC analysis, the composition and content of the lignan glycoside in the aqueous methanol extract were determined using sesamin as an external standard, and sesaminol triglycoside (structural formula (II-a)), sesaminol diglycoside (Structural Formula (II-b)) and Sesaminol monoglycoside (Structural Formula (II-c)), which are present in the aqueous methanol extract in an amount of 80 mg and have a composition of 40 mg of sesaminol triglycoside. %, Sesaminol diglycoside 50%, sesaminol monoglycoside 10%
Met.

The chemical structure of each lignan glycoside component was confirmed by the following method using each purified product purified to a single component by preparative HPLC under the same conditions as described above. That is, 1N hydrochloric acid was added to each purified product, hydrolyzed at 100 ° C. for 30 minutes, extracted with ethyl acetate, and separated into an ethyl acetate layer and an aqueous layer. The ethyl acetate layer was concentrated to dryness at 40 ° C. or lower, subjected to trimethylsilylation treatment with TMS-PZ (manufactured by Tokyo Chemical Industry Co., Ltd.), and subjected to gas chromatography (GLC) to quantitatively analyze lignan (external standard: sesamin).

The GLC conditions are as follows. GLC apparatus: Hewlett-Packard 5890, column: D
B-17HT (15mx0.319mm, film t
kickness: 0.15 μm, J & W SCIEN
TIFIC), injection method: split method (split ratio 1/10), column temperature: 270 ° C., carrier gas:
helium.

Further, the aqueous layer was subjected to a pretreatment filter for HPLC (pore size: 0.2 μm, Meishoridisk W-13).
2, Tosoh Corporation), add 5 ml of acetone to the filtrate, concentrate under reduced pressure to dryness, and then TMS-PZ (same as above)
And subjected to GLC for quantitative analysis of sugars (external standard: glucose, galactose,
Fructose).

The GLC conditions are as follows: Column: DB-170
1 (15m x 0.25mm, film thickne
ss: 1.0 μm, manufactured by J & W SCIENTIFIC) Injection method: split method (split ratio 1/5)
0), except that the column temperature was set to 180 ° C.

Reference Example 2 Production of Crude Lignan Glycoside The aqueous methanol extract obtained in the same manner as in Reference Example 1 was dispersed in 100 ml of water, and the same volume of n-hexane was added, followed by vigorous shaking. This extraction operation was repeated three times to remove fat-soluble substances. To the residual solution from which the n-hexane layer was completely removed, the same volume of n-butanol which had been saturated with water in advance was added, and the mixture was vigorously shaken. This extraction operation was repeated twice to remove water-soluble substances. After washing the n-butanol layer twice with the same volume of water,
It was concentrated to dryness under reduced pressure to obtain a crude lignan glycoside.

According to HPLC analysis by the method described in Reference Example 1, the lignan glycoside in the crude lignan glycoside contains sesaminol triglycoside, sesaminol diglycoside and sesaminol monoglycoside, which are crude lignan glycosides. 80 mg was present in the glycoside, and the composition was 40% sesaminol triglycoside, 50% sesaminol diglycoside, and 10% sesaminol monoglycoside.

Reference Example 3 Production of Purified Product of High Purity Lignan Glycoside The crude lignan glycoside obtained by the method described in Reference Example 2 was
The resultant was subjected to partition chromatography using ODS as a carrier.
YMC-GEL ODS-A (Yamamura Chemical Co., Ltd.) 60
g was packed in a glass column having a diameter of 3 cm and a length of 50 cm, and equilibrated by flowing water. To this, 1 g of the crude lignan glycoside was loaded on the top of the column. The fraction components were eluted by a step elution method in which the methanol concentration was sequentially increased from water. Fractions eluted with 30-60% (v / v) methanol were collected and concentrated under reduced pressure to obtain about 100 mg of a column fraction.

This was repeatedly subjected to preparative HPLC, and purification was performed until each lignan glycoside component became single.
As a result, 5 to 10 mg of each purified lignan glycoside of sesaminol triglycoside, sesaminol diglycoside and sesaminol monoglycoside was obtained. The content of all these lignan glycoside components was 2.0% (wt / wt) per dried germination product and 4.5% (wt / wt) per hydrated methanol extract.

REFERENCE EXAMPLE 4 Production of Hamamelis Extract A leaf and bark of Hamamelis (10 g) were minced, and the water content was 50%.
100 ml of ethanol (% / v / v) was added, extracted for 3 days with occasional stirring, and filtered to obtain a Hamamelis extract.

Reference Example 5 Production of Kudjin Extract 100 ml of 50% (v / v) water-containing ethanol was added to 10 g of crude powder of Kudjin Pharmaceutical Co., Ltd.
Extracted for days and filtered to get kujin extract

Reference Example 6 Production of Melissa Extract Melissa leaves (10 g) were minced, and the water content was 50% (v / v).
v) 100 ml of ethanol was added, and the mixture was extracted with stirring at 40 ° C. for 24 hours, followed by filtration to obtain a Melissa extract.

Reference Example 7 Production of Dokudami Extract 10 g of the above-ground portion of Dokudami was cut into small pieces, and the water content was 50% (v
/ V) 100 ml of 1,3-butylene glycol was added,
Extraction was carried out at room temperature for 5 days with occasional stirring, followed by filtration to obtain a Dokudami extract.

Reference Example 8 Production of Tea Tree Extract Tea tree leaves were subjected to steam distillation to obtain a tea tree extract.

Example 1 Cream A cream was prepared by the composition shown in Table 1 and by the following method, and its antibacterial effect on microorganisms resident on the skin was examined. The results are also shown in Table 1.

[0036]

[Table 1] * 1: Manufactured in Reference Example 2 * 2: Manufactured in Reference Example 4 * 3: Manufactured in Reference Example 5

(Production method) A. Components (1) to (7) are mixed and heated to 70 ° C. B. Mix components (11) to (13) and heat to 70 ° C
To keep. C. Add B to A, mix and cool. D. (8) to (10) and (12) were added to C to obtain a cream.

(Test Method) 27 per test cream
A panel of 15 women aged ~ 54 years, apply an appropriate amount of cream to fingers. After allowing to stand for 30 minutes, the cream is wiped off with gauze previously sterilized, and the fingertip is pressed against a gravy plate agar medium that has been prepared aseptically in advance. This medium was cultured at 37 ° C. for 24 hours, and the antibacterial effect on microorganisms resident on the skin was evaluated according to the following criteria.

(Evaluation Criteria) <Evaluation> <Contents> Effective Little growth of microorganisms is observed. Slightly effective growth of microorganisms is observed. Ineffective Many microorganisms are growing.

As shown in the results in Table 1, the products 1 and 2 of the present invention, when applied to the skin, suppress the growth of microorganisms resident on the skin and have excellent antibacterial and antibacterial activities. It became clear.

Example 2 Emulsion: An emulsion was prepared according to the composition shown in Table 2 and by the following method, and its acne-preventing effect was examined.
The results are also shown in Table 2.

[0042]

[Table 2] * 1: Manufactured in Reference Example 1 * 2: Osaka Chemical Co., Ltd. * 3: Kanto Chemical Co., Ltd.

(Production method) Heat and mix components (6), (7), (10) and (14) and keep at 70 ° C. B. Components (1) to (5), (8), (9) and (11)
Is heated and mixed and kept at 70 ° C. C. Add the above B to the above A, mix, add the component (13), emulsify uniformly, cool to 30 ° C. and mix the component (12)
And mix uniformly to obtain an emulsion.

(Test method) 18 to 2 per test emulsion
A panel of 15 2-year-old women, twice daily, morning and night,
After washing the face for 12 weeks, an appropriate amount of the test emulsion was applied to the face. The acne prevention effect of the application was evaluated according to the following criteria.

[Evaluation] [Content] Effective Acne is hardly observed. Slightly effective Acne formation is rarely observed. Ineffective No change from before use.

As shown in the results in Table 2, the products 3 and 4 of the present invention
It was found that applying these to the skin prevented the formation of acne.

Example 3 Shampoo: Shampoos were prepared according to the compositions shown in Table 3 and by the following method, and their dandruff-preventing effects were examined. The results are also shown in Table 3.

[0048]

[Table 3] * 1: Manufactured in Reference Example 3 * 2: Manufactured by Sigma * 3: Manufactured in Reference Example 6

(Production method) The components (1) to (5) and (13) are mixed by heating and uniformly dissolved. B. A is cooled, and components (6) to (12) are added and uniformly mixed to obtain a shampoo.

(Test method) 2 per test shampoo
A panel of 15 women aged 5 to 54 years old.
The hair was washed with the test shampoo for a week. The anti-dandruff effect of washing the hair was evaluated according to the following criteria.

[Evaluation] [Content] Effective Almost no dandruff is observed. Slightly effective There is little occurrence of dandruff. Ineffective No change from before use.

As shown in Table 3, the products of the present invention 5 and 6
It was clarified that dandruff was prevented by washing hair with them.

Example 4 Lotion: (Formulation) (%) (1) Glycerin 2.0 (2) 1,3-butylene glycol 3.0 (3) Polyoxyethylene (20EO) Sorbitan 0.5 Monolaurate (4) Ethyl alcohol 8.0 (5) Crude lignan glycoside * 1 10.0 (6) Resorcinol * 2 0.001 (7) Preservative proper amount (8) Flavor proper amount (9) Purified water residue Amount * 1 Manufactured in Reference Example 2 * 2 Kokusan Chemical

(Production method) Components (3), (4), (6), (7) and (8) are mixed and dissolved. B. Components (1), (2), (5) and (9) are mixed and dissolved. C. A and B were mixed and made uniform to obtain a lotion.

The lotion of Example 4 was excellent in bactericidal effect, and effectively suppressed comed formation when applied to the skin.

Example 5 Ointment: (Formulation) (%) (1) Stearic acid 18.0 (2) Cetanol 4.0 (3) Triethanolamine 1.0 (4) Glycerin 5.0 (5) High purity Lignan glycoside purified product * 1 1.0 (6) Dokudami extract * 2 3.0 (7) Remaining purified water * 1 Produced in Reference Example 3 * 2 Produced in Reference Example 7

(Production method) A. A part of components (3) to (5) and (7) are mixed by heating and kept at 75 ° C. B. Heat mix components (1) and (2) and maintain at 75 ° C. C. Add A slowly to B. D. While cooling C, (6) dissolved in the remainder of (7) was added to obtain an ointment.

The ointment of Example 5 was effective in suppressing acne formation when applied to the skin.

Example 6 Pack: (Formulation) (%) (1) Polyvinyl alcohol 20.0 (2) Ethyl alcohol 20.0 (3) Glycerin 5.0 (4) Kaolin 6.0 (5) Crude lignan distribution Saccharide * 1 0.05 (6) Benzalkonium chloride * 2 0.05 (7) Preservative appropriate amount (8) Flavor appropriate amount (9) Purified water balance * 1 Manufactured in Reference Example 2 * 2 Sigma Made

(Production method) A. Mixing components (1), (3), (4) and (9),
Heat to 70 ° C. and stir. B. Mix components (2), (7) and (8). C. The above B was added to the above A, mixed, cooled, and (5) and (6) were uniformly dispersed to obtain a pack.

The pack of Example 6 had an excellent acne-preventing effect when applied to the skin.

Example 7 Detergent: (Formulation) (%) (1) Stearic acid 10.0 (2) Palmitic acid 8.0 (3) Myristic acid 12.0 (4) Lauric acid 4.0 (5) Oleyl alcohol 1.5 (6) Purified lanolin 1.0 (7) Perfume proper amount (8) Preservative proper amount (9) Glycerin 18.0 (10) Potassium hydroxide 6.0 (11) Hydrous methanol extract * 15 2.0 (12) Sodium benzoate * 2 1.0 (13) Remaining purified water * 1 Manufactured in Reference Example 1 * 2 Manufactured by Kanto Chemical Co.

(Production Method) Mix components (9), (10) and (13) and mix
Heat to ° C. B. Ingredients (1) to (6), (8) and (12), 70
Heat to ° C. C. The above B was added to the above A, kept at 70 ° C. for a while, cooled to 50 ° C. after the reaction was completed, and the components (7) and (1)
1) was added and cooled to obtain a washing agent.

The cleaning agent of Example 7 had an excellent bactericidal effect, and was effective in suppressing acne formation by washing the face.

Example 8 Hair tonic: A hair tonic was prepared by the following formulation and the following method. (Prescription) (%) (1) Crude lignan glycoside * 1 5.0 (2) Tea tree extract * 2 0.1 (3) Menthol 0.1 (4) Ethanol 40.0 (5) Perfume (6) Remaining purified water * 1 manufactured in Reference Example 2 * 2 manufactured in Reference Example 8

A. Components (3) to (5) are mixed and dissolved. B. Components (1), (2) and (6) are mixed and dissolved. C. A was added to B and mixed uniformly to obtain a hair tonic.

The hair tonic of Example 8 had an excellent antidandruff effect when applied to the scalp.

[0068]

According to the present invention, since the composition of the present invention containing a bactericide is stable and has an excellent antibacterial and bacteriostatic action, it has a more excellent external acne-preventing effect. When used for hair, it has an excellent dandruff preventing effect. As described above, the composition of the present invention can sufficiently exhibit the intrinsic performance of a medicinal agent, and is extremely useful in beauty and medicine.

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[Procedure amendment]

[Submission date] February 6, 1998

[Procedure amendment 1]

[Document name to be amended] Statement

[Correction target item name] 0036

[Correction method] Change

[Correction contents]

[0036]

[Table 1] * 1: Manufactured in Reference Example 2 * 2: Manufactured in Reference Example 4 * 3: Manufactured in Reference Example 5

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI A61K 7/075 A61K 7/075 7/50 7/50 35/78 35/78 X ADB ADBQ ADN ADNJ (72) Inventor Masami Senoo (26) Inventor Kumi Kameyama 4-11-9-512, Kamiikebukuro, Toshima-ku, Tokyo

Claims (6)

[Claims] 1. A composition comprising the following components (A) and (B): (A) a lignan glycoside (B) a medicinal agent selected from sebum secretion regulators and / or fungicides. 2. A lignan glycoside having the following structural formula (I):
The composition according to claim 1, which is a sesaminol glycoside represented by the formula: Embedded image 3. A lignan glycoside having the following structural formula (II)
The composition according to claim 1 or 2, which is a lignan glycoside containing one or more of sesaminol glycosides represented by -a), (II-b) or (II-c) as a main component. . Embedded image Embedded image Embedded image 4. The lignan glycoside is a hydrated lower alcohol extract of sesame seeds, humidified or germinated bodies thereof, crushed products thereof, or defatted products thereof.
4. The composition according to 2 or 3. 5. The sebum secretion regulator is pyridoxine or a derivative thereof, a salt thereof, biotin, zinc oxide, aluminum chloride, sodium chloride, aluminum hydroxychloride, citric acid or a salt thereof, seawater dried product, aloe extract, ebuki 1 selected from Tranoh extract, oak extract, watercress extract, Melissa extract, Hamamelis extract, black tea extract, green tea extract, oolong tea extract, horsetail extract, hop extract, rosemary extract
5. The composition according to claim 1, 2, 3 or 4, which is a species or two or more species. 6. The bactericide is benzoic acid or a derivative thereof or a salt thereof, benzalkonium chloride, isopropylmethylphenol, resorcinol, bis (2-pyridylthio-1-).
Oxide) The composition according to claim 1, 2, 3 or 4, wherein the composition is at least one selected from zinc, sulfur, ginger extract, kudin extract, tea tree extract, eucalyptus extract and dokudami extract. .