JP2001072552A - Hair growth composition - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a hair growth composition having prophylactic effects on alopecia and hair growth effects by including a stilbene-based compound abundantly contained in a plant of the family Polygonaceae or Vitaceae or Veratrum album as an essential ingredient. SOLUTION: This hair growth composition is obtained by including one or more kinds selected from a stilbene-based compound represented by the formula (A and B are each a halogen, amino or the like; n and m are each an integer of 0-5), its polymer and plant extracts containing the same. For example, the compound represented by the formula is resveratrol, polydatin or α-viniferin and can be synthesized by the Wittig reaction of the corresponding phosphonium salt with the corresponding aldehyde. A dried material, an extract, etc., prepared by carrying out a treatment such as drying, extraction or purification from a suitable site of a rhizome, a fruit, etc., of the plant containing the compound represented by the formula (e.g. Polygonum multiflorum which is a plant of the family Polygonaceae, Vistis vinifra species of the family Vitaceae or Veratrum album) may be used. The stilbene-based compound is preferably contained in an amount of 0.0001-5 wt.% in the composition.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a hair growth composition containing a stilbene compound useful for a hair growth effect and a hair loss prevention effect.

[0002]

2. Description of the Related Art Various hair restorative compositions have been proposed and used for the purpose of suppressing hair loss and promoting hair growth. For example, application of compounds having blood circulation promoting action such as assembly extract, capsaicin and benzyl nicotinate, vitamin E acetate, minoxidil, application of vitamins such as pantothenic acid and biotin, application of keratin and amino acid which are constituents of hair, Application of a compound having an androgen-suppressing effect can be mentioned.

However, in the case of a compound having a blood circulation promoting action, a satisfactory hair growth effect cannot be obtained because the amount of the compound is limited due to skin irritation or the blood circulation promoting effect is temporary. In addition, when keratin, amino acid, or vitamin, which is a constituent component of hair, is applied, it is difficult to penetrate into the hair root, and a hair growth effect cannot be obtained, and even when penetrated, the effect is weak. In the case of a compound having an androgen-suppressing effect, there is a risk of exerting an undesired effect on other than the hair root.

[0004]

Means for Solving the Problems The present inventors have conducted intensive studies on physiologically active substances contained in plant components, and as a result, have found that stilbene-based compounds, which are often contained in Polygonaceae plants, grape plants, and diatomaceous plants, are widely used. The present inventors have found that a hair loss preventing effect and a hair growth effect exist, and have completed the present invention. That is, the present invention provides a hair growth composition comprising a stilbene compound as an essential component.

The present invention provides an invention based on the following items. Item 1 (a) General formula (1):

[0006]

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Wherein A and B are the same or different and each is a halogen atom, an amino group, an amidino group, an anilinoamide group,
Mercapto group, sulfonic acid group, phosphoric acid group, hydroxy C
1-5 alkyl group, a sugar residue or -OR ₁ (. R ₁ is a hydrogen atom, C ₁ -C ₅ alkyl group, a hydroxy C ₁ -C ₅ alkyl or C ₂ -C ₅ alkenyl group) or - O
COR ₂ (R ₂ represents a hydrogen atom, a C ₁ -C ₅ alkyl group, a hydroxy C ₁ -C ₅ alkyl group or a C ₂ -C ₅ alkenyl group). n and m are the same or different and are 0
Represents an integer of from 5 to 5. A hair growth composition comprising one or more selected from the group consisting of a stilbene compound represented by the formula [I], a multimer thereof, and a plant extract containing the same.

Item 2 The compound represented by the general formula (1) is
At least 3, 5, and 4 'position are the same or different and a hydroxyl group, a sugar residue or -OCOR ₂ [R ₂ are as defined above. ] The hair-growth composition characterized by being the compound substituted by these.

Item 3 The compound represented by the general formula (1) is
A hair-growing composition characterized by being derived from one or more plants selected from the group consisting of Polygonaceae, grape, and diatomaceous.

[0010]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Stilbene used in the present invention (stilbene)
The bene) -based compound has the general formula (1):

[0011]

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Wherein A and B are the same or different and are each a halogen atom, an amino group, an amidino group, an anilinoamide group,
Mercapto group, sulfonic acid group, phosphoric acid group, hydroxy C
1-5 alkyl group, a sugar residue or -OR ₁ (. R ₁ is a hydrogen atom, C ₁ -C ₅ alkyl group, a hydroxy C ₁ -C ₅ alkyl or C ₂ -C ₅ alkenyl group) or - O
COR ₂ (R ₂ represents a hydrogen atom, a C ₁ -C ₅ alkyl group, a hydroxy C ₁ -C ₅ alkyl group or a C ₂ -C ₅ alkenyl group). n and m are the same or different and are 0
Represents an integer of from 5 to 5. ] And a multimer thereof, and a plant extract containing the same.

Each group in the general formula (1) is specifically as shown below.
Examples include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. Examples of the alkyl group having 1 to 5 carbon atoms include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, and n-pentyl. And a branched alkyl group.
Examples of the hydroxyalkyl group having 1 to 5 carbon atoms include linear or branched such as hydroxymethyl group, hydroxyethyl group, hydroxy n-propyl group, hydroxyisopropyl group, hydroxy n-butyl group, and hydroxy n-pentyl group. And hydroxyalkyl groups. 2 carbon atoms
Examples of the alkenyl group of 5 include linear or branched such as a vinyl group, an isopropenyl group, an allyl group, a 2-butenyl group, a 3-butenyl group, a 1-methylallyl group, a 2-pentenyl group, and a 3-pentenyl group. An alkenyl group is mentioned.
Examples of the sugar residue include monosaccharides such as pentose and hexose and derivatives thereof (eg, deoxy sugar, amino sugar, uronic acid, sugar alcohol, etc.), disaccharides, trisaccharides and the like.

The sugar residue in the formula is a group in which the hydrogen atom of the hydroxyl group bonded to the glycoside carbon atom at the reducing end of the sugar is removed, and examples of pentose include D-arabinose, L-arabinose, and D-arabinose. Xylose, L-xylose, D-ribose, D-ribulose and the like. Examples of hexose include D-galactose, L-galactose, D-glucose, D-fructose, D-mannose, D-talose, L-sorbose, D-tagalose and the like. Examples of deoxysugars include the deoxysugars of the monosaccharides described above, for example, D-2-deoxyribose, L-rhamnose, L-fucose, and the like.

Examples of amino sugars include the amino sugars of the monosaccharides described above, for example, N-acetylglucosamine, N-acetylgalactosamine, N-acetylneuraminic acid and the like. Examples of uronic acids include glucuronic acid, mannuronic acid, galacturonic acid, iduronic acid and the like. Examples of sugar alcohols include D-glucitol, D-mannitol, ribitol, galactitol and the like. Examples of disaccharides include disaccharides obtained by appropriately combining the monosaccharides described above. For example, it is represented by sucrose, lactose, trehalose, maltose, soloobiose, xylobiose, melibiose, rutinose, vicianose, trehalosamine, chondrosin and the like. Examples of trisaccharides include trisaccharides obtained by appropriately combining the monosaccharides described above. For example, it is represented by raffinose, maltotriose, cellotriose, manninotriose and the like.

In the general formula (1), n and m each represent an integer of 0 to 5, but may be the same or different.
The composition of the present invention may contain a multimer such as a dimer or trimer of the compound represented by the general formula (1). As a dimer, α-viniferin (α-Viniferin; a dimer of Resveratrol); as a trimer, a ε-viniferin (ε-Viniferin; a trimer of resveratrol) ); As tetramers, Hopephenol (Hopeaphenol; Resveratrol (Resvera
trol) tetramer).

Preferred stilbene compounds represented by the general formula (1) and their multimers are shown below.

(1) Compound wherein n and m are both 0
[That is, stilbene (2) a stilbene compound in which n and m are the same or different and are integers of 0 to 5, and all substituents are hydroxyl groups (however, n and m are not simultaneously 0). As a specific example, 4,4′-stilbenediol (4,4-stilbenedio
l), 3,5-stilbenediol,
Resveratrol [that is, 3,5,4'-stilbenetriol (3,5,4'-stilbenetriol)] and the like. (3) A stilbene compound in which n and m are the same or different and are each an integer of 0 to 5, and one of the substituents is a sugar residue (however, n and m are not simultaneously 0).
As a specific example, Rhaponticin (ie,
4'-methoxy-3,3 ', 5-stilbenetriol-3-glucoside)], polydatin (ie, pie seed
d) or 3,5,4'-stilbenetriol-5-glucoside (3,5,4'-stilbenetriol-5-glucoside)], 3,4'5-stilbenetriol-4'-glucoside (3,4 '5-stilbenetr
iol-4'-glucoside), 2,3,5,4'-stilbenetetraol-2-glucoside (2,3,5,4'-stilbenetetraol-2-glucos)
ide).

(4) n and m are the same or different and 0
A stilbene compound having a substituent at least at the 3-, 5-, and 4'-positions (provided that the sum of n and m is 3 or more). Specific examples include resveratrol, rapontisine, polydatin, 3,4'5-stilbenetriol-4'-glucoside, 2,3,5,4'-stilbenetetraol-2-glucoside, and the like. (5) A stilbene compound in which n and m are the same or different and are each an integer of 1 to 5, and a substituent is present at least at the 4- and 4-positions. As a specific example, stilbamidine (St
ilbamidine) [ie, 4,4'-diamidinostilbene (4,4 '
-diamidinostilbene)], 4,4'-diaminostilbene (4,
4'-diaminostilbene), 4,4'-stilbenediol (4,
4'-stilbenediol) and the like. (6) A stilbene compound in which n and m are the same or different and are each an integer of 0 to 5, and one of the substituents is a sulfonic acid group or a carboxy group (n and m are not simultaneously 0). Specific examples include 4,4′-diamino-2,2′-stilbene disulfonic acid (4,4′-diamino-2,
2'-stilbenedisulfonic acid), 2-carboxy-3, 4'-stilbenediol (2-carboxy-3, 4'-stilbenediol) and the like.

(7) n and m are the same or different and 0
A stilbene compound in which one of the substituents is an alkoxy group (n and m are not simultaneously 0). Specific examples include 4-methoxystilbene, 2,5′-dimethoxy-4,4′-stilbenediol (2,5′-methoxy-4, 4′-stilbenediol)
And the like. (8) stilbene compound substituent is -OR _1. (9) Dimers of the compounds of (1) to (8). A specific example is α-viniferin which is a dimer of resveratrol.

Among the compounds shown above, (2)
The stilbene compounds of (3) and (4) are preferred, and among the compounds contained therein, the substituents at the 3-, 5- and 4'-positions are the same or different, and a hydroxyl group, -OSO
A stilbene compound which is R ₂ or a sugar residue is preferred, and resveratrol and polydatin are particularly preferred. As the multimer, α-vinyliferin and ε-vinyliferin are preferable.

The stilbene compound represented by the general formula (1) can be synthesized by a known method, for example, by a Wittig reaction of a corresponding phosphonium salt with a corresponding aldehyde.
(See E. Reimann "Tetrahedron Letters" 47, 4051 (1970)).

As the compound represented by the general formula (1), a dried product, an extract, or the like obtained by subjecting a plant containing the compound to a treatment such as drying, extraction, and purification may be used. good. In the present invention, the case where such a dried product, extract or the like also passes is referred to as “plant-derived”. As such a plant, for example, a plant that contains about 0.0001% by weight or more of the compound of the general formula (1) in a dried product can be used. Examples include plants and diatoms. The Polygonum tinc is not particularly limited as long as it contains a stilbene compound represented by the general formula (1).
torium ) Ibukinotranoo ( Polygonum bistorta ), Buckwheat ( Fagopyrum esculentum ), Rhubarb ( Rheum sp. )
p. ), Tsurukudami ( Polygonum multiflorum ), Knotweed ( Polygonum cuspidatum ) and the like. Among them, especially rhubarb ( Rheum spp. ), Turkudami ( Polygonum multiflorum ), knotweed ( Polygonum cus )
pidatum ) is preferred because of its high content of stilbene-based compounds, and more preferably turkudokumi ( Polygonum multiflorum ) and knotweed ( Polygonum cuspidatum ), which contain a large amount of resveratrol. The site to be used is not particularly limited, but a rhizome or a root is preferable.

The grape plant (Vitaceae) is not particularly limited as long as it contains a stilbene compound represented by the general formula (1). Species (Vitis spp.). Specifically, European and Middle Eastern varieties of Vistis vinifera ( V.vinifra ) and North American varieties of Vistis Labrusca ( V.labrusca ). Vistis California (VC
alifornia). Two varieties represented by V. Munsoniana, a North American mucadin species. Three varieties typified by the Asian varieties Vistis Amurensis (V. Amurensis) are listed. Among these, Vistini Vinifera species ( V.vini
fra), Bisutisu Vitis labrusca (V.labrusca) and varieties that have been developed in Japan is preferred. Specifically, Airen, Aligote, Riesling
ling), Sauvignon blanc,
Trebbiano, Chardonna
y), Cheninblanc, Semion (Sem)
illon), Muscat, Cabernet Sauvignon, Carignan, Cinsaut, Grenache Noir
Noir), Merlot, Mataro, Pinot Noir, Sangiovese
e), Syrah, Gamay, Tempranillo, Trebbian
o), Gewurtraminer, Zweigltrebe, Muller-Thurgau, Grolleau, Cabernet Franc, Petit Verdo
t), Koshu, Muscat Berry A, and Gluck Queen. Among them, Cabernet Sauvignon (Cabernet Sauvin) of Vistis Vinifera species ( V.vinifra )
ignon), Pinot Noir, Syra
h), Merlot, Grenache,
Carignan, Nebbiolo,
Sangiovese, Gamay, Bistis labrusca species, V. labrusca, Muscat berry A, and Gluck queen are preferable because they contain a large amount of stilbene compounds. The site to be used is not particularly limited, but leaves or fruits (including pericarp and seeds)
Is preferred. In the case of fruits, immature ones are preferable because they contain more stilbene compounds.

The diatomaceous plant ( Veratrum album ) is a plant of the lily family, and the site to be used is not particularly limited, but a rhizome is preferable. For mulberry, fruit is preferred.

Plants containing the above-mentioned stilbene compounds may be used as they are after natural drying, hot-air drying, freeze-drying or fermentation, or may be concentrated, extracted, powdered, etc. according to a conventional method. The product obtained by performing the above process is used. Examples of such a method include a method described in JP-A-61-171427.

The amount of the stilbene compound of the general formula (1) in the composition of the present invention is not particularly limited as long as the desired effects of the present invention can be obtained. It can be set appropriately according to the requirements.
0001-5% by weight, further 0.001-1% by weight,
Particularly, 0.005 to 1% by weight is preferable. These ranges are preferable from the viewpoint of solubility, palatability and the like.

The hair growth composition of the present invention includes purified water, lower alcohols such as ethanol, polyhydric alcohols such as propylene glycol, oils and fats such as vegetable oil and animal oil,
Esters made by condensing fatty acids and alcohols, surfactants such as anionic surfactants, cationic surfactants, nonionic surfactants, amphoteric surfactants, l-menthol, menthyl malonate, l-menthyl Lactate,
Cooling agents such as camphor, warming agents such as vanillyl alcohol butyl ester, blood circulation promoters such as capronium chloride and benzyl nicotinate, extract of extract, vitamin E acetate, capsaicin, and thickeners such as cellulose derivatives and polysaccharide derivatives Keratolytic agents such as salicylic acid and urea, antidandruff agents such as zinc pyrithione, pyroctone olamine, sulfur, trichlorocarbanilide, and triclosan; antihistamine agents such as diphenhydramine hydrochloride and isotipendyl hydrochloride; amino acids; chitin derivatives and chitosan derivatives; Hair setting agents such as polymer resins, natural polymer resins, cellulose derivatives, polysaccharide derivatives, moisturizing agents such as hyaluronic acid, urea, glycerin, sodium pyrrolidonecarboxylate, oxendrone and spironolactone,
Anti-androgens such as diproterone acetate; antioxidants such as ascorbic acid and vitamin E; dibutylhydroxytoluene; anti-inflammatory agents such as dipotassium glycyrrhetinate, allantoin and guaiazulene; preservatives such as sodium benzoate and paraoxybenzoate , UV absorbers such as oxybenzone and cinnamate,
Chelating agents such as EDTA, hydrokiethane-1, 1-diphosphonic acid and phytic acid, dyes, fragrances and the like can be blended within a range that does not impair the effects of the present invention.

The hair restoring composition of the present invention can be prepared by a conventional method, for example, a hair restorer, hair tonic, scalp lotion,
It can be manufactured and used in the form of hair cream, shampoo, scalp cleansing, rinse, treatment, hair gel, mist, hair foam, hair spray, ointment and the like.

[0030]

EXAMPLES Hereinafter, the present invention will be described in more detail based on examples and comparative examples, but the present invention is not limited to these examples. [%] Means [% by weight] unless otherwise specified.

Experimental Example 1: Mouse back hair regenerating effect Male C3H / HeN Crj mice (49 days old) were preliminarily reared for one week and used for other experiments. Breeding was allowed to freely ingest commercially available solid feed (NMS: manufactured by Oriental Yeast Co., Ltd.) and tap water. The back of a group of 10 animals was completely shaved using an electric clipper and an electric shaver so as not to damage the skin. From the next day, 0.001% and 0.01%,
0.1% trans-Resveratrol water / ethanol solution or 0.1 ml water / ethanol solution as a control,
It was applied to the hair removal site twice a day. For the measurement of hair regeneration, a photograph of the hair removal site was taken, and then the area of the hair removal site and the hair regeneration site were measured with a planimeter, and then the regeneration rate was calculated. The obtained data was expressed as mean ± standard deviation and standard error, and a significance test was performed. As a result of the experiment, any test group showed a significant effect of promoting hair regeneration as compared with the control, and the effect was particularly remarkable at 0.01% or more. In addition, comparing the number of days until the hair in the depilated portion was completely grown, it was confirmed that the effect was almost dose-dependent in the range of 0.001% to 0.1%.

Example 1 Hair Tonic for Hair Growth A hair tonic for hair growth was prepared according to a conventional method by mixing the components according to the following formulation. Ingredients Amount (%) Ethyl alcohol 55.00 Vine leaf extract 10.00 (Stilbene compound content 0.5%) 1,3-butylene glycol 2.00 POE (12) POP (6) 1.00 Decyltetradecyl Ether Methyl parahydroxybenzoate 0.10 Pyroctone olamine 0.10 Fragrance 0.05 Purified water Remainder Total 100.00

Example 2: Hair restoration lotion Each component was mixed according to the following formulation to prepare a hair restoration lotion according to a conventional method. Ingredient Content (%) Grape fruit extract 30.00 (resveratrol content 0.05) Propylene glycol 5.00 Carbopol 940 (1% aqueous solution) 5.00 Squalene 4.00 Glycerin triisooctanoate 4.00 Water Sodium oxide (0.1% aqueous solution) 2.50 POE (20) Sorbitan monostearate 1.00 Glycerin monostearate 1.00 Stearic acid 0.50 Methyl parahydroxybenzoate 0.10 Butyl paraoxybenzoate 0.10 Purification Water balance Total 100.00

Example 3 Scalp Cleansing for Hair Growth Scalp cleansing for hair growth was prepared according to a conventional method by mixing the components according to the following formulation. Ingredients Amount (%) POE (3) lauryl 20.00 magnesium sulfosuccinate glycerin 5.00 coconut oil fatty acid diethanolamide 4.00 1-menthol 1.00 mixture of resveratrol and its glycoside 0.50 benzoic acid Sodium 0.50 Disodium EDTA 0.05 Pepper tincture (10% solution) 0.02 Purified water Remainder Total 100.00

[0035]

According to the present invention, a hair restoration composition having an excellent hair restoration effect by blending a stilbene compound represented by the general formula (1), a multimer thereof, and a plant extract containing them. Can be provided.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (reference) A61P 43/00 107 A61P 43/00 107 F term (reference) 4C083 AA111 AA112 AB032 AC012 AC031 AC102 AC122 AC211 AC242 AC312 AC341 AC422 AC442 AC471 AC482 AC532 AC551 AC641 AC642 AC771 AC791 AC792 AC811 AC842 AC891 AD052 AD092 AD391 AD392 AD532 CC37 DD23 DD38 EE22 FF05 4C088 AB43 AB50 AB56 AB85 AC11 AC13 BA08 CA03 MA07 MA63 ZA92

Claims (3)

[Claims] (A) General formula (1): Wherein A and B are the same or different and each is a halogen atom, an amino group, an amidino group, an anilinoamide group, a mercapto group, a sulfonic acid group, a phosphoric acid group, a hydroxy C1-5 alkyl group, a sugar residue or -OR ₁ ( R ₁ is a hydrogen atom, C _1-
C ₅ alkyl group, a hydroxy C ₁ -C ₅ alkyl or C ₂ -C ₅ alkenyl group. ) Or -OCOR
₂ (R ₂ is a hydrogen atom, a C ₁ -C ₅ alkyl group, a hydroxy C
Shows the ₁ -C ₅ alkyl or C ₂ -C ₅ alkenyl group. ). n and m are the same or different, and
Indicates an integer of 5. A hair growth composition comprising one or more selected from the group consisting of a stilbene compound represented by the formula [I], a multimer thereof, and a plant extract containing the same. 2. The compound represented by the general formula (1) is the same or different at least at the 3-, 5- and 4'-positions, and a hydroxyl group, a sugar residue or -OCOR ₂ [R ₂ is the same as described above. The composition according to claim 1, which is a compound substituted by the formula: 3. The compound represented by the general formula (1) is derived from one or more plants selected from the group consisting of a Polygonaceae plant, a grape plant, and a diatomaceous plant. 3. The composition according to any one of 2.