CN1311834C - Melanogenesis inhibitors and whitening agents comprising ergosterol derivatives and compositions containing ergosterol derivatives - Google Patents
Melanogenesis inhibitors and whitening agents comprising ergosterol derivatives and compositions containing ergosterol derivatives Download PDFInfo
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- CN1311834C CN1311834C CNB028273133A CN02827313A CN1311834C CN 1311834 C CN1311834 C CN 1311834C CN B028273133 A CNB028273133 A CN B028273133A CN 02827313 A CN02827313 A CN 02827313A CN 1311834 C CN1311834 C CN 1311834C
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- ergosterol
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/63—Steroids; Derivatives thereof
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- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
- A23L33/11—Plant sterols or derivatives thereof, e.g. phytosterols
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
Abstract
It is intended to provide substances which are efficacious in whitening the sunburned skin after UV-irradiation and preventing, relieving and treating pigmentation in the skin such as spots caused by sunburn or the like, freckles and liver spots, and compositions containing the same. The above object is achieved by using melanogenesis inhibitors and whitening agents comprising ergosterol derivatives; melanogenesis inhibitors and whitening agents containing the above ergosterol derivatives; melanogenesis inhibitory compositions and whitening compositions containing the above ergosterol derivatives; cosmetics, drugs, external skin preparations, melanogenesis inhibitory foods and whitening foods containing the above ergosterol derivatives; and the above-described compositions, cosmetics, drugs, external skin preparations, melanogenesis inhibitory foods and whitening foods containing the above ergosterol derivatives together with whitening component(s) other than the ergosterol derivatives. Thus, novel melanogenesis inhibitors and whitening agents as well as compositions having a melanogenesis inhibitory effect and a whitening effect such as cosmetics, drugs, external skin preparations and foods can be obtained.
Description
Technical field
The present invention relates to Melanin inhibitor and the whitening agent that forms by the ergosterol derivant and the compositions that contains the ergosterol derivant, particularly cosmetics, pharmaceuticals, skin preparations for extenal use, food.More specifically relating to the melanin that can suppress in the melanocyte generates, whiten tanning behind the ultraviolet radiation, prevention, improve and treatment because of Melanin inhibitor and the whitening agent and the compositions of the pigementation of skins such as the senile plaque that produces such as tanned, freckle, chloasma hepaticum, particularly cosmetics, pharmaceuticals, skin preparations for extenal use and food.
Background technology
The pigementation of skins such as the senile plaque that produces because of tanned grade, freckle, chloasma hepaticum occurs with advancing age, increases with advancing age or is difficult to disappear, and middle-aged and elderly people has been become one big worried.Though the mechanism of production of these pigementations is at present also indeterminate, but the melanin of being commonly considered as in the melanogenic granule that is called as melanosome in the melanocyte that sunray (particularly ultraviolet) tanning etc. causes being present in epidermis cell produces, and the melanin of generation is diffused in the adjacent cell again and produces.
Wish to develop and to make this pigementation revert to the material of the normal colour of skin, the commercialization of present most of materials.For example, known have L-ascorbic acid, kojic acid or a hydroquinone etc.
But the stability of L-ascorbic acid is not good, though kojic acid has some effects, effect a little less than.In addition,, have zest and anaphylaxis, have safety hidden danger, mix existing problems as medicament though hydroquinone also has certain effect.Therefore, also do not have the material appearance that effect was prevented and improved to sufficient pigementation at present.
Though chemical compound of the present invention is a compound known, but it is not known (for example that it has the effect and the skin-whitening effect that suppress the melanin generation, with reference to Koji Ohta, Yasunori Yaoita and Masao Kikuchi etc., Natural Medicines (Japan), 1996,50 volumes, p.336).
The present invention is the invention of In view of the foregoing finishing, its objective is provides the whitening of the tanning behind the ultraviolet radiation, because of the sedimentary preventions of skin pigment such as senile plaque, freckle and chloasma hepaticum, improvement and the treatment effective substances of generation such as tanned and contain the compositions of this material.
The announcement of invention
The present inventor conscientiously studies the back discovery in order to address the above problem, and the ergosterol derivant with ad hoc structure has stronger melanin and generates inhibitory action and whitening function, has found result of the above problems, thereby has finished the present invention.
That is, the present invention is by following formula (1)
Melanin inhibitor and whitening agent that the ergosterol derivant of expression forms.
In addition, the present invention is Melanin inhibitor, the whitening agent that contains the ergosterol derivant of aforementioned formula (1) expression.
In addition, the present invention is that the melanin generation that contains the ergosterol derivant of aforementioned formula (1) expression suppresses with compositions, whitens and use compositions.
In addition, the present invention is the cosmetics that contain the ergosterol derivant of aforementioned formula (1) expression, and these cosmetics can be used for suppressing melanic generation and whiten.
In addition, the present invention is the pharmaceuticals that contain the ergosterol derivant of aforementioned formula (1) expression, and these pharmaceuticals can be used for suppressing melanic generation and whiten.
In addition, the present invention is the skin preparations for extenal use that contains the ergosterol derivant of aforementioned formula (1) expression, and this skin preparations for extenal use can be used for suppressing melanic generation and whitens.
In addition, the present invention suppresses with food for the melanin of the ergosterol derivant that contains aforementioned formula (1) expression generates and whitens and use food.
In addition, the melanin that contains the ergosterol derivant of aforementioned formula (1) expression of the present invention generate suppress with compositions, whiten with compositions, melanin generate suppress with and whiten cosmetics, melanin such as use to generate to suppress with and whiten pharmaceuticals, melanin such as use to generate to suppress with and whiten and skin preparations for extenal use, melanin such as use to generate to suppress, whiten with also containing the ergosterol derivant whitening agent composition in addition that aforementioned formula (1) is represented in the compositionss such as food with food.Also using of ergosterol derivant by this whitening agent composition and aforementioned formula (1) expression cooperates, and can further improve the melanin generation and suppress effect and whitening effect.
The best mode that carries out an invention
Below, embodiments of the present invention are elaborated.
Used following formula (1) among the present invention
The ergosterol derivant (being designated hereinafter simply as the ergosterol derivant) of expression is a known substances, for example can separate from mushroom.The generation of ergosterol derivant can be used all mushrooms that contain the ergosterol derivant, is preferably and for example uses Folium Isatidis pleat umbrella (chlorophyllum molybdites).In addition, also can modulate by chemosynthesis.Isolating the ergosterol derivant from the mushroom that contains the ergosterol derivant can carry out according to following steps.Promptly, after being preferably in a sporophore or parts such as mycelia, spore of pulverizing mushroom, immerse it in extractant or reflux in extractant, filter then, remove insoluble matter by centrifugalize etc., according to circumstances the gained extraction solution is concentrated again, adopt known separation and purification means to separate then.
The solvent that is used to extract can adopt the solvent of the extraction that is generally used for mushroom, plant etc., for example, can be used alone or in combination alcohols such as methanol, ethanol, organic solvent and water such as acetoneand ethyl acetate.Extracting process can adopt conventional method, and general extraction temperature is 0～100 ℃, is preferably 40～70 ℃, and the extraction time is 1～168 hour, is preferably 24～72 hours.For example can be undertaken from the separation of extraction solution by reverse-phase chromatography, gel filtration chromatography, liquid chromatography isochrome spectrometry.
Below, illustrate the object lesson of the generation of ergosterol derivant.
[refining example (from the separation of mushroom)]
After the sporophore of Folium Isatidis pleat umbrella of cultivation pulverized, it is immersed in methanol, in 40 ℃ of extractions of carrying out 72 hours.Then, by removing by filter insoluble matter, after the gained extraction solution concentrates, refining by reverse-phase chromatography.The structure of refining thing can be determined by mass spectral analysis gas chromatography and NMR.This chemical compound be aforementioned formula (1) expression (22E, 24R)-5a, 8a-epidioxy Ergota-6,9, the 22-triolefin, it is the derivant of ergosterol.
Aforementioned ergosterol derivant of the present invention has melanin described later and generates inhibitory action and whitening function.Therefore, can use as Melanin inhibitor and whitening agent.Also can be applicable to contain the Melanin inhibitor and the whitening agent of ergosterol derivant.The melanin that these Melanin inhibitors and whitening agent can suppress in the melanocyte generates, the tanned skin behind the ultraviolet radiation of whitening, prevention, improve and treatment because of the pigementation of skins such as the senile plaque that produces such as tanned, freckle, chloasma hepaticum.In addition, can be applicable to the melanin that contains the ergosterol derivant as compositions and generate to suppress with compositions and whiten and use compositions, and contain various cosmetics, pharmaceuticals, skin preparations for extenal use, melanin in the cosmetics, pharmaceuticals, field of food of ergosterol derivant generate inhibition with food, whiten with food etc.The inhibition melanin that aforementioned cosmetics, pharmaceuticals and skin preparations for extenal use can be used for having the function of aforementioned ergosterol derivant generates and whitens.Foregoing is to be used to prevent and the compositions of processing with the aforementioned inhibition melanin generation and the relevant symptom of whitening etc.
These 2 kinds of forms of oral (interior usefulness) or non-oral (external) that compositions of the present invention can adopt.Compositions of the present invention can be modulated into for example form such as pharmaceuticals or food when oral, non-ly can be modulated into forms such as cosmetics, medicine for external use, pharmaceuticals, skin preparations for extenal use when oral.
When compositions of the present invention is gone in the fusion of ergosterol derivant, but the pure ergosterol derivant of fusion also can contain the extract of plant, mushroom etc. of ergosterol derivant or the form fusion of extraction extractum.
The aforementioned compositions that contains the ergosterol derivant of the present invention, be that melanin generates the inhibition compositions, whiten and use compositions, melanin generate to suppress with and the cosmetics of whitening and using etc., melanin generate to suppress with and the pharmaceuticals of whitening and using etc., melanin generate to suppress with and the skin preparations for extenal use of whitening and using etc., melanin generates and suppresses to use food, whiten with also containing aforementioned ergosterol derivant whitening agent composition (being designated hereinafter simply as the whitening agent composition) in addition in the compositionss such as food, cooperate by also using of aforementioned ergosterol derivant and whitening agent composition, can further improve melanin and generate inhibition effect and whitening effect.
Aforementioned whitening agent composition is not particularly limited; for example ascorbic acid and derivant thereof and their salt are (for example; ascorbic acid; ascorbic acid 2-glucoside; magnesium L-ascorbyl-2-phosphate salt; sodium ascorbate; hard ester acid acid ascorbyl ester; ascorbic palmitate; two ascorbic palmitate; VC-IP; Magnesium ascorbate; the chitosan ascorbic acid; ascorbic acid methyl-monosilane alcohol pectate; the ascorbic acid polypeptide; two Azelaic Acid acid ascorbyl esters; the ascorbic acid polyphosphate; the ascorbic acid polyoxyethylene deriv; the ricinoleic acid acid ascorbyl ester; Ascorbic acid 2-sulfate sodium salt etc.); hydroquinone and derivant thereof and their salt are (for example; arbutin etc.); cysteine and derivant thereof and their salt are (for example; the L-cysteine; N, N '-diacetyl cystine dimethyl etc.); placentin; kojic acid and derivant thereof; retinal; ellagic acid and derivant thereof; glycosamine and derivant thereof; Azelaic Acid and derivant thereof; hydroxycinnamic acid and derivant thereof; glutathion; plant extract (anthemidis flos extract; the Arnica montana extract; Radix Scutellariae extract; Rhizoma Chuanxiong extract; Cortex Mori extract; Radix Bupleuri extract; Radix Saposhnikoviae extract; the glehnia littoralis extract; the forest Gymnema sylvestre extract; the tilia extract; the leaf of Fructus Persicae extract; Radix Sophorae Flavescentis extract; チ ユ extract; Radix Angelicae Sinensis extract; Semen Coicis extract; the leaf of Diospyros kaki L.f. extract; Radix Et Rhizoma Rhei extract; Cortex Moutan extract; the Radix Hamamelidis Mollis extract; the Aesculus chinensis Bunge extract; Resina garciniae extract; the Herba lamii barbati extract; Radix Glycyrrhizae extract; セ Application プ Network カ extract; ケ イ ケ Star ト ウ extract; サ Application ペ Application ズ extract; Rhizoma Bistortae extract; Radix Sophorae Flavescentis extract; Fructus Crataegi extract; white Bulbus Lilii extract; the hops extract; Flos rosae multiflorae extract etc.); glabridin; glabranin; liquiritin; isoliquiritin; the hydrophobic licorice flavonoid; licochalcone A; intacellin etc.The whitening agent composition can be selected arbitrarily to mix more than a kind or 2 kinds.Fusion the proportional quantity (content) of the whitening agent composition during the whitening agent composition be preferably 0.0001～10 weight % of foregoing total amount, more preferably 0.001～5 weight %.Its amount is to be converted into the amount of removing the dry thing weight after desolvating from extracting solution during for extract.
Below, the branch purposes describes the of the present invention concrete compositions that contains the ergosterol derivant again.
As the cosmetics of the 1st purposes of the present invention, for example can be used as skin preparations for extenal use such as ointment, solution, cream, emulsion, astringent, lotion, jello, essence (beautifying liquid), foundation cream, skin lotion facial film, lipstick, lip pomade, bath gel etc. and in comprising the broad range of medicine for external use, use.
The dosage form of cosmetics can adopt solution system, can dissolve be, emulsion type, powder system, powder disperse system, fluid system, gel system, ointment system, aerosol system, water-oily 2 series of strata, water-oil-more dosage forms such as powder 3 series of strata.
The proportional quantity of the ergosterol derivant in the cosmetics of the present invention is preferably 0.001～20 weight % of cosmetics total amount, and more preferably 0.01～16 weight % is well 0.1～12 weight % again, is preferably 1～10 weight %.Cosmetics of the present invention generate inhibitory action and whitening function owing to have melanin, suppress to apply some make up and whiten the use that applies some make up so can be used as the melanin generation.In addition, use, suppress to use with skin preparations for extenal use and Dermatologic preparation for beautifying so be used as the melanin generation because cosmetics of the present invention are particularly suitable as skin preparations for extenal use.
Any administering mode in oral administration, the non-oral administration can be adopted as the pharmaceuticals of the 2nd purposes of the present invention, the pharmaceutical dosage form that is fit to this dual mode respectively can be formed.As pharmaceutical preparation, can exemplify aqueous dosage forms such as solution, syrup, injection, inhalant, Emulsion, solid dosage formss such as tablet, powder, granule, capsule, inhalant, skin preparations for extenal use such as ointment, external agent such as suppository etc.
The proportional quantity of the ergosterol derivant in the pharmaceutical preparation is preferably 0.001～30 weight % of pharmaceutical preparation total amount, and more preferably 0.01～20 weight % is preferably 0.1～10 weight %.Dosage can according to patient's age and body weight, be suitable for approach, advancing of disease trend and carry out simultaneously other handle and do suitably to change, it is not particularly limited, about general 1 day administration 4～10ml, can 1 administration in 1 day also can divide 2～3 administrations, be not particularly limited.Pharmaceuticals of the present invention generate inhibitory action and whitening function owing to have melanin, generate and suppress with pharmaceuticals and whiten and use with pharmaceuticals so can be used as melanin.Because pharmaceuticals of the present invention are particularly suitable as skin preparations for extenal use and use, suppress to use with skin preparations for extenal use and Dermatologic preparation for beautifying so can be used as the melanin generation.
Food as the 3rd purposes of the present invention can be used as so-called healthy function food use.For example, can be extensively as uses such as the processed goods of beverages such as cake, refreshment drink, vegetable or fruit, poultry meat product, flavouring agents.Its form is powder, solid shape goods and solution etc.The proportional quantity of the ergosterol derivant in the food can be made appropriate change according to purpose and goods form etc.When being generally solution such as beverage, for example in 30ml, contain 0.001～10mg, be preferably 0.01～5mg, more preferably 0.15～1mg.During for powder solid goods such as tablets, for example in 300mg, contain 0.001～10mg, be preferably 0.01～5mg, more preferably 0.1～1mg.Generate inhibitory action and whitening function because food of the present invention has melanin, generate and suppress with food and whiten and use with food so be used as melanin.
Under the prerequisite that does not influence effect of the present invention, in the compositionss such as cosmetics of the present invention, pharmaceuticals, food except above-mentioned ergosterol derivant, but also fusion is generally used for other compositions of cosmetics, pharmaceuticals, skin preparations for extenal use, food etc.
For example, but adjust agent, active ingredient, saccharide, antiseptic, vitamins, spice, water etc. as cosmetics fusion oil content, powder, surfactant, wetting agent, viscosifier, lower alcohols, film agent, UV absorbent, sequestering agent, organic amine, pH.
The example of oil content can exemplify Jojoba oil, olive oil, American Avocado Tree oil, Oleum Ricini, Oleum Cocois, Adeps Bovis seu Bubali, solidified oil, natural oil and derivants thereof such as aqueous agnolin, Brazil wax, Cera Flava, wax classes such as lanoline, liquid paraffin, microwax, three decanes, hydro carbons such as vaseline, senior fatty acids such as hard ester acid, hexadecanol, senior alcohols such as octadecanol, monostearin, tricaprylin, monoolein, isopropyl myristate, the malic acid diisopstearate, two 2-heptyl hendecanoic acid glyceride, three 2 ethyl hexanoic acid trimethylolpropanes, three sad trimethylolpropanes, esters such as the own ester of decanedioic acid two 2-methyl, Oleum menthae, Oleum Rosae Rugosae, quintessence oil classes such as citronellal, dimethyl polysiloxane, silicone oils such as decamethylcyclopentasiloxane etc.The proportional quantity of oil content in cosmetics can be done suitably to select according to the form of cosmetics and dosage form etc., but can account for 0.1～95 weight % in the cosmetics total amount usually.
The example of powder can exemplify Pulvis Talci, Muscovitum, Kaolin, silicon dioxide, zinc oxide, mica titanium, titanium oxide, ferrum oxide, nylon powder etc.
The example of surfactant can exemplify non-ionic surface active agents such as polyoxyethylene alkyl ether, polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, fatty acid glyceride, polyoxyethylene curing Oleum Ricini, polyoxyethylene sorbitol fatty acid ester, polyoxyalkylene modified polyorganosiloxane, anion surfactants such as sodium palmitate, cationic surfactants such as chlorination stearoyl trimethyl ammonium, amphoteric surfactantes such as betanin, amide betaine, sulfobetaines, imidazolium salts.
The example of wetting agent can exemplify glycerol, 1,3 butylene glycol, Polyethylene Glycol, dipropylene glycol, Sorbitol etc.
The example of viscosifier can exemplify water soluble polymers such as CVP Carbopol ETD2050, carboxy methyl cellulose, polyvinyl alcohol, clay minerals such as bentonite etc.
The example of UV absorbent can exemplify para-amino benzoic acid (being designated hereinafter simply as PABA), glyceryl PABA, ethyl dihydroxypropyl PABA, octyl methoxycinnamate, 2-ethoxyethyl group p-methoxycinnamic acid ester, 2,4-dihydroxy benaophenonel, 2-hydroxyl-4-methoxy benzophenone, 2-hydroxyl-4-methoxyl group-4-methyldiphenyl ketone, 2-hydroxyl-4-methoxyl group-4-methyldiphenyl ketone sulfonate, urocanic acid ethyl ester, 2-phenyl-5-methyl benzoxazol, 4-methoxyl group-4-tert-butyl group DBM, ethylhexyl-p-methoxycinnamate etc.
The example of sequestering agent can exemplify sequestrene Na4 and citric acid etc.The example of lower alcohol can exemplify ethanol etc.The example of organic amine can exemplify-ethanolamine, triethanolamine etc.The example that pH adjusts agent can exemplify buffer agents such as lactic acid-sodium lactate, citric acid-sodium citrate.
The example of active ingredient can exemplify pantoyl ether, glycyrrhetate etc.The example of vitamins can exemplify vitamin E or derivatives thereof etc.The example of antioxidant can exemplify vitamin E class, dibenzylatiooluene, propyl gallate etc.
The example of saccharide can exemplify erithritol, sucrose, hyaluronic acid etc.Examples of preservatives can exemplify ethyl p-Hydroxybenzoate, butyl p-Hydroxybenzoate, sodium benzoate etc.But other also fusion be selected from the composition of the composition that can be added into pharmaceuticals described later and food.
But fusion excipient, stabilizing agent, wetting agent, emulsifying agent, absorption enhancer, pH adjust various adding ingredients such as agent, surfactant, carrier in the pharmaceuticals.The object lesson of these adding ingredients comprises alcohols such as water, ethanol and 1,3 butylene glycol and polyglycols such as cellulose derivatives such as saccharides such as starch, lactose, magnesium sulfate, Pulvis Talci, gelatin, hydroxypropyl cellulose, soybean oil and Semen Sesami wet goods vegetable oil, animal oil or artificial oil, rubber, normal saline solution etc.But other also fusion be selected from the composition of the composition that can be added into aforementioned cosmetics and food described later.
But fusion sweeting agent, acidic flavoring agent, preservative agent, spice, coloring agent, excipient, stabilizing agent, wetting agent, emulsifying agent, absorption enhancer, pH adjust various adding ingredients such as agent, surfactant, diluent, carrier in the food.The object lesson of these adding ingredients can exemplify various food extracts solution such as mushroom extracting solution, Radix Ginseng extractive solution, ginger extract, Mel, aqueous food, the cyclic oligosaccharide as saccharide, reduction maltose, trehalose, lactose, sucrose fatty acid ester etc.But other also fusion be selected from the composition of the composition that can be added into aforementioned cosmetics, pharmaceuticals.
Mixed in the foregoing of the present invention of the present invention must composition and aforementioned any formulated component in more than a kind or 2 kinds, can modulate form and dosage form arbitrarily according to conventional method.
Below, exemplify embodiment the present invention is specifically described.As there not being special record, then represent in the proportional quantity of compositions with weight %.
[embodiment 1] melanin generates and suppresses effect
[melanin in the B16 melanoma cells generates inhibitory action]
Employing is from the melanin cellulation B16 10F7 melanoma cells (obtaining from autumn fields county composite food institute transfer) of mice, solution effects after making in aforementioned refining example purified ergosterol derivant with the culture fluid dilution is in this cell, observe melanic generation situation, suppress the evaluation of melanin nucleus formation.With PBS washing 70% cell that converges, add trypsin and peel off the B-16 cell, added the interpolation commensurability the culture medium of serum (E-MEM+10%FBS) again with trypsin, concentrated cell carries out centrifugal (800rpm, 5 minutes).Counting cells is adjusted into about 10 with it
4Cell/ml (E-MEM+10%FBS).The dilution of ergosterol derivative solution is to divide the sterilization PBS that injects 20 μ l in Tissue Culture Dish (inoculating cell is used), gets the ergosterol derivative solution dilution several times (ultimate density in the culture fluid is 100 μ g/ml～0.0012 μ g/ml) of 20 μ l.Liquid uses arbutin (ultimate density in the culture fluid is 140 μ g/ml～0.22 μ g/ml) in contrast, and methanol carries out same dilution.
Each cell suspending liquid that injects 80 μ l that divides in the culture dish of this diluent of having packed into.In 37 ℃, at CO
2Cultivated 72 hours in the calorstat, with the melanic generation in the microscope observing cell.Generating under the melanic situation, remove culture medium, with the NaOH dissolving melanin of the 1N of 300 μ l, by measuring the ultra-violet absorption evaluation melanin growing amount of 470nm.With making value as the reaction of the methanol of solvent as 100%, the consumption of ergosterol derivant and arbutin is changed, under least concentration, obtain and show and suppress the synthetic concentration of melanin that its result is as shown in table 1.
Table 1
| Arbutin | The ergosterol derivant | |
| Minimal inhibitory concentration | 0.88μg/ml | 0.5μg/ml |
Can find out that from table 1 the ergosterol derivant shows with melanin as the arbutin equal extent of Melanin inhibitor the melanoma b16 cell and generates inhibitory action (whitening function), can be used as Melanin inhibitor and whitening agent and uses.
Can find out that from microphotograph ergosterol derivant and arbutin have equal inhibitory action to the black of B16 cell, confirm that it has good melanin and generates inhibition effect and whitening effect.
The mensuration of [embodiment 2～3, comparative example 1～2] whitening effect
Composition proportion amount (weight %)
(pure phase)
Ethanol 25.0
Polyoxyethylene (25 moles) solidifies Oleum Ricini 2.0
Antioxidant is an amount of
Antiseptic is an amount of
Spice is an amount of
The amount of test compound (being recorded in table 2) table 2 record
(water)
Glycerol 5.0
Sodium hexameta phosphate is an amount of
The ion exchange water surplus
(method for making) modulate respectively in the prescription of above-mentioned composition water and alcohol mutually after, mix both, make their dissolvings, obtain compositions (lotion).
(test method) make 20 experimenters at 11 at noon summer in 1 time of afternoon, be exposed under the sunlight in continuous 2 days and amount to 4 hours.As object, after 5 days that begin to be exposed under the sunlight, every day, each once was coated with above-mentioned composition (lotion) sooner or later, lasted for 5 weeks with the inboard arm skin of the experimenter after the Exposure to Sunlight.
(evaluation methodology) estimated the result of the test after using according to following determinating reference.
(determinating reference) is very effective: almost do not see pigementation, effectively: pigementation becomes very shallow, more effective: pigementation becomes more shallow, and is invalid: no change.
(judgement) ◎: have among the experimenter to show effectively above effect more than 16 people, zero: have 11～15 people to show effectively above effect among the experimenter, △: there are 6～10 people to show effectively above effect among the experimenter, *: have among the experimenter to show effectively above effect below 5 people.
Evaluation result is as shown in table 2.
Table 2
| Test compound | Proportional quantity (weight %) | Effect | |
| Embodiment 2 | The ergosterol derivant | 0.2 | ○ |
| Embodiment 3 | The ergosterol derivant | 1.0 | ◎ |
| Comparative example 1 | Do not have and add | _ | × |
| Comparative example 2 | Hydroquinone | 1.0 | △ |
Can find out that from table 2 compositions (lotion) that contains the ergosterol derivant can prevent melanin deposition, show melanin and generate inhibitory action and whitening function.On the other hand, test compound is under the situation of do not have adding (comparative example 1), and fusion under the situation of hydroquinone (comparative example 2), all do not show effect.
The mensuration of [embodiment 4～7, comparative example 3～4] whitening effect
Emulsification composition according to conventional method following composition of preparation and proportional quantity.The proportional quantity of ergosterol derivant is with also the composition title and the proportional quantity of the whitening agent composition of usefulness are shown in table 3.
Composition proportion amount (weight %)
Polyethylene Glycol one hard ester acid esters 2.0
Glycerol one hard ester acid esters 5.0
Tadenan 5.5
Three decanes 8.0
Tricaprylin 8.0
Glycerol 5.0
Citric acid 0.1
Sodium citrate 0.9
P-Hydroxybenzoate 0.2
The surplus branch of Purified Water
The amount of ergosterol derivant table 3 record
The amount of whitening agent composition (seeing Table 3) table 3 record
Table 3 (proportional quantity (weight %))
| Composition | Embodiment | Comparative example | ||||
| 4 | 5 | 6 | 7 | 3 | 4 | |
| The ergosterol derivant | 0.01 | 0.005 | 0.005 | 0.01 | _ | _ |
| Ascorbic acid 2-glucoside | 0.02 | 0.01 | _ | _ | 0.02 | _ |
| Magnesium L-ascorbyl-2-phosphate salt | _ | _ | 0.01 | _ | _ | 0.02 |
(test method) has the healthy volunteer of tangible senile plaque and freckle to be divided into 6 groups with 30, every group 5 people, and every day, 2 difference were coated with the compositions of embodiment 4～7, comparative example 3～4 to them in the morning and before sleeping.Then, the photochrome after taking day on-test and 4 weeks under the state of not making up, the visual state that compares to determine the colour of skin of comparing with day on-test.
(result) result of determination is shown in table 4.Table 4 is depicted as the number that meets each critical item according to judgement.
Table 4
| Critical item | Embodiment | Comparative example | ||||
| 4 | 5 | 6 | 7 | 3 | 4 | |
| Compare obvious desalination with beginning day | 5 | 4 | 3 | 3 | 0 | 0 |
| Compare slightly light with beginning day | 0 | 1 | 2 | 2 | 2 | 2 |
| No change or denseer | 0 | 0 | 0 | 0 | 3 | 3 |
Can find out obviously that from table 4 ergosterol derivant and ascorbic acid 2-glucoside or fusion of magnesium L-ascorbyl-2-phosphate salt and usefulness can further improve the whitening effect of ergosterol derivant, promptly melanin generates and suppresses effect.
The following stated is for to modulate the embodiments of the invention of the compositions of various prescriptions according to conventional method.Arbitrary embodiment shows good melanin and generates inhibition effect and whitening effect.
[embodiment 8] cream
Composition proportion amount (weight %)
Hard ester acid 6.0
Glycerol one hard ester acid esters 2.0
Polyoxyethylene (20 moles) 2.0
The sorbitan monostearate
1,3 butylene glycol 10.0
Ergosterol derivant 5.0
Isopropyl myristate 12.0
Three decanes 5.0
Liquid paraffin 3.0
Vitamin E 0.05
Sodium sulfite is an amount of
Antiseptic is an amount of
Spice is an amount of
The surplus branch of ion exchange water
[embodiment 9] emulsion
Composition proportion amount (weight %)
Octadecanol 2.0
Three decanes 5.0
Aqueous agnolin 3.0
Three sad trimethylolpropanes 2.0
Tricaprylin 5.0
Monoolein 2.0
Polyoxyethylene (20 moles) 1.0
The anhydrosorbitol monooleate ester
Vitamin C 0.1
Antiseptic is an amount of
Ergosterol derivant 8.0
Para-amino benzoic acid 0.1
Spice is an amount of
Sodium sulfite is an amount of
Glycerol 5.0
CVP Carbopol ETD2050 0.2
Triethanolamine 1.0
The surplus branch of Purified Water
[embodiment 10] jello
Composition proportion amount (weight %)
Dipropylene glycol 10.0
PEG1500 5.0
CVP Carbopol ETD2050 1.0
Ethanol 2.0
The oily ether 2.0 of polyoxyethylene (50 moles)
Potassium hydroxide 0.15
Ergosterol derivant 1.0
2-hydroxyl-4-methoxyl group 0.05
The benzophenone sodium sulfonate
Antiseptic is an amount of
EDTA3Na is an amount of
Spice is an amount of
The surplus branch of ion exchange water
[embodiment 11] jello
Composition proportion amount (weight %)
Dipropylene glycol 10.0
PEG1500 5.0
CVP Carbopol ETD2050 1.0
Ethanol 2.0
The oily ether 2.0 of polyoxyethylene (50 moles)
Potassium hydroxide 0.15
Ergosterol derivant 1.0
Ascorbic acid 2-glucoside 0.01
2-hydroxyl-4-methoxyl group 0.05
The benzophenone sodium sulfonate
Antiseptic is an amount of
EDTA3Na is an amount of
Spice is an amount of
The surplus branch of ion exchange water
[embodiment 12] essence
Composition proportion amount (weight %)
Glycerol 5.0
Dipropylene glycol 10.0
Ethanol 10.0
CVP Carbopol ETD2050 0.2
Hyaluronate sodium 0.5
Potassium hydroxide 0.1
Polyoxyethylene (20 moles) 0.5
The anhydrosorbitol monooleate ester
Polyoxyethylene (20 moles) 1.0
The octyl group lauryl ether
Olive oil 0.15
Vitamin e acetate 0.1
Ergosterol derivant 3.0
Sodium sulfite is an amount of
Antiseptic is an amount of
EDTA3Na is an amount of
Spice is an amount of
The surplus branch of Purified Water
[embodiment 13] skin lotion
Composition proportion amount (weight %)
Venamul 15.0
Polyvinyl alcohol 10.0
Dipropylene glycol 5.0
Sorbitol 5.0
Tocopherol acetate E 0.2
Olive oil 1.0
Three decanes 3.0
Polyoxyethylene (20 moles) 1.5
The anhydrosorbitol monooleate ester
Titanium dioxide 5.0
Pulvis Talci 10.0
Ethanol 7.0
Ergosterol derivant 3.0
Antiseptic is an amount of
Spice is an amount of
The surplus branch of Purified Water
[embodiment 14] astringent
Composition proportion amount (weight %)
1,3 butylene glycol 6.0
Glycerol 5.0
Hyaluronate sodium 0.3
Polyoxyethylene (20 moles) 1.5
Sorbitan one hard ester acid esters
Polyoxyethylene (20 moles) 0.5
The octyl group lauryl ether
Ethanol 15.0
Ergosterol derivant 4.0
Antiseptic is an amount of
Spice is an amount of
The surplus branch of Purified Water
[embodiment 15] astringent
Composition proportion amount (weight %)
1,3 butylene glycol 6.0
Glycerol 5.0
Hyaluronate sodium 0.3
Polyoxyethylene (20 moles) 1.5
Sorbitan one hard ester acid esters
Polyoxyethylene (20 moles) 0.5
The octyl group lauryl ether
Ethanol 15.0
Ergosterol derivant 4.0
Ascorbic acid 2-glucoside 0.05
Ascorbic acid 2-sulfate sodium salt 0.05
Antiseptic is an amount of
Spice is an amount of
The surplus branch of Purified Water
[embodiment 16] ointment
Composition proportion amount (weight %)
Polyoxyethylene (30 moles) solidifies Oleum Ricini 2.0
Monostearin 10.0
Three decanes 10.0
Vaseline 40.0
Hexadecanol 6.0
Ergosterol derivant 5.0
1,3 butylene glycol 10.0
The surplus branch of ion exchange water
Antiseptic is an amount of
Spice is an amount of
[embodiment 17] ointment
Composition proportion amount (weight %)
Polyoxyethylene (30 moles) solidifies Oleum Ricini 2.0
Monostearin 10.0
Three decanes 10.0
Vaseline 40.0
Hexadecanol 6.0
Ergosterol derivant 5.0
Ascorbic acid 2-glucoside 0.003
Chamomile extract (dry thing weight) 0.002
1,3 butylene glycol 10.0
The surplus branch of ion exchange water
Antiseptic is an amount of
Spice is an amount of
[embodiment 18] foundation cream
Composition proportion amount (weight %)
Pulvis Talci 3.0
Titanium dioxide 5.0
Iron oxide red 0.5
Iron oxide yellow 1.5
Iron oxide black 0.1
Bentonite 0.5
Polyoxyethylene (20 moles) 1.0
The sorbitan monostearate
Triethanolamine 1.0
Glycerol 5.0
Propylene glycol 5.0
Hard ester acid 2.0
Glycerol one hard ester acid esters 10.0
Liquid paraffin 10.0
Dimethyl polysiloxane 5.0
Polyoxyalkylene modified polyorganosiloxane 3.0
Ergosterol derivant 3.0
The surplus branch of Purified Water
Antiseptic is an amount of
Spice is an amount of
[embodiment 19] healthy beverage
Composition proportion amount (among the 30ml)
Ergosterol derivant 0.085mg
Radix Ginseng extractive solution 50mg
Cordyceps extracting solution 100mg
Ginger extract 300mg
Mel 150mg
Cyclic oligosaccharide 300mg
Sweeting agent is an amount of
Acidic flavoring agent is an amount of
Preservative agent is an amount of
Spice is an amount of
The surplus branch of water
[embodiment 20] healthy beverage
Composition proportion amount (among the 30ml)
Ergosterol derivant 0.085mg
Vitamin C 1000mg
Radix Ginseng extractive solution 50mg
Cordyceps extracting solution 100mg
Ginger extract 300mg
Mel 150mg
Cyclic oligosaccharide 300mg
Sweeting agent is an amount of
Acidic flavoring agent is an amount of
Preservative agent is an amount of
Spice is an amount of
The surplus branch of water
[embodiment 21] healthy beverage
Composition proportion amount (among the 30ml)
Ergosterol derivant 0.5mg
Radix Ginseng extractive solution 50mg
Cordyceps extracting solution 100mg
Ginger extract 300mg
Mel 150mg
Cyclic oligosaccharide 300mg
Sweeting agent is an amount of
Acidic flavoring agent is an amount of
Preservative agent is an amount of
Spice is an amount of
The surplus branch of water
[embodiment 22] health food tablet
Composition proportion amount (among the 300mg)
Ergosterol derivant 0.025mg
Reduction maltose 87.8mg
Trehalose 41.2mg
Lactose 16.5mg
Sucrose fatty acid ester 6.2mg
Dextrin 148.275mg
[embodiment 23] health food tablet
Composition proportion amount (among the 300mg)
Ergosterol derivant 0.025mg
Vitamin C 100mg
Reduction maltose 87.8mg
Trehalose 41.2mg
Lactose 16.5mg
Sucrose fatty acid ester 6.2mg
Dextrin 48.275mg
[embodiment 24] health food tablet
Composition proportion amount (among the 300mg)
Ergosterol derivant 0.025mg
L-cysteine 40mg
Reduction maltose 87.8mg
Trehalose 41.2mg
Lactose 16.5mg
Sucrose fatty acid ester 6.2mg
Dextrin 108.275mg
[embodiment 25] health food tablet
Composition proportion amount (among the 300mg)
Ergosterol derivant 0.5mg
Reduction maltose 87.8mg
Trehalose 41.2mg
Lactose 16.5mg
Sucrose fatty acid ester 6.2mg
Dextrin 147.8mg
The possibility of utilizing on the industry
As mentioned above, the present invention has obtained new Melanin inhibitor, whitening agent and has had the composition of check melanin nucleus formation and whitening function. Also obtain to have melanin and generated inhibitory action and whitening function, to the whitening of the postradiation tanning of ultraviolet ray, and cosmetics, pharmaceuticals, skin preparations for extenal use and food that the pigementation because of skins such as the age mark that produces such as tanned, freckle, chloasma hepaticums is had good prevention, improvement and result for the treatment of. In addition, composition of the present invention can further improve melanin and generate inhibition and whitening effect by fusion and the usefulness of ergosterin derivative and whitening agent composition.
Claims (6)
1. the application of the ergosterol derivant of following formula (1) expression in the preparation Melanin inhibitor,
2. application according to claim 1 is characterized in that described Melanin inhibitor is a whitening agent.
3. application according to claim 1 and 2 is characterized in that, described Melanin inhibitor is the used for cosmetic Melanin inhibitor.
4. application according to claim 1 and 2 is characterized in that, described Melanin inhibitor is the pharmaceuticals Melanin inhibitors.
5. application according to claim 4 is characterized in that described medicine is a skin preparations for extenal use.
6. application according to claim 1 and 2 is characterized in that, the ergosterol derivant of formula (1) expression and other whitening agent composition are used in combination.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2001370989 | 2001-12-05 | ||
| JP370989/2001 | 2001-12-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1615138A CN1615138A (en) | 2005-05-11 |
| CN1311834C true CN1311834C (en) | 2007-04-25 |
Family
ID=19180115
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB028273133A Expired - Fee Related CN1311834C (en) | 2001-12-05 | 2002-12-03 | Melanogenesis inhibitors and whitening agents comprising ergosterol derivatives and compositions containing ergosterol derivatives |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPWO2003047593A1 (en) |
| KR (1) | KR20040073459A (en) |
| CN (1) | CN1311834C (en) |
| AU (1) | AU2002354353A1 (en) |
| WO (1) | WO2003047593A1 (en) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2006182731A (en) * | 2004-12-28 | 2006-07-13 | Ichimaru Pharcos Co Ltd | Cosmetic composition or food and drink |
| CN103845234A (en) * | 2014-02-13 | 2014-06-11 | 上海珍馨化工科技有限公司 | Hyaluronic acid whitening cream |
| KR102493245B1 (en) * | 2020-10-30 | 2023-01-30 | 주식회사 지엠엑스 | Composition for skin whitening comprising carvedilol |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58113118A (en) * | 1981-12-26 | 1983-07-05 | Nonogawa Shoji:Kk | Cosmetic |
| JPH0249710A (en) * | 1988-05-20 | 1990-02-20 | Narisu Keshohin:Kk | Cosmetic |
| JPH07316035A (en) * | 1994-03-31 | 1995-12-05 | Usuki Seiyaku Kk | Skin external agent |
| US5733558A (en) * | 1995-04-20 | 1998-03-31 | L'oreal | Method for treatment of acne and/or the effects of ageing using HMG-coenzyme A-reductase inhibitor and compositions for performing the same |
| JPH11199499A (en) * | 1998-01-07 | 1999-07-27 | Kanebo Ltd | Fat synthetic promoter and composition for external use for skin for breast-enlargement |
| JP2000319191A (en) * | 1999-03-05 | 2000-11-21 | Takeda Chem Ind Ltd | Cyclic gmp specific phosphodiesterase inhibitor and sexual dysfunction-improving drug |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4115656B2 (en) * | 2000-10-11 | 2008-07-09 | 株式会社坂本バイオ | Melanin production inhibitor and whitening agent comprising ergosterol derivative |
-
2002
- 2002-12-03 KR KR10-2004-7008661A patent/KR20040073459A/en not_active Application Discontinuation
- 2002-12-03 CN CNB028273133A patent/CN1311834C/en not_active Expired - Fee Related
- 2002-12-03 JP JP2003548848A patent/JPWO2003047593A1/en active Pending
- 2002-12-03 WO PCT/JP2002/012647 patent/WO2003047593A1/en active Application Filing
- 2002-12-03 AU AU2002354353A patent/AU2002354353A1/en not_active Abandoned
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS58113118A (en) * | 1981-12-26 | 1983-07-05 | Nonogawa Shoji:Kk | Cosmetic |
| JPH0249710A (en) * | 1988-05-20 | 1990-02-20 | Narisu Keshohin:Kk | Cosmetic |
| JPH07316035A (en) * | 1994-03-31 | 1995-12-05 | Usuki Seiyaku Kk | Skin external agent |
| US5733558A (en) * | 1995-04-20 | 1998-03-31 | L'oreal | Method for treatment of acne and/or the effects of ageing using HMG-coenzyme A-reductase inhibitor and compositions for performing the same |
| JPH11199499A (en) * | 1998-01-07 | 1999-07-27 | Kanebo Ltd | Fat synthetic promoter and composition for external use for skin for breast-enlargement |
| JP2000319191A (en) * | 1999-03-05 | 2000-11-21 | Takeda Chem Ind Ltd | Cyclic gmp specific phosphodiesterase inhibitor and sexual dysfunction-improving drug |
Non-Patent Citations (4)
| Title |
|---|
| Effect of endoperoxides from marine origin on2 hydroxy methylgltarul coareductase activity ofinfant skin BIOMED PHARMACOTHE,Vol.40 No.5 1986 * |
| Effect of endoperoxides from marine origin on3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) activity ofinfant skin fibroblasts in culture. Guyot,M.,Loriette,C.,Lapous,D.,et al,Biomed. Pharmacother. CAN:106:12483,Vol.40 No.5 1986 * |
| Minor and trace sterols in marine invertebrates.26.Isolationand structure elucidation of nine new 5a,8a-epidioX sterolsfrom four marine organisms. Leslie Gunatilaka A. A.,Copichand Y.,Schmitz F. J.,et al,J. Orgb. Chem.,Vol.46 No.19 1981 * |
| Novel phytotoxins produced by the causal fungus of theshoot blight of larches. Otomo N.,Sato Hi.,Sakamura S.,Agric. Biol. Chem.,Vol.47 No.5 1983 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2002354353A1 (en) | 2003-06-17 |
| WO2003047593A1 (en) | 2003-06-12 |
| KR20040073459A (en) | 2004-08-19 |
| JPWO2003047593A1 (en) | 2005-04-14 |
| CN1615138A (en) | 2005-05-11 |
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