CN1784215A - Melanogenesis promoter and melanogenesis promoter composition - Google Patents
Melanogenesis promoter and melanogenesis promoter composition Download PDFInfo
- Publication number
- CN1784215A CN1784215A CNA2004800123491A CN200480012349A CN1784215A CN 1784215 A CN1784215 A CN 1784215A CN A2004800123491 A CNA2004800123491 A CN A2004800123491A CN 200480012349 A CN200480012349 A CN 200480012349A CN 1784215 A CN1784215 A CN 1784215A
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- compositions
- melanin
- agent
- short melanin
- short
- Prior art date
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- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
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Abstract
A substance excelling in the efficacy of melanogenesis promotion and being effective in hair graying prevention and amelioration and in skin melanism; and a composition making effective use of the substance. In particular, such a substance consists of a melanogenesis promoter comprising as an active ingredient a Lactuca indica extract or a lupeol fatty acid ester and/or an isomer thereof. There are provided the above melanogenesis promoter and a melanogenesis promoter composition comprising as an active ingredient a Lactuca indica extract or a lupeol fatty acid ester and/or an isomer thereof. This melanogenesis promoter composition can be used as a hair graying prevention composition or a skin melanism composition and can find appropriate application in cosmetics, drugs or food products.
Description
Technical field
The present invention relates to the Herba Lactucae Indicae extract and active component hexadecanoic acid feather fan alcohol ester is the application of the fatty acid feather fan alcohol ester of representative, also relate to not only can promote melanocytic melanin to generate, but also the short melanin that can prevent and improve poliosis, U.S. casting skin generates agent and short melanin such as cosmetics, pharmaceuticals and food generates compositions.
Background technology
The depth of hair and skin color depends on the melanin amount that exists in hair and the skin.And melanin is in the pigment cellulation (melanocyte) of the ball top portion of hair and stratum basale, and through the process of tyrosine to DOPA, the catalytic action by tryrosinase is synthesized.
Therefore, if because the activation of melanocytic superfunction or tryrosinase, melanic growing amount increases, and then hair color is deepened, and then prevents that poliosis from taking place, or improves poliosis.Up to now, as the method that makes medicine for curing poliosis, existing much prevent or improve the report (reference example such as patent documentation 1,2,3) that the one-tenth of poliosis grades, but still lack effectiveness and safety.
In addition, if increase dermal melanin amount, the then color burn of skin.Follow popular trend, have many people to like brown skin, generally accept ultraviolet radiation or by being that the skin tanning agent of main constituent achieves the goal with dihydro acetone by sun tan or tanned beauty treatment etc.But there are a lot of problems in these methods in safety.
In sum, if find the composition of the safety of increase hair and dermal melanin amount, just can realize safety, prevent effectively and improve poliosis that it is brown that skin is become.
In the research of short melanin material up to now, the research relevant with the present invention has: for example, the methanolic extract of the root of the Compositae Dandelion common dandelion (Taraxacum officinale) that the inventor did in the experiment of cell cultivation level, have the active report that short melanin generates, and the effective ingredient of described extract is accredited as lupeol and similar substance (with reference to non-patent literature 1,2) thereof.In addition, similarly in the experiment of cell cultivation level, the Compositae lettuce belongs in the extract separately of continue disconnected chrysanthemum (Sonchus asper) and Herba Sonchi Oleracei (Sonchus oleraceus) and has detected the activity that short melanin generates, but the wild carraway of same Compositae belongs to red autumnal leaves umbrellas (Cacalia delphiniiforia) and do not find identical activity (with reference to non-patent literature 1) in the Senecio Herba Senecionis Vulgaris (Senecio vulgaris) of Compositae equally.But even the activity that has short melanin to generate, its effectiveness is also insufficient.In addition, the short melanin that contains dihydro lupeol derivant in addition generates the report (reference example such as patent documentation 4) of agent, but this material is not a natural materials, renders a service still not strong yet.
Patent documentation 1: the Japan Patent spy opens the 2000-169348 communique
Patent documentation 2: the Japan Patent spy opens the 2002-47130 communique
Patent documentation 3: the Japan Patent spy opens the 2002-212039 communique
Patent documentation 4: the Japan Patent spy opens the 2002-3381 communique
Non-patent literature 1: Hata favour department (Keishi Hata) etc., Biological and PharmaceuticalBulletin.2000,23 volumes, No. 8, p.962～967
Non-patent literature 2: Hata favour department (Keishi Hata) etc., Journal of Natural Products.2002,65 volumes, p.645～648
The announcement of invention
The problem that invention will solve
The present invention In view of the foregoing carries out, its purpose be to provide short melanin nucleus formation good, can be used to prevent again and improve the material of poliosis, U.S. casting skin and effectively use the compositions of this material.
For solving above-mentioned problem, the inventor has carried out conscientiously research, found that the Herba Lactucae Indicae extract has very strong short melanin nucleus formation, further find behind the active component of its extract of research, the fatty acid feather fan alcohol ester of ad hoc structure has very strong short melanin nucleus formation, they can be used for prevention and improve poliosis, U.S. casting skin, thereby have finished the present invention.
That is, the present invention includes by Herba Lactucae Indicae extract or following general formula
The short melanin that the fatty acid feather fan alcohol ester of (in the formula, R represents the acyl group of carbon number 12～22) expression or its isomer constitute generates agent.
In addition, the present invention also comprises and contains described Herba Lactucae Indicae extract or contain following general formula
The fatty acid feather fan alcohol ester of (in the formula, R represents the acyl group of carbon number 12～22) expression and/or its isomer generate agent as the short melanin of effective ingredient.
Described short melanin generates in the agent, and the R in the represented fatty acid feather fan alcohol ester of described general formula better is the acyl group of carbon number 14～18.Be more preferably the acyl group of the carbon number 14～18 that contains saturated hydrocarbons, good especially is hexadecanoyl.
In addition, the present invention comprises that also the short melanin that contains described short melanin generation agent generates compositions.
In addition, the present invention also comprises and contains above-mentioned Herba Lactucae Indicae extract or following general formula
The fatty acid feather fan alcohol ester of (in the formula, R represents the acyl group of carbon number 12～22) expression and/or the short melanin of its isomer generate compositions.
Described short melanin generates in the compositions, and the R in the represented fatty acid feather fan alcohol ester of described general formula better is the acyl group of carbon number 14～18.Be more preferably the acyl group of the carbon number 14～18 that contains saturated hydrocarbons, good especially is hexadecanoyl.
Described short melanin generates compositions and can be used as the compositions that compositions that the prevention poliosis uses or U.S. casting skin are used.
Described compositions is suitable as cosmetics, pharmaceuticals or the food of the non-drug class that comprises.
Adopting the present invention can obtain novel short melanin generates agent and has the compositions of short melanin nucleus formation.Particularly, can obtain having good preventing and the cosmetics, pharmaceuticals and the food that improve poliosis, U.S. casting skin effect by short melanin nucleus formation.
The best mode that carries out an invention
Below describe embodiments of the present invention in detail.
Herba Lactucae Indicae extract of the present invention can use Herba Lactucae Indicae, and with method commonly used in the plant extract, promptly the method for Herba Lactucae Indicae being extracted by solvent etc. obtains.
Used Herba Lactucae Indicae is the plant of Compositae Lactuca (Lactuca indica) among the present invention.Described Herba Lactucae Indicae is an annual herb, is distributed widely in East Asia and Southeast Asia, also can both find in Japanese various places.And be up to the macrophyte about 60cm～2m.Described Herba Lactucae Indicae is grown in sun-drenched place in wilderness, river bank, waste exhausted dry land, the open country.In 9～October, the yellow-white flower is opened on the top of stem.Day real name band " lettuce " word of Herba Lactucae Indicae, but on taxonomy, with the Herba Lactucae versicoloris that is all Compositae and the disconnected chrysanthemum different genus not of the same race that continue.Because open closely similar flower, so got similar name.Herba Lactucae Indicae be used as for a long time domestic animal feedstuff, the very high plant of safety, but its short melanin nucleus formation is also not known.
The extract part of Herba Lactucae Indicae can use whole strain, leaf, stem, root, flower and seed etc.Especially, consider, better be to use whole strain from aspects such as effectiveness, extraction efficiencies.In addition, the form of Herba Lactucae Indicae can adopt the fresh plant of for example gathering, chop up the plant of pulverizing etc. behind the plant of having shredded, dry plant, drying when obtaining extract, but be not limited thereto, in the scope of not destroying effect of the present invention, also can use other form.Among the present invention, better be after making the high form of extraction efficiencies such as drying, powder, for solvent extraction.
The solvent that is used to extract is not particularly limited, and can exemplify for example alcohols such as ethanol, methanol, isopropyl alcohol, 1,3 butylene glycol, hydro carbons such as hexane, heptane, cyclohexane extraction, esters such as ethyl acetate, ketones such as acetone, water etc., these solvents can separately or mix more than 2 kinds and use.In the described solvent, ethanol, methanol or their mixed solvent can be brought into play effectiveness of the present invention, so be ideal.
During extraction, can use methods such as infiltration, solvent refluxing in solvent.In addition, extract temperature and be not particularly limited, under from the room temperature to the normal pressure, carry out in the scope of the boiling point of solvent.Extraction time is not particularly limited, and carries out with random time.After solvent extraction, with filtering or method such as centrifugalize removes the residue of extraction from extracting solution after, extract solvent and obtain extract by removing.
Following general formula of the present invention
The shown fatty acid feather fan alcohol ester and the R of isomer thereof are the acyl groups of carbon number 12～22, better are the acyl groups of carbon number 14～18.The alkyl that constitutes acyl group can contain unsaturated bonds such as two keys, also can be straight chain shape or branch's chain.The object lesson of described acyl group can exemplify lauroyl, tetradecanoyl, hexadecanoyl, stearyl, oleoyl, isostearoyl base, docosane acyl group, Caulis et Folium Lini acyl group etc.Among the present invention, R is more preferably the acyl group of the carbon number 14～18 with saturated hydrocarbyl, and described alkyl can be straight chain shape or branch's chain, better is directly catenate.Good especially is the acyl group with carbon number 16 of saturated hydrocarbyl.Hexadecanoyl preferably.
Fatty acid feather fan alcohol ester that above-mentioned general formula is represented (below, be called for short fatty acid feather fan alcohol ester) and isomer thereof can obtain with for example method of acidylate lupeol.Carry out with method commonly used in the method for acidylate, also can carry out esterification plant or its extract that contains lupeol.Extract is except to remove the dry thing of the extraction desolvate from the solvent extraction liquid of plant, be outside the form use of extract, can also directly use the form of the extracting solution that obtains with solvent extraction, perhaps make with solvent and dilute extraction diluent that obtains or the spissated extraction concentrated solution use of the solvent of removing any amount with arbitrary proportion.In addition, in the scope of not destroying effect of the present invention, also can carry out operation back uses such as deodorize again.
Among the present invention; have hexadecanoyl as the hexadecanoic acid feather fan alcohol ester of the R of described fatty acid feather fan alcohol ester (below; be called for short hexadecanoic acid feather fan alcohol ester) be composition contained in the described Herba Lactucae Indicae, can from described Herba Lactucae Indicae extract of the present invention, separate obtaining with known method.Can be by for example the extract of Herba Lactucae Indicae being used repeatedly the separation of column chromatography etc., separation obtains, but is not limited thereto.The inventor finds that for the first time the hexadecanoic acid feather fan alcohol ester among the present invention is present in the Herba Lactucae Indicae.
The extract of Herba Lactucae Indicae that is used for separating described hexadecanoic acid feather fan alcohol ester is except removing the dry thing of the extraction of desolvating with the solvent extraction liquid from plant, be outside the form use of extract, can also directly use the form of the extracting solution that obtains with solvent extraction, perhaps make with solvent and dilute extraction diluent that obtains or the spissated extraction concentrated solution use of the solvent of removing any amount with arbitrary proportion.In addition, in the scope of not destroying effect of the present invention, also can carry out operation back uses such as deodorize again.
The preferred hexadecanoic acid feather fan alcohol ester that uses among the present invention, except from described Herba Lactucae Indicae extracts, also can by for example from the plant that contains hexadecanoic acid feather fan alcohol ester except that Herba Lactucae Indicae additive method such as separation grade obtain.
Herba Lactucae Indicae extract of the present invention and fatty acid feather fan alcohol ester and isomer thereof as described later, have good short melanin nucleus formation.Therefore, they can be generated agent as short melanin.Should short melanin generate the new application that agent is based on the described new function of the Herba Lactucae Indicae extract found and fatty acid feather fan alcohol ester and isomer thereof, and by containing Herba Lactucae Indicae extract or fatty acid feather fan alcohol ester and/or its isomer generate agent as short melanin as the effective ingredient performance effect.Described short melanin generates agent to have the melanin that promotes in the black cell and generates, prevent or improve poliosis, be U.S. dark hair, make functions such as skin overstrike.
The range of application that short melanin of the present invention generates agent is extremely wide, can be applied to every field.The cosmetics that for example comprise the non-drug class, medicine, food etc. can be enumerated in described field, and these are ideal.
When using short melanin of the present invention and generating agent, the type of service of Herba Lactucae Indicae extract and fatty acid feather fan alcohol ester and isomer thereof, in the Herba Lactucae Indicae extract, except from the solvent extraction liquid of plant, to remove the dry thing of the extraction desolvate, be outside the form use of extract, can also directly use the form of the extracting solution that obtains with solvent extraction, perhaps make with solvent and dilute extraction diluent that obtains or the spissated extraction concentrated solution use of the solvent of removing any amount with arbitrary proportion.In addition, in the scope of not destroying effect of the present invention, also can carry out operation backs such as deodorize (deodorize thing), purification (purification thing) again and use.In addition, also useable solvents is made the solution use of extracting dry thing after dissolving dry thing with any concentration.In addition, also can use purification such as column chromatography, make separator even active component and use.
In addition, fatty acid feather fan alcohol ester and isomer thereof can be used as the plant of effective ingredient and fatty acid feather fan alcohol ester that contain the concentration that can effectively bring into play short melanin nucleus formation and/or its isomer or the form of its extract to contain fatty acid feather fan alcohol ester and/or its isomer.As long as satisfy described condition, this extract can be any one following form: the form of solvent extraction liquid, its concentrated solution, make the separator arbitrarily that contains fatty acid feather fan alcohol ester and/or its isomer by purified extract (extracting solution).
Short melanin of the present invention generates agent and is mixed with in the compositions as the composition that short melanin generates, and can form new, the useful compositions with short melanin nucleus formation, and promptly short melanin generates compositions.It is obvious especially to hair and skin effect that short melanin among described the present invention generates compositions.In hair, make the hair blackening, can be as the compositions of preventing poliosis to use.In addition, in skin, make skin darkening (turing brown), can be with the compositions of helping casting skin to use.Described compositions is not particularly limited, and can be arbitrarily, can exemplify the cosmetics that for example comprise the non-drug class, pharmaceuticals, food etc., and these are ideal.Concrete compositions can exemplify short melanin generate apply some make up, short melanin generates with pharmaceuticals, short melanin and generates the food of usefulness, cosmetics that the prevention poliosis is used, pharmaceuticals that the prevention poliosis is used, prevents the pharmaceuticals that the food that poliosis uses, the cosmetics that U.S. casting skin is used, U.S. casting skin use, the food that U.S. casting skin is used etc.
Thereby short melanin of the present invention is generated agent be mixed with compositions when obtaining promoting that melanin generates compositions, the content of Herba Lactucae Indicae extract (converting by extracting dry thing) and fatty acid feather fan alcohol ester and isomer thereof is according to purposes, dosage form, preparation purpose etc. and different, but generally be preferably 0.00001～20 weight % of total composition, more preferably 0.0001～10 weight %.
Dosage about as pharmaceuticals the time, can appropriate change according to the progress of patient's age and body weight, administering mode, the state of an illness and the treatment carried out simultaneously, be not particularly limited, but generally can be with 1～10ml every day (liquid) or 1～20mg (paste, the ointment shape) about, divide every day 1 time or 2～3 administrations, but be not limited thereto.
In cosmetics in the short melanin generation compositions of the present invention, pharmaceuticals, the food etc., in the scope of not destroying effect of the present invention, can add other compositions commonly used in cosmetics, pharmaceuticals, the food.
For example, as other relevant compositions of cosmetics, wherein contained concrete composition has and has multiple situation simultaneously, and for example can exemplifying, oiliness composition, surfactant, wetting agent, polyhydric alcohol, viscosifier, water soluble polymer, tunicle form the U.S. black composition of agent, water-insoluble macromolecule, powder, pigment, dyestuff, lake, lower alcohol, UV absorbent, metal ion chelation agent, organic amine, pH regulator agent, active ingredient, saccharide, other hairs or skin, antiseptic, antioxidant, spice, water etc.
The oiliness composition can exemplify for example Jojoba oil (Jojoba oil), olive oil, American Avocado Tree oil, Oleum Ricini, Oleum Cocois, Adeps Bovis seu Bubali, sclerosis wet goods natural oil and derivant thereof, aqueous lanoline, Brazil wax, Cera Flava, wax classes such as lanoline, liquid paraffin, three decanes, vaseline, Witcodur 272, hydro carbons such as solid paraffin, stearic acid, senior fatty acid such as behenic acid, hexadecanol, stearyl alcohol, 16/18 mixed alcohols senior aliphatic alcohols such as (cetostearyl alcohol), tricaprylin, isopropyl myristate, malic acid two isooctadecanol esters, 2-triethyl group caproin, two isostearic acids, two glyceride, 2-triethyl group caproic acid trihydroxy methyl propyl ester, three sad trihydroxy methyl propyl ester, esters such as decanedioic acid 2-ethylhexyl, dimethyl polysiloxane, methyl phenyl silicone, silicone oils such as decamethylcyclopentasiloxane etc.
The powder composition can exemplify for example Talcum, Muscovitum, Kaolin, silicon dioxide, zinc white, mica titanium, titanium oxide, ferrum oxide, nylon powder etc.
Surfactant can exemplify for example anion surfactants such as nonionic surfactant, hexadecanoic acid sodium such as poly(ethylene oxide) (hereinafter to be referred as POE) alkyl ether, POE fatty acid ester, POE sorbitan fatty acid ester, fatty glyceride, POE hardened castor oil, POE Sorbitol fatty acid ester, polyalkylene oxide modified polyorganosiloxane, cationic surfactants such as chlorination stearoyl trimethyl ammonium, amphoteric surfactantes such as betanin, amido betaine, imidazolinium compounds, sulfobetaines.
The example of wetting agent can exemplify glycerol, 1,3 butylene glycol, Polyethylene Glycol (hereinafter to be referred as PEG), dipropylene glycol, Sorbitol etc.
The example of viscosifier can exemplify mineral clays such as water soluble polymer, bentonite such as poly-carboxyl ethylene, carboxymethyl cellulose, polyvinyl alcohol.
The example of UV absorbent can exemplify para-amino benzoic acid (hereinafter to be referred as PABA), PABA glyceride, PABA ethyl dihydroxy propyl ester, octyl methoxycinnamate, p-methoxycinnamic acid-2-ethoxy ethyl 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 benzothiazole, 4-methoxyl group-4-tert-butyl group DBM, ethylhexyl-p-methoxycinnamate etc.
The example of metal ion chelation agent can exemplified by ethyl enediamine tetraacethyl four sodium, citric acid etc.The example of lower alcohol can exemplify ethanol etc.The example of organic amine can exemplify ethanolamine, triethanolamine etc.The example of pH regulator agent can exemplify buffer agents such as lactic acid-sodium lactate, citric acid-sodium citrate.
The example of active ingredient can exemplify pantoyl ether (pantotenyl-ethyl ether), glycyrrhetate (glycyrrhetinic acid), nicotinate etc.Examples of antioxidants 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 ethylparaben, butyl p-hydroxybenzoate, sodium benzoate etc.In addition, select in the composition that can also from aftermentioned pharmaceuticals and food, can add to add.
Then, as other relevant compositions of pharmaceuticals, wherein contained concrete composition has and has multiple situation simultaneously, can exemplify various adding ingredients such as for example excipient, stabilizing agent, wetting agent, emulsifying agent, absorption enhancer, pH regulator agent, surfactant, diluent, carrier, cosolvent, flavoring agent, preservative agent, aromatic, coloring agent, sugar-coat agent and water etc.The object lesson of these adding ingredients can exemplify saccharides such as starch, lactose, cellulose derivatives such as magnesium sulfate, Talcum, gelatin, hydroxypropyl cellulose, soybean oil and Semen Sesami wet goods vegetable oil, animal oil or artificial oil, the natural gum class, ethanol, 1,3 butylene glycol, poly alkylene glycol alcohols such as (poly alkylene glycol).In addition, select in the composition that can also from above-mentioned cosmetics and aftermentioned food, can add to add.
Then, as other relevant compositions of food, wherein contained concrete composition has and has multiple situation simultaneously, can exemplify for example various adding ingredients such as sweeting agent, acidic flavoring agent, preservative agent, spice, coloring agent, excipient, stabilizing agent, wetting agent, emulsifying agent, absorption enhancer, pH regulator agent, surfactant, diluent, carrier and water etc.The object lesson of these adding ingredients can exemplify for example various extracting solution such as Radix Ginseng extractive solution, ginger extract, Mel, cyclic oligosaccharide, saccharides such as reduction maltose, trehalose, lactose, sucrose fatty acid ester.In addition, select in the composition that can from above-mentioned cosmetics and medicine, can add to add.
Described compositions among the present invention can be mixed with various forms of preparations.
For example, cosmetics can be suitable in the very wide scope of for example emulsifiable paste, washing liquid, emulsion, ointment, solution, astringent, gel, foam, essence (beautifying liquid), foundation cream, facial film, spraying etc.
In addition, the dosage form of cosmetics can adopt the solution class, can dissolve class, emulsifying class, powdery type, powder disperse class, fluid class, gel-like, ointments, spray-like, foam class, lip pomade class, water-2 layers of class of oil, water-oil-3 layers of multiple dosage forms such as class of powder.
In addition, pharmaceuticals can adopt oral or non-oral administration mode, can adopt the form of corresponding pharmaceutical preparation respectively.Pharmaceutical preparation can exemplify for example aqueous dosage forms such as liquid type type, syrup dosage form, injection type, liquid inhalant type, emulsion-type, solid dosage formss such as tablet form, powder-type, granule dosage form, capsule formulation, ointment dosage form, solid inhalant dosage form, suppository type etc.
In addition, as food, can be used for called function food, for example can be used as, beverage such as dessert, refreshment drink, vegetable or processing fruits goods, poultry meat products, flavoring agent etc. extensively are suitable for.Its form has powder, solid-state product, solution etc.
Described compositions of the present invention is especially suitable for use as external preparation such as cosmetics, pharmaceuticals.For example, the compositions of prevention poliosis better is with for example forms such as emulsifiable paste, washing liquid, emulsion, ointment, solution, gel, spraying, foam, makes hair cream, hair conditioner (hair tonic), the water of haircuting, shampoo (hair rinse), shampoo, hairdressing gel (hair treatment), hair conditioner products such as (hair conditioner).The compositions of U.S. casting skin better is to make product with for example forms such as emulsifiable paste, washing liquid, emulsion, ointment, jello, facial film, foam, solution, essence, lip pomade, powder.
Described compositions of the present invention can be mixed with form, dosage form arbitrarily according to a conventional method.
Below, exemplify embodiment and specify the present invention.In the addition of compositions, what not do not specify is weight %.
[preparation example 1; Herba Lactucae Indicae extract]
With the herb lyophilization of Herba Lactucae Indicae, pulverize with fiber destructor (fiber mixer).In this powder of 10g, add 100ml methanol, leave standstill under the room temperature after 30 minutes and extract.After the extraction, obtain 0.26g by filtration, drying under reduced pressure and extract powder (extracting dry thing).
[preparation example 2; Hexadecanoic acid feather fan alcohol ester]
With the herb lyophilization of Herba Lactucae Indicae, pulverize with the fiber destructor.Add 3L methanol to this powder of 300g, left standstill under the room temperature 90 minutes, its filtrate decompression drying is obtained extracting powder.Add 3L methanol again in the Herba Lactucae Indicae powder after the filtration, left standstill under the room temperature 90 minutes, its filtrate decompression drying is obtained extracting powder once more.Repeat this extraction operation 5 times, obtain 33.7g altogether and extract powder.
Then, use chloroform: methanol: the dicyandiamide solution of the volume ratio of water=4: 4: 3 distributes extraction, obtains the dry thing of 13.6g from chloroform layer (lower floor).To silica gel column chromatography separation, the purification of this dry product with 4 stages.That is, collect activated part and dry in each stage, carry out the next stage chromatography again.Used dicyandiamide solution is followed successively by chloroform: methanol=5: 1, normal hexane: ethyl acetate=5: 1, normal hexane: ethyl acetate=20: 1 and normal hexane: chloroform=10: 1.Separate at last and obtain the reactive compound that identify at the 99.4mg end.
With
1H-NMR (400MHz, Fig. 1) and
13(100MHz Fig. 2) analyzes described chemical compound to C-NMR, is accredited as lupeol.In addition, analyze (table 1) with high-resolution EI-MS, molecular weight 664.6125 and 665.6163 position probing go out tangible peak value.Combine the molecular formula C of the chemical compound hexadecanoic acid feather fan alcohol ester that hexadecanoic acid forms on these data and the C-3 position according to lupeol
46H
80O
2(carbon atom all is the molecular weight that calculates
12During C) 664.6158 1 carbon atoms are
13Molecular weight 665.6192 during C is very approaching.In conjunction with angle-of-rotation measuring, the spectrometric result of IR, know that described chemical compound is the ester that conjugated fatty acid forms on the C-3 position of lupeol, thinks hexadecanoic acid feather fan alcohol ester.The ester bond of the described chemical compound of basic hydrolysis again, and analyze free fatty acid with FID-GC, be accredited as hexadecanoic acid.In addition, with purification by silica gel column chromatography triterpene rare part, also confirm as lupeol with NMR etc.
[table 1]
| Determining molecular weight | Molecular formula | Calculate molecular weight | Error (mmu) |
| 664.6125 | C 46H 80O 2 | 664.6158 | 3.3 |
| 665.6163 | C 45H 80 13CO 2 | 665.6192 | 2.9 |
According to above analysis, the compound identification that obtains is a hexadecanoic acid feather fan alcohol ester.
Promote melanin to generate effect-1
In order to the short melanin nucleus formation in the following method evaluation B16 melanoma cells.
(method)
The high susceptibility cell strain of the melanotropin B16 2F2 that will screen from mouse black-in tumor cell strain B16, sets up uses to contain the clear Dulbecco improvement Eagle culture medium of 10% N of fetal blood and cultivate under 37 ℃, 5%/conditions of air.Separate the B16 2F2 cell of cultivating in advance with trypsin, reclaim, count, be used for following cultivation.The Herba Lactucae Indicae extract or the Radix Taraxaci extract (use with the Herba Lactucae Indicae same procedure and handle the extraction powder that obtains from the Radix Taraxaci of ウ チ ダ oriental drug Co., Ltd. purchase) of preparation in the aforementioned preparation example 1 are mixed with the methanol solution that concentration is 20mg/ml, and add in the culture medium by following mode.
To B16 2F2 cell (1 * 10
5Add and mix the extract or the Radix Taraxaci extract of Herba Lactucae Indicae in the culture fluid of cell/ml), making its concentration is 20 μ g/ml, and cultivation was used to measure cell number and melanin content after 72 hours in 24 well culture plates (0.5ml/ hole).The melanin content of B16 2F2 cell by add 1N NaOH solution (300 μ l/ hole) in 4 well culture plates, was placed 60 minutes under the room temperature, made intracellular melanin dissolving, measured the absorption of 470nm, thereby quantitatively.In contrast, use the methanol of same amount to replace the extract of Herba Lactucae Indicae or Radix Taraxaci extract to add, similarly experimentize.The result as shown in Figure 3.
(result)
As shown in Figure 3, the extract of Herba Lactucae Indicae is compared with the Radix Taraxaci extract, makes the about 3 times melanin of B16 2F2 cell induction.Even when increasing the addition of Radix Taraxaci extract, melanic growing amount does not almost change yet.
Embodiment 2
Short melanin generates effect-2
[the short melanin nucleus formation in the B16 melanoma cells]
(method)
Identical with embodiment 1, use mouse black-in tumor cell B16 2F2 to estimate the short melanin nucleus formation of hexadecanoic acid feather fan alcohol ester.With separating the Herba Lactucae Indicae extract that the hexadecanoic acid feather fan alcohol ester that obtains replaces use among the embodiment 1 in the preparation example 2, add in the culture medium with the concentration of 10 μ M, 20 μ M or 30 μ M.Its result as shown in Figure 4.
(result)
As shown in Figure 4, hexadecanoic acid feather fan alcohol ester is induced melanic generation in the B16 2F2 cell consumingly.
Below, exemplify embodiment with the compositions of the various prescriptions of common method preparation.Herba Lactucae Indicae extract in the formula components except that specified otherwise is arranged, is the Herba Lactucae Indicae extract (extracting dry thing) that obtains in the described preparation example 1.The ethanol extraction of Herba Lactucae Indicae herb also is by the preparation of the method for described preparation example.In addition, all demonstrate good short melanin among all embodiment and generate effect, when being used for hair, showing and prevent that hair from bleaching, poliosis is had the effect of improving poliosis, when being used for skin, show the effect of U.S. casting skin.
Emulsifiable paste
Composition proportion amount (weight %)
Stearyl alcohol 6.0
Stearic acid 2.0
Agnolin 4.0
Three decanes 9.0
Octyldodecanol 10.0
1,3 butylene glycol 6.0
PEG1500 4.0
POE (25) hexadecane alcohol ether 3.0
Glyceryl monostearate 2.0
Herba Lactucae Indicae extract 5.0
Antiseptic is an amount of
Antioxidant is an amount of
Spice is an amount of
The ion exchange water surplus
Embodiment 4
Emulsifiable paste
Composition proportion amount (weight %)
Stearyl alcohol 6.0
Stearic acid 2.0
Agnolin 4.0
Three decanes 9.0
Octyldodecanol 10.0
1,3 butylene glycol 6.0
PEG1500 4.0
POE (25) hexadecane alcohol ether 3.0
Glyceryl monostearate 2.0
Hexadecanoic acid feather fan alcohol ester 0.003
Antiseptic is an amount of
Antioxidant is an amount of
Spice is an amount of
The Purified Water surplus
Emulsion
Composition proportion amount (weight %)
Stearic acid 2.0
Hexadecanol 1.5
Vaseline 4.0
Three decanes 5.0
Tricaprylin 2.0
Anhydrosorbitol monooleate ester 2.0
Glycerol 5.0
PEG1500 3.0
Triethanolamine 1.0
Herba Lactucae Indicae extract 0.08
Antiseptic is an amount of
Antioxidant is an amount of
Spice is an amount of
The Purified Water surplus
Gel
Composition proportion amount (weight %)
Dipropylene glycol 7.0
PEG1500 8.0
Poly-carboxyl ethylene 0.4
Methylcellulose 0.2
The oily ether 1.0 of POE (25)
Potassium hydroxide 0.1
Herba Lactucae Indicae extract 1.0
Antiseptic is an amount of
Antioxidant is an amount of
Chelating agen is an amount of
Spice is an amount of
The Purified Water surplus
Embodiment 7
Gel
Composition proportion amount (weight %)
Dipropylene glycol 7.0
PEG1500 8.0
Poly-carboxyl ethylene 0.4
Methylcellulose 0.2
The oily ether 1.0 of POE (25)
Potassium hydroxide 0.1
Hexadecanoic acid feather fan alcohol ester 0.1
Antiseptic is an amount of
Antioxidant is an amount of
Chelating agen is an amount of
Spice is an amount of
The Purified Water surplus
Embodiment 8
Washing liquid
Composition proportion amount (weight %)
1,3 butylene glycol 6.0
Glycerol 4.0
Isooctadecanol 0.1
Hyaluronate sodium 0.3
POE (20) sorbitan one dodecylate 0.5
POE (20) dodecane ether 0.5
Ethanol 10.0
The ethanol extract 0.5 of Herba Lactucae Indicae herb
(to extract dry thing weight)
Antiseptic is an amount of
Antioxidant is an amount of
Spice is an amount of
The Purified Water surplus
Embodiment 9
Washing liquid
Composition proportion amount (weight %)
1,3 butylene glycol 6.0
Glycerol 4.0
Isooctadecanol 0.1
Hyaluronate sodium 0.3
POE (20) sorbitan one dodecylate 0.5
POE (20) dodecane ether 0.5
Ethanol 10.0
Hexadecanoic acid feather fan alcohol ester 0.5
Antiseptic is an amount of
Antioxidant is an amount of
Spice is an amount of
The Purified Water surplus
Hair cream
Composition proportion amount (weight %)
Liquid paraffin 15.0
Vaseline 15.0
Cera Flava 2.0
Poly-carboxyl ethylene 0.1
Xanthene natural gum 0.1
1,3 butylene glycol 5.0
POE (20) ten or twenty dioxane ether 2.0
POE (40) four oleic acid sorbitol esters 1.0
Herba Lactucae Indicae extract 4.0
Antiseptic is an amount of
Antioxidant is an amount of
Spice is an amount of
The Purified Water surplus
Embodiment 11
Hair care washing liquid (hair treatment lotion)
Composition proportion amount (weight %)
Glycerol 2.0
1,3 butylene glycol 1.0
Chlorination stearoyl trimethyl ammonium 0.5
Methyl phenyl silicone 1.0
Collagen hydrolysate 1.0
Ethanol 50.0
Herba Lactucae Indicae extract 0.1
The Purified Water surplus
Spice is an amount of
Embodiment 12
The hair care washing liquid
Composition proportion amount (weight %)
Glycerol 2.0
1,3 butylene glycol 1.0
Chlorination stearoyl trimethyl ammonium 0.5
Methyl phenyl silicone 1.0
Collagen hydrolysate 1.0
Ethanol 50.0
Hexadecanoic acid feather fan alcohol ester 0.5
The Purified Water surplus
Spice is an amount of
Embodiment 13
Hair conditioner
Composition proportion amount (weight %)
Ethanol 70.0
POE (60) hardened castor oil 0.5
L-menthol 0.05
Acetic acid dl-alpha-tocopherol 0.05
Enoxolone dicalcium 0.05
1,3 butylene glycol 0.5
Glycerol 0.5
The ethanol extract 1.5 of Herba Lactucae Indicae herb
(to extract dry thing weight)
The Purified Water surplus
Spice is an amount of
Embodiment 14
Hair conditioner
Composition proportion amount (weight %)
Ethanol 70.0
POE (60) hardened castor oil 0.5
L-menthol 0.05
Acetic acid dl-alpha-tocopherol 0.05
Enoxolone dicalcium 0.05
1,3 butylene glycol 0.5
Glycerol 0.5
Hexadecanoic acid feather fan alcohol ester 0.5
The Purified Water surplus
Spice is an amount of
Hair growth promoter
Composition proportion amount (weight %)
Ethanol 60.0
Thujaplicin is an amount of
Herba swertiae extract is an amount of
Vitamin B
6In right amount
Vitamin e derivative is an amount of
1,3 butylene glycol 2.0
Glycerol 0.5
POE (60) hardened castor oil 0.5
Herba Lactucae Indicae extract 0.5
The Purified Water surplus
Spice is an amount of
Embodiment 16
Hair growth promoter
Composition proportion amount (weight %)
Ethanol 60.0
Thujaplicin is an amount of
Herba swertiae extract is an amount of
Vitamin B
6In right amount
Vitamin e derivative is an amount of
1,3 butylene glycol 2.0
Glycerol 0.5
POE (60) hardened castor oil 0.5
Hexadecanoic acid feather fan alcohol ester 3.0
The Purified Water surplus
Spice is an amount of
Embodiment 17
Oral liquid
Composition proportion amount (among the 30ml)
The dry thing 0.085mg of the ethanol extraction of Herba Lactucae Indicae herb
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
Water surplus
Embodiment 18
Oral liquid
Composition proportion amount (among the 30ml)
The dry thing 0.5mg of the ethanol extraction of Herba Lactucae Indicae herb
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
Water surplus
Embodiment 19
Oral liquid
Composition proportion amount (among the 30ml)
Hexadecanoic acid feather fan alcohol ester 0.05mg
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
Water surplus
The food tablet
Composition proportion amount (among the 300mg)
The dry thing 0.025mg of the ethanol extraction of Herba Lactucae Indicae herb
Reduction maltose 87.8mg
Trehalose 41.2mg
Lactose 16.5mg
Sucrose fatty acid ester 6.2mg
Dextrin 148.275mg
Embodiment 21
The food tablet
Composition proportion amount (among the 300mg)
The dry thing 0.5mg of the ethanol extraction of Herba Lactucae Indicae herb
Reduction maltose 87.8mg
Trehalose 41.2mg
Lactose 16.5mg
Sucrose fatty acid ester 6.2mg
Dextrin 147.8mg
Embodiment 22
The food tablet
Composition proportion amount (among the 300mg)
Hexadecanoic acid feather fan alcohol ester 0.05mg
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
Can obtain new short melanin generates agent and has the composition that promotes the melanin nucleus formation, especially can be applicable to by short melanin nucleus formation, have good prevention and improve cosmetics, pharmaceuticals and the food etc. of the effect of white hair, U.S. casting skin.
The simple declaration of accompanying drawing
[Fig. 1] Fig. 1 is a hexadecanoic acid feather fan alcohol ester
1The H-NMR collection of illustrative plates.
[Fig. 2] Fig. 2 is a hexadecanoic acid feather fan alcohol ester
13The C-NMR collection of illustrative plates.
[Fig. 3] Fig. 3 is the sketch map that the short melanin of Herba Lactucae Indicae extract generates effect.
[Fig. 4] Fig. 4 is the sketch map that the short melanin of hexadecanoic acid feather fan alcohol ester generates effect.
Claims (16)
1. short melanin generates agent, it is characterized in that, described short melanin generates agent and is made of the Herba Lactucae Indicae extract.
2. short melanin generates agent, it is characterized in that, described short melanin generates agent and contains the Herba Lactucae Indicae extract as effective ingredient.
3. short melanin generates agent, it is characterized in that, described short melanin generates agent by following general formula
The fatty acid feather fan alcohol ester of expression or its isomer constitute, and in the formula, R represents the acyl group of carbon number 12～22.
4. short melanin generates agent, it is characterized in that, described short melanin generates agent and contains following general formula
The fatty acid feather fan alcohol ester of expression and/or its isomer are as effective ingredient, and in the formula, R represents the acyl group of carbon number 12～22.
5. generate agent as claim 3 or 4 described short melanin, its feature is that also R is carbon number 14～18 alkanoyls.
6. generate agent as claim 3 or 4 described short melanin, its feature is that also R is the acyl group with carbon number 14～18 of saturated hydrocarbyl.
7. generate agent as claim 3 or 4 described short melanin, its feature is that also R is a hexadecanoyl.
8. short melanin generates uses compositions, it is characterized in that, described compositions contains any the short melanin described in the claim 1～7 and generates agent.
9. short melanin generates uses compositions, it is characterized in that described compositions contains the Herba Lactucae Indicae extract.
10. short melanin generates uses compositions, it is characterized in that described compositions contains following general formula
Fatty acid feather fan alcohol ester and/or its isomer of expression, in the formula, R represents the acyl group of carbon number 12～22.
Use compositions, its feature also to be 11. short melanin as claimed in claim 10 generates, R is the acyl group of carbon number 14～18.
Use compositions, its feature also to be 12. short melanin as claimed in claim 10 generates, R is the acyl group with carbon number 14～18 of saturated hydrocarbyl.
13. generating, short melanin as claimed in claim 10 use compositions, its feature to be that also R is a hexadecanoyl.
14. use compositions, its feature also to be as each the described short melanin generation in the claim 8～13, described compositions is prevention poliosis compositions.
15. use compositions, its feature also to be as each the described short melanin generation in the claim 8～13, described compositions is U.S. casting skin skin composition.
16. use compositions, its feature also to be as each the described short melanin generation in the claim 8～15, described compositions is cosmetics, pharmaceuticals or food.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP136439/2003 | 2003-05-14 | ||
| JP2003136439A JP4517249B2 (en) | 2003-05-14 | 2003-05-14 | Melanin production promoter and composition for promoting melanin production |
| PCT/JP2004/006436 WO2004112815A1 (en) | 2003-05-14 | 2004-05-13 | Melanogenesis promoter and melanogenesis promoter composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1784215A true CN1784215A (en) | 2006-06-07 |
| CN1784215B CN1784215B (en) | 2010-10-06 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2004800123491A Expired - Fee Related CN1784215B (en) | 2003-05-14 | 2004-05-13 | Melanogenesis promoter and melanogenesis promoter composition |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP4517249B2 (en) |
| KR (1) | KR101112006B1 (en) |
| CN (1) | CN1784215B (en) |
| BR (1) | BRPI0410251A (en) |
| WO (1) | WO2004112815A1 (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008138200A1 (en) * | 2007-05-11 | 2008-11-20 | Hong Kong University Of Science & Technology | Nmda and mc receptor antagonists exhibiting neuroprotective and memory enhancing activities |
| CN108113927A (en) * | 2018-02-28 | 2018-06-05 | 周海英 | A kind of composition with white-skinned face function in cosmetics and preparation method thereof |
| CN108815066A (en) * | 2018-06-14 | 2018-11-16 | 广州植境生物科技有限公司 | A kind of draft Haircare composition of the seed extract containing millet |
| CN111387505A (en) * | 2020-04-21 | 2020-07-10 | 中国农业科学院都市农业研究所 | Lettuce extract for inhibiting melanin synthesis and lettuce matching cultivation method |
| CN111658593A (en) * | 2019-03-08 | 2020-09-15 | 伊德姆有限公司 | Leukotrichia-suppressing and ameliorating agent and phosphorylated MITF/MITF production ratio increasing agent |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5428000B2 (en) * | 2007-06-27 | 2014-02-26 | 株式会社スカイライト・バイオテック | Lupeol-containing pharmaceutical composition, food and feed |
| JP6027752B2 (en) * | 2011-02-21 | 2016-11-16 | 第一三共ヘルスケア株式会社 | AGEs production inhibitor |
| JP6142342B2 (en) * | 2013-02-22 | 2017-06-07 | 株式会社東洋新薬 | Novel uses of Akinonogeshi extract |
| KR101692851B1 (en) * | 2015-10-16 | 2017-01-05 | 경상대학교산학협력단 | Composition for skin whitening comprising amorphigeni as effective component |
| WO2020032297A1 (en) * | 2018-08-10 | 2020-02-13 | 탑월드(주) | Composition for alleviating vitiligo symptoms and preparation method thereof |
| KR102249072B1 (en) * | 2019-07-11 | 2021-05-06 | 인하대학교 산학협력단 | Pharmaceutical composition for preventing or treating vitiligo or canities comprising extract of Cichorium intybus as an active ingredient |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4504520B2 (en) * | 2000-06-26 | 2010-07-14 | 花王株式会社 | Melanin production promoter |
| JP2002308753A (en) * | 2001-04-10 | 2002-10-23 | Mitsui Chemicals Inc | Elastase activity inhibitor, estrogenic activator and anti- aging agent for skin containing the same inhibitor or the same activator |
-
2003
- 2003-05-14 JP JP2003136439A patent/JP4517249B2/en not_active Expired - Lifetime
-
2004
- 2004-05-13 WO PCT/JP2004/006436 patent/WO2004112815A1/en active Application Filing
- 2004-05-13 KR KR1020057021403A patent/KR101112006B1/en not_active IP Right Cessation
- 2004-05-13 BR BRPI0410251-7A patent/BRPI0410251A/en active Search and Examination
- 2004-05-13 CN CN2004800123491A patent/CN1784215B/en not_active Expired - Fee Related
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008138200A1 (en) * | 2007-05-11 | 2008-11-20 | Hong Kong University Of Science & Technology | Nmda and mc receptor antagonists exhibiting neuroprotective and memory enhancing activities |
| GB2462235A (en) * | 2007-05-11 | 2010-02-03 | Univ Hong Kong Science & Techn | NMDA and MC receptor antagonists exhibiting neuroprotective and memory enhancing activities |
| GB2462235B (en) * | 2007-05-11 | 2011-09-28 | Univ Hong Kong Science & Techn | Receptor modulators exhibiting neuroprotective and memory enhancing activities |
| US8637474B2 (en) | 2007-05-11 | 2014-01-28 | The Hong Kong University Of Science And Technology | Receptor modulators exhibiting neuroprotective and memory enhancing activities |
| US8642567B2 (en) | 2007-05-11 | 2014-02-04 | The Hong Kong University Of Science And Technology | Receptor modulators exhibiting neuroprotective and memory enhancing activities |
| CN108113927A (en) * | 2018-02-28 | 2018-06-05 | 周海英 | A kind of composition with white-skinned face function in cosmetics and preparation method thereof |
| CN108815066A (en) * | 2018-06-14 | 2018-11-16 | 广州植境生物科技有限公司 | A kind of draft Haircare composition of the seed extract containing millet |
| CN108815066B (en) * | 2018-06-14 | 2019-10-15 | 广州植境生物科技有限公司 | A kind of draft Haircare composition of the seed extract containing millet |
| CN111658593A (en) * | 2019-03-08 | 2020-09-15 | 伊德姆有限公司 | Leukotrichia-suppressing and ameliorating agent and phosphorylated MITF/MITF production ratio increasing agent |
| CN111387505A (en) * | 2020-04-21 | 2020-07-10 | 中国农业科学院都市农业研究所 | Lettuce extract for inhibiting melanin synthesis and lettuce matching cultivation method |
| CN111387505B (en) * | 2020-04-21 | 2023-04-07 | 中国农业科学院都市农业研究所 | Lettuce extract for inhibiting melanin synthesis and lettuce matching cultivation method |
Also Published As
| Publication number | Publication date |
|---|---|
| BRPI0410251A (en) | 2006-05-16 |
| JP2004345959A (en) | 2004-12-09 |
| WO2004112815A1 (en) | 2004-12-29 |
| KR101112006B1 (en) | 2012-03-13 |
| KR20060014397A (en) | 2006-02-15 |
| CN1784215B (en) | 2010-10-06 |
| JP4517249B2 (en) | 2010-08-04 |
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