CN102186457A - Skin-whitening composition comprising an extract, fraction or compound derived from lindera erythrocarpa - Google Patents
Skin-whitening composition comprising an extract, fraction or compound derived from lindera erythrocarpa Download PDFInfo
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- CN102186457A CN102186457A CN2009801412078A CN200980141207A CN102186457A CN 102186457 A CN102186457 A CN 102186457A CN 2009801412078 A CN2009801412078 A CN 2009801412078A CN 200980141207 A CN200980141207 A CN 200980141207A CN 102186457 A CN102186457 A CN 102186457A
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- fructus
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- chemical compound
- linderae glaucae
- extract
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- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
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- 239000011787 zinc oxide Substances 0.000 description 1
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- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/54—Lauraceae (Laurel family), e.g. cinnamon or sassafras
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- 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
- A61K8/96—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution
- A61K8/97—Cosmetics or similar toiletry preparations characterised by the composition containing materials, or derivatives thereof of undetermined constitution from algae, fungi, lichens or plants; from derivatives thereof
- A61K8/9783—Angiosperms [Magnoliophyta]
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- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
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- A23V2200/00—Function of food ingredients
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Abstract
The present invention relates to a skin-whitening composition comprising an extract, a fraction or a compound derived from Lindera erythrocarpa. More specifically, the present invention relates to a skin-whitening composition comprising having an active ingredient consisting of an ethanol extract obtained by using ethanol to extract Lindera erythrocarpa, a solvent fraction obtained therefrom, or a compound isolated and purified therefrom.
Description
Technical field
The present invention relates to comprise the skin whitening composition of the extract, part or the chemical compound that are derived from Fructus Pyracanthae Fructus Linderae Glaucae (Lindera erythrocarpa).More specifically, the present invention relates to comprise ethanol extraction as active component from the Fructus Pyracanthae Fructus Linderae Glaucae, separate and the skin whitening composition of the chemical compound of purification from the solvent part of described ethanol extraction or from described ethanol extraction.
Background technology
The physiologically active compound from natural product is paid close attention in a large amount of research.Plant resources is widely used in treatment of diseases and prevention or auxiliary as health.For example, alpha-tocopherol, vitamin C, carotenoid and flavonoid are as natural antioxidant.Found to have the chemical compound of antioxidant activity in the animal and plant of wide region, particularly a large amount of researchs are from plant.Experiment shows that the secondary metabolite from plant suppresses or removing free radical and oxygen production, the anti-thus inductive cell injury of oxidation in the body.
Bao Dao most of naturally occurring antioxidant is from plant and be mainly polyphenolic substance up to now.Particularly, flavonoid has the function that stops lipid oxidation and oxidative stress and removing active oxygen, prevention or slow down aging, blocking-up cancer and cardiopathic generation or progress thus.Thus, flavonoid has been used to various fields, comprises food industry, pharmaceuticals industry and cosmetics industry.In addition, melanin is at the ubiquitous polymerization phenols of nature pigment, its see comprise animal, plant and even most of biologies of microorganism, and as the radiating important thing against sunshine (photoprotectant) of protection body antagonism UV.
Melanin strengthens the survival ability of antagonism UV radiation, drying and extreme temperature, and has strengthened the quality of coffee, tea and cigar.On the other hand, the excessive melanic synthetic known generation that can cause generation, the promotion skin aging of body freckle and speckle and participate in skin carcinoma.The plurality of enzymes that comprises tryrosinase is regulated melanic biosynthesis.Among these enzymes, tryrosinase is responsible for the early stage oxidation of dihydroxy indole afterwards of biosynthesis, and wherein tyrosine is converted into L-DOPA quinine.In this, the research of searching tyrosinase inhibitor occupies part and parcel in the exploitation of skin whitener.The tyrosinase inhibitor of exploitation comprises hydroquinone, 4-hydroxyanisol, ascorbic acid derivates, kojic acid, Azelaic Acid, corticosteroid, biostearin, arbutin, catechin and 3,4,5-trimethoxy cinnamic acid Herba thymi vulgaris phenolic ester at present.Yet, because the problem of their safety and economic benefit is difficult to use them.
The Fructus Pyracanthae Fructus Linderae Glaucae is the plant that belongs to Lauraceae (Lauraceae family).Known 45 genus and 1500 kinds that have Lignum cinnamomi camphorae in the whole world, and in Korea S's 6 genus of existence and 12 kinds.In Korea S, no matter be male or female Fructus Pyracanthae Fructus Linderae Glaucae, great majority were left lurid flower and are born the erythrocarpus that size is about 8mm in JIUYUE in April to May.The Fructus Pyracanthae Fructus Linderae Glaucae is the high deciduous tree of about 5m and originates in Korea S south, Japan and Chinese warm area.The dry fruit of tree has distinctive fragrance and bitter in the mouth, they is used as be good for the stomach medicine and neuralgic analgesic in Japan.It is reported that the leaf of Fructus Pyracanthae Fructus Linderae Glaucae and the ethanol extraction of fruit and Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone (lucidone) (a kind of cyclopentanedione) have potential anti-inflammatory activity (Wang et al., 2008).Known have active anticancer (Oh et al., 2005 from the isolating cyclopentanedione chemical compound of Fructus Pyracanthae Fructus Linderae Glaucae; The 10-0658519 Korean Patent).
After considering background technology comprehensively, the inventor has obtained to originate in the ethanol extraction of Fructus Pyracanthae Fructus Linderae Glaucae of Korea S's Jizhou Island and follow-up solvent part thereof and from the cyclopentanedione chemical compound and the cyclopentanedione derivant of described solvent part, the antioxidant activity of the above material of detection and active in B16F10 mouse melanin tumor cell and RAW264.7 cell to the biosynthetic inhibition of melanin, and find that finally above material can be used as the functional activity material of skin whitening cosmetics, food and pharmaceutical composition, thereby finish the present invention.
Disclosure
Technical problem
Therefore, the purpose of this invention is to provide and comprise as the solvent of the extract of the Fructus Pyracanthae Fructus Linderae Glaucae of active component, described extract part or from the skin whitening composition of isolating cyclopentanedione chemical compound of described solvent part or derivant.
Technical scheme
According to an aspect of the present invention, the invention provides the skin whitening composition that comprises as the solvent part of the extract of the Fructus Pyracanthae Fructus Linderae Glaucae of active component or described extract.
In the present invention, the solvent that is used for obtaining from the Fructus Pyracanthae Fructus Linderae Glaucae extract is selected from water, such as methanol or alcoholic acid lower alcohol and above combination, and preferred alcohol.According to the present invention, the extract solution that obtains from extraction, the diluent of extract solution or concentrated solution, the residue that obtains by dry extract solution, all fall in the scope of extract from the material of the thick purification of extract solution with from the material of the purification of extract solution.
In embodiments of the invention, can be prepared as follows extract: pulverized, under room temperature, the Fructus Pyracanthae Fructus Linderae Glaucae of pulverizing immersed with Fructus Pyracanthae Fructus Linderae Glaucae drying, with exsiccant Fructus Pyracanthae Fructus Linderae Glaucae with hot blast in 70% the ethanol three days and follow stirring exudate to be provided, exudate is filtered and the concentrating under reduced pressure filter liquor from the Fructus Pyracanthae Fructus Linderae Glaucae.
In embodiments of the invention, can be prepared as follows solvent part from the extract of Fructus Pyracanthae Fructus Linderae Glaucae: will be suspended in the distilled water from the extract of Fructus Pyracanthae Fructus Linderae Glaucae, and with the normal hexane that comes from non-polar solven (n-Hex), dichloromethane (CH
2Cl
2), ethyl acetate (EtOAc) and n-butyl alcohol (n-BuOH) be the suspension part.
In one embodiment of the invention, be prepared as follows each solvent part: the ethanol extraction of Fructus Pyracanthae Fructus Linderae Glaucae is suspended in the distilled water, uses separatory funnel, be used to normal hexane (n-Hex), dichloromethane (CH from non-polar solven from the extract of Fructus Pyracanthae Fructus Linderae Glaucae
2Cl
2), ethyl acetate (EtOAc) and n-butyl alcohol (n-BuOH) be the extract part, filter and with gained part concentrating under reduced pressure.
According to a further aspect in the invention, the invention provides at least a skin whitening composition that is selected from the chemical compound in the represented chemical compound of following Chemical formula 1 to 10 that comprises as active component:
Chemical formula 4
Chemical formula 7
In order to use in the present invention, can from the Fructus Pyracanthae Fructus Linderae Glaucae, separate and the above chemical compound of purification.Perhaps, can perhaps can synthesize them by commercially available prod acquisition all above-claimed cpds except that chemical compound 10 by known synthetic method.
According to the preferred embodiment of the invention, compositions of the present invention is the cosmetics preparation.
Except extract from the Fructus Pyracanthae Fructus Linderae Glaucae, the solvent of extract partly or from the extract isolated compound also is used as active component, cosmetics compositions of the present invention can comprise conventional cosmetics composition, for example Chang Gui adminicle and carrier, for example antioxidant, stabilizing agent, solubilizing agent, vitamin, coloring agent and aromatic.Above cosmetics compositions can also comprise the skin absorption promoter of the cosmetic result that is used for the enhanced activity composition.
Any preparation that can cosmetics compositions preparation cost of the present invention field is commonly used.For example, it can be mixed with solution, suspension, emulsion, paste, gel, emulsifiable paste, lotion, powder, soap, the cleaning agent that contains surfactant, oil, foundation cream, foundation emulsion, foundation cream wax and spray, but be not limited thereto.The instantiation of preparation comprises astrigent lotion, nutrition washing liquid, nourishing cream, massage cream, essence, eye cream, cleansing cream, cleaning foam, clean water, facial film, spray or powder.
When this compositions is formulated into paste, emulsifiable paste or gel, can be with animal oil, vegetable oil, wax, paraffin, starch, Tragacanth, cellulose derivative, Polyethylene Glycol, silicon, bentonite, silicon dioxide, Talcum or zinc oxide as carrier.
When preparation is the form of powder or spray, can be with lactose, Talcum, silicon dioxide, aluminium hydroxide, calcium silicates or polyamide powder as carrier.Especially, under the situation of spray, can also comprise propellant such as Chlorofluorocarbons (CFCs), propane/butane or dimethyl ether.
For the preparation of solution or emulsion form, can be with solvent, solubilizing agent or emulsifying agent as carrier.The example of carrier comprises: water, ethanol, isopropyl alcohol, ethyl carbonate, ethyl acetate, benzylalcohol, benzyl benzoate, propylene glycol, 1, the fatty acid ester of 3-butyl glycol oil, glycerin fatty ester, Polyethylene Glycol or sorbitan.
Preparation for form of suspension, carrier can comprise the liquid diluent such as water, ethanol or propylene glycol, such as the suspending agent of ethoxylation isooctadecanol, polyoxyethylene sorbitol ester and polyoxyethylene sorbitan esters, microcrystalline Cellulose, aluminium hydroxide oxide (aluminum methahydroxide), bentonite, agar or Tragacanth etc.
For the preparation of the cleaning agent form that contains surfactant, carrier can comprise fatty alcohol sulfate, fatty alcohol ether sulfate, sulfosuccinic acid monoesters, isethionate, imdazole derivatives, methyl tauride, sarcosinate, fatty acyl amidogen ether sulfuric ester, alkyl amido betaine, aliphatic alcohol, fatty glyceride, fatty diglycollic amide, vegetable oil, lanolin derivative or ethoxylated glycerol fatty acid ester etc.
According to the preferred embodiments of the invention, compositions of the present invention is pharmaceutical preparation.
When being formulated as pharmaceutical preparation, compositions of the present invention can comprise pharmaceutically acceptable carrier.The normally used pharmaceutically acceptable carrier in this area can be included in the pharmaceutical composition.The example of the pharmaceutically acceptable carrier that uses in the compositions comprises lactose, glucose, sucrose, Sorbitol, mannitol, starch, arabic gum, calcium phosphate, alginate, gelatin, calcium silicates, microcrystalline Cellulose, polyvinylpyrrolidone, cellulose, water, syrup, methylcellulose, methyl hydroxybenzoate, propyl hydroxybenzoate, Talcum, magnesium stearate and mineral oil, but is not limited thereto.In addition to these, pharmaceutical composition of the present invention can also comprise lubricant, wetting agent, sweeting agent, flavoring agent, emulsifying agent, suspending agent and/or antiseptic.
Can give pharmaceutical composition of the present invention by various oral or parenteral route, for example, oral administration or percutaneous dosing.Yet, preferably by giving pharmaceutical composition by parenteral route, percutaneous dosing particularly, and more preferably by local application.
According to comprise dosage form, administering mode, age, body weight, sex, the multiple factor of the disease of patient situation for the treatment of and diet, administration time, route of administration, excretion rate and reaction sensibility, when pharmaceutical composition of the present invention is used, when spraying or administration, its proper dosage can be different.When making oral formulations, can carry out single dose administration every day or be divided into a plurality of dosage carrying out administration with adult's dosage every day of 5mg/kg to 30mg/kg and adult's dosage every day of being preferably 10mg/kg with the solvent part of the extract of Fructus Pyracanthae Fructus Linderae Glaucae, this extract or from this solvent part isolated compound.For adult's local application, can carry out single dose with dosage every day of 1.0ml to 3.0ml and use and maybe can be divided into five dosage of as many as and use, continue to use at least one month.
According to well known to a person skilled in the art method, pharmaceutical composition of the present invention can be formulated as unit dosage forms with pharmaceutically acceptable carrier and/or excipient and maybe can be included in the multiple-unit container.Under this background, pharmaceutical composition can be formulated as the peroral dosage form such as powder, granule, tablet, capsule, suspension, emulsion, syrup, aerosol etc., such as the topical formulations or the suitable form of any pharmacy of ointment, emulsifiable paste etc., and can comprise dispersant or stabilizing agent.
In the preferred embodiment of the invention, compositions of the present invention is a food formulation.
When the food prepared therefrom preparation, except that as the part of the extract from the Fructus Pyracanthae Fructus Linderae Glaucae of active component, this extract or from this extract isolated compound, compositions of the present invention comprises the composition that preparation food adds usually, for example protein, carbohydrate, lipid, nutrient, flavoring agent and flavorant.Examples of carbohydrates comprises the monosaccharide such as glucose and fructose, and such as the disaccharide of maltose, sucrose, oligosaccharide is such as the polysaccharide of dextrin, cyclodextrin etc. with such as the sugar alcohol of xylitol, Sorbitol, erythritol etc.Flavorant can be natural [thaumatin (thaurmatin), Stevia rebaudiana (Bertoni) Hemsl extract (for example, stevioside A, glycyrrhizin etc.)] and synthetic (glucide, aspartame etc.).
According to other aspects of the invention, the invention provides the represented chemical compound of following Chemical formula 10:
[Chemical formula 1 0]
In the present invention, can be from the Fructus Pyracanthae Fructus Linderae Glaucae and preferred from the bark of Fructus Pyracanthae Fructus Linderae Glaucae the chemical compound of separation chemistry formula 10.
According to other aspects of the invention, the invention provides the method for the chemical compound of separation chemistry formula 10 from the Fructus Pyracanthae Fructus Linderae Glaucae.
[Chemical formula 1 0]
In preferred embodiments, the method for the chemical compound of separation chemistry formula 10 can may further comprise the steps:
The Fructus Pyracanthae Fructus Linderae Glaucae is immersed in the solvent so that the extract from the Fructus Pyracanthae Fructus Linderae Glaucae to be provided, and described solvent is selected from water, C
1To C
4Lower alcohol or its combination;
With hexane, dichloromethane, ethyl acetate and butanols with described Fructus Pyracanthae Fructus Linderae Glaucae extract part, to provide branch other solvent part;
Use hexane and ethyl acetate gradient as eluent, described Fructus Pyracanthae Fructus Linderae Glaucae solvent is partly carried out elementary silica gel column chromatography, so that the chromatography part to be provided; And
The mixture that uses hexane and ethyl acetate carries out purification with the part of elementary silica gel column chromatography by secondary silica gel column chromatography as eluent, so that the polymethoxy phenolic compounds of new Chemical formula 10 to be provided.
In the method for the invention, " Fructus Pyracanthae Fructus Linderae Glaucae " is meant the bark of Fructus Pyracanthae Fructus Linderae Glaucae.
In the present invention, can use and be selected from following solvent and obtain Fructus Pyracanthae Fructus Linderae Glaucae extract: water, such as methanol or alcoholic acid C
1To C
4Lower alcohol or above combination, or preferably use ethanol.In the present invention, extract comprise be selected from following any: diluent by extracting the extract solution that obtains, extract solution or concentrated solution, the residue that obtains by dry extract solution, from the material of the thick purification of extract solution or from the material of the purification of extract solution.
According to embodiment of the present invention, can following acquisition Fructus Pyracanthae Fructus Linderae Glaucae extract: pulverized, under room temperature, the Fructus Pyracanthae Fructus Linderae Glaucae of pulverizing immersed with Fructus Pyracanthae Fructus Linderae Glaucae drying, with exsiccant Fructus Pyracanthae Fructus Linderae Glaucae with hot blast in 70% the ethanol three days and follow stirring exudate to be provided, exudate is filtered and the concentrating under reduced pressure filter liquor.
In embodiments of the invention, can be prepared as follows the solvent part of Fructus Pyracanthae Fructus Linderae Glaucae extract: Fructus Pyracanthae Fructus Linderae Glaucae extract is suspended in the distilled water, uses normal hexane (n-Hex), dichloromethane (CH from non-polar solven
2Cl
2), ethyl acetate (EtOAc) and n-butyl alcohol (n-BuOH) be the suspension part.
In embodiments of the invention, can be prepared as follows each solvent part of Fructus Pyracanthae Fructus Linderae Glaucae extract: the ethanol extraction of Fructus Pyracanthae Fructus Linderae Glaucae is suspended in the distilled water, uses separatory funnel, be used to normal hexane (n-Hex), dichloromethane (CH from non-polar solven
2Cl
2), ethyl acetate (EtOAc) and n-butyl alcohol (n-BuOH) be the extract part, filter with concentrating under reduced pressure to provide branch other solvent part.
Useful effect
Comprise cyclopentanedione or derivatives thereof as active component based on the skin whitening composition from extract, part or the chemical compound of Fructus Pyracanthae Fructus Linderae Glaucae, what it showed is higher than conventional skin whitener arbutin to the synthetic inhibition activity of melanin.
Description of drawings
Fig. 1 schematically illustrates the flow chart that obtains the process of ethanol extraction and solvent part thereof from the Fructus Pyracanthae Fructus Linderae Glaucae.
Fig. 2 shows the HPLC analytical data of Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction of the present invention.
Fig. 3 shows the HPLC analytical data of the normal hexane part that is derived from Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction.
Fig. 4 shows the HPLC analytical data of the dichloromethane part that is derived from Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction.
Fig. 5 shows the HPLC analytical data of the ethyl acetate part that is derived from Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction.
Fig. 6 shows the HPLC analytical data of the n-butyl alcohol part that is derived from Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction.
Fig. 7 shows the HPLC analytical data of the water section that is derived from Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction.
Fig. 8 shows the HPLC data that are used for chemical compound 1 quantitative analysis.
Fig. 9 shows chemical compound 1
1H and
13The C-NMR spectrum.
Figure 10 shows the HPLC data that are used for chemical compound 2 quantitative analyses.
Figure 11 shows chemical compound 2
1H and
13The C-NMR spectrum.
Figure 12 shows the HPLC data that are used for chemical compound 3 quantitative analyses.
Figure 13 shows chemical compound 3
1H and
13The C-NMR spectrum.
Figure 14 shows the HPLC data that are used for chemical compound 4 quantitative analyses.
Figure 15 shows chemical compound 4
1H and
13The C-NMR spectrum.
Figure 16 shows the HPLC data that are used for chemical compound 5 quantitative analyses.
Figure 17 shows chemical compound 5
1H and
13The C-NMR spectrum.
Figure 18 shows the HPLC data that are used for chemical compound 6 quantitative analyses.
Figure 19 shows chemical compound 6
1H and
13The C-NMR spectrum.
Figure 20 shows the HPLC data that are used for chemical compound 7 quantitative analyses.
Figure 21 shows chemical compound 7
1H and
13The C-NMR spectrum.
Figure 22 shows the HPLC data that are used for chemical compound 8 quantitative analyses.
Figure 23 shows chemical compound 8
1H and
13The C-NMR spectrum.
Figure 24 shows the HPLC data that are used for chemical compound 9 quantitative analyses.
Figure 25 shows chemical compound 9
1H and
13The C-NMR spectrum.
Figure 26 is the figure of demonstration with the vigor of the B16F10 cell of Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and solvent section processes thereof.Data are three mean+SD of measuring.
The inhibition active figure of Figure 27 for showing that Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and solvent thereof part generates melanin in the B16F10 cell.Data are three mean+SD of measuring.
Figure 28 is for showing the inhibition active figure of Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and solvent thereof part to tryrosinase in the B16F10 cell.Data are three mean+SD of measuring.
Figure 29 is the figure of demonstration with the vigor of the B16F10 cell of Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone processing.Data are three mean+SD of measuring.
Figure 30 is the figure of demonstration with the vigor of the B16F10 cell of Radix Linderae cyclopentenes diketone methyl ether (methyllinderone) processing.Data are three mean+SD of measuring.
Figure 31 is the figure of demonstration with the vigor of the B16F10 cell of Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative (kanakugiol) processing.Data are three mean+SD of measuring.
The inhibition active figure of Figure 32 for showing that Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone generates melanin in the B16F10 cell.Data are three mean+SD of measuring.
The inhibition active figure of Figure 33 for showing that Radix Linderae cyclopentenes diketone methyl ether generates melanin in the B16F10 cell.Data are three mean+SD of measuring.
The inhibition active figure of Figure 34 for showing that Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative generates melanin in the B16F10 cell.Data are three mean+SD of measuring.
Figure 35 is for showing the inhibition active figure of Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone to tryrosinase in the B16F10 cell.Data are three mean+SD of measuring.
Figure 36 is for showing the figure use from the vigor of the B16F10 cell of the compound treatment of the isolating Chemical formula 10 of Fructus Pyracanthae Fructus Linderae Glaucae.
Figure 37 is for showing the active figure of inhibition that melanin the B16F10 cell is generated from the chemical compound of the isolating Chemical formula 10 of Fructus Pyracanthae Fructus Linderae Glaucae.
Figure 38 shows from the chemical compound of the isolating Chemical formula 10 of the Fructus Pyracanthae Fructus Linderae Glaucae inhibition activity to tryrosinase, TRP-1 and TRP-2 gene expression the B16F10 cell.C and Arb represent contrast and arbutin.
The mode of invention
Can understand the present invention better by following examples, following examples are to illustrate for example, and should not be construed as restriction the present invention.
Embodiment 1: the preparation of Fructus Pyracanthae Fructus Linderae Glaucae extract
For the vegetable material that uses, obtain the Fructus Pyracanthae Fructus Linderae Glaucae by living resources extract storehouse, Jizhou (Jeju Bio-Resource Extract Bank).
At first, with flowing water washing tree material (Fructus Pyracanthae Fructus Linderae Glaucae), with hot blast in 40 ℃ dry three days and use the pulverizer pulverizing down.Under room temperature, the exsiccant material of 200g was immersed in 70% ethanol three days and follow stirring so that exudate to be provided.This exudate is filtered.To ooze out and the filter process triplicate.The gained filter liquor is carried out concentrating under reduced pressure, thereby obtain the ethanol extraction of 60g.
Embodiment 2: separate the solvent part from Fructus Pyracanthae Fructus Linderae Glaucae extract
Be used for the isolating solvent of part in this embodiment available from Merk Co., Junsei Co. and Hyman Co..
The ethanol extraction of Fructus Pyracanthae Fructus Linderae Glaucae is carried out following solvent partly to be separated:
At first, the 42g in the 60g Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction (70% ethanol extraction) of preparation among the embodiment 1 is suspended in the distilled water, and use separatory funnel, utilize normal hexane (n-Hex), dichloromethane (CH
2Cl
2), ethyl acetate (EtOAc) carries out part with n-butyl alcohol (n-BuOH) and separates.Filter subsequently and concentrating under reduced pressure, the amount that obtains each solvent part is as follows: be 8.56g, use CH with n-Hex
2Cl
2For 1.47g, be 4.14g, be 10.2g and use H with n-BuOH with EtOAc
2O is 14.58g (referring to Fig. 1).
Each extract and part are carried out the HPLC analysis, and in Fig. 2 to 7, provide the result.
In subsequent experimental, hexane part, dichloromethane part or the ethyl acetate of powder type are partly dissolved in 100% ethanol, simultaneously butanols part or water section are dissolved in 100% ethanol: 1 * phosphate buffer (PBS, pH 7.4) be in 1: 1 the mixture, before using, filter subsequently.
Embodiment 3: separate and authenticating compound from the solvent part of Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction
Use kieselguhr, utilize dichloromethane, ether, ethyl acetate and acetone that ethyl acetate part layer (4.0g) is carried out part again to separate.Use chloroform and methanol the ether part in the gained part to be divided into subdivision on purification on normal-phase silica gel as launching solvent.Use purification on normal-phase silica gel, utilize chloroform and methanol that part-5 wherein is further purified.Respectively from part-1 and separating compound 1 and 2-3 partly.Use preparation HPLC, utilize 30% methanol solution that part-2 is further purified, with separating compound 3 and 4.
Use purification on normal-phase silica gel, utilize the solvent gradient of hexane and ethyl acetate that dichloromethane part layer (2.53g) is further divided into 10 subdivisions.Use purification on normal-phase silica gel, utilize hexane and ethyl acetate to incite somebody to action part-2 purification with separating compound 5 as developing solvent.Use purification on normal-phase silica gel, utilize chloroform and methanol as launching solvent separating compound 6 from part-5.To part-6 and part-7 recrystallization respectively so that chemical compound 7 and 8 to be provided.Use chloroform and methanol part-8 to be carried out the purification on normal-phase silica gel chromatography so that two parts to be provided as launching solvent.Part-8-2 wherein is used for separating compound 9.When analyzing by HPLC and NMR, it is pure being proved to be by nine kinds of chemical compounds of above acquisition.
In brief, the leaf with the Fructus Pyracanthae Fructus Linderae Glaucae of 70% ethanol extraction 200g has obtained the 60g extract, separates the kind chemical compound coldest days of the year end from the 60g extract.
In following table 1, summed up the yield of separated portions and chemical compound.
The yield of the extract of table 1. Fructus Pyracanthae Fructus Linderae Glaucae and part thereof
| Material | Yield (%) |
| The normal hexane part | 20.400 |
| The dichloromethane part | 6.000 |
| The ethyl acetate part | 9.800 |
| The n-butyl alcohol part | 24.200 |
| Water section | 34.700 |
| |
0.600 |
| |
0.060 |
| |
0.002 |
| Chemical compound 4 | 0.720 |
| |
0.020 |
| |
0.030 |
| Chemical compound 7 | 0.240 |
| |
0.090 |
| |
0.110 |
(Bruker Co.500MHz NMR) obtains chemical compound to use the NMR instrument
1H,
13C, COSY, HMQC, HMBC spectrum, and analyze to determine the structure of chemical compound.Carry out high performance liquid chromatography (HPLC) and be used for quantitative analysis.
In Fig. 8 to 25, provided chemical compound HPLC result and
1H,
13The C-NMR spectrum.
Therefore, chemical compound 1 is accredited as the Quercetin with following Chemical formula 1:
[Chemical formula 1]
[Chemical formula 2]
[chemical formula 3]
Chemical compound 4 is accredited as the Quercetin-3-O-arabinofuranosyl glycosides with following chemical formula 4:
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
Chemical compound 7 is accredited as the Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone with following chemical formula 7:
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
EXPERIMENTAL EXAMPLE 1: the antioxidant activity of Fructus Pyracanthae Fructus Linderae Glaucae extract and part is measured
1) 1,1-diphenyl-2-picryl hydrazine (DPPH) free radical scavenging is measured
Measure electron donation according to the Blosis method by the DPPH free radical scavenging.With the sample aliquot of variable concentrations in the ethanol is every hole 100 μ L, and the 0.4mM DPPH solution of equal volume is also added in 96 orifice plates, leaves standstill under room temperature 10 minutes, measures absorbance then under 517nm.Butylatedhydroxyanisole (BHA) is used as positive control.Calculate the DPPH free radical scavenging activity and the absorbance that activity is expressed as DPPH is reduced the concentration (IC of 50% o'clock sample according to following formula 1
50).
DPPH free radical scavenging activity (%)=(A
Contrast-A
Sample)/A
Contrast* 100
Wherein
A
Sample=comprise the solution absorbency of sample,
A
Contrast=comprise ethanol and do not comprise the solution absorbency of sample.
The measurement result that has shown the antioxidant activity of Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and further part thereof in the following table 2.For ethanol extraction and further part thereof, the free radical scavenging activity of DPPH increases in dose-dependent mode.In further part, ethyl acetate partly makes DPPH show to be higher than the free radical scavenging activity that contrasts BHA.Except dichloromethane part and hexane part, observe other parts and show remarkable high activity, IC
50Value is 7.43 (ethyl acetate), 16.88 (ethanol), 18.54 (butanols) and 66.77 μ g/mL (water) (table 2).
2) xanthine oxidase inhibitory activity and superoxides are removed active mensuration
With allopurinol (Sigma) in contrast, the absorbance that increases down by 290nm is measured the uric acid generation by xanthine oxidase.Use tetrazole indigo plant (NBT) reducing process under 560nm, to measure the amount of superoxides.Sample, 0.5mM xanthine and 1mM EDTA by each concentration of dissolving in 100 μ L 200mM phosphate buffers (pH 7.5) come preparation feedback solution.In order to induce the generation of uric acid, the 50mU/ml xanthine oxidase is added in the reaction solution.Remove activity in order to measure superoxides, 0.5mM NBT is added in the reaction solution.Xanthine oxidase inhibitory activity and superoxides are removed active be expressed as the respectively uric acid of formation and the concentration (IC that superoxides reduces by 50% o'clock sample
50).Each sample is measured and is calculated the meansigma methods of measuring for three times in triplicate.
Shown in the table 2 that the ethanol extraction of Fructus Pyracanthae Fructus Linderae Glaucae and the xanthine oxidase inhibitory activity and the superoxide radical of further part thereof remove active measurement result.All Fructus Pyracanthae Fructus Linderae Glaucae ethanol extractions and further part thereof show the xanthine oxidase inhibitory activity that concentration relies on mode.Although at hexane part (＞1000 μ g/mL) and dichloromethane part (IC
5086.21 detect low activity μ g/mL), but other parts show high activity, the IC of suppressing
50Value is 5.55 μ g/mL to 9.79 μ g/mL (table 2).Remove activity for superoxides, detect IC
50Value is 16.86 μ g/mL (ethyl acetate parts), and this comparison is according to allopurinol (IC
50=3.82 μ g/mL) low slightly (table 2).
As previous report ground, lipid oxidation and oxidative stress and removing active oxygen are relevant with stoping, antioxidant activity causes prevention or slow down aging or blocking-up cancer and cardiopathic generation or progress, and has application prospect in a plurality of fields that comprise food industry, pharmaceutical industries and cosmetics industry.Therefore, consider the antioxidant activity of Fructus Pyracanthae Fructus Linderae Glaucae, it can be used in and prevents esoteric various oxidative stress and disease.
Table 2
EXPERIMENTAL EXAMPLE 2: the cytotoxicity MTT of Fructus Pyracanthae Fructus Linderae Glaucae extract and part measures
Use the B16F10 mouse melanin tumor cell of buying from American type culture collection (ATCC) in the present embodiment.At 5%CO
2In the incubator under 37 ℃ contain 10% hyclone (FBS, Gibco), cultivate the B16F10 cell among the DMEM (Gibco) of 1% antibiotic-antifongin (Gibco), L-glutaminate and sodium bicarbonate.In addition, buy RAW 264.7 cells of mouse macrophage from KCLB (Korea S cell line storehouse), and at 5%CO
2In the DMEM (Gibco) that is containing 10%FBS, 100 units/mL penicillin and 100 μ g/mL streptomycins under 37 ℃, cultivate in the incubator.
In 24 orifice plates with 2 * 10
4The density of cells/well inoculation B16F10 cell and at 5%CO
2Cultivated 24 hours down in 37 ℃ in the incubator, hatched 72 hours with the sample of every hole 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL concentration then.The 2mg/mL MTT of 200 μ L is added into cell.After hatching 4 hours under the same conditions, culture medium removed and with PBS with twice of cell washing.In every hole, add the DMSO of 200 μ L, then by ELISA analyzer (μ Quant, USA) absorbance under the mensuration 570nm.
In order to detect the influence of Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and further part thereof, the extract of cell and 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL variable concentrations and part were hatched three days to B16F10 cell line vigor.Then, measure cell viability by MTT.As shown in Figure 2, under the concentration of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL of extract and part, observe the 81%-103% that cell viability is the control cells vigor, and therefore high slightly or be lower than contrast slightly.Because they do not cause the remarkable change of cell viability when using the concentration of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL, Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction then of the present invention and further part thereof are low cytotoxicity and the composition that therefore can be used as skin whitener.
EXPERIMENTAL EXAMPLE 3: Fructus Pyracanthae Fructus Linderae Glaucae extract and part are for the active mensuration of the biosynthetic inhibition of melanin
In 24 orifice plates with 2 * 10
4The density of cells/well inoculation B16F10 cell and at 5%CO
2Cultivated 24 hours down in 37 ℃ in the incubator, hatched three days with the sample of every hole 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL concentration subsequently.Culture medium removed and with PBS with twice of cell washing.In every hole, add the 1N NaOH of 500 μ L, under 56 ℃, hatch 30 minutes subsequently with dissolved cell.(μ Quant USA) reads absorbance under the 405nm to use the ELISA analyzer.
Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and further part thereof are applied to cell after three days with the variable concentrations of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL, measure it to the biosynthetic inhibition activity of melanin, the Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction of above-mentioned concentration and further part thereof are all observed pair cell in EXPERIMENTAL EXAMPLE 2 be avirulent.As shown in Figure 3, when using the concentration of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL, Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction shows 0.6%, 7.9%, 31.6% and 45.8% melanin inhibition respectively, and when the known contrast arbutin as skin whitener of the concentration of using 100 μ g/mL, arbutin is 31% to the inhibition that melanin produces.Simultaneously, concentration be the further part of 100 μ g/mL show respectively 33%, 49%, 24%, 31% and 28% to the biosynthetic inhibition of melanin, this be better than or similar in appearance to the contrast the inhibition activity.Because Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction or its further part have to melanin biosynthetic good inhibition activity and low cytotoxicity, so they can be used as the natural skin brightening agent.
EXPERIMENTAL EXAMPLE 4: Fructus Pyracanthae Fructus Linderae Glaucae extract and part are to the active mensuration of the inhibition of tryrosinase
In 24 orifice plates with 2 * 10
4The density of cells/well inoculation B16F10 cell and at 5%CO
2Cultivated 24 hours down in 37 ℃ in the incubator, hatched three days with the sample of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL concentration subsequently.After culture medium removed, with twice of cell washing and centrifugal, add lysis buffer (0.1M sodium phosphate buffer, 0.2mM PMSF, 1% triton x-100) to cell precipitation group then so that cell precipitation group to be provided with PBS.Cell in the lysis buffer placed carry out lysis on ice.After centrifugal, supernatant is used to measure enzymatic activity.Each sample is added in the reaction buffer (12.5mM L-DOPA, 1.5mM L-tyrosine, 67mM sodium phosphate buffer (pH6.8)) and under 37 ℃, hatched 1 hour, then, (μ Quant USA) measures absorbance down in 405nm to use the ELISA analyzer.
After Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and further part processing, melanin terminal level's reduction has reflected the active reduction that participates in the synthetic enzyme of melanin.As shown in Figure 4, when with the sample treatment B16F10 cell of the variable concentrations of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL in the time of three days, ethanol extraction shows the inhibition to tryrosinase up to 13.9%, 15.9%, 36.8% and 42.5% respectively, and the contrast arbutin is 19% to the inhibition of tryrosinase.Under the concentration of 100 μ g/mL, part is respectively 40%, 21%, 19%, 41% and 26% to the inhibition of tryrosinase, and this demonstrates the antityrosinase activity that is better than contrasting.The biosynthetic reduction of the melanin that Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction and further part cause among the data acknowledgement B16F10 is mainly owing to they inhibition activity to tryrosinase.
EXPERIMENTAL EXAMPLE 5: use MTT to measure the cytotoxicity of the cyclopentanedione chemical compound in measurement Fructus Pyracanthae Fructus Linderae Glaucae source
1) Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone (chemical compound 1)
In order to detect the influence of the one matter that is separated into Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone to B16F10 cell line vigor, this chemical compound of cell and 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL variable concentrations was hatched three days, measure cell viability by MTT subsequently.As shown in figure 29, under the caffeic acid concentration of 1.25,2.5,5 and 10 μ g/mL, observe the 96%-106% that cell viability is the control cells vigor, and therefore high slightly or low slightly and contrast.Because do not cause the remarkable change of cell viability when using the one matter that is separated into Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone of the present invention with the concentration of 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL, therefore the one matter that is separated into Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone of the present invention is low cytotoxicity and the composition that therefore can be used as skin whitener.
2) Radix Linderae cyclopentenes diketone methyl ether (chemical compound 2)
In order to detect the influence of the one matter that is separated into Radix Linderae cyclopentenes diketone methyl ether to B16F10 cell line vigor, this chemical compound of cell and 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL variable concentrations was hatched three days, measure cell viability by MTT subsequently.As shown in figure 30, under the caffeic acid concentration of 1.25,2.5,5 and 10 μ g/mL, observe the 93%-99% that cell viability is the control cells vigor, and therefore be lower than contrast slightly.Because do not cause the remarkable change of cell viability when using the one matter that is separated into Radix Linderae cyclopentenes diketone methyl ether of the present invention with the concentration of 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL, therefore the one matter that is separated into Radix Linderae cyclopentenes diketone methyl ether of the present invention is low cytotoxicity and the composition that therefore can be used as skin whitener.
3) Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative (chemical compound 3)
In order to detect the influence of the one matter that is separated into Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative to B16F10 cell line vigor, this chemical compound of cell and 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL variable concentrations was hatched three days, measure cell viability by MTT subsequently.As shown in figure 31, under the caffeic acid concentration of 1.25,2.5,5 and 10 μ g/mL, observe the 91%-96% that cell viability is the control cells vigor, and therefore be lower than contrast slightly.Because do not cause the remarkable change of cell viability when using the one matter that is separated into Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative of the present invention with the concentration of 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL, therefore the one matter that is separated into Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative of the present invention is low cytotoxicity and the composition that therefore can be used as skin whitener.
EXPERIMENTAL EXAMPLE 6: the cyclopentanedione chemical compound in Fructus Pyracanthae Fructus Linderae Glaucae source is to the active mensuration of the biosynthetic inhibition of melanin
1) Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone (chemical compound 1)
For detect be separated into Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone one matter to the biosynthetic inhibitory action of melanin in the B16F10 cell line, the melanin biosynthesis was hatched three days and analyzed to this chemical compound of cell and 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL variable concentrations.
Shown in figure 32, when using Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone with 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL, it shows the inhibition up to 3%, 19%, 37% and 53% respectively, and when the concentration use with 50 μ g/mL was known as the contrast arbutin of skin whitener, biosynthetic inhibition was 23.5% to arbutin to melanin.Compare with the contrast arbutin, this chemical compound has stronger also can be used as natural skin whitener to biosynthetic inhibitions of melanin is active.
2) Radix Linderae cyclopentenes diketone methyl ether (chemical compound 2)
For detect be separated into Radix Linderae cyclopentenes diketone methyl ether one matter to the biosynthetic inhibitory action of melanin in the B16F10 cell line, the melanin biosynthesis was hatched three days and analyzed to this chemical compound of cell and 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL variable concentrations.
As shown in figure 33, when using Radix Linderae cyclopentenes diketone methyl ether with 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL, it shows the inhibition up to 1%, 14%, 38% and 62% respectively, and when the concentration use with 50 μ g/mL was known as the contrast arbutin of skin whitener, biosynthetic inhibition was 23.5% to arbutin to melanin.Compare with the contrast arbutin, this chemical compound has stronger also can be used as natural skin whitener to biosynthetic inhibitions of melanin is active.
3) Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative (chemical compound 3)
For detect be separated into Fructus Pyracanthae Fructus Linderae Glaucae chalcone derivative one matter to the biosynthetic inhibitory action of melanin in the B16F10 cell line, respectively the melanin biosynthesis was hatched three days and analyzed to this chemical compound of cell and 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL variable concentrations.
As shown in figure 34, when using Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone with 1.25 μ g/mL, 2.5 μ g/mL, 5 μ g/mL and 10 μ g/mL, it shows the inhibition up to 2%, 16%, 29% and 61% respectively, and when the concentration use with 50 μ g/mL was known as the contrast arbutin of skin whitener, biosynthetic inhibition was 23.5% to arbutin to melanin.Compare with the contrast arbutin, this chemical compound has stronger also can be used as natural skin whitener to biosynthetic inhibitions of melanin is active.
EXPERIMENTAL EXAMPLE 7: the cyclopentanedione chemical compound in Fructus Pyracanthae Fructus Linderae Glaucae source is to the active mensuration of the inhibition of tryrosinase
As shown in figure 35, when with the sample treatment B16F10 cell of 12.5 μ g/mL, 25 μ g/mL, 50 μ g/mL and 100 μ g/mL variable concentrations in the time of three days, Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone shows 10%, 17%, 26.4% and 48.9% the inhibition to tryrosinase respectively, and the contrast arbutin is 19% to the inhibition of tryrosinase.Based on these data, think that the biosynthetic reduction of melanin is mainly owing to its inhibition activity to tryrosinase from the B16F10 that the isolating Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone of Fructus Pyracanthae Fructus Linderae Glaucae causes.
Embodiment 4: from leaf and the extract of bark and the preparation of solvent part thereof of Fructus Pyracanthae Fructus Linderae Glaucae
To be used as vegetable material by the Fructus Pyracanthae Fructus Linderae Glaucae that living resources extract storehouse, Jizhou obtains.Extracting solvent is the product of Merk Co..
With the fresh leaf of flowing water washing Fructus Pyracanthae Fructus Linderae Glaucae, with hot blast 40 ℃ dry three days down, and use pulverizer to pulverize.Under room temperature, the drying material of 200g immersed in 70% ethanol three days and follow stirring, so that exudate to be provided.This exudate is filtered, and will ooze out and the filter process triplicate.With gained filter liquor concentrating under reduced pressure, to obtain the 60g ethanol extraction.42g in the 60g Fructus Pyracanthae Fructus Linderae Glaucae ethanol extraction (70% ethanol extraction) is suspended in the distilled water, and with normal hexane (n-Hex), dichloromethane (CH
2Cl
2), ethyl acetate (EtOAc) carries out part with n-butyl alcohol (n-BuOH) and separates.Filter and vacuum concentration, the amount of the extract of acquisition is as follows: use n-Hex to be 8.56g, use CH
2Cl
2For 1.47g, use EtOAc as 4.14g, use n-BuOH to be 10.2g and use H
2O is 14.58g.
In the mode identical with leaf, the dry and pulverizing with the bark of Fructus Pyracanthae Fructus Linderae Glaucae.Under the same conditions, the sample that uses 560g to pulverize obtains 70% ethanol extraction of 68.2g and carries out part with solvent and separate.
Embodiment 5: separate and authenticating compound from the solvent part of Fructus Pyracanthae Fructus Linderae Glaucae
The filler that uses in the separation of this embodiment is purification on normal-phase silica gel 60 (0.063-0.200mm, Merck Co.).Analytical tool is for being equipped with XTerra
The HPLC (Alliance2695, Waters Co.) of C18 3.5 μ m 4.6 * 100mm.The detector that PDA Model 2998 usefulness of Waters are performed an analysis.Use the solvent and the reagent of HPLC level.NMR (nuclear magnetic resonance, NMR) device that is used for structural analysis is the JNM-LA500 of Burker (German Co.).With methanol-d
4And chloroform-d
1Solvent as the NMR analysis.
The solvent gradient of use purification on normal-phase silica gel, utilizing hexane/ethyl acetate (v/v) is further divided into 10 subdivisions with the dichloromethane part layer (2.5g) that obtains from the leaf of Fructus Pyracanthae Fructus Linderae Glaucae among the embodiment 4.Part-6 wherein is further purified so that chemical compound 10 (21.8mg) to be provided by recrystallization.
In addition, the solvent gradient of use purification on normal-phase silica gel, utilizing hexane/ethyl acetate (v/v) is further divided into 8 subdivisions with the dichloromethane part layer (7g) that obtains from the bark of Fructus Pyracanthae Fructus Linderae Glaucae among the embodiment 4.Further place purification on normal-phase silica gel (hexane/ethyl acetate is 3/2) so that part to be provided part-2 wherein.Part-2-2 wherein is used for separating compound 12 (59.6mg), simultaneously separating compound 11 from part-2-3.
By the structure of HPLC, NMR (1D, 2D NMR) and LR/HR FAB-MS analysis of compounds 10 to 12, and analyze the purity and the content of chemical compound 10 to 12 in the ethanol extraction by HPLC.
As a result, chemical compound 10 is accredited as Ganoderma lucidum (Leyss. Ex Fr.) Karst. ketone, is cyclopentanedione; Chemical compound 11 is accredited as Radix Linderae cyclopentenes diketone methyl ether, also is cyclopentanedione; Chemical compound 12 is accredited as the cyclopentanedione derivant by the modification of following Chemical formula 10 expression, the noval chemical compound (N2) that it is not reported before being.The IUPAC name of this noval chemical compound is called 2,3,4,5-tetramethoxy-6-(1-methoxyl group-3-phenylpropyl) phenol], and be called as Jizhou-Polymethoxylated-phenol.The 1D and the 2D NMR data of chemical compound 12 are provided in following table 3.
[Chemical formula 1 0]
Character:
1) IUPAC name: 2,3,4,5-tetramethoxy-6-(1-methoxyl group-3-phenylpropyl) phenol;
2) color: bottle green;
3) abnormal smells from the patient: slight putrid abnormal smells from the patient;
4) dissolubility: be dissolved in organic solvent such as methanol, acetone, chloroform etc.;
5) only be distributed in the bark of Fructus Pyracanthae Fructus Linderae Glaucae;
6) common name: Jizhou-Polymethoxylated-phenol.
The 1D of table 3. chemical compound 12 and 2D NMR data
In following table 4, summed up the yield of the chemical compound of ethanol extraction, solvent part and Chemical formula 10 from the leaf of Fructus Pyracanthae Fructus Linderae Glaucae and bark.
Table 4
As shown in table 4, the yield of chemical compound in bark of finding Chemical formula 10 be up to 0.71%, and do not find this chemical compound in leaf.
To be dissolved in the DMSO fully from the isolating unification compound of Fructus Pyracanthae Fructus Linderae Glaucae, and filter to be used for subsequent experimental.
EXPERIMENTAL EXAMPLE 8: the Cytotoxic MTT of the chemical compound of Chemical formula 10 measures
According to following, the noval chemical compound of not reporting so far carried out toxicity detect in B16F10 cell line.
Use the B16F10 mouse melanin tumor cell of buying from American type culture collection (ATCC) in the present embodiment.At 5%CO
2In the incubator, under 37 ℃, contain 10% hyclone (FBS, Gibco), cultivate the B16F10 cell among the DMEM (Gibco) of 1% antibiotic-antifongin (Gibco), L-glutaminate and sodium bicarbonate.
In 24 orifice plates with 2 * 10
4The density inoculation B16F10 cell of cells/well, and at 5%CO
2Cultivated 24 hours down in 37 ℃ in the incubator, hatched 72 hours with the sample of 5 μ g/mL, 10 μ g/mL, 20 μ g/mL and 30 μ g/mL concentration then.The 2mg/mL MTT of 200 μ L is added into cell.After hatching 4 hours under the same conditions, culture medium removed and with PBS with twice of cell washing.In every hole, add the DMSO of 200 μ L, utilize ELISA analyzer (μ Quant, USA) absorbance under the mensuration 570nm then.
As shown in figure 36, under the concentration of 5 μ g/mL, 10 μ g/mL, 20 μ g/mL and 30 μ g/mL of extract and part, observe the 97%-103% that cell viability is the control cells vigor, and therefore high slightly or be lower than contrast slightly.Owing to do not cause the remarkable change of cell viability when using the chemical compound of Chemical formula 10 of the present invention with the concentration of 5 μ g/mL, 10 μ g/mL, 20 μ g/mL and 30 μ g/mL, therefore the chemical compound of Chemical formula 10 of the present invention is low cytotoxicity and the composition that therefore can be used as skin whitener.
EXPERIMENTAL EXAMPLE 9: the chemical compound of Chemical formula 10 is to the active mensuration of the biosynthetic inhibition of melanin
In 24 orifice plates with 2 * 10
4The density inoculation B16F10 cell of cells/well, and at 5%CO
2Cultivated 24 hours down in 37 ℃ in the incubator, hatched three days with sample subsequently.Culture medium removed and with PBS with twice of cell washing.In every hole, add the 1N NaOH of 500 μ L,, under 56 ℃, hatch 30 minutes with dissolved cell, using ELISA analyzer (μ Quant, USA) absorbance under the mensuration 405nm then.
Therefore, as shown in figure 37, when using noval chemical compound of the present invention with the concentration of 5 μ g/mL, 10 μ g/mL, 20 μ g/mL and 30 μ g/mL, it shows 19%, 32%, 51% and 59% the biosynthetic inhibition of melanin respectively, and when using known contrast arbutin as skin whitener with the concentration of 50 μ g/mL, biosynthetic inhibition is 33.6% to arbutin to melanin.Because noval chemical compound of the present invention has for contrasting the active to the biosynthetic good inhibition of melanin of 2 times of arbutin, therefore can be used as the natural skin brightening agent.
EXPERIMENTAL EXAMPLE 10: the active mensuration of inhibition that the chemical compound of Chemical formula 10 is expressed the mRNA that is responsible for the biosynthetic gene of melanin
Use the B16F10 mouse melanin tumor cell of buying from American type culture collection (ATCC) in the present embodiment.At 5%CO
2In the incubator, under 37 ℃, contain 10% hyclone (FBS, Gibco), cultivate the B16F10 cell among the DMEM (Gibco) of 1% antibiotic-antifongin (Gibco), L-glutaminate and sodium bicarbonate.
After the cultivation, with PBS washed twice or three times, and (Invitrogen, USA) pair cell carries out total RNA and separates to use TRIzol reagent with cell.Mix centrifugal then (12,000rpm, 15 minutes) with cell homogenization and with chloroform with TRIzol-reagent.Add the isopropyl alcohol of equal volume in supernatant, centrifugal then (12,000rpm, 10 minutes) are with precipitated rna.With the washing with alcohol RNA precipitate that 75% pyrocarbonic acid diethyl ester (DEPC) is handled, be dried and be dissolved in the water that DEPC handles.Determine the amount of RNA by the absorbance under the measurement 260nm.With A260/A280nm ratio is that unique RNA component of 1.6 to 1.9 is used for reverse transcription.By means of Improm-II
TM(Promega USA) carries out cDNA and synthesizes cDNA test kit (kit).In this process, at 1 RNA of unit enzyme inhibitor and Improm-II
TMUnder the existence of reverse transcription (2U), the isolating total RNA of 1 μ g, widow's (dT) primer and dNTP (0.5 μ M) in 25 ℃ of heating 5 minutes, were heated 60 minutes down at 37 ℃ then, stopped reverse transcription in 10 minutes by heating down then at 70 ℃, thus synthetic cDNA.By polymerase chain reaction (PCR) from synthetic cDNA amplification tryrosinase, TRP-1, TRP-2 and beta-actin.For this process, with the synthetic cDNA of 1 μ L, 4 μ M 5 '-and 3 '-primer, 10 * buffer (10mM Tris-HCl, pH 8.3,50mM KCl, 0.1% triton x-100), 250 μ M dNTP, 25mM MgCl
2With 1 Taq of unit polymerase (Promega USA) mixes with deionized water forming the cumulative volume of 25 μ L, and with it at the enterprising performing PCR of Perkin-Elmer thermal cycler.PCR carries out 20 to 25 circulations, and each circulation is: 94 ℃/30 seconds, 50 ℃-55 ℃/45 seconds and 72 ℃/45 seconds.Thus obtained PCR product is carried out electrophoresis and use ethidium bromide staining on 1.2% agarose gel to show particular bands.
In melanocyte, the NO that keratinocyte produces in response to the UV irradiation increases melanin by the cGMP approach and generates.In addition, known melanocyte can increase the expression of tryrosinase and TRP-1, and induces the expression of tryrosinase mRNA.Whether come from the inhibition that mRNA is expressed in order to detect the inhibitory action that melanin the B16F10 mouse melanin tumor cell is generated from the isolating unification compound of Fructus Pyracanthae Fructus Linderae Glaucae, thereby carry out RT-PCR.The known TRP-1 that plays an important role in melanin generates and the expression of TRP-2 and tyrosinase cdna are suppressed.
In this context, as shown in figure 38, tryrosinase and TRP-1 mRNA level reduce in the mode that concentration relies on.In the synthetic process of melanin, it is reported that the function of TRP-2 is that dopachrome is converted into carboxylic acid derivant 5,6-dihydroxy indole-2-carboxylic acid (DHICA).Yet the expression of observing TRP-2 mRNA remains on constant level, and is irrelevant with sample concentration.
Therefore,, find to express by the mRNA that reduces tryrosinase and TRP-1 and suppress melanin and generate, this mechanism and TRP-2 have nothing to do (Figure 38) from the isolating new chemical compound of Fructus Pyracanthae Fructus Linderae Glaucae.In a word, more than the data acknowledgement of Huo Deing has from the isolating new chemical compound of Fructus Pyracanthae Fructus Linderae Glaucae melanin the B16F10 melanoma cell is generated and the strong inhibitory activity of tryrosinase, and therefore can be used as the functional components of skin whitening.
Industrial applicibility
Shown in embodiment and EXPERIMENTAL EXAMPLE, discovery comprises from the skin whitening composition of the present invention of the isolating extract of Fructus Pyracanthae Fructus Linderae Glaucae, part or chemical compound and has cyclopentanedione chemical compound or derivatives thereof as active component, highly suppresses melanin thus and generates and tyrosinase activity.Therefore, the present invention can be applicable to comprise a plurality of fields of cosmetics industry, pharmaceutical industries and food industry.
Claims (13)
1. skin whitening composition, comprise as active component from the extract of Fructus Pyracanthae Fructus Linderae Glaucae (Lindera erythrocarpa) or the solvent part of described extract.
2. skin whitening composition as claimed in claim 1, wherein said extract from the Fructus Pyracanthae Fructus Linderae Glaucae is the ethanol extraction of Fructus Pyracanthae Fructus Linderae Glaucae.
3. skin whitening composition as claimed in claim 1, wherein said solvent partly are selected from hexane part, dichloromethane part, ethyl acetate part, butanols part, water section and above combination.
4. skin whitening composition comprises at least a chemical compound that is selected from the represented chemical compound of following Chemical formula 1 to 10:
[Chemical formula 1]
[Chemical formula 2]
[chemical formula 3]
[chemical formula 4]
[chemical formula 5]
[chemical formula 6]
[chemical formula 7]
[chemical formula 8]
[chemical formula 9]
[Chemical formula 1 0]
5. skin whitening composition as claimed in claim 4, wherein said chemical compound separates and purification from the Fructus Pyracanthae Fructus Linderae Glaucae.
6. as each described skin whitening composition in the claim 1 to 5, described skin whitening composition is used to the cosmetics preparation.
7. as each described skin whitening composition in the claim 1 to 5, described skin whitening composition is used to pharmaceutical preparation.
8. as each described skin whitening composition in the claim 1 to 5, described skin whitening composition is used to food formulation.
9. by the represented chemical compound of following Chemical formula 10:
[Chemical formula 1 0]
10. chemical compound as claimed in claim 9, the chemical compound of wherein said Chemical formula 10 are isolating from the Fructus Pyracanthae Fructus Linderae Glaucae.
11. chemical compound as claimed in claim 9, the chemical compound of wherein said Chemical formula 10 are isolating from the bark of Fructus Pyracanthae Fructus Linderae Glaucae.
12. separate the method for the chemical compound of claim 9 from Fructus Pyracanthae Fructus Linderae Glaucae (Lindera erythrocarpa):
The Fructus Pyracanthae Fructus Linderae Glaucae is immersed in the solvent so that the extract from the Fructus Pyracanthae Fructus Linderae Glaucae to be provided, and described solvent is selected from water, C
1To C
4Lower alcohol and combination thereof;
With hexane, dichloromethane, ethyl acetate and butanols with described Fructus Pyracanthae Fructus Linderae Glaucae extract part, to provide branch other solvent part;
Use hexane and ethyl acetate gradient as eluent, described Fructus Pyracanthae Fructus Linderae Glaucae solvent is partly carried out elementary silica gel column chromatography so that the chromatography part to be provided; And
The mixture that uses hexane and ethyl acetate makes described elementary silica gel column chromatography part carry out purification by secondary silica gel column chromatography, so that new polymethoxy phenolic compounds to be provided as eluent.
13. method as claimed in claim 12, wherein said Fructus Pyracanthae Fructus Linderae Glaucae are the bark of Fructus Pyracanthae Fructus Linderae Glaucae.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020080087480A KR101069907B1 (en) | 2008-09-04 | 2008-09-04 | A composition for skin whitening comprising extract, fraction or compound from Lindera erythrocarpa |
| KR10-2008-0087480 | 2008-09-04 | ||
| PCT/KR2009/005027 WO2010027221A2 (en) | 2008-09-04 | 2009-09-04 | Skin-whitening composition comprising an extract, fraction or compound derived from lindera erythrocarpa |
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| Publication Number | Publication Date |
|---|---|
| CN102186457A true CN102186457A (en) | 2011-09-14 |
| CN102186457B CN102186457B (en) | 2014-10-08 |
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| JP (1) | JP5627585B2 (en) |
| KR (1) | KR101069907B1 (en) |
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| CN107602645A (en) * | 2017-11-17 | 2018-01-19 | 周静宜 | A kind of method that juglanin is extracted from apple flower |
| CN114847309A (en) * | 2022-05-20 | 2022-08-05 | 湖北工程学院 | Application of mixed extract of lindera glauca leaves and fruits, wild chrysanthemum extract and mixture thereof in prevention and treatment of strawberry diseases |
| CN117491535A (en) * | 2023-12-22 | 2024-02-02 | 山东省食品药品检验研究院 | Quality evaluation method of external gel bulk drug of lindera root |
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| KR101042005B1 (en) * | 2009-09-24 | 2011-06-16 | 재단법인 제주테크노파크 | Compound from Lindera erythrocarpa, method for isolating thereof, and composition for skin whitening comprising the same |
| KR102096788B1 (en) | 2017-11-02 | 2020-04-03 | 콜마비앤에이치 주식회사 | Composition for skin whitening comprising beauvericin or beauvericin derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN107602645A (en) * | 2017-11-17 | 2018-01-19 | 周静宜 | A kind of method that juglanin is extracted from apple flower |
| CN114847309A (en) * | 2022-05-20 | 2022-08-05 | 湖北工程学院 | Application of mixed extract of lindera glauca leaves and fruits, wild chrysanthemum extract and mixture thereof in prevention and treatment of strawberry diseases |
| CN117491535A (en) * | 2023-12-22 | 2024-02-02 | 山东省食品药品检验研究院 | Quality evaluation method of external gel bulk drug of lindera root |
| CN117491535B (en) * | 2023-12-22 | 2024-03-22 | 山东省食品药品检验研究院 | Quality evaluation method of external gel bulk drug of lindera root |
Also Published As
| Publication number | Publication date |
|---|---|
| WO2010027221A9 (en) | 2010-09-16 |
| KR101069907B1 (en) | 2011-10-05 |
| WO2010027221A3 (en) | 2010-07-15 |
| JP2012502022A (en) | 2012-01-26 |
| CN102186457B (en) | 2014-10-08 |
| JP5627585B2 (en) | 2014-11-19 |
| WO2010027221A2 (en) | 2010-03-11 |
| KR20100028440A (en) | 2010-03-12 |
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