CN105377263A - Composition for antioxidation or skin whitening containing 21-O-angeloyltheasapogenol E3 ingredient derived from green tea seed - Google Patents
Composition for antioxidation or skin whitening containing 21-O-angeloyltheasapogenol E3 ingredient derived from green tea seed Download PDFInfo
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- CN105377263A CN105377263A CN201380078158.4A CN201380078158A CN105377263A CN 105377263 A CN105377263 A CN 105377263A CN 201380078158 A CN201380078158 A CN 201380078158A CN 105377263 A CN105377263 A CN 105377263A
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- theasapogenol
- radix angelicae
- angelicae sinensis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
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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)
- A61K36/82—Theaceae (Tea family), e.g. camellia
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/37—Esters of carboxylic acids
- A61K8/375—Esters of carboxylic acids the alcohol moiety containing more than one hydroxy group
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/96—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]
- A61K8/9789—Magnoliopsida [dicotyledons]
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/02—Preparations for care of the skin for chemically bleaching or whitening the skin
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
Abstract
The present invention relates to a composition for antioxidation or skin whitening containing, as an active ingredient, an 21-O-angeloyltheasapogenol E3 ingredient derived from a green tea seed, and more specifically, to a composition containing, as an active ingredient, a 21-O-angeloyltheasapogenol E3 ingredient derived from a green tea seed and is obtained from an extract of a seed having distinguishing characteristics through decomposition using an acid, a base, an enzyme, or a microorganism producing the enzyme, and thereby having excellent antioxidation and skin-whitening effects.
Description
Technical field
The present invention relates to a kind of 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 composition containing being derived from green tea seed as the antioxidation of effective ingredient or skin-whitening compositions, more specifically, relate to a kind of containing by utilizing acid, alkali, enzyme or producing the decomposition reaction of microorganism of above-mentioned enzyme, the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 composition obtained from green tea species seed extract as effective ingredient, thus has excellent antioxidation and the compositions of skin whitening efficacy.
Background technology
With advancing age, the skin of the mankind is according to various endogenous cause of ill and thus changing outward.That is, say from inside, for regulating the secretion of metabolic various hormone to reduce, the function of immunocyte and the activity of cell reduce, thus cause the biosynthesis of the protein of the immune protein needed for organism and formation organism to reduce; Say from outside, due to the destruction of ozone layer, cause the ultraviolet content arriving earth's surface in sunray to increase, environmental pollution is day by day serious and cause free radical and activity to be harmful to the increase of oxygen etc., thus causes various skin problem.Superoxide anion radical (superoxideanionradical, O is converted into due to environment and biochemical factors etc. such as enzyme, reductive metabolism, chemical drugs, public hazards material, photochemical reactions with the oxygen that stable state exists
2 -), hydroxyl (hydroxylradical, OH
-), hydrogen peroxide (hydrogenperoxide, H
2o
2), singlet oxygen (singletoxygen,
1o
2) active oxygen (reactiveoxygenspecies:ROS) that isoreactivity is large, will destroy as the protein of human body cell constituent, lipid and DNA etc. non-reversiblely.The effect of above-mentioned active oxygen can be passed through as the superoxide dismutase (superoxidedismutase defending instrument in body, SOD), the antioxidant such as non-oxidizability enzyme and vitamin C (vitaminC, ascorbic acid (ascorbicacid)), vitamin E (tocopherol) such as catalase (catalase), peroxidase (peroxidase), glutathion (glutathione) effect and be minimized.But, when known this organism phylactic power defensive power generation exception or over-exposure are in active oxygen, residual or superfluous active oxygen produces fatal oxygen toxicity to organism, and induce the lipid as cellularity composition, protein, sugar, DNA etc. produce destruction that is non-selective and non reversibility, and then not only cause aging, also can cause the apoplexy comprising cancer, the encephalopathys such as parkinson disease, heart disease, ischemia, arteriosclerosis, dermatosis, digestive system disease, inflammation, rheumatism, various disease (the Crossetal. such as autoimmune disease, Ann.Intern.Med., 1987, 107, 526, Aldersonetal., Proc.Natl.Acad.Sci.USA, 1988,85,2706).
In order to develop the Natural antioxidant, people have studied the raw material being much derived from natural materials, but reality is the raw material that major part is derived from natural materials to be used with the form of simple extract in the past, correctly do not show which kind of material is effect that its extract demonstrates be caused by, but be used in cosmetics etc. by experience and oral instructions.
In addition, in the colour of skin of decider, relevant with many factors.Wherein, inside and outside generating the activeness of melanic melanocyte (melanocyte), the distribution of blood vessel, skin thickness and the human body such as carotenoid, bilirubin, the factors such as whether pigment contains are particularly important.
Wherein, most important factor is the pigment being called as melanic black generated by the effect of the multiple enzymes such as tryrosinase in melanocyte in human body.The environmental factorss such as the physiologic factor that inherited genetic factors, hormone secretion, pressure etc. are relevant and ultraviolet radiation can have an impact to described melanic formation.
The melanin generated by the melanocyte of body skin is the phenols polymer substance of the complex form with black pigment and protein; it is responsible for and blocks from the ultraviolet shined upon; thus while skin organ below protection corium, also play and catch the protection skin internal protein of the free radical that generates in skin organism etc. and the beneficial effect of gene.
As mentioned above, even if the melanin produced due to the stress stimulation inside and outside skin is a kind of after stress eliminating, can not removed stable material before externally discharging in percutaneous keratinization.But, when melanin generates in a large number to exceed required amount, nevus can be brought out, freckle, speckle waited pigmentation disease, thus bring bad result to beauty treatment aspect.
In addition, make to like the increasing number of people movable out of doors along with the increase of leisure population, the demand of the melanin pigmentation caused for ultraviolet blocking-up also increases day by day.
In order to cater to this demand, in the past just start ascorbic acid, kojic acid, arbutin, hydroquinone, glutathion or their derivant, or have tryrosinase hinder active material and cosmetics or pharmaceuticals with the use of, but due to they insufficient whitening effect, to the stability problem of skin, coordinate the problems such as the dosage form that occurs during cosmetics and stability, its use is restricted.
Summary of the invention
The technical problem solved
For this reason, the present inventor is in order to solve the problem, and find the result that the material and carrying out that can demonstrate more excellent antioxidation and skin whitening effects studies, confirm by utilize acid, alkali, enzyme or generate above-mentioned enzyme microorganism decomposition reaction and the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 composition that obtains from green tea species seed extract has excellent antioxidation and skin whitening effects, this completes the present invention.
Therefore, the object of the invention is to, a kind of antioxidation or skin-whitening compositions of the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 composition containing obtaining from green tea species seed extract is provided.
Technical scheme
In order to solve the problem, the invention provides a kind of containing the antioxidation Dermatologic preparation composition of 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 as effective ingredient.
In addition, the invention provides a kind of containing 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 as the skin-whitening Dermatologic preparation composition of effective ingredient.
Beneficial effect
21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of the present invention, except having the antioxidant effect of suppression diphenyl picryl phenylhydrazine (DPPH) and active oxygen (ROS) generation etc., also demonstrates simultaneously and generates based on check melanin, improve by ultraviolet (ultravioletrays; UV) skin whitening effects of excellence of the Pigmented effect generated, thus 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 can be used as antioxidation effectively, skin-whitening applies some make up the Dermatologic preparation composition such as compositions or pharmaceutical composition or food compositions according to of the present invention.
Detailed description of the invention
The invention provides a kind of containing the compositions of 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 (21-O-angeloyltheasapogenolE3) shown in following chemical formula 1 as effective ingredient:
Chemical formula 1
Described 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 preferred source is from green tea seed.
The 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 used in the present invention is prepared by the method comprised the steps, the method comprises: utilize water or organic solvent from plant, obtain the first step of saponin crude extract; And utilize acid, alkali, enzyme or produce the microorganism of above-mentioned enzyme, said extracted thing is hydrolyzed, thus the second step of separation 21-O-Radix Angelicae Sinensis acyl theasapogenol E3.
First step: the acquisition of saponin crude extract
From plant, especially from green tea seed, obtain saponin crude extract.Now, Extraction solvent can use water or organic solvent, organic solvent can use the mixture being selected from more than one organic solvent in ethanol, methanol, butanols, ether (ether), ethyl acetate and chloroform or they and water, preferably uses 50% ethanol.
In order to utilize water or organic solvent to obtain saponin crude extract from plant, in plant, adding water or the organic solvent of about 1 to 6 times, preferably adding water or the organic solvent of about 3 times, and stir at normal temperatures and extract 1 to 5 time, thus making plant defat.In the plant of defat, add water or the organic solvent of about 1 to 8 times, preferably add water or the organic solvent of about 4 times, and carry out reflux, extract, 1 to 5 time, then at 10 to 20 DEG C, precipitate 1 to 3 day.Then, be separated residue and filtrate by filtering with centrifugalize, the filtrate reduced in volume be separated is obtained extracts (extract), after being suspended in water by the extracts obtained, utilize ether etc. to remove pigment.After water layer is with an organic solvent extracted 1 to 5 time, by the organic solvent layer concentrating under reduced pressure obtained, thus obtain organic solvent extracts, then this extracts is dissolved in a small amount of methanol, ethanol, propanol, butanols etc.Then, add a large amount of ethyl acetate, acetonitrile (acetonitrile) etc. and generate precipitate, by this drying precipitate, thus obtain saponin crude extract of the present invention.
second step: the separation of 21-O-Radix Angelicae Sinensis acyl theasapogenol E3
The saponin crude extract obtained in above-mentioned first step be hydrolyzed, thus can be separated 21-O-Radix Angelicae Sinensis acyl theasapogenol E3, the microorganism that said hydrolyzed can utilize acid, alkali, enzyme or produce above-mentioned enzyme is carried out.
Described acid can use more than one the acid be selected from hydrochloric acid, sulphuric acid and nitric acid, or these sour mixed solvents with being selected from more than one the alcohol in ethanol, methanol and butanols, preferably uses the mixed solvent of above-mentioned acid and 50% ethanol.
When utilizing acid to be hydrolyzed, in saponin crude extract, add the acid of 0.1 ~ 2N concentration, preferably add the acid of 1N concentration; Or add the acid of amount and the mixed solvent of alcohol of 1 ~ 10%, and at 50 ~ 100 DEG C, preferably reflux 0.5 ~ 8 hour in the water bath of 80 DEG C, preferably 1 hour.
Described alkali can use more than one the alkali be selected from Feldalat NM, sodium hydroxide and potassium hydroxide, or these alkali be selected from the mixed solvent of more than one the alcohol in ethanol, methanol and butanols, preferably use the mixed solvent of butanols of above-mentioned alkali and 50%.
When utilizing alkali to be hydrolyzed, saponin crude extract is dissolved in after in the mixed solvent of water or water and ethanol, add the alkali of 0.1 ~ 2N concentration, the alkali of preferred interpolation 1N concentration, or with 1 ~ 10% amount add the mixed solvent of alkali and alcohol after, at 50 ~ 100 DEG C, preferably reflux 0.5 ~ 24 hour in the water bath of 100 DEG C, preferably 12 hours.
Described enzyme is the enzyme decomposing glycosidic bond, and its feature to remove the part of sugar in green tea saponin, thus generates 21-O-Radix Angelicae Sinensis acyl theasapogenol E3.This enzyme can use commercially available or prepare use as required, particularly can obtain from the microorganism generating above-mentioned enzyme.
In addition, above-mentioned enzyme can be more preferably use and be selected from glucosidase (glucosidase), arabinosidase (arabinosidase), rhamnosidase (rhamnosidase), xylosidase (xylosidase), cellulase (cellulase), hesperidin enzyme (hesperidinase), naringinase (naringinase), glucuronidase (glucuronidase), pectase (pectinase), more than one in tilactase (galactosidase) and amyloglucosidase (amyloglucosidase).
In addition, the microorganism of producing described enzyme can use and be selected from aspergillus (Aspergillus), Bacillus (Bacillus), Penicillium (Penicillium), Rhizopus (Rhizopus), Rhizomucor (Rhizomucor), Talaromyces (Talaromyces), Bifidobacterium (Bifidobacterium), Mortierella (Mortierella), Cryptococcus (Cryptococcus), Microbacterium (Microbacterium), more than one in Leuconostoc (Leuconostoc) and genus lactubacillus (Lactobacillus).
When utilizing enzyme to be hydrolyzed, saponin crude extract is dissolved in 5 to 20 times, preferably in the acidic buffer solution of about 10 times, then adds the enzyme of 0.001 ~ 10%.Then by it about 25 ~ 37 DEG C of stirred in water bath about 40 to 55 hours, preferably about 48 hours, utilize thin layer chromatography to confirm the elimination factor of substrate, treat that substrate disappears completely, heating 5 to 15 minutes cessation reactions in hot water (80 ~ 100 DEG C).
When utilizing microorganism to be hydrolyzed, saponin crude extract is dissolved in 5 to 10 times, preferably in the ionized water of about 10 times, then at 121 DEG C, sterilizing was cooled to 30 DEG C after 30 minutes.Then, by pre-incubated microorganism to be that the amount of 5 ~ 10 % by weight is inoculated relative to amount of liquid, cultivate 2 to 5 days at 20 ~ 30 DEG C, preferably cultivate 5 days, then, utilize thin layer chromatography to confirm the elimination factor of substrate, treat that substrate disappears completely, with 5,000 ~ 10,000rpm centrifugalize culture fluid, by the precipitate distilled water wash 3 times reclaimed, then obtains precipitate by centrifugalize.
As mentioned above, after utilizing acid, alkali, enzyme or the microorganism of producing above-mentioned enzyme to be hydrolyzed, concentrating under reduced pressure is carried out to reactant liquor, thus removal solvent, and in residue, add ethanol and stir 1 ~ 5 time.Then, by filtering the salt removing precipitation, the filtrate reduced in volume of filtration is obtained thick product, is separated the thick product of acquisition by silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1), thus 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 can be obtained.
Compositions of the present invention comprises with the amount of 0.0001 of composition total weight ~ 10 % by weight the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 prepared as said method.Above-mentioned containing quantity not sufficient 0.0001 % by weight time, antioxidation or skin whitening effects that mentioned component brings cannot be obtained; Even if content is more than 10 % by weight, the lifting of the effect that the increase of content brings is little.
Compositions of the present invention can be used as antioxidant composition, and its inhibition generated DPPH and ROS is excellent.
In addition, compositions of the present invention can be used as skin-whitening compositions, and its check melanin generates, and improves the Pigmented excellent effect generated because of ultraviolet (ultravioletrays:UV).
Compositions of the present invention contains medium or base material that cosmeceutical or Dermatology allow, dosage form can turn to cosmetic composition or pharmaceutical compositions.It can for being suitable for all dosage forms of topical application, such as, can be provided as solution, gel, solid, the anhydrous product of pasty state, in aqueous phase, disperse oil phase and the emulsion, suspension, microemulsion, microcapsule, subparticle ball or the ion-type (liposome) that obtain or nonionic folliculus dispersant form, or frost, astringent, lotion, powder, ointment, spraying or hide flaw clavate state.In addition, also can use with foam (foam) form or the aerosol composition form further containing compressed propellant.These compositionss are prepared by method well known in the art.
In addition, the present composition can also contain fatty material, organic solvent, lytic agent, concentrating agents, gelating agent, softening agent, antioxidant, suspensoid, stabilizing agent, foaming agent (foamigagent), aromatic, surfactant, water, ion-type or nonionic emulsifier, filler, chelating agen, chelating agent, preservative agent, vitamin, blocker, wetting agent, quintessence oil, dyestuff, pigment, hydrophilic or lipophile activating agent, lipid folliculus or any one other composition being generally used for cosmetics etc. are at the normally used auxiliary agent of cosmeceutical or Dermatology field.Above-mentioned auxiliary agent adds with the normally used amount of cosmeceutical or Dermatology field.
In addition, compositions of the present invention, in order to increase antioxidation or skin whitening effects, can also contain skin absorption enhancement material.
In addition, compositions of the present invention dosage form can turn to food compositions, such as, dosage form can turn to the form of various foodstuff, beverage, chewing gum, tea, compound vitamin, healthy functions foodstuff and numerous food additive.
Food compositions of the present invention contains 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 as outside required composition divided by disclosed ratio, and for other composition, there is no particular limitation, can contain the supplementary element such as various flavouring agent or natural carbon hydras as common beverage.The example of above-mentioned natural carbon hydras has and comprises the such as monosaccharide such as glucose, fructose; The such as disaccharide such as maltose, sucrose; And the common saccharide of the such as polysaccharide such as dextrin, cyclodextrin; And the sugar alcohol such as xylitol, Sorbitol, erythritol.Flavouring agent than that described above can use natural flavours (Talin, Flos Chrysanthemi extract (such as, RA, glycyrrhizin etc.)) and synthesis flavouring agent (glucide, aspartame etc.).The ratio of above-mentioned natural carbon hydras is relative to compositions 100ml of the present invention, usually containing the 1 ~ 20g that has an appointment, preferably containing the 5 ~ 12g that has an appointment, but be not limited thereto.
In addition, food compositions of the present invention, can containing other composition main efficacy results being played to castering action in the scope not affecting main efficacy results of the present invention.Such as, the additives such as spice, pigment, antibacterial, antioxidant, antiseptic, wetting agent, thickening agent, inorganic pigment, emulsifying agent and synthesis macromolecule can be contained further in order to improve physical property.In addition, the auxiliary elements such as water soluble vitamins, fat soluble vitamin, macromolecule peptide, macromolecule polysaccharide and zostera marina extracts can also be contained.Mentioned component according to dosage form or application target, those skilled in the art can easily suitably select and with the use of, its addition can be selected in the scope not affecting the object of the invention and effect.Such as, the addition of mentioned component can be relative to composition total weight 0.01 ~ 5 % by weight, more specifically, can be 0.01 ~ 3 % by weight scope.
, further describe the present invention by embodiment and experimental example below, but scope of the present invention does not limit thus.
[embodiment 1]: the preparation of green tea species seed extract
In the green tea seed of 2kg, add the caproic acid of 6L, carrying out defat 3 times by stirring extraction at normal temperatures, in the green tea seed of the defat of 1kg, adding 50% ethanol of 4L, after reflux, extract, 3 times, at 15 DEG C, precipitate 1 day.Then, be separated with filtrate by residue with centrifugalize by filter-cloth filtering, then by carrying out concentrating under reduced pressure to the filtrate be separated, the extracts that obtains suspends in water, and utilizes the ether extraction 5 times of 1L, thus removal pigment, the n-butyl alcohol of water layer 500ml is extracted 3 times.Thus obtained whole n-butyl alcohol layer is carried out concentrating under reduced pressure, thus obtain n-butyl alcohol extracts, the n-butyl alcohol extracts of above-mentioned acquisition is dissolved in a small amount of methanol, add a large amount of ethyl acetate to precipitate, by drying precipitate, obtain 300g green tea species seed extract (saponin crude extract) thus.
[embodiment 2]: prepare 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 by acid hydrolysis process
[2-1] adds the 1NHCl-50% methanol solution (v/v) of 20 times (v/w) in the green tea species seed extract obtained from above-described embodiment 1 of 10g, and in 80 DEG C of water baths reflux 8 hours, make to be incorporated into the sucrose solution solution on the thick saponin of green tea seed.Reactant liquor concentrating under reduced pressure is removed solvent, in residue, then adds ethanol (200ml) and stir 3 times, then by filtering the salt removing precipitation.The filtrate reduced in volume of filtration is obtained thick product, then utilizes silica gel column chromatography (chloroform: methanol=7:1 ~ 3:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.55g.
[2-2] adds the 1MH of 20 times (v/w) in the green tea species seed extract obtained from above-described embodiment 1 of 10g
2sO
4-30% aqueous solution (v/v), reflux 8 hours in 90 DEG C of water baths, makes to be incorporated into the sucrose solution solution on the thick saponin of green tea seed.Reactant liquor concentrating under reduced pressure is removed solvent, in residue, then adds ethanol (200ml) stir 3 times, then by filtering the salt removing precipitation.The filtrate reduced in volume of filtration is obtained thick product, then utilizes silica gel column chromatography (chloroform: methanol=7:1 ~ 3:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.59g.
[2-3] adds the 1MHNO of 20 times (v/w) in the green tea species seed extract obtained from above-described embodiment 1 of 10g
3-10%
watersolution (v/v), and in 90 DEG C of water baths reflux 8 hours, make to be incorporated into the sucrose solution solution on the thick saponin of green tea seed.Reactant liquor concentrating under reduced pressure is removed solvent, in residue, then adds ethanol (200ml) stir 3 times, then by filtering the salt removing precipitation.The filtrate reduced in volume of filtration is obtained thick product, then utilizes silica gel column chromatography (chloroform: methanol=7:1 ~ 3:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.39g.
[embodiment 3] prepares 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 by Base hydrolysis method
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in anhydrous pyridine (500ml) by [3-1], Feldalat NM (sodiummethoxide) (powder is added at this, 10g), and in oil bath back flow reaction 8 hours, make to be incorporated into the sucrose solution solution on the thick saponin of green tea seed.Reactant liquor concentrating under reduced pressure is removed solvent, filters after washing 3 times with Purified Water, thus obtain filtrate, in residue, add ethanol (200ml) and stir 3 times, then by filtering the salt removing precipitation.The filtrate reduced in volume of filtration is obtained thick product, then utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 3:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.35g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the 1MNaOH-20% aqueous solution (v/v) of 20 times (v/w) by [3-2], and at 80 DEG C back flow reaction 8 hours, make to be incorporated into the sucrose solution solution on the thick saponin of green tea seed.Reactant liquor concentrating under reduced pressure is removed solvent, filters after washing 3 times with Purified Water, thus obtain filtrate, in residue, add ethanol (200ml) and stir 3 times, then by filtering the salt removing precipitation.The filtrate reduced in volume of filtration is obtained thick product, then utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.31g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the 1MKOH-20% aqueous solution (v/v) of 20 times (v/w) by [3-3], and at 80 DEG C back flow reaction 8 hours, make to be incorporated into the sucrose solution solution on the thick saponin of green tea seed.Reactant liquor concentrating under reduced pressure is removed solvent, filters after washing 3 times with Purified Water, thus obtain filtrate, in residue, add ethanol (200ml) stir 3 times, then by filtering the salt removing precipitation.The filtrate reduced in volume of filtration is obtained thick product, then utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.25g.
[embodiment 4] prepares 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 by enzyme decomposition method
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the 0.1M hac buffer (pH4.5) of 100ml by [4-1], 2.5g enzyme (0.5g hesperidin enzyme is added at this, 0.5g naringinase, 0.5g cellulase, β-the glucuronidase of 0.2g, the beta galactosidase of 0.5g, 0.3g amyloglucosidase, Sigma manufactures), and 37 DEG C of stirred in water bath 48 hours, periodically confirmed by thin layer chromatography simultaneously, treat that green tea saponin disappears, heat 10 minutes and cessation reaction in hot water (80 ~ 100 DEG C).Reactant liquor concentrating under reduced pressure is removed solvent, in residue, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.After the filtrate reduced in volume of filtration is obtained thick product, utilize silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 1.02g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the 0.1M hac buffer (pH6.5) of 100ml by [4-2], 3.5g enzyme (1g glucosidase, 0.5g arabinosidase, 1g rhamnosidase, 0.5g xylosidase, 0.5g pectase) is added at this, and 27 DEG C of stirred in water bath 48 hours, periodically confirmed by thin layer chromatography simultaneously, treat that green tea saponin disappears, heat 10 minutes and cessation reaction in hot water (80 ~ 100 DEG C).Reactant liquor concentrating under reduced pressure is removed solvent, in residue, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.After the filtrate reduced in volume of filtration is obtained thick product, utilize silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 1.53g.
[embodiment 5] prepares 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 by microorganism
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the ionized water of 100ml by [5-1], and sterilizing 30 minutes at 121 DEG C, after being cooled to 30 DEG C, being that the amount of 5 ~ 10% is to inoculate pre-incubated aspergillus niger (Aspergillusniger) KCCM11885 relative to amount of liquid, and cultivate at 30 DEG C after 5 days, utilize thin layer chromatography to confirm the elimination factor of substrate, after substrate to be confirmed disappears completely, with 5, 000 ~ 10, the precipitate that the rotating speed of 000rpm carrys out centrifugalize culture fluid and reclaims utilizes distilled water wash 3 times, then carry out centrifugalize and obtain precipitate.In this precipitate, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.The filtrate reduced in volume of filtration is obtained thick product, utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.72g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the ionized water of 100ml by [5-2], and sterilizing 30 minutes at 121 DEG C, after being cooled to 27 DEG C, being that the amount of 5 ~ 10% is to inoculate pre-incubated Rhizopus oryzae (Rhizopusoryzae) relative to amount of liquid, and cultivate at 27 DEG C after 5 days, utilize thin layer chromatography to confirm the elimination factor of substrate, after substrate to be confirmed disappears completely, with 5, 000 ~ 10, the precipitate that the rotating speed of 000rpm carries out centrifugalize culture fluid and reclaims utilizes distilled water wash 3 times, then carry out centrifugalize and obtain precipitate.In this precipitate, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.The filtrate reduced in volume of filtration is obtained thick product, utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.92g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the ionized water of 100ml by [5-3], and sterilizing 30 minutes at 121 DEG C, after being cooled to 27 DEG C, being that the amount of 5 ~ 10% is to inoculate pre-incubated bacillus subtilis (Bacillussubtilis) relative to amount of liquid, and cultivate at 27 DEG C after 2 days, utilize thin layer chromatography to confirm the elimination factor of substrate, after substrate to be confirmed disappears completely, with 5, 000 ~ 10, the precipitate that the rotating speed of 000rpm carrys out centrifugalize culture fluid and reclaims utilizes distilled water wash 3 times, then carry out centrifugalize and obtain precipitate.In this precipitate, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.The filtrate reduced in volume of filtration is obtained thick product, utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.72g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the ionized water of 100ml by [5-4], and sterilizing 30 minutes at 121 DEG C, after being cooled to 27 DEG C, being that the amount of 5 ~ 10% is to inoculate pre-incubated Leuconostoc mesenteroides (Leuconostocmesenteroides) relative to amount of liquid, and cultivate at 27 DEG C after 2 days, utilize thin layer chromatography to confirm the elimination factor of substrate, after substrate to be confirmed disappears completely, with 5, 000 ~ 10, the precipitate that the rotating speed of 000rpm carrys out centrifugalize culture fluid and reclaims utilizes distilled water wash 3 times, then carry out centrifugalize and obtain precipitate.In this precipitate, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.After the filtrate reduced in volume of filtration is obtained thick product, utilize silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.52g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the ionized water of 100ml by [5-5], and sterilizing 30 minutes at 121 DEG C, after being cooled to 27 DEG C, being that the amount of 5 ~ 10% is to inoculate pre-incubated long bifidus bacillus (Bifidobacteriumlongum) relative to amount of liquid, and cultivate at 27 DEG C after 2 days, utilize thin layer chromatography to confirm the elimination factor of substrate, after substrate to be confirmed disappears completely, with 5, 000 ~ 10, the precipitate that the rotating speed of 000rpm carrys out centrifugalize culture fluid and reclaims utilizes distilled water wash 3 times, then carry out centrifugalize and obtain precipitate.In this precipitate, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.The filtrate reduced in volume of filtration is obtained thick product, utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.52g.
The green tea species seed extract obtained from above-described embodiment 1 of 10g is dissolved in the ionized water of 100ml by [5-6], and sterilizing 30 minutes at 121 DEG C, after being cooled to 27 DEG C, being that the amount of 5 ~ 10% is to inoculate pre-incubated Lactobacillus plantarum (Lactobacillusplantarum) relative to amount of liquid, and cultivate at 27 DEG C after 2 days, utilize thin layer chromatography to confirm the elimination factor of substrate, after substrate to be confirmed disappears completely, with 5, 000 ~ 10, the precipitate that the rotating speed of 000rpm carrys out centrifugalize culture fluid and reclaims utilizes distilled water wash 3 times, then carry out centrifugalize and obtain precipitate.In this precipitate, adding ethanol (200ml) and after stirring 3 times, removing precipitate by filtering.The filtrate reduced in volume of filtration is obtained thick product, utilizes silica gel column chromatography (chloroform: methanol=8:1 ~ 4:1) to be separated the thick product of above-mentioned acquisition, thus obtain the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.42g.
[experimental example 1] DPPH generates inhibition test (DPPH experiment)
The absorbance change produced by the reduction reaction (antioxidant oxidation) of organic free radical DPPH (1,1-diphenyl-2-picryl phenylhydrazine, 1,1-diphenyl-2-picrylhydrazyl) is used to evaluate the method for oxidation resistance.By measuring the oxidation of DPPH and being suppressed, absorbance compares the degree that matched group reduces to antioxidation degree, to demonstrate the concentration (IC of absorbance of less than 50% relative to matched group absorbance
50) be evaluated as effective antioxidation concentration.
In 100 μMs of (being dissolved in ethanol) DPPH solution of 190 μ l, mix the green tea species seed extract of the embodiment 1 of 10 μ l, the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of embodiment 2 to 5 and control sample respectively and prepared reactant liquor.The reactant liquor of mixing is reacted 30 minutes at 37 DEG C, then measures absorbance at 540nm place.Control sample uses the watermiscible vitamin E (Trolox) being extensively used as synthetized oxidation preventive agent.Respective DPPH analysis result is represented in table 1 below.
Table 1
| Sample | IC 50(ppm) |
| Embodiment 1 | 450.24 |
| Embodiment 2-1 | 7.73 |
| Embodiment 3-1 | 7.52 |
| Embodiment 4-1 | 7.47 |
| Embodiment 5-1 | 7.53 |
| Watermiscible vitamin E | 8.64 |
Can know from the result of upper table 1,21-O-Radix Angelicae Sinensis acyl theasapogenol E3 has very excellent oxidation resistance, and compared with known antioxidant watermiscible vitamin E, oxidation resistance is more excellent.
[experimental example 2] utilizes fluorescent material to carry out reactive oxygen species (reactiveoxygenspecies; ROS) generation rejection ability experiment
Cell line for testing is Human keratinocytes HaCaT cell line (HumankeratinocytesHaCaTcellline), by it with every hole 2.0x10
4individual amount is seeded in fluoremetry with on 96 hole blackboards, uses DMEM (DulbeccosModificationofEaglesMedium, the FBS10%) culture medium that with the addition of penicillin/streptomycin, and at 37 DEG C, 5%CO
2cultivate under condition after 1 day and process by test sample.Use the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of the green tea species seed extract of the embodiment 1 of 50ppm, embodiment 2 to 5 and control sample as test sample respectively, control sample employs the watermiscible vitamin E being widely used as synthetized oxidation preventive agent.Then use the serum-free DMEM (not containing FBS) that with the addition of penicillin/streptomycin as culture medium, at 37 DEG C, 5%CO
2cultivate 1 day under condition.
After interpolation experimental sample cultivates 24 hours, wash with HCSS (HEPES-bufferedcontrolsaltsolution (hydroxyethyl piperazine second sulfacid-buffered control salt solution)), thus remove remaining culture medium, the off-the-shelf 20 μMs of DCFH-DA (2' of 100 μ l are added in HCSS, 7'-dichloro-dihydro is for fluorescein(e) diacetate (2', 7'-dichlorodihydro-fluoresceindiacetate), molecular probe company limited (MolecularProbes, Inc)), then at 37 DEG C, 5%CO
2cultivate 20 minutes under condition, wash with HCSS.Afterwards, add the HCSS with 100 μ l of sample pretreating, the fluorescence of then utilize fluorescence spectrophotometer (Ex=485nm, Em=530nm) to measure DCF (dichlorofluorescein, dichlorofluorescein) that initial oxidation is ROS.Irradiation ultraviolet radiation (UVB) (30mJ/cm afterwards
2), the fluorescence after utilizing the just process of fluorescence spectrophotometer (Ex=485nm, Em=530nm) mensuration or after 3 hours.
As a control group, the ROS trying to achieve each substances as benchmark generates rejection ability (% of matched group) to the situation that will use dimethyl sulfoxide (DMSO), and experimental result is shown in following table 2.
Table 2
| Sample (50ppm) | Generate rejection ability (%) |
| Matched group (DMSO) | 00 |
| Embodiment 1 | 25 |
| Embodiment 2-1 | 61.7 |
| Embodiment 3-1 | 61.5 |
| Embodiment 4-1 | 61.2 |
| Embodiment 5-1 | 62.1 |
| Watermiscible vitamin E | 51.7 |
Can know from the result of upper table 2, the ROS of 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 generates rejection ability excellence, and compared with known antioxidant watermiscible vitamin E, the ability suppressing ROS to generate is more excellent.
The inhibition that [experimental example 3] utilizes the chromatophorous melanin of mice to generate measures
Mus pigment cell (the Mel-Abcell) (Dooley of C57BL/6 mice will be derived from, T.P.etal, Skinpharmacol, 7, pp188-200) be to the addition of in DMEM in the culture medium of 10% hyclone, 100nM12-O-Tetradecanoylphorbol (tetradecanoylphorbol)-13-acetate, 1nM cholera toxin (choleratoxin), at 37 DEG C, 5%CO
2cultivate under condition.By cultivate Mel-Ab cell with 0.25% trypsin-EDTA peel off, with 10
5the concentration of cells/well is cultivated in 24 orifice plates, adds each test sample of 10ppm from the 2nd day for three days on end.Test sample uses the green tea species seed extract of embodiment 1, the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of embodiment 2-5 and control sample, control sample employs hydroquinone as known whitening agent as positive controls, using do not process test sample as negative control group.After adding test sample, at 37 DEG C, 5%CO
2cultivate 1 day under condition, then remove liquid medium, and with PBS washing, then use 1N sodium hydroxide dissolved cell, measure absorbance at 400nm place.The result of mensuration is calculated melanin generating suppression according to following mathematical expression 1, the results are shown in following table 3 (method of Du Li (Dooley)).
Mathematical expression 1
Melanin generating suppression (%)=100-(absorbance of the absorbance/negative control group of each substances) × 100
Table 3
| Substances | Melanin generating suppression (%) |
| Non-process group (negative control group) | 00.0 |
| Embodiment 1 | 75.3 |
| Embodiment 2-1 | 75.2 |
| Embodiment 3-1 | 75.7 |
| Embodiment 4-1 | 74.9 |
| Embodiment 5-1 | 75.1 |
| Hydroquinone (positive controls) | 41.1 |
Can confirm from upper table 3,21-O-Radix Angelicae Sinensis acyl theasapogenol E3 demonstrates excellent melanin generating suppression, compared with known whitening agent hydroquinone, demonstrates more excellent melanin generating suppression.
[test example 4] skin whitening effects to human body skin is tested
In order to confirm that the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 obtained in above-described embodiment 4 is to the skin whitening effects of human body skin, has carried out following experiment.
First, with 12 healthy males for object, diameter is had to be the opaque adhesive tape in the hole of 1.5cm at the upper arm position adhesive band of subject, then the upper arm of subject is irradiated to the ultraviolet (UVB) of 1.5 ~ 2 times of degree of minimal erythema dose (MinimalErythemaDose), the melanism of induced skin.
After irradiation ultraviolet radiation, (solvent is 1 to smear the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of the embodiment 4-1 of 1% respectively, 3-butanediol: ethanol=7:3), 1% hydroquinone and 1% solvent (matched group (vehicle)) (negative control group), an other place is under the state of not smearing anything, observes state change 10 weeks.In units of 1 week, color difference meter CR2002 (Japan, Minolta company) is utilized to measure skin colour change.
Then calculate above-mentioned each substances coating according to following mathematical expression 2 to start time point and applied the skin aberration (△ L*) of time point, this is shown in following table 4.In addition, the △ L* that whitening effect smears position and matched group position by sample relatively judges, when △ L* value is about 2, is the obvious situation of whiteningization to precipitation pigment, can be judged as having whitening effect when more than 1.5.
Mathematical expression 2
△ L*=has smeared the L* value of time point-smear the L* value starting time point
Table 4
| Substances | The colour of skin puies forward brightness level (△ L*) |
| Embodiment 4-1 | 1.80±0.21 |
| Hydroquinone (positive controls) | 1.90±0.11 |
| Solvent (contrast (Vehicle)) (negative control group) | 0.50±0.15 |
Can confirm from the result of upper table 4,21-O-Radix Angelicae Sinensis acyl theasapogenol E3 makes the colour of skin highlight, and demonstrates the colour of skin similar to known whitening agent hydroquinone and highlights degree.This can be judged as that the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 used in the present invention is by improving the pigmentation generated by ultraviolet, thus bright color.
Claims (7)
1. containing the antioxidation Dermatologic preparation composition of the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 shown in following chemical formula 1 as effective ingredient:
[chemical formula 1]
2. containing the skin-whitening Dermatologic preparation composition of the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 shown in following chemical formula 1 as effective ingredient:
[chemical formula 1]
3. Dermatologic preparation composition according to claim 1 and 2, wherein, in composition total weight, containing the described 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 of 0.0001 ~ 10 % by weight.
4. Dermatologic preparation composition according to claim 1 and 2, wherein, described 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 is derived from green tea seed.
5. will remove the Dermatologic preparation composition described in 4 according to right, wherein, described 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 utilizes acid, alkali, enzyme or produces the microbial decomposition green tea species seed extract of above-mentioned enzyme and obtain.
6. containing the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 shown in following chemical formula 1 as effective ingredient Dermatologic preparation composition for the application in antioxidation:
[chemical formula 1]
7. containing the 21-O-Radix Angelicae Sinensis acyl theasapogenol E3 shown in following chemical formula 1 as effective ingredient Dermatologic preparation composition for the application in skin-whitening:
[chemical formula 1]
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| KR101824897B1 (en) * | 2011-09-30 | 2018-02-05 | (주)아모레퍼시픽 | External composition for skin containing saponin derived from the root of Camellia sinensis |
| KR101921903B1 (en) * | 2012-04-23 | 2018-11-26 | (주)아모레퍼시픽 | Composition for antioxidation or whitening containing 21-O-angeloyltheasapogenol E3 from green tea seed |
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