CN105997556A - Cosmetics and/ or skin care product containing fat soluble tea polyphenol - Google Patents
Cosmetics and/ or skin care product containing fat soluble tea polyphenol Download PDFInfo
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- CN105997556A CN105997556A CN201610520129.4A CN201610520129A CN105997556A CN 105997556 A CN105997556 A CN 105997556A CN 201610520129 A CN201610520129 A CN 201610520129A CN 105997556 A CN105997556 A CN 105997556A
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- tea polyphenol
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- soluble tea
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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
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4973—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom
- A61K8/498—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with oxygen as the only hetero atom having 6-membered rings or their condensed derivatives, e.g. coumarin
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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
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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
Abstract
The invention discloses fat soluble tea polyphenol. The content of total tea polyphenol in the fat soluble tea polyphenol is 60-95%. The invention also discloses a preparation method of the fat soluble tea polyphenol, and the application of the fat soluble tea polyphenol in the field of cosmetics. The fat soluble tea polyphenol takes green tea as a raw material and takes a polar or nonpolar solvent as a solution medium, extraction is carried out for multiple times under a certain temperature condition to prepare water-soluble tea polyphenol, and then, the water-soluble tea polyphenol is subjected to acylation to obtain the fat soluble tea polyphenol. The fat soluble tea polyphenol provided by the invention has good anti-aging capability, can accelerate secretion of collagen and also can clear free radicals in skin cells. In addition, the fat soluble tea polyphenol provided by the invention also has good moisturizing and whitening functions, and can be added into the cosmetics as an additive.
Description
Technical field
The invention belongs to biochemical field, relate to a kind of cosmetics and/or skin care item, particularly relate to a kind of bag
Cosmetics containing fat-soluble tea polyphenol and/or skin care item.
Background technology
Aging refers to each organ dysfunction of body process universal, that be gradually lowered, with advancing age, old and feeble
Unavoidably, but, good living habit and hygienic measures can slow down aging effectively.In the market
The product of defying age also emerges in an endless stream.
The topmost performance of skin aging is to produce wrinkle, and skin aging is mainly due to the growth at age or the external world
The interference of factor, the NTx albumen of skin corium emiocytosis reduces or collagen hydro enzyme increases, and cell lacks
The support of weary collagen protein, horny layer and epidermal area cave in and form wrinkle.At present it is generally believed that because of oneself
The oxidation being attacked biomembrane polyunsaturated fatty acid, DNA, protein and other biological macromole by base and cause
Damage, is to cause organism aging process and the principal element of many infirmitiess of age.
Ancient times rises, cosmetic formulations existing book on Chinese herbal medicine composition.Along with scientific development, the most existing the most novel
Technology can be used for treating skin aging.But, natural herbal product still has very because of features such as its high-efficiency low-toxicities
Big captivation and wide market.Research has proven to increasing book on Chinese herbal medicine chemical substance and skin is had benefit
Place, a lot of extracts and compound have the potentiality significantly treating skin aging, and the most tentatively illustrate its mechanism.
Green tea (Green Tea), is one of Chinese main teas, refers to take the young leaves of Camellia sinensis or bud,
The most fermented, through completing, shaping, the technique such as drying and the beverage that makes.Often drink green tea can give protection against cancer, blood fat reducing with
Fat-reducing, also can alleviate its nicotine being subject to and injure smoker.
The tea polyphenols (Tea polyphenols) contained in green tea is a kind of Natural antioxidant, to anti-aging,
Anti-cancer, anticancer, sterilization, antiinflammatory etc. have a special-effect, but owing to tea polyphenols is soluble in water, ethanol, third
Ketone, ether, ethyl acetate equal solvent, be insoluble in the characteristic of oils and fats and make it apply to be restricted.Solve at present
Tea polyphenols is insoluble in the method for oils and fats mainly solvent method, emulsion process and a molecular modification method, but prior art system
Standby product otherwise fat-soluble instability, however preparation method is complicated, and product purity is the highest.
Summary of the invention
The problem existed for prior art, the present invention provides a kind of fat-soluble tea polyphenol, and have studied this liposoluble
Property tea polyphenols application in cosmetic field.
The first aspect of the invention is to provide a kind of cosmetics of everyday use, and described cosmetics of everyday use includes that fat-soluble tea is many
Phenol, in the most described cosmetics and/or skin care item, it is also possible to include nutritive additive.
As a preferred embodiment of the present invention, in described cosmetics and/or skin care item, described fat-soluble tea
The content of polyphenol is 0.001%-60%, such as 0.003%, and 50%, preferably 0.005%-40%, such as 20%,
30% etc..
As a preferred embodiment of the present invention, the formula of described fat-soluble tea polyphenol is formula (I):
Wherein: R1、R3、R4、R5Independently, for H, C6-C14Any one in fatty acyl group；
R2For H ,-OH, C6-C14Any one in fatty acyl group；
R1、R2、R3、R4、R5In at least one be C6-C14Fatty acyl group.
The second aspect of the invention is to provide the application of any one fat-soluble tea polyphenol above-mentioned.
Described fat-soluble tea polyphenol is preferably applied to skin appearance face, is more preferably applied to preparation and is coated on skin
The goods of skin outer surface.
Wherein, fat-soluble tea polyphenol of the present invention is applied to prepare cosmetics of everyday use, is preferably applied to preparationization
Cosmetic and/or skin care item.
As a preferred embodiment of the present invention, described fat-soluble tea polyphenol includes logical formula (I):
Wherein: R1、R3、R4、R5Stand alone as H, C6-C14Any one in fatty acyl；
R2For H ,-OH, C6-C14Any one in fatty acyl；
R1、R2、R3、R4、R5In at least one be C6-C14Fatty acyl group.
The third aspect of the invention is to provide a kind of fat-soluble tea polyphenol, and described fat-soluble tea polyphenol includes leading to
Formula (I):
Wherein: R1、R3、R4、R5Stand alone as H, C6-C14Any one in fatty acyl；
R2For H ,-OH, C6-C14Any one in fatty acyl；
R1、R2、R3、R4、R5In at least one be C6-C14Fatty acyl group.
As a preferred embodiment of the present invention, in described fat-soluble tea polyphenol, the content of total tea polyphenols is
60%-95%, such as 65%, 90%, preferably 70%-85%, such as 75%, 80% etc..
The fourth aspect of the invention is to provide the preparation method of a kind of fat-soluble tea polyphenol, described preparation method
Including:
The solvent adding 5-20 volume multiplying power in green tea extracts, and obtains extracting solution；
Described extracting solution prepared by purification, and it is concentrated under reduced pressure to give concentrated solution；
Concentrated solution described in saponification, filters, is dried, obtain intermediate product；
Acylated intermediate product, is slowly added to described intermediate product in acylating agent, reacts certain time, obtains institute
State fat-soluble tea polyphenol.
As a preferred embodiment of the present invention, described solvent is water, ethanol, methanol, ether, surpasses and face
Any one or a few combination in boundary's carbon dioxide.
As a preferred embodiment of the present invention, the number of times of described extraction is at least 2 times, preferably 3-5 time,
Extract and merge each extracting solution after terminating, obtain mixed extract.
As a preferred embodiment of the present invention, in described saponification process, the saponifier of addition can be inorganic
Any one or a few combination in alkali, organic base, such as ammonia, carbamide, ethanolamine etc., preferably inorganic base,
Aqueous solution or ethanol solution, the aqueous solution of potassium hydroxide or alcoholic solution, ammonia etc. such as sodium hydroxide.
As a preferred embodiment of the present invention, described acylating agent prepare reagent include for carboxylic acid, carboxylic acid anhydrides,
Any one or a few combination in acyl chlorides etc., such as acetic acid, ethanedioic acid, benzoic acid, acetic anhydride etc., is preferably
Acyl chlorides, such as phosphorus pentachloride, Phosphorous chloride., phosphorous oxychloride, thionyl chloride etc..
As a preferred embodiment of the present invention, described acylating agent under the conditions of organic base, with acyl chlorides and
C6-C10Prepared by fatty acid.
As a preferred embodiment of the present invention, described fatty acid is preferably C6-C10Satisfied fatty acid, more
It is preferably linear saturated fatty acids.
As a preferred embodiment of the present invention, the temperature conditions of described acylation process is 20 DEG C-50 DEG C.
As a preferred embodiment of the present invention, after described acylation process, also include abstraction purification technique,
The extractant of described abstraction purification technique can be in ethyl acetate, tributyl phosphate, benzene, carbon tetrachloride etc.
Any one or a few combination.
As a preferred embodiment of the present invention, after acylated described intermediate product, it is also possible to include concentrating reaction
Liquid, any one or a combination thereof of being dried in the reactant liquor after concentrating.
As a preferred embodiment of the present invention, the condition of described concentration of reaction solution is 5-20kPa, 20-50 DEG C
Rotary evaporation 10-50min.
As a preferred embodiment of the present invention, the condition being dried the reactant liquor after concentrating is spray drying, institute
The condition stating spray drying is: under 60-120MPa pressure, concentrated solution is injected into the microgranule of 100-400 μm,
Microgranule is passed through the hot-air dry 5-30s of 50-90 DEG C.
The fat-soluble tea polyphenol that the present invention provides, has excellent defying age ability, it is possible to promote collagen protein
Secretion, it is also possible to remove the free radical in Skin Cell.It addition, the fat-soluble tea polyphenol that the present invention provides also has
There is excellent performance of keeping humidity, can join in cosmetics as additive.
Accompanying drawing explanation
Fig. 1 is the impact that under naturalness, I-type collagen is secreted by fat-soluble tea polyphenol；
Fig. 2 is the hydrogen peroxide impact on cell survival rate；
Fig. 3 is the fat-soluble tea polyphenol impact on the HDF cell survival rate of Hydroperoxide injury；
Fig. 4 is the fat-soluble tea polyphenol impact on the HDF cell MMP-1 content of Hydroperoxide injury；
Fig. 5 is the fat-soluble tea polyphenol impact on the HDF cell MDA content of Hydroperoxide injury；
Fig. 6 is the fat-soluble tea polyphenol impact on DPPH clearance rate；
Fig. 7 is the fat-soluble tea polyphenol impact on LOR content；
Fig. 8 is the fat-soluble tea polyphenol suppression ratio to TYR enzyme.
Detailed description of the invention
The preparation of fat-soluble tea polyphenol
Embodiment one
The green tea that will newly pluck, clean water 2 times, during cleaning, in clear water, implantation concentration is 100ppm's
Chlorine dioxide, cleans green tea, sterilization, and uses the cleaned green tea of 65 DEG C of hot air dryings, obtains
The water content dry green tea below 5%, and the dry green tea of preparation is pulverized, cross 60 mesh sieves, standby.
Take the dry green tea 10kg after pulverizing, and be added thereto to the water of 10 times of volumes, at 80 DEG C, 1.01MPa
Extract 2h under pressure, extract and after terminating, add 60% ethanol water of 8 times of volumes, 80 DEG C,
Carry out second extraction under 1.01MPa pressure, extract 2h, extract after terminating, merge twice extracting solution, will be mixed
Extracting solution after conjunction in D-101 type macroporous adsorbent resin, 25 DEG C be adsorbed to saturated, the most respectively with anhydrous
Ethanol, 60% ethanol water, 50% ethanol water, 30% ethanol water eluting, the flow velocity of eluent
For 3BV/h, normal temperature and pressure eluting macroporous adsorbent resin is after eluting terminates, dense under 5kPa, slight boiling condition
Contracting eluent, removes ethanol therein, to 6kg, adds the hydroxide of 1.5L 0.1mol/L in concentrated solution
Sodium water solution, 90 DEG C, 1.01MPa react 2h, filter, obtain filter cake, by filter cake 0.5MPa,
60 DEG C of hot air dryings, to mass conservation, obtain intermediate product.
To 300g CH3(CH2)5COOH adds 285g SOCl2With 7.3g dimethylformamide,
30-50 DEG C of reaction 5h, after reaction terminates, Rotary Evaporators removes SOCl therein2, obtain
CH3(CH2)5COCl。
The CH that will obtain3(CH2)5COCl is dissolved in 25L ethyl acetate, is slowly added to obtain under room temperature
Intermediate product, reacts 2h, is warming up to 35 DEG C, and reaction to no acidic gas produces, and reaction terminates.Rotated
Evaporation and concentration removes ethyl acetate therein, then adds and the isopyknic deionized water of concentrated solution in concentrated solution
And ethyl acetate, stratification after stirring mixing, remove supernatant liquid, layer liquid adds and subnatant still further below
The isopyknic ethyl acetate of body, extraction lower floor liquid 3 times, combining extraction liquid, 5kPa, 20 DEG C of concentrated by rotary evaporations
To 2.5kg, then spray-dried to constant weight in 85 DEG C, obtain fat-soluble tea polyphenol.
Wherein, the condition of spray drying is: under 100MPa pressure, and concentrated solution is injected into the micro-of 150 μm
Grain, passes through the hot-air dry 15s of 70 DEG C by microgranule.
Detect through ultraviolet scanner, determine that in this fat-soluble tea polyphenol, Determination of Polyphenols is 90%.
Analyzing through LC-MS instrument, this fat-soluble tea polyphenol includes C22H26O7Quasi-molecular ions,
M/e=402.17.
Embodiment two
The green tea that will newly pluck, clean water 2 times, during cleaning, in clear water, implantation concentration is 100ppm's
Chlorine dioxide, cleans green tea, sterilization, and uses the cleaned green tea of 65 DEG C of hot air dryings, obtains
The water content dry green tea below 5%, and the dry green tea of preparation is pulverized, cross 80 mesh sieves, standby.
Take the dry green tea 10kg after pulverizing, and be added thereto to the dehydrated alcohol of 5 times of volumes, 80 DEG C,
Extract 2h under 1.5MPa pressure, extract after terminating, add 60% ethanol water of 8 times of volumes 80 DEG C,
Carry out second extraction under 1.1MPa pressure, extract 2h, extract after terminating, mix the extracting solution obtained for twice,
By mixed extracting solution evaporation and concentration 1h under the conditions of 5kPa, micro-boiling, obtaining concentrated solution, concentrated solution exists
In AB-8 type macroporous adsorbent resin, 25 DEG C be adsorbed to saturated, the most respectively with dehydrated alcohol, 60% ethanol water
Solution, 50% ethanol water, 30% ethanol water eluting, the flow velocity of eluent is 3BV/h, and room temperature is normal
Compress and wash de-macroporous adsorbent resin.
After eluting terminates, concentrate eluant under 5kPa, slight boiling condition, remove ethanol therein, to 6kg,
Obtain concentrated solution two, the condition identical with the present embodiment in AB-8 type macroporous adsorbent resin by concentrated solution two
Secondarily purified, after eluting terminates, under the conditions of the micro-boiling of 5kPa, concentrate secondary eluent, obtain concentrated solution three, to
In concentrated solution three add 0.8L 0.1mol/L potassium hydroxide aqueous solution, 90 DEG C, 1.01MPa react 2h,
Filter, obtain filter cake, by filter cake at 0.5MPa, 60 DEG C of hot air dryings to mass conservation, obtain intermediate product.
To 0.75kg CH3(CH2)9COOH adds 0.5kg PCl3With 3.7g dimethylformamide,
30-50 DEG C of reaction 5h, after reaction terminates, Rotary Evaporators removes PCl therein3, obtain
CH3(CH2)9COCl。
The CH that will obtain3(CH2)9COCl is dissolved in 15L ethyl acetate, is slowly added to obtain under room temperature
Intermediate product, reacts 2h, is warming up to 35 DEG C, and reaction to no acidic gas produces, and reaction terminates.Through 20 DEG C,
5kPa rotary evaporation concentrates and removes ethyl acetate therein, obtains fat-soluble tea polyphenol.
Detect through ultraviolet scanner, determine that in this fat-soluble tea polyphenol, Determination of Polyphenols is 60%.
Analyzing through LC-MS instrument, this fat-soluble tea polyphenol includes C26H34O7Quasi-molecular ions,
M/e=458.54.
Embodiment three
The green tea that will newly pluck, clean water 2 times, during cleaning, in clear water, implantation concentration is 100ppm's
Chlorine dioxide, cleans green tea, sterilization, and uses the cleaned green tea of 65 DEG C of hot air dryings, obtains
The water content dry green tea below 5%, and the dry green tea of preparation is pulverized, cross 100 mesh sieves, standby.
Take the dry green tea 10kg after pulverizing, and be added thereto to the ether of 20 times of volumes, at 40 DEG C, 1.2MPa
Extract 2h under pressure, extract after terminating, add 30% ethanol water of 10 times of volumes 80 DEG C,
Carrying out second extraction under 1.1MPa pressure, extract 2h, extraction terminates.
Repeat said extracted method, extract 4 times altogether.
Merge each extracting solution, use 200 mesh silica column purification, make with the ethyl acetate of 2BV/h flow velocity
For flowing phase, at 25 DEG C, normal pressure eluting enriched layer, in concentrated solution, add the ammonia spirit of 1L 0.1mol/L,
70 DEG C, 1.01MPa react 2h, filter, obtain filter cake, by filter cake at 0.5MPa, 60 DEG C of hot air dryings
Dry to mass conservation, obtain intermediate product.
To 1.5kg CH3(CH2)11COOH adds 0.8kg POCl3With 7.3g dimethylformamide,
30-50 DEG C of reaction 5h, after reaction terminates, Rotary Evaporators removes POCl therein3, obtain
CH3(CH2)11COCl。
The CH that will obtain3(CH2)11COCl is dissolved in 25L ethyl acetate, is slowly added to obtain under room temperature
Intermediate product, reacts 2h, is warming up to 35 DEG C, and reaction to no acidic gas produces, and reaction terminates.Rotated
Evaporation and concentration removes ethyl acetate therein, then adds and the isopyknic deionized water of concentrated solution in concentrated solution
And ethyl acetate, stratification after stirring mixing, remove supernatant liquid, ethyl acetate extracts lower floor's liquid 3
Secondary, combining extraction liquid, it is concentrated to give fat-soluble tea polyphenol.
Detect through ultraviolet scanner, determine that in this fat-soluble tea polyphenol, Determination of Polyphenols is 75%.
Analyzing through LC-MS instrument, this fat-soluble tea polyphenol includes C28H38O7Quasi-molecular ions,
M/e=486.60.
Comparative example
Weigh 10kg to cross the green tea dust of 30 mesh sieves and be placed in extraction tank, be added thereto to 200L 30% ethanol water
Solution, reflux 3h, and sucking filtration obtains tea polyphenol extract liquid, adds 0.415mol/L in tea polyphenol extract liquid
Solder(ing)acid, shake up, by sodium bicarbonate aqueous solution that mass fraction is 15% regulation acidity to pH value
=5.0, it is centrifuged and obtains tea polyphenols-zinc salts precipitate, in tea polyphenols-zinc salts precipitate, add a certain amount of sulfuric acid solution,
Dissolution precipitation, a small amount of gelatinous precipitate of centrifugal segregation, obtain tea polyphenols acid and turn liquid, use the sodium bicarbonate of 15%
Aqueous solution regulation acidity, then extract the most at twice by ethyl acetate, combining extraction liquid, in ethyl acetate
Add the VC aqueous solution that mass fraction is 2%, the non-2:1 of both volume ratios in mutually, wash twice, at 60 DEG C
Under be vacuum dried, obtain the green tea extract that 1.3kg comprises tea polyphenols.
Detect through ultraviolet scanner, determine that in this green tea extract, Determination of Polyphenols is 60%.
Analyzing through LC-MS instrument, this green tea extract includes C15H14O6Quasi-molecular ions, its molal weight
It is 290.26.
Fat-soluble tea polyphenol is on HDF cell and the impact of Hacat cell survival rate
Trophophase, the concentration of taking the logarithm is 105People's HDF cell of individual/mL, is inoculated in 96 porocytes by cell
In culture plate, every porocyte liquid 100 μ L.The cell hole count finally spread depends on that sample number, each sample set
3 multiple holes.
96 orifice plates are placed in adhere-wall culture 6h in the cell culture incubator of 37 DEG C.
The fat-soluble tea polyphenol of final concentration of 1mg/mL, 0.1mg/mL and 0.01mg/mL is joined 96
In porocyte culture plate, add isopyknic cell culture fluid to matched group.In 37 DEG C, comprise 5%CO2
Cell culture incubator in hatch 48h.
Then in every hole, add the MTT100 μ L of 0.5mg/mL, in 37 DEG C, comprise 5%CO2Thin
Born of the same parents' incubator hatches 4h under dark condition.Removing supernatant, add 150 μ L DMSO, concussion is with 570
Nm is experiment wavelength, and 630nm is with reference to wavelength, detects absorbance.
Calculating cell survival rate, result is as shown in table 1:
Table 1, fat-soluble tea polyphenol is on HDF cell and the impact of Hacat cell survival rate
With cell survival rate higher than 80% for people's HDF cell and the standard of Hacat cytotoxic, by table 1
Understanding, the fat-soluble tea polyphenol that the present invention provides is 0.01mg/mL to the maximum concentration of people's HDF cytotoxic,
The fat-soluble tea polyphenol that the present invention provides is 0.01mg/mL to the maximum concentration of people's HDF cytotoxic, because of
This, determine that the maximum concentration 0.01mg/mL of fat-soluble tea polyphenol is follow-up experimental concentration.
The defying age performance of fat-soluble tea polyphenol
The fat-soluble tea polyphenol impact on HDF collagen secretion under naturalness
In order to investigate the fat-soluble tea polyphenol impact on HDF collagen secretion that the present invention provides, this enforcement
Test is divided into blank group, experimental group, control experiment group and criterion group by example.
Trophophase, the concentration of taking the logarithm is 105Individual/mL cell, every hole 100 μ L, in 37 DEG C, containing CO2
Cell culture incubator in cultivate 24h, take out supernatant afterwards, with the centrifugation 10min of 3000rpm,
Take supernatant.
In criterion group, add 50 μ L titers, add in experimental group 10 μ L of supernatant liquid and 40 μ L this
The diluent of the fat-soluble tea polyphenol of bright offer, adds 10 μ L of supernatant liquid and 40 μ L couple in control experiment group
The ratio diluent of the green tea extract that embodiment provides, is not added with sample in blank group, hatches 1h respectively at 37 DEG C,
And wash plate 5 times, often group sample sets 3 multiple holes.
Biotin labeled anti-lgG antibody 50 μ L it is separately added in four groups of samples, in 37 DEG C of incubation 30min,
Wash 5 times.
In four groups of samples, it is separately added into streptomycin and the element-HRP of 50 μ L, shakes mixing gently, in 37 DEG C
Incubation 30min, washs 5 times.
In four groups of samples, it is separately added into each 50 μ L of developer A and developer B, shakes mixing gently, in
37 DEG C of lucifuges hatch 30min, add stop buffer 50 μ L in four groups of samples.
Return to zero with blank group, after terminating reaction in 15min, at the absorbance that 450nm wavelength measurement is respectively organized,
Result is as shown in table 2.
Table 2, the impact that HDF cell I-type collagen is secreted by fat-soluble tea polyphenol
Collagen protein mainly includes that type i collagen and type III collagen, extraneous induction promote to aoxidize in hypodermal cell water
Flat raising is the principal element of cell injury, and the direct result that oxidation level improves is reduction of I-type collagen
Expression and I-type collagen degraded by matrix metalloproteinase MPP-1, the result that two kinds of situations cause is equal
Reduce for I-type collagen content in skin, and the minimizing of I-type collagen content is skin formation wrinkle
Main cause.From table 2 and Fig. 1, the concentration that adding the present invention in HDF cell provides is
After 0.01mg/mL fat-soluble tea polyphenol, the I-type collagen content in skin is 129.93%, and ratio is existing
In tea polyphenols prepared by technology, the content 106.52% of I-type collagen, exceed 23%, illustrate that the present invention carries
The fat-soluble tea polyphenol of confession can the most significantly promote the expression of I-type collagen.
The hydrogen peroxide impact on HDF cell survival rate
Choose the hydrogen peroxide of variable concentrations, as 50 μMs, 100 μMs, 200 μMs, 400 μMs, 600 μMs,
800 μMs and 1000 μMs, jointly hatch different time with HDF cell, such as 3h, 6h and 9h etc., use
The impact on HDF cell survival rate of the hydrogen peroxide of mtt assay detection variable concentrations.
Taking cultivation to concentration is 105The HDF cell of individual/mL, is inoculated in 96 porocyte culture plates, every hole
100μL.In 37 DEG C, containing CO2Incubator in adhere-wall culture 6h, every plate does 3, multiple hole.
The hydrogen peroxide using variable concentrations hatches modeling 3h, 6h and 9h respectively；Add in each sample well
Enter the MTT 100 μ L that concentration is 0.5mg/mL, in 37 DEG C, containing CO2Incubator in, dark bar
4h is hatched under part.
Remove supernatant, in sample, add 150 μ L DMSO, concussion, with 570nm for experiment wavelength,
630nm is with reference to wavelength, detects the absorbance of each sample, calculates cell survival rate.
Test result is as in figure 2 it is shown, people's HDF cell is hatched altogether in the hydrogen peroxide that concentration is 50-800 μM
After 3-9h, the survival rate of people's HDF cell is decreased obviously, and when hatching concentration more than 400 μMs, cell is deposited
Motility rate is less than 50%.After 200 μMs of hydrogen peroxide effect 6h, cell survival rate drops to 70%.
The fat-soluble tea polyphenol impact on the HDF cell survival rate through Hydroperoxide injury
Taking cultivation to density is 105The HDF cell of individual/mL is inoculated in 96 orifice plates, every hole 100 μ L.In
37 DEG C, containing CO2Incubator in adhere-wall culture 6h.
Add, to experimental group, the fat-soluble tea polyphenol that the present invention provides, add comparative example to control experiment group and carry
The green tea extract of confession, utilizes Hydroperoxide injury to model, and adds the MTT 100 of 0.5mg/mL to every hole
μ L, in 37 DEG C, 5%CO2Dark condition under hatch 4h.Remove supernatant, add DMSO 150 μ L,
Concussion detection absorbance.Calculate cell survival rate, and for the survival rate mapping of examination thing variable concentrations and cell,
Result is as shown in Figure 3.
After hydrogen peroxide is hatched, the survival rate of HDF cell is reduced to less than 70%, and to through peroxidating
After the HDF cell that hydrogen damage is crossed adds the fat-soluble tea polyphenol that the present invention provides, the survival of people's HDF cell
Rate reaches 80%, after adding tea polyphenols prepared by prior art in the HDF cell crossed through Hydroperoxide injury,
The survival rate of people's HDF cell is 73%, and the fat-soluble tea polyphenol that i.e. present invention provides is relative to prior art system
Standby tea polyphenols can significantly alleviate the hydrogen peroxide damage to HDF cell.
The fat-soluble tea polyphenol impact on the HDF matrix metalloproteinases (MMP-1) of Hydroperoxide injury
Material and reagent
Cell culture fluid 24 porocyte culture plate
Cell culture incubator hydrogen peroxide
Centrifuge ELISA kit
Testing procedure
It is divided into criterion group, blank group, experimental group and control experiment group.
The concentration of trophophase of taking the logarithm is 105The HDF cell of individual/mL is inoculated in 24 well culture plates, often
Hole 1mL, in 37 DEG C, containing CO2Cell culture incubator in cultivate 6h.
Add, to experimental group, the fat-soluble tea polyphenol that the present invention provides, add comparative example to control experiment group and carry
The green tea extract of confession, adds reference material to criterion group, and blank group is without other samples.
Hydroperoxide injury model is set up in induction.Careful Aspirate supernatant culture medium, centrifugal, say according to test kit
Bright book, takes 10 μ L cell suspension and tests.Return to zero with blank well, after termination of the reaction in 15min,
Absorbance with each hole of 450nm wavelength measurement.Concentration according to MMP-1 corresponding to standard substance and correspondence
Absorbance, calculates the linear regression equation of standard curve, further according to the absorbance of sample, in recurrence side
The concentration of MMP-1 in experimental group is calculated in journey.
As shown in Figure 4, after hydrogen peroxide stimulates, the MMP-1 level in HDF cell significantly rises to
The 170% of normal cell level, adds what the present invention provided in the HDF cell stimulated through hydrogen peroxide
After fat-soluble tea polyphenol, the content of MMP-1 is reduced to less than 100%, is 93.45%.And it is existing to add employing
After having green tea extract prepared by technology, the content of MMP-1 is 120.38%.This explanation, at oxidative stress
Under the conditions of, the fat-soluble tea polyphenol that the present invention provides, compared with tea polyphenols prepared by prior art, has more excellent
Suppression MMP-1 express performance.
Fat-soluble tea polyphenol is on the impact of malonaldehyde (MDA) in the HDF cell of Hydroperoxide injury
When MDA heats in acid condition, can be condensed with thiobarbituricacidα-(TBA), form redness and produce
Thing 3,5,5-trimethyl oxazole-2,4-diketone, at 532nm, there is maximum absorption band.Because substrate is that sulfur is for bar ratio
Appropriate acid (TBA), therefore this method is called TBA method.
Trophophase, the concentration of taking the logarithm is 105The HDF cell of individual/mL, is inoculated in 6 porocyte culture plates,
Every hole 2mL, cultivates 6h, the fat-soluble tea prepared through the present invention that fresh culture dilutes to experimental group addition
Polyphenol, adds green tea extract prepared by comparative example to control experiment group, and Hydroperoxide injury is set up in induction
Model.It is centrifuged 10min with 1000rpm, collects the cell in medium supernatant and attached cell, carefully
Adding 500 μ L PBS in born of the same parents' precipitation, reverse mixing, at 4 DEG C, is centrifuged 10min with 2000rpm gently,
Reject supernatant retains bottom precipitation.500 μ L PBS are added in precipitation, sonicated cells (400A,
5s/ time, gap 10s 3～5 times repeatedly), prepare cell homogenates；
Test according to test kit description.Reagent is mixed, with preservative film, test tube mouth is tightened, use syringe needle
Acanthopore is breathed freely, and uncaps with pot and boils 40min, and after taking-up, flowing water cooling, is centrifuged 10min with 4000rpm,
Make precipitation complete.Take supernatant, use the absorbance at spectrophotometry 532nm wavelength；Utilize
BCA protein detection kit, the fat-soluble tea polyphenol dilution that the present invention is prepared by method to specifications is suitably
Multiple, measures the protein content in cell；
Table 3, the fat-soluble tea polyphenol impact on the HDF cell MDA content of Hydroperoxide injury
| Group | MDA concentration (%) |
| Blank group | 100 |
| Negative control group | 326.33 |
| Positive controls | 262.35 |
| Experimental group | 216.56 |
| Control experiment group | 262 |
From table 3 and Fig. 5, after Hydroperoxide injury, MDA concentration rapid increase, during 6h, MDA contains
Amount increases to Normocellular 326.33%, as shown in negative control group.And the increasing of MDA after adding retinoic acid
Add and be inhibited, finally stable 262.35%.This is added in the HDF cell of Hydroperoxide injury
After the tea polyphenols that invention and comparative example provide, MDA content is all low than add after retinoic acid, and fat is described
Dissolubility tea polyphenols has the ability that the suppression MDA of excellence increases, and the fat-soluble tea polyphenol that the present invention provides presses down
The tea polyphenols that the ability of MDA processed is prepared also superior to prior art.
Fat-soluble tea polyphenol removes the performance of free radical
1,1-diphenyl-2-trinitrophenyl-hydrazine (DPPH) is the free radical at the most stable a kind of nitrogen center, it
Stability essentially from the Resonance Stabilization action of 3 phenyl ring and spatial obstacle, makes on the nitrogen-atoms that is clipped in the middle not
Paired electronics can not play its due electronics and act in pairs.As a kind of stable free radical, it can be clear
Free radical except other.It is now widely used in quantitative determination Biosample and the oxidation resistance of food.This method is
Having single electron according to DPPH free radical, have the last one to absorb at 517nm, its alcoholic solution is the characteristic of purple.
In the presence of having free radical scavenger, make it absorb fade away owing to matching with its single electron, its journey of fading
The electron amount that degree accepts with it becomes quantitative relationship, thus available spectrophotometer carries out quick quantitative analysis.
Material and reagent
DPPH dehydrated alcohol
Dd water 200 μ L suction nozzle
96 orifice plate 8 passage sample loading guns
Microplate reader
Testing procedure
With the DPPH solution of dehydrated alcohol configuration 0.2mmol/L, keep in Dark Place, configuration 0.01mg/mL's
Epigallocatechin gallate (EGCG) (EGCG) solution.
To experimental group add the fat-soluble tea polyphenol solution that provides for the 0.01mg/mL present invention of 20uL concentration with
In DPPH ethanol solution 180uL to 96 orifice plate of 0.2mmol/L, in blank group 1, add 180uL
The fat-soluble tea polyphenol solution that dehydrated alcohol provides with the 20uL present invention, adds 180uL in criterion group
DPPH solution and 20uL distilled water, every hole arranges at least 3 multiple holes, shakes up respectively, and under room temperature, dark place is quiet
Put 30min, measure the absorbance of each group.
Adding 20uL concentration to controlled trial group is that the green tea that 0.01mg/mL uses prior art to prepare extracts
In DPPH ethanol solution 180uL to 96 orifice plate of thing solution and 0.2mmol/L, add in blank group 2
Adding the green tea extract solution that 180uL dehydrated alcohol uses prior art to prepare with 20uL, every hole is arranged at least
3 multiple holes, shake up respectively, and under room temperature, dark place stands 30min, measures the absorbance of each group.
The Scavenging activity of DPPH free radical is according to the following formula:
Wherein, during the DPPH clearance rate of experiment with computing group, test specimens absorbance is the absorbance of experimental group,
Blank group absorbance is respectively the absorbance of blank group 1；
When calculating the DPPH clearance rate of control experiment group, test specimens absorbance is the absorbance of control experiment group,
Blank group absorbance is the absorbance of blank group 2；
Clearance rate shows that the most greatly oxidation resistance is the strongest, result as shown in Figure 6, when solution does not exist DPPH
During free radical, the DPPH clearance rate of blank group is 0, and the clearance of DPPH free radical is by EGCG
47.23%, the fat-soluble tea polyphenol that the present invention provides is 80.63% to the clearance of DPPH free radical, adopts
The tea polyphenols prepared by prior art less than 70%, illustrates that fat-soluble tea is many to the clearance of DPPH free radical
Phenol has the ability of the strongest removal DPPH free radical, and the tea polyphenols provided relative to prior art,
Fat-soluble tea polyphenol prepared by the present invention has more excellent DPPH clearance rate.
The performance of keeping humidity of fat-soluble tea polyphenol
In skin, the number of the content of moisture, directly affects the elasticity of skin, glossiness etc., the epidermis of skin,
Skin is all maintained moisture to play a different role by corium, subcutaneous tissue.During skin moisture-keeping, mainly have
Two kinds of machine-processed skin maintenance effects to water that affect:
1) skin is as the natural cover for defense, it is to avoid water loss；
Epiderm skin is the natural cover for defense of people, and wherein skin lock outlet capacity is risen by clear layer, granular layer and horny layer
To important function.Clear layer contains phospholipid substance and keratoprotein, it is possible to prevent moisture and electrolyte etc. from passing through
Skin.The cell arrangement of granular layer is fine and close, to storage moisture, prevents moisture penetration to have important effect.Angle
Matter layer is to be formed thin layer structure tough and tensile, resilient by cutin, intracellular is filled with keratin.
2) skin exists many Moisture factor, absorb and pin moisture.
In dermal layer of the skin, hyaluronic acid (HA) is the aminopolysaccharide that content is more, and HA viscosity is high
And can bound water molecule in high proportion, the content of HA directly affects the content of moisture in skin.As in skin
Important moisturizing ingredient, it has remarkable effect to propagation, the differentiation of Skin Cell, to just maintaining Skin Cell
Often metabolism is most important.
Horny layer is the tough and tensile resilient layer structure being made up of keratinocyte, intracellular is filled with angle egg
In vain.Keratin is non-water-soluble scleroprotein, has the effect blending body fluid extravasation in stoping chemical substance, wherein
The keratin that content is the highest is called loricrin, accounts for keratic 80%, and the content of loricrin can be directly
Affect the loss situation of moisture of skin.
This test investigates what the present invention provided by investigating the expression of Hacat cell loricrin (LOR)
The performance of keeping humidity of fat-soluble tea polyphenol.This test is divided into blank group, experimental group, test control group and criterion group.
Take the logarithm the Hacat cell that concentration is 105/mL of trophophase, the cell of cultivation is inoculated in 24
In orifice plate, every porocyte liquid 1mL, in 37 DEG C, containing CO2Cell culture incubator in cultivate 6h.
The fat-soluble tea polyphenol that a certain amount of present invention provides is added in experimental group Cell sap, thin to control experiment group
Cytosol adds the green tea extract that a certain amount of comparative example provides, is placed in 37 DEG C, containing 5%CO2And it is full
With the cell culture incubator of humidity is cultivated 24h respectively；
Reject supernatant, rinses cell twice with pre-cooling PBS, adds 100 μ L lysates in culture hole,
Cell lysis 10min on ice, collects cell pyrolysis liquid, is centrifuged 10min with 13000rpm, takes supernatant standby
With.
According to ELISA kit description, take cell pyrolysis liquid and test；
The different group protein content of BCA test kit detection, each group LOR expression is utilized to use protein content to rectify
Just, result is as shown in table 4.
Table 4, the impact that LOR is expressed by fat-soluble tea polyphenol
| For examination species | LOR content (%) |
| Experimental group | 107.43 |
| Control experiment group | 105.36 |
| Blank group | 100 |
From table 4 and Fig. 7, after adding the green tea extract of the present invention and comparative example's offer, people Hacat
In cell, LOR content has increased, and illustrates that tea polyphenols has the effect promoting LOR secretion, and the present invention carries
The fat-soluble tea polyphenol of confession is close with the activity of the tea polyphenols that comparative example provides.
The whitening function of fat-soluble tea polyphenol extract
Tryrosinase is the major rate-limiting enzyme of melanin genesis, by suppressing the activity of tryrosinase, it is possible to reduce black
The generation of element, tyrosinase activity detection method has: radioisotope method, Immunological Method and biochemical-Enzymic method,
With the relatively simple maturation of biochemical-Enzymic method.Biochemical-Enzymic method measures the principle of tyrosinase activity suppression: cheese ammonia
Acid or DOPA acid are converted into DOPA quinone under the effect of tryrosinase, judge that tryrosinase is lived by colorimetric method for determining
Property suppression ratio, the method is by the activity of external test tryrosinase, simple and fast.
Material and reagent
The phosphate buffer of Mushroom Tyrosinase pH value=6.8
Levodopa (L-DOPA) 200 μ L suction nozzle
96 orifice plate 8 passage sample loading guns
Microplate reader
Operating procedure
Measure the tyrosinase inhibitory action of the liposoluble extract that the present invention provides
This test is divided into blank group, blank reference group, experimental group and experiment reference group.
Preparation mass concentration is the L-DOPA aqueous solution of 0.1%, and the phosphate of secure ph=6.8 delays
Dissolved liquid.
The fat-soluble tea polyphenol that adding the present invention that 5 μ L concentration are 0.1mg/mL in experimental group provides carries
Take thing, in experiment reference group, add the fat-soluble tea that the present invention that 5 μ L concentration are 0.1mg/mL provides
Polyphenol extract and the phosphate buffered solution of 45 μ L pH value=6.8, add 5 μ L to blank reference group
The phosphate solution of Mushroom Tyrosinase, and the phosphate buffered solution of 45 μ L pH value=6.8, to sky
White group adds the phosphate buffered solution of 50 μ L pH value=6.8.
It is placed in 20min in 37 DEG C of air baths, adds 50 μ L to every hole, mass concentration is 0.1%
L-DOPA aqueous solution, stands 20min in 37 DEG C of air baths, measures the suction often organized under 475nm
Shading value, and calculate the present invention provide fat-soluble tea polyphenol extract the activity of Mushroom Tyrosinase is pressed down
Rate processed.
Identical method of testing is used to calculate the fat-soluble tea polyphenol using comparative example's (prior art) to prepare
Extract and the positive controls kojic acid suppression ratio to tryrosinase.
Result as shown in Figure 8, the fat-soluble tea polyphenol extract suppression to Mushroom Tyrosinase that the present invention provides
Rate is 80.63%, and the suppression ratio of Mushroom Tyrosinase is by the green tea extract using prior art to prepare
63.28%, illustrate that the fat-soluble tea polyphenol extract that the present invention provides has the whitening function of excellence, Ke Yizuo
Add in cosmetics for additive.
To sum up, the fat-soluble tea polyphenol that the present invention provides has excellent defying age performance, and removes free radical
Ability, additionally, also have performance of keeping humidity and whitening function, the fat-soluble tea polyphenol that the present invention provides can conduct
Additive joins in cosmetics.
Being described in detail the specific embodiment of the present invention above, but it is intended only as example, the present invention is also
It is not restricted to particular embodiments described above.To those skilled in the art, any the present invention is carried out
Equivalent modifications and substitute the most all among scope of the invention.Therefore, without departing from the spirit of the present invention and model
Enclose lower made impartial conversion and amendment, all should contain within the scope of the invention.
Claims (9)
1. cosmetics and/or skin care item, it is characterised in that comprise fat-soluble in described cosmetics and/or skin care item
Tea polyphenols, the content of described fat-soluble tea polyphenol is 0.001%-60%.
Cosmetics the most according to claim 1 and/or skin care item, it is characterised in that described fat-soluble tea polyphenol
Including logical formula (I):
Wherein: R1、R3、R4、R5Stand alone as H, C6-C14Any one in fatty acyl group；
R2For H ,-OH, C6-C14Any one in fatty acyl group；
R1、R2、R3、R4、R5In at least one be C6-C14Fatty acyl group.
3. a fat-soluble tea polyphenol, it is characterised in that described fat-soluble tea polyphenol includes logical formula (I):
Wherein: R1、R3、R4、R5Stand alone as H, C6-C14Any one in fatty acyl；
R2For H ,-OH, C6-C14Any one in fatty acyl；
R1、R2、R3、R4、R5In at least one be C6-C14Fatty acyl group.
Fat-soluble tea polyphenol the most according to claim 3, it is characterised in that total in described fat-soluble tea polyphenol
The content of tea polyphenols is 60%-95%.
5. the preparation method of the fat-soluble tea polyphenol as described in claim 3 or 4, it is characterised in that described
Method includes:
The solvent adding 5-20 volume multiplying power in green tea extracts, and obtains extracting solution；
Described extracting solution prepared by purification, and it is concentrated under reduced pressure to give concentrated solution；
Concentrated solution described in saponification, filters, is dried, obtain intermediate product；
Acylated intermediate product, is slowly added to described intermediate product in acylating agent, reacts certain time, obtains institute
State fat-soluble tea polyphenol.
Preparation method the most according to claim 5, it is characterised in that also include after described acylation process
Abstraction purification technique, the extractant of described abstraction purification technique can be ethyl acetate, tributyl phosphate, benzene,
Any one or a few combination in carbon tetrachloride etc..
Preparation method the most according to claim 5, it is characterised in that after acylated described intermediate product, also may be used
To include concentration of reaction solution, any one or a combination thereof of being dried in the reactant liquor after concentrating, described concentration is reacted
The condition of liquid is 5-20kPa, 20-50 DEG C of rotary evaporation 10-50min.
8. the application of the fat-soluble tea polyphenol as described in claim 3 or 4, it is characterised in that described liposoluble
Property tea polyphenols is applied to prepare the goods being coated on skin appearance face.
The application of fat-soluble tea polyphenol the most according to claim 8, it is characterised in that liposoluble in described goods
The content of property tea polyphenols is 0.001%-60%.
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