CN105581919A - Ferulic acid and phospholipid complex and application thereof to preparation of skin-whitening cosmetics - Google Patents
Ferulic acid and phospholipid complex and application thereof to preparation of skin-whitening cosmetics Download PDFInfo
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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
- A61K8/55—Phosphorus compounds
- A61K8/553—Phospholipids, e.g. lecithin
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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
- A61K8/36—Carboxylic acids; Salts or anhydrides thereof
- A61K8/365—Hydroxycarboxylic acids; Ketocarboxylic acids
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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
- 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
- A61K2800/59—Mixtures
- A61K2800/596—Mixtures of surface active compounds
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Abstract
The invention discloses a ferulic acid and phospholipid complex and application thereof to preparation of skin-whitening cosmetics. The ferulic acid and phospholipid complex is obtained after ferulic acid and phospholipid are heated, stirred and compounded in a non-protonic solvent and the non-protonic solvent is removed. The invention also provides the skin-whitening cosmetics containing the ferulic acid and phospholipid complex. The cosmetics include skin oil, emulsion and cream with the skin whitening effect. According to the ferulic acid and phospholipid complex, ferulic acid and phospholipid are compounded, so that physicochemical properties of ferulic acid are changed, fat solubility, stability and water dispersibility of the complex are enhanced, the transmembrane transport performance of the complex is improved, and then the bioavailability of the complex is increased. After 30 female volunteers at the age of 25-45 use the skin-whitening and skin-caring emulsion containing the ferulic acid and phospholipid complex for 30 days, the melanin content of their faces is lowered obviously, the brightness of their skin is increased, the MI value, L* value and ITA degree value of their skin are remarkably different from original values (P<0.05), and it is indicated that the skin-whitening emulsion has a good human body skin whitening effect.
Description
Technical field
The present invention relates to a kind of preparation method of forulic acid phosphatide complexes, also relate to and contain forulic acid phosphatide complexesSkin-lightening cosmetic and preparation method thereof. The invention belongs to cosmetics technical field.
Background technology
Forulic acid is a kind of phenolic acid being prevalent in natural plant cells wall, is asafoetide, Ligusticum wallichii, Radix Angelicae Sinensis, literFiber crops are waited one of Effective Component of Chinese Medicine, because its good effect such as anti-oxidant, antibacterial, anticancer is widely usedFood and medicine industry. In recent years, along with to the going deep into of forulic acid bioactivity research, find that it not only has veryGood pharmacological effect also has good skin-care effect. The one, forulic acid has good ultraviolet near 290～330nmLine absorption, can add in sunlight screening skin-protecting product and protect skin to avoid the damage of UVB; The 2nd, forulic acid has very strong resistingOxidation, can remove the free radical that causes human body diseases, aging as superoxides, hydroxyl, hydroxyl peroxideCompound etc.; The 3rd, there is the effect of restraint of tyrosinase. Therefore, forulic acid can be used as sun-proof, anti-ageing, whitening meritEffect composition is applied in cosmetics. At present, Japan is applied to forulic acid in cosmetics as sun-screening agent. ThoughSo forulic acid can improve skin quality, makes its exquisiteness, gloss, high resilience, but because of its fat-soluble poor, materializationCharacter is unstable, makes its application in cosmetics be subject to certain limitation.
Phosphatide is biomembranous basis, is extensively present in nature animals and plants seed, has source wide, nothingThe advantages such as poison, phospholipid molecule has a hydrophilic head and two hydrophobic long-chains, has because it is amphipathicEmulsification, disperse, help and the characteristic such as ooze, soak. Phosphatide is applied to cosmetics, be on the one hand the surface-active of utilizing it,Natural sex and colloidal nature, it is the proper constituent of Skin Cell on the other hand, at cellular metabolism and membrane permeabilityProperty regulate important role, and skin is also had to certain physiological action. Phosphatide is risen in cosmeticsFunction is summed up as follows: antioxidant, emulsifying agent, softening agent, emollient, bleeding agent, stabilizing agent,Embedding medium, nutritional supplement and the vitamin source of lubricant, superfatting agent, liposome. Phosphatide is considered to skin skySo the basis of NMF (NMF), is the neccessary composition that maintains skin normal function, to maintaining cellThe metabolism of water balance and coordination cell plays an important role. Phosphatide has hygroscopicity and is easy to infiltrate through skinIn ability, therefore can fetter the moisture in skin, prevent dry skin, and then keep skin soft smooth and health.
Phosphatide complexes is a kind of drug delivery system taking phosphatide as carrier, and from solid pharmaceutical preparation angle, phosphatide is multipleCompound is a kind of comparatively special solid dispersions, and much research is found, very eurypalynous active skull cap components and phosphorusBetween fat, there is special affinity. By preparing phosphatide complexes, can improve the bioavilability of active component,Active component is had and see through better keratoderma, performance skin-care effect.
Summary of the invention
One of the object of the invention be to provide a kind of forulic acid phosphatide complexes being composited by forulic acid and phosphatide andIts preparation method, to improve forulic acid hydrophilic and oleophilic physicochemical property, improves the solubility property of forulic acid, improves its lifeThing availability, can effectively solve it and be difficult for the problem absorbing, and keeps or strengthen its anti-oxidant in varying environmentProperty.
Above-mentioned purpose realizes by following technical scheme:
A kind of forulic acid phosphatide complexes of the present invention, it is multiple in non-protonic solvent by forulic acid and phosphatideAfter closing, remove non-protonic solvent, obtain;
Wherein, described phosphatide is selected from soybean lecithin, egg yolk lecithin, phosphatidyl-ethanolamine, phosphatidyl silk ammoniaA kind of in acid, hydrogenated soy phosphatidyl choline, DPPC and DPPE orMultiple, be preferably soybean lecithin;
Wherein, described non-protonic solvent is selected from chloroform, ether, carrene, acetone, ethanol, tetrahydrochysene furanMutter and ethyl acetate in one or more, be preferably ethanol;
Wherein, the mol ratio of described forulic acid and phosphatide is 1:0.5～10, is preferably 1:0.5～4.
In the present invention, preferred, described forulic acid is cis forulic acid or trans-ferulaic acid, more preferably transForulic acid.
Further, the invention allows for a kind of method of preparing described forulic acid phosphatide complexes, comprise withLower step:
A) forulic acid and phosphatide are added to thermal agitation in non-protonic solvent compound;
B) remove the non-protonic solvent in the product that step a) obtains, obtain forulic acid phosphatide complexes.Method according to claim 3, is characterized in that the concentration of described forulic acid in described aprotic solvent isBelow 8mg/mL, be preferably 1～4mg/mL.
In the present invention, preferred, described compound temperature is 20～60 DEG C, more preferably 40～60 DEG C; DescribedThe compound time is 15min～4h, more preferably 15min～2h.
In the present invention, preferred, described in the aprotic solvent removed in the product that step a) obtains comprise that decompression is denseThe product that contracting step a) obtains, until aprotic solvent steams, is then dried 24h by it in a vacuum.
Compared to prior art, beneficial effect of the present invention is:
1) preparation technology is simple, reproducible: forulic acid phosphatide complexes provided by the invention is forulic acid and phosphatideWith the compound of mol ratio 1:0.5～10, described phosphatide is natural phospholipid or synthetic phospholipid.
2) be applicable to suitability for industrialized production: it is raw material that the present invention adopts forulic acid, makes with suitable preparation method with phosphatideForulic acid phosphatide complexes, has improved the hydrophilic and oleophilic physicochemical property of forulic acid, strengthens dissolubility and stability, carriesThe high bioavilability of forulic acid.
3) of many uses: forulic acid phosphatide complexes prepared by the present invention can be used as cosmetic industry raw material, for U.S.In vain, in sun-proof, the anti-ageing cosmetic emulsion of waiting for a long time, cream frost, skin care wet goods product, multiple by preparing forulic acid phosphatideCompound can improve forulic acid in cosmetic applications process, and solubility does not add, and is applied on skin assimilation effectThe defect such as not good.
4) solubility experiment proves that forulic acid phosphatide complexes of the present invention has improved the dissolving of forulic acid phosphatide complexesPerformance, can effectively solve it and be difficult for the problem absorbing.
Two of object of the present invention is to provide described forulic acid phosphatide complexes in the purposes of preparing in cosmetics, excellentChoosing, described cosmetics are the cosmetics with whitening effect, comprise the skin care oil, emulsion with whitening effect withAnd cream frost.
Above-mentioned purpose realizes by following technical scheme:
A whitening and skin-protecting oil that contains forulic acid phosphatide complexes, it is by by forulic acid phosphorus of the present inventionFat complexes is further dissolved in oil phase or joins in the oil phase that contains both sexes parent surfactant and is prepared from;
Wherein, preferred, described forulic acid phosphatide complexes and oil phase or the oil that contains amphiphilic surfactantThe mass ratio of phase is 1:1～2;
Wherein, preferred, described oil phase is medium chain or long-chain fat acid glyceride, and described medium chain fatty acid is sweetGrease be selected from have that the fatty acid glycerine of 8～10 carbon atom chains is single, double, three esters or its mixture; Described lengthChain fatty acid triglyceride be selected from have that the glycerine of 12～18 carbon atom chain lengths is single, double, three esters or its mixture;
Wherein, preferred, described amphiphilic surfactant, is selected from oleic acid LABRAFIL M 1944CS, single stearicOne or more in acid propylene glycol, Labraso.
A whitening emulsion that contains forulic acid phosphatide complexes, it is by by forulic acid phosphatide of the present inventionCompound adds in emulsification system and is prepared from as Effect raw material;
Concrete, described whitening emulsion prepares by the following method:
A is under agitation heated to 80 DEG C mutually, after stirring, starts homogeneous A phase, and slowly add B phase,Under 17000rpm, continue homogeneous 2 minutes, stir and make it cooling; At 40 DEG C, C is added to, and at 17000rpmLower homogeneous 30 seconds, obtains the whitening emulsion that contains forulic acid phosphatide complexes;
Wherein, A is by synthetic saualane, caprylic/capric triglyceride, and the own ester of palm acid ethyl, cetostearyl alcohol,Dimethyl silicone polymer, forulic acid phosphatide complexes, vitamin E and methyl hydroxybenzoate or ethylparaben composition;Described B is by glycerine, butanediol, trehalose and deionized water composition; Described C by triethanolamine withAnd azone/Cremophor RH40 composition; Preferably, the quality percentage composition of each raw material is as follows:
A whitening cream frost that contains forulic acid phosphatide complexes, it is by by forulic acid phosphatide of the present inventionCompound is prepared into whitening cream frost as Effect raw material according to the conventional preparation method of cosmetics.
The present invention is by by forulic acid and the compound physicochemical property that changes forulic acid of phosphatide, strengthened that it is fat-soluble,Stability and water dispersible, improved its transmembrane transport performance, thereby improved its bioavilability. System of the present inventionThe standby whitening and skin-protecting oil that contains forulic acid phosphatide complexes, emulsion and the cream frost obtaining, has good human body whiteningEffect. 30 25～45 female volunteers are used the whitening emulsion 30 days that contains this forulic acid phosphatide complexes, facePortion's melanin content obviously reduces, and skin brightness increases, and skin MI value, L* value and ITA ° of value are compared with initial valueThere is significant difference (P < 0.05).
Brief description of the drawings
Fig. 1 uses the volunteer of the whitening emulsion that contains forulic acid phosphatide complexes of the present invention at different times skinThe variation of skin L* value;
Fig. 2 uses the volunteer of the whitening emulsion that contains forulic acid phosphatide complexes of the present invention at different times skinThe variation of skin ITA ° value;
Fig. 3 uses the volunteer of the whitening emulsion that contains forulic acid phosphatide complexes of the present invention at different timesThe variation of skin MI value.
Detailed description of the invention
Further describe the present invention below in conjunction with specific embodiment, advantage and disadvantage of the present invention will be along with descriptionAnd it is more clear. But embodiment is only exemplary, scope of the present invention is not formed to any restriction. This areaTechnical staff it should be understood that lower without departing from the spirit and scope of the present invention can be to technical solution of the present inventionDetails and form are modified or are replaced, but these amendments and replacement all fall within the scope of protection of the present invention.
Embodiment 1: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 150mg, adds absolute ethyl alcohol 40ml, and 40 DEG C add thermal agitation2h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 2: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 150mg, adds absolute ethyl alcohol 80ml, and 40 DEG C add thermal agitation2h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 3: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 300mg, adds absolute ethyl alcohol 20ml, and 60 DEG C add thermal agitation1h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 4: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 300mg, adds absolute ethyl alcohol 40ml, and 60 DEG C add thermal agitation2h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 5: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 600mg, adds absolute ethyl alcohol 40ml, and 60 DEG C add thermal agitation1h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention
Embodiment 6: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 600mg, adds absolute ethyl alcohol 40ml, and 40 DEG C add thermal agitation2h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 7: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 900mg, adds absolute ethyl alcohol 40ml, and 60 DEG C add thermal agitation1h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 8: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 900mg, adds absolute ethyl alcohol 80ml, and 60 DEG C add thermal agitation2h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 9: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 900mg, adds absolute ethyl alcohol 80ml, and 60 DEG C add thermal agitation1h, revolves and steams except desolventizing, and vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 10: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 1200mg, adds absolute ethyl alcohol 20ml, and 60 DEG C of heating are stirredMix 2h, revolve and steam except desolventizing, vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 11: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 1200mg, adds absolute ethyl alcohol 40ml, and 40 DEG C of heating are stirredMix 1h, revolve and steam except desolventizing, vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
Embodiment 12: the preparation of forulic acid phosphatide complexes
Take forulic acid 77.67mg, soybean lecithin 1200mg, adds absolute ethyl alcohol 80ml, and 40 DEG C of heating are stirredMix 2h, revolve and steam except desolventizing, vacuum drying 24h, obtains forulic acid phosphatide complexes of the present invention.
The preparation of the whitening and skin-protecting oil that embodiment 13 contains forulic acid phosphatide complexes
Take the forulic acid phosphatide complexes 1g that embodiment 1 prepares, add 5g caprylic/capric glyceryl ester,The vitamin E of 1g olive fruit oil, 2.9g Unigly GO 102S and 0.1g, is stirred to and forms transparent solution shape,Obtain the whitening and skin-protecting oil that contains forulic acid phosphatide complexes.
The preparation of the whitening and skin-protecting oil that embodiment 14 contains forulic acid phosphatide complexes
Take the forulic acid phosphatide complexes 1g that embodiment 2 prepares, add 2g caprylic/capric glyceryl ester,2g sher butter, 1g jojoba oil, 2g oleic acid LABRAFIL M 1944CS, 1.9 olive fruit oil and 0.1g support one's familyElement C, is stirred to and forms transparent solution shape, obtains the whitening and skin-protecting oil that contains forulic acid phosphatide complexes.
The preparation of the whitening and skin-protecting oil that embodiment 15 contains forulic acid phosphatide complexes
Take the forulic acid phosphatide complexes 0.8g that embodiment 3 prepares, add propylene glycol monostearate 3.4g,Labraso 2.8g, olive oil 2.2g, caprylic/capric glyceryl ester and the 0.1g of 0.7gVitamin E, be stirred to and form transparent solution shape, obtain the whitening and skin-protecting oil that contains forulic acid phosphatide complexes.
The preparation of the whitening emulsion that embodiment 16 contains forulic acid phosphatide complexes
Raw material and consumption:
Preparation method: under stirring condition, by A heat phase to 80 DEG C, after stirring, start homogeneous A phase, andSlowly add B phase, continue homogeneous 2 minutes at 17000rpm, under stirring, make it cooling. At 40 DEG C, C is addedEnter, and 17000rpm homogeneous 30 seconds, obtain the whitening emulsion that contains forulic acid phosphatide complexes.
The preparation of the whitening emulsion that embodiment 17 contains forulic acid phosphatide complexes
Raw material and consumption:
Preparation method: under stirring condition, by A heat phase to 80 DEG C, after stirring, start homogeneous A phase, andSlowly add B phase, continue homogeneous 2 minutes at 17000rpm, under stirring, make it cooling. At 40 DEG C, C is addedEnter, and 17000rpm homogeneous 30 seconds, obtain the whitening emulsion that contains forulic acid phosphatide complexes.
The apparent solubility experiment of test example 1 forulic acid phosphatide complexes
Weigh respectively excessive forulic acid, forulic acid phosphatide complexes, the forulic acid of equal proportion and the physics of phosphatide mixedCompound is dissolved in 10ml and goes in distilled water, under room temperature, stirs 48h, the each sample of sample thief 5ml respectively, 12000rmin-1Centrifugal 5min, accurate absorption after the dilution of supernatant 1ml absolute ethyl alcohol, UV measures.
The solubility test of the physical mixture of forulic acid, phosphatide complexes, forulic acid and phosphatide in water the results are shown inTable 1, as seen from table all molten in water than forulic acid of the solubility in water of physical mixture and phosphatide complexesSolution degree is high, illustrates that forulic acid is prepared into phosphatide complexes has increased its solubility in water.
The mixture of table 1 forulic acid, forulic acid phosphatide complexes, forulic acid and phosphatide is the solubility (n=3) of 25 DEG C
The removing experiment of test example 2 forulic acid phosphatide complexes to DPPH free radical
Experimental results show that forulic acid phosphatide complexes of the present invention can keep below by DPPH radicals scavenging orTo a certain degree increase the antioxygenic property of material.
Weigh respectively a certain amount of forulic acid, forulic acid phosphatide complexes absolute ethyl alcohol is mixed with respectively 5 concentrationSample liquid. Take 20mgDPPH, add anhydrous alcohol solution constant volume in 250mL volumetric flask; 0-4 DEG CUnder keep in Dark Place, now with the current, in 4h effectively. Operate by following experimental procedure:
1) get the liquid to be measured of 1mL and the DPPH solution of 1mL and mix (A1 pipe);
2) get the absolute ethyl alcohol of 1mL and the DPPH solution of 1mL and mix (A2 pipe);
3) get the absolute ethyl alcohol of 1mL and the liquid to be measured of 1mL and mix (A3 pipe);
4) after reaction 20min, under 517nm, survey A1, A2, A3 pipe absorbance.
Clearance rate computing formula is:
Clearance rate (%)=[(A2+A3)-A1]/A2.
Contained asafoetide in forulic acid phosphatide complexes in forulic acid and phosphatide complexes DPPH radicals scavenging experiment thereofAcid is identical with monomer ferulic acid amount. Result is as shown in table 2 below:
Table 2 forulic acid, forulic acid phosphatide complexes, phosphatide are to DPPH free radical scavenging activity (n=3)
The external tyrosinase inhibition test of test example 3 forulic acid phosphatide complexes
Experimental results show that below by external tyrosinase inhibition test forulic acid phosphatide complexes of the present invention can protectHold the tyrosinase activity of material, thereby by this approach performance white-skinned face function.
The external tyrosinase of forulic acid and phosphatide complexes thereof suppresses experiment, adds solubilizer HPS in course of dissolution,In forulic acid phosphatide complexes, contained forulic acid is identical with monomer ferulic acid amount. Experimental procedure is as described below:
1) according to following table 3, prepare respectively C1, C1, T1 and T2 tetra-group reagents, tyrosinase adds after being;
2), after C2 pipe prepares and shakes up, heating water bath 10min in 37 DEG C of water-baths, returns to zero under wavelength 475nm.
3) C1 pipe solution prepares and shakes up, and after 37 DEG C of water-bath 10min, adds tyrosinase 1ml, continues 25 points of water-bathsClock, measures C1 absorbance.
4), by (2) (3) same method, measure T1 absorbance with T2 zeroing.
5) the maximum inhibition T (%) of calculation sample to tyrosinase. Formula: T (%)=(C1-T1)/C1 ×100％
Table 3 reagent proportioning table
| Unit (mL) | C1 | C2 | T1 | T2 |
| TYR | 2 | 2 | 2 | 2 |
| Sample | 0 | 0 | 2 | 2 |
| PBS | 4 | 5 | 2 | 3 |
| Tyrosinase | 1 | 0 | 1 | 0 |
| Cumulative volume | 7 | 7 | 7 | 7 |
Note: C1 and T1 add 1mL tyrosinase, and enzyme is lived as 100U/mL.
Result is as shown in table 4 below.
Table 4 forulic acid, the forulic acid phosphatide complexes inhibiting rate (n=3) to tyrosinase
Test example 4 forulic acid phosphatide complexes are to the melanic inhibition test of cell
Prove that below by cell melanin inhibition test forulic acid phosphatide complexes of the present invention can reduce melanocyteThe melanic generation of oncocyte.
Forulic acid, forulic acid phosphatide complexes suppress experiment to melanin in MC and (in course of dissolution, addEnter solubilizer HPS. In forulic acid phosphatide complexes, contained forulic acid is identical with monomer ferulic acid amount), experimental procedureAs described below:
1) according to the cell concentration of counting gained, cell is diluted, add in 6 orifice plates, make every porocyteQuantity approximately 105Individual. To the nutrient solution that adds 1ml in 6 orifice plates, after add the cell suspending liquid of 1ml. 37 DEG C,Under 5%CO2 condition, hatch 24 hours.
2) plant plate and cultivate after 24h, take out Tissue Culture Plate, renew nutrient solution 1800ul, after add 200ul differenceThe sample of concentration, each sample do three parallel. 37 DEG C, under 5%CO2 condition, hatch 72 hours.
3) discard cell conditioned medium liquid, PBS cleans 2 times, adds the PBS of 0.5ml and the trypsase of 0.5ml,37 DEG C, under 5%CO2 condition, digest 3～5 minutes, to pat and make cell detachment, collecting cell liquid is in the EP of 2ml pipeIn, again clean 6 orifice plates with the PBS of 1ml, itself and the cell liquid of collecting are for the first time merged. The condition of 4 DEG CUnder, 5000 turn-min, centrifugal 5 minutes. Abandoning supernatant. Get after the PBS that above-mentioned cell adds 1ml again fromThe heart, abandoning supernatant, collects and obtains mouse black-in tumor cell. Attention: in the end a step abandoning supernatant is collectedIn the process of cell, can use liquid-transfering gun to draw remaining PBS in EP pipe, avoid after the too low impact of cell concentrationContinuous experiment.
4) in the mouse black-in tumor cell obtaining to collection, add the 1NNaOH of 50ul, 60 DEG C of concussion 2h, make thinBorn of the same parents are fully broken, and discharge melanin and other intracellular protein. Getting 50ul cell pyrolysis liquid with liquid-transfering gun transfers toIn 96 orifice plates, under 405nm, measure light absorption value. 50ul1NNaOH does blank.
5) mensuration of total protein
The solution 10ul getting in 96 orifice plates of measuring melanin content transfers in 96 new orifice plates, and use is examinedMaas light blue kit measurement total protein content (making protein content calibration curve) is measured under 595nm conditionIts light absorption value. 10ul1NNaOH does blank.
Melanin synthesizes inhibiting rate=[1-A1/C1*C0/A0] * 100%
A1: sample melanin content light absorption value
A0: solvent blank contrast light absorption value
C1: sample protein matter content
C0: solvent blank control protein content
Result is as shown in table 5 below.
The inhibiting rate (n=3) that table 5 forulic acid, forulic acid phosphatide complexes generate melanin
The external inhibition hyaluronidase test of test example 5 forulic acid phosphatide complexes
Prove that below by external inhibition hyaluronidase test forulic acid phosphatide complexes of the present invention has inhibition thoroughlyThe activity of phaneroplasm acid enzyme, has potential anti-inflammatory efficacy.
Forulic acid, the external experiment of the inhibition to hyaluronidase activity of forulic acid phosphatide complexes, sample preparation processIn, add solubilizer HPS, wherein in forulic acid phosphatide complexes, contained forulic acid is identical with monomer ferulic acid amount.Experimental procedure is as described below:
Adopt hyaluronidase body outer suppressioning experiment Elson-Morgan method to carry out. Get 0.1mL0.25mmol/LCaCl2Solution and 37 DEG C of heat insulating culture 20min of 0.5mL hyaluronidase liquid; Add sample liquid 0.5mL, continue 37 DEG C of guarantorsTemperature is cultivated 20min; Add 37 DEG C of insulation 30min of 0.5mL Sodium Hyaluronate liquid, normal temperature is placed 5min; Add0.1mL0.4mol/LNaOH solution and 0.5mL acetylacetone,2,4-pentanedione solution, be placed in boiling water bath and heat after 15min immediatelyCarry out cooling 5min with frozen water; Add Ehrlich's reagent 1.0mL also to dilute with 3.0mL absolute ethyl alcohol,Place 20min colour developing, measure its absorbance with spectrophotometer 582nm.
Result is as shown in table 6 below.
Table 6 forulic acid, the forulic acid phosphatide complexes inhibiting rate (n=3) to hyaluronidase activity
The permeability experiment of test example 6 forulic acid phosphatide complexes
Test to prove that below by permeability forulic acid phosphatide complexes of the present invention has good permeance property,Can be good at infiltrating into skin, and there is slowly-releasing forulic acid, thereby reach effect of long effect.
The preparation of rat skin in vitro, gets 180～220gWistar rat, and ♀ ♂ dual-purpose is put to death, in belly depilation,Skin after clip depilation, eliminates hypodermis and fat,, soaks to without white casse thing with physiological saline cyclic washingIn physiological saline, in 4 DEG C of refrigerators, preserve, in 1 week, use. Before experiment, check the integrality of mouse skin, must notThere is breakage.
For the preparation of feeding, take excessive forulic acid and forulic acid phosphatide complexes, be mixed with for feeding, whereinTwo kinds of amounts for the contained forulic acid of feeding are identical.
The upper storage reservoir of diffusion device and transdermal penetration test transdermal diffusion instrument is tubular supply pool, and lower chamber is coniformReception tank, therebetween bark pocket skin fixing. Transdermal penetration area is 3.14cm2, maintain with submersible type magnetic stirrerThe dynamic environment of reception tank. In reception tank, precision adds 6.6mL physiological saline, put in 37 DEG C of waters bath with thermostatic control,Start magnetic stirrer and keep constant speed to stir (200rmin-1), get for feeding 1mL in supply pool, in0.5,1,2,4,8, the accurate acceptable solution 2mL (adding equivalent physiological saline) that draws respectively when 12h, 24h,With 0.45 μ m filtering with microporous membrane, ultraviolet spectrometry degree method is measured light absorption value, calculates acceptable solution concentration. And ask to calculate and tire outLong-pending infiltration capacity Qn (μ gcm-2), result is as shown in table 7 below.
Table 7 forulic acid, the time dependent amount of forulic acid phosphatide complexes transdermal penetration amount
As shown in Table 7, forulic acid phosphatide complexes transdermal penetration amount is obviously greater than forulic acid, and is smearing for feedingAfter forulic acid phosphatide complexes 24h, its entrained forulic acid still can see through skin, this explanation forulic acid phosphorusFat complexes can increase forulic acid through skin uptake, simultaneously can extend action time.
The whitening effect evaluation of the whitening emulsion that test example 7 contains forulic acid phosphatide complexes
1 material and instrument
The whitening emulsion that what sample: embodiment 16 prepared contain forulic acid phosphatide complexes
1.2 tester
Dermal melanin and ferroheme tester (MexameterMX18), German CK company produces; Multi-functionalSkinanalysis apparatus and colourity test probe MPA9, German CK company produces.
2 experimental techniques:
Bibliography carries out: Wu Jinhao, Liu Qi, Deng Yingmei etc., the research of whitening cosmetics effect evaluation method[C], the tenth China cosmetic scientific seminar collection of thesis, 2014:276-280.
2.1 volunteer
Experimenter amounts to 30 people, 25 years old-45 years old women. Volunteer's exclusion condition meets " cosmetics contact skinScorching diagnostic criteria and treatment principle " include in, exclusion standard.
2.2 test index
Dermal melanin content (MI) value is used for characterizing melanin index, and MI value more represents that dermal melanin containsMeasure higher. Skin brightness L value, ITA ° value. The L* that color instrument records characterizes brightness, is used for representing skin black and whiteColourity, its numerical value is larger, and skin color is deflection white more; A* represents red green degree, and it changes expression whitening productThe variation of red green degree before and after using ,+a* represents redness ,-a* represents green; B* represents blue yellow chromaticity, its variationRepresent that whitening product uses the variation of the blue yellow chromaticity of front and back skin ,+b* represents yellow, and-b* represents blueness. By recordingL*, a* and b* numerical value can calculate ITA ° of value, thereby the relatively variation of crowd's skin color, ITA ° of value is moreGreatly, skin is brighter, otherwise skin is darker and more gloomy.
2.3 test environment
Test environment requires: constant-temperature constant-humidity environment, temperature: 1 DEG C, 22 DEG C of soil, humidity: 50% soil 5%. Before testExperimenter will wait for 20min under this environment.
2.4 method of testing
Test position is face, requires product to smear evenly, uses whitening emulsion, and experimenter is in the every day of each painting sooner or laterSmear once, life cycle is 4 weeks. Within test period, tested position is not used other any cosmetics.
2.5 data acquisition
Test is carried out altogether 5 times, be divided into initial value and make to apply some make up one week, after two weeks, three weeks and surrounding, everyZhou Tongyi time experimenter will smear position and clean, by tester's use test Instrument measuring spreader portion bit value.
2.6 data statistics
Adopt SigmaStat3.5 data analysis component software to carry out variance analysis. Statistics contains by dermal melaninAmount and skin colour change, the white-skinned face function of reaction cosmetics.
3 results and discussion
3.1 skin L*a*b*, ITA ° colorimetric analysis test result, this experiment is screened altogether 30 people and is included this research in,Do not have to come off between group. Experimental result is in table 8 and Fig. 1, and tested position is used after sample, and sample sets test value is with justInitial value is compared, and in the time range of the 0th week to the 4th week experimental period, skin L* value is rising trend, andWhile testing the 3rd week, there is significant difference (P < 0.05).
The variation (x ± s, n=30) of table 8 different experiments skin in period L* value
(note: with Normal group comparison, * P < 0.05)
Experimental result is in table 9 and Fig. 2, and tested position is used after sample, sample sets test value compared with initial value,0 week experimental period, in the time range of the 4th week, skin value was rising trend.
The variation (x ± s, n=30) of TA ° of value of table 9 different experiments skin I in period
(note: with Normal group comparison, * P < 0.05)
3.2 melanin index analysis test results
30 experimenters are screened in this experiment altogether. Experimental result is in table 10 and Fig. 3, and tested position is used after sample,Sample sets test value compared with initial value, in the time range of the 0th week to the 4th week experimental period, skin blackCellulose content MI value is reduction, and within the 3rd week, has significant difference (P < 0.05) in experiment.
The variation (x ± s, n=30) of table 10 different experiments dermal melanin in period content MI value
(note: with Normal group comparison, * P < 0.05)
Claims (10)
1. a forulic acid phosphatide complexes, it is characterized in that by forulic acid and phosphatide multiple in non-protonic solventAfter closing, remove non-protonic solvent, obtain;
Wherein, described phosphatide is selected from soybean lecithin, egg yolk lecithin, phosphatidyl-ethanolamine, phosphatidyl silk ammoniaA kind of in acid, hydrogenated soy phosphatidyl choline, DPPC and DPPE orMultiple, be preferably soybean lecithin;
Wherein, described non-protonic solvent is selected from chloroform, ether, carrene, acetone, ethanol, tetrahydrochysene furanMutter and ethyl acetate in one or more, be preferably ethanol;
Wherein, the mol ratio of described forulic acid and phosphatide is 1:0.5～10, is preferably 1:0.5～4.
2. forulic acid phosphatide complexes according to claim 1, is characterized in that, described forulic acid is cisForulic acid or trans-ferulaic acid, be preferably trans-ferulaic acid.
3. prepare a method for forulic acid phosphatide complexes claimed in claim 1, it is characterized in that comprising followingStep:
A) forulic acid and phosphatide are added to thermal agitation in non-protonic solvent compound;
B) remove the non-protonic solvent in the product that step a) obtains, obtain forulic acid phosphatide complexes.
4. method according to claim 3, is characterized in that described forulic acid is in described aprotic solventConcentration is, below 8mg/mL, to be preferably 1～4mg/mL.
5. method according to claim 3, is characterized in that, described compound temperature is 20～60 DEG C, excellentElect 40～60 DEG C as; The described compound time is 15min～4h, is preferably 15min～2h.
6. method according to claim 3, is characterized in that, described in remove in the product that step a) obtainsAprotic solvent comprise product that reduced pressure concentration step a) obtains until aprotic solvent steams, then by it veryAerial dry 24h.
7. the forulic acid phosphatide complexes described in claim 1 or 2 is in the purposes of preparing in cosmetics, preferred,Described cosmetics are the cosmetics with whitening effect, comprise skin care oil, emulsion and the cream frost with whitening effect.
8. contain a whitening and skin-protecting oil for forulic acid phosphatide complexes, it is characterized in that by by claimForulic acid phosphatide complexes described in 1 or 2 is further dissolved in oil phase or joins and contains both sexes parent surfactantOil phase in be prepared from;
Wherein, preferred, described forulic acid phosphatide complexes and oil phase or the oil that contains amphiphilic surfactantThe mass ratio of phase is 1:1～2;
Wherein, preferred, described oil phase is medium chain or long-chain fat acid glyceride, and described medium chain fatty acid is sweetGrease be selected from have that the fatty acid glycerine of 8～10 carbon atom chains is single, double, three esters or its mixture; Described lengthChain fatty acid triglyceride be selected from have that the glycerine of 12～18 carbon atom chain lengths is single, double, three esters or its mixture;
Wherein, preferred, described amphiphilic surfactant, is selected from oleic acid LABRAFIL M 1944CS, single stearicOne or more in acid propylene glycol and caprylic/capric LABRAFIL M 1944CS.
9. contain a whitening emulsion for forulic acid phosphatide complexes, it is characterized in that by by claim 1Or forulic acid phosphatide complexes described in 2 adds in emulsification system and is prepared from as Effect raw material;
Concrete, described whitening emulsion prepares by the following method:
A is under agitation heated to 80 DEG C mutually, after stirring, starts homogeneous A phase, and slowly add B phase,Under 17000rpm, continue homogeneous 2 minutes, stir and make it cooling; At 40 DEG C, C is added to, and at 17000rpmLower homogeneous 30 seconds, obtains the whitening emulsion that contains forulic acid phosphatide complexes;
Wherein, A is by synthetic saualane, caprylic/capric triglyceride, and the own ester of palm acid ethyl, cetostearyl alcohol,Dimethyl silicone polymer, forulic acid phosphatide complexes, vitamin E and methyl hydroxybenzoate or ethylparaben composition;Described B is by glycerine, butanediol, trehalose and deionized water composition; Described C by triethanolamine withAnd azone/Cremophor RH40 composition; Preferably, the quality percentage composition of each raw material is as follows:
10. contain a whitening cream frost for forulic acid phosphatide complexes, it is characterized in that by by claim 1Or forulic acid phosphatide complexes described in 2 is prepared into whitening as Effect raw material according to the conventional preparation method of cosmeticsCream frost.
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| CN114869795A (en) * | 2022-03-29 | 2022-08-09 | 上海肤徕生物高科技有限公司 | Preparation method of whitening composition for improving solubility of active components, product and application thereof |
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| CN114869795B (en) * | 2022-03-29 | 2024-01-26 | 上海肤徕生物高科技有限公司 | Preparation method of whitening composition, product and application thereof |
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