CN108543079A - A kind of astaxanthin-collagen couplings and its preparation method and application - Google Patents
A kind of astaxanthin-collagen couplings and its preparation method and application Download PDFInfo
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- A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
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- A61K47/6435—Drug-peptide, drug-protein or drug-polyamino acid conjugates, i.e. the modifying agent being a peptide, protein or polyamino acid which is covalently bonded or complexed to a therapeutically active agent the peptide or protein in the drug conjugate being a connective tissue peptide, e.g. collagen, fibronectin or gelatin
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Abstract
The invention discloses a kind of astaxanthin collagen couplings and its preparation method and application, this method is that will be enriched in the raw material of astaxanthin to mix with water-miscible organic solvent, removes insoluble composition；By collagen water dissolution；Above two solution is added dropwise under 4~60 DEG C of temperature, acid condition and is mixed, so that collagen and astaxanthin is dissolved in mixing reaction solution, and be protected from light and be stirred to react；By the astaxanthin collagen couplings generated in above-mentioned reaction solution isolate and purify to get.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to the preparation of a kind of astaxanthin-collagen couplings and pre-
Anti-, treatment skin photoage application.
Background technology
Skin photoage is that skin is irradiated with caused accumulated damage for a long time, and excessive ultraviolet light irradiates meeting
Make skin collagen, hyaluronic acid and elastin degradation, skin appearance is caused to change, severe patient can lead to basal-cell carcinoma, black
The formation of the tumor diseases such as plain cytoma and squamous cell carcinoma.Currently, prevention and treatment light aging has become medicine, cosmetics
With the hot spot of technical field of biological material research, it is the one of presently relevant industrial research to develop safe and effective prevention light ageing prod
A important directions.
Astaxanthin (3,3 '-dihydroxy -4,4 '-diketos-beta carotene, Astaxanthin, hereinafter referred to as astaxanthin)
UV-induced skin injury can be reduced, skin collagen function, effective delay skin aging are improved.However, astaxanthin
Originally be applied directly to skin using when significantly limit it in the various development and application including anti-skin photoage
Direct use.It is protected using the technologies such as microcapsule embedded, host-guest inclusion complexing and nanoprecipitation and low-temperature dark
Deposit, the methods of fat-soluble solvent dissolving preserves and low dose of coating uses, although astaxanthin can be solved to a certain extent
Applied defect, but high high or use cost, convenience and the deficient validity are required to technology level.Therefore, city at present
It is rare using astaxanthin as the dermatologic product or cosmetics of main active ingredient on field.Basic reason therein is：Astaxanthin
Exist still in the form of unstable initial molecule in existing various applications, physical method can not inherently solve astaxanthin and answer
Limitation.
Invention content
One of the objects of the present invention is to provide a kind of preparation methods of astaxanthin-collagen couplings.
The second object of the present invention is to provide the application of astaxanthin-collagen couplings of above method preparation.
The technical solution used in the present invention is：
A kind of preparation method of astaxanthin-collagen couplings, includes the following steps：
1) raw material that will be enriched in astaxanthin is mixed with water-miscible organic solvent, removes insoluble composition；Collagen is used
Water dissolution；
2) above two solution is added dropwise under 4~60 DEG C of temperature, acid condition and is mixed, collagen and astaxanthin is made to exist
It is dissolved in reaction solution, and is protected from light and is stirred to react；
3) astaxanthin generated in above-mentioned reaction solution-collagen couplings are isolated and purified, obtains astaxanthin-collagen egg
White couplings.
Further, in step 2), the molar ratio of astaxanthin and collagen addition is 1 in reaction solution:1~10:1.
Further, in step 2), the volume ratio of water-miscible organic solvent and water is 0.5 in reaction solution:1~4:1.
Further, the water-miscible organic solvent is selected from ethyl alcohol, acetone, methanol, ethylene glycol, dimethyl sulfoxide (DMSO), tetrahydrochysene
Furans.
Further, the content of astaxanthin is no less than 1%w/w in the raw material rich in astaxanthin.
Astaxanthin-collagen couplings prepared by any of the above-described method.
Astaxanthin described above-collagen couplings answering in the product for preparing prevention and treatment skin photoage
With.
A kind of product of prevention and treatment skin photoage, astaxanthin-collagen described above is contained in the product
Couplings.
Further, the product of above-mentioned prevention and treatment skin photoage is by the shrimp described in 0.5~2.0 part of claim 6
Green element-collagen couplings, 16~19 parts of oil phases, 5~7 parts of emulsifiers, 74~77 parts of water phases are made.
Further, the oil phase by 8~12 parts of stearic acid, 1~2 part of hexadecanol, 0.8~1.2 part of lanolin, 4~6 parts
Paraffin group at；
The emulsifier is made of 4~5 parts of glycerin monostearates, 1~2 part of lauryl sodium sulfate；
The water phase is made of 2~3 parts of glycerine, 70~75 parts of water.
The beneficial effects of the invention are as follows：
(1) astaxanthin of preparation of the present invention-collagen couplings, which have, is different from collagen raw material (214nm)
With the ultraviolet characteristic absorption peak of astaxanthin (480nm), water-soluble, non-coloring.
(2) astaxanthin of preparation of the present invention-collagen couplings have better anti-photooxidation, can be preferably
The skin thickness that illumination causes is reduced, MDA contents is reduced, improves SOD and GSH-Px antioxidase activities.Shrimp prepared by the present invention
Green element-collagen couplings have the function of preventing and treating skin photoage, be carried for the application of collagen and astaxanthin
Market prospects are supplied.
(3) preparation method step of the present invention is simple, and operating condition is easily-controllable.
Description of the drawings
Fig. 1 is gel filtration chromatography figure of the astaxanthin of the present invention-collagen couplings under different Detection wavelengths, in figure
Coupling indicates that collagen-astaxanthin couplings group of the present invention, Collagen peptide indicate collagen polypeptide,
Astaranthin astaxanthins；
Fig. 2 mouse skins thickness (Thickness of skin) changes, wherein A：Normal group；B：Model control group；
C：Matrix control group；D：Astaxanthin group；E：Free collagen and astaxanthin group, (w/w) containing 4% free astaxanthin；F：This hair
Bright collagen-astaxanthin couplings group；G：Vitamin E group；Compared with Normal group, * * * p<0.001, * * p<0.01, * p
<0.05；Compared with model control group, ###p<0.001, ##p<0.01, #p<0.05)；
Skin histopathology's slice HE dyeing of each experimental mices of Fig. 3；
MDA changes of contents in the skin histology of each experimental mices of Fig. 4；
SOD (I) and GSH-Px (II) vigour changes in the skin histology of each experimental mices of Fig. 5.
Specific implementation mode
A kind of preparation method of astaxanthin-collagen couplings, includes the following steps：
1) raw material that will be enriched in astaxanthin is mixed with water-miscible organic solvent, removes insoluble composition；Collagen is used
Water dissolution；
2) above two solution is added dropwise under 4~60 DEG C of temperature, acid condition and is mixed, collagen and astaxanthin is made to exist
It is dissolved in reaction solution, and is protected from light and is stirred to react；
3) astaxanthin generated in above-mentioned reaction solution-collagen couplings are isolated and purified, obtains astaxanthin-collagen egg
White couplings.
Preferably, in step 2), it is 3.0~6.0 that acid condition, which refers to pH, more preferable 4.5~5.5, most preferably 5.0.
Preferably, preferably 4~45 DEG C of the temperature in step 2), most preferably 37 DEG C.
Preferably, in step 2), the molar ratio of astaxanthin and collagen addition is 1 in reaction solution:1~10:1.
Preferably, in step 2), the volume ratio of water-miscible organic solvent and water is 0.5 in reaction solution:1~4:1.
Preferably, it in step 2), is protected from light and is stirred to react the time for 0.5~2h, more preferably 0.5~1.5h, most preferably
0.75h。
Preferably, in step 3), it is described isolate and purify including using organic solvent deposit, salting out method, membrane filter method and/or
Column chromatography is isolated and purified.
Preferably, the water-miscible organic solvent is selected from ethyl alcohol, acetone, methanol, ethylene glycol, dimethyl sulfoxide (DMSO), tetrahydrochysene furan
It mutters.
Preferably, the content of astaxanthin is no less than 1%w/w in the raw material rich in astaxanthin.
It is furthermore preferred that the raw material rich in astaxanthin is：Different Cis-trans structures [(3S, 3S '), (3R, 3S ') and (3R,
3R ')] astaxanthin monomer and combinations thereof, haematococcus algae powder, snow algae powder, the algae extract rich in astaxanthin, green rich in shrimp
The crust bio-extract of element.
Preferably, the collagen includes：The Hydrolyzed Collagen or/and molecular weight that molecular weight is 500~20000 be
500~20000 gelatin.
Astaxanthin-collagen couplings prepared by any of the above-described method.
Astaxanthin described above-collagen couplings answering in the product for preparing prevention and treatment skin photoage
With.
Preferably, the product includes skin care item, cosmetics.
A kind of product of prevention and treatment skin photoage, astaxanthin-collagen described above is contained in the product
Couplings.
Preferably, the product of above-mentioned prevention and treatment skin photoage is by 0.5~2.0 part of astaxanthin-glue described above
Former protein coupled object, 16~19 parts of oil phases, 5~7 parts of emulsifiers, 74~77 parts of water phases are made.
Preferably, the oil phase is by 8~12 parts of stearic acid, 1~2 part of hexadecanol, 0.8~1.2 part of lanolin, 4~6 parts of stones
Wax oil forms；
The emulsifier is made of 4~5 parts of glycerin monostearates, 1~2 part of lauryl sodium sulfate；
The water phase is made of 2~3 parts of glycerine, 70~75 parts of water.
With reference to specific embodiment, the present invention is further illustrated.
A kind of preparation method of 1 astaxanthin of embodiment-collagen couplings
(3S, the 3S ') astaxanthin monomer in haematococcus pluvialis source is dissolved with ethyl alcohol, centrifugation removal insoluble composition will
The Hydrolyzed Collagen water dissolution that average molecular weight is 15600.Above two pH value of solution is adjusted to 5.0, is added dropwise at 25 DEG C
It mixes, the molar ratio of astaxanthin and collagen addition is 10 in mixed liquor:1, and in mixed liquor ethyl alcohol and water volume ratio
It is 2:1, after being protected from light stirring 2 hours, saturated ammonium sulfate solution is added into reaction solution to albumen precipitation, it is heavy to collect albumen
It forms sediment, freeze-drying is kept in dark place at low temperature.
After testing, the ultraviolet characteristic absorption peak of upper prepared astaxanthin-collagen couplings near 418nm (see
Fig. 1), there is the ultraviolet characteristic absorption peak different from collagen (214nm) and astaxanthin monomer (480nm), water-soluble, nothing
Coloring.
A kind of preparation method of 2 astaxanthin of embodiment-collagen couplings
Haematococcus pluvialis powder (content astaxanthin 3%w/w) is mixed with acetone, is stirred, 40min, centrifugation are vibrated at 4 DEG C
(4000r/min, 10min), takes supernatant.The Hydrolyzed Collagen water dissolution for being 5000 by number-average molecular weight.It adjusts above-mentioned
To 4.0 mixing is added dropwise, it is 5 that molar ratio, which is added, with collagen in mixed astaxanthin in pH value of solution at 4 DEG C:1, acetone and water
Volume ratio be 1:1, after being protected from light stirring 1 hour, continues to be added dropwise cold acetone into reaction solution to albumen precipitation, collect albumen
Precipitation, freeze-drying are kept in dark place at low temperature.
After testing, the ultraviolet characteristic absorption peak of upper prepared astaxanthin-collagen couplings is near 390nm,
With the ultraviolet characteristic absorption peak different from collagen raw material (214nm) and astaxanthin (480nm), water-soluble, non-coloring
Property.
A kind of preparation method of 3 astaxanthin of embodiment-collagen couplings
It will be enriched in the crust bio-extract (astaxanthin monomer content 26%, astaxanthin ester content 9%, w/w) of astaxanthin
It is dissolved with methanol, 0.4mol/L NaOH-CH is added3OH solution, solid-liquid ratio 1:2 (v/v) are kept for 20 minutes at 10 DEG C, centrifugation
(4000r/min, 10min), takes supernatant.PH value is adjusted to 4.5, by number-average molecular weight be 10000 gelatin hydrolysate with water-soluble
Solution.PH value of solution is adjusted to 4.5, is mixed with the crust bio-extract methanol solution dropwise addition after saponification at 37 DEG C.It is mixed
It is 2.5 that molar ratio, which is added, with collagen in astaxanthin:1, the volume ratio of methanol and water is 3:1, after being protected from light stirring 1 hour,
It uses molecular cut off for 5000 organic membrane filtration, collects and retain liquid, volatilize solvent, low-temperature dark is protected after collecting sample
It deposits.
After testing, the ultraviolet characteristic absorption peak of upper prepared astaxanthin-collagen couplings is near 407nm,
With the ultraviolet characteristic absorption peak different from collagen raw material (214nm) and astaxanthin (480nm), water-soluble, non-coloring
Property.
A kind of product of prevention and treatment skin photoage of embodiment 4
This product is by 1 part of astaxanthin of the present invention-collagen couplings, 17.5 parts of oil phases, 6 parts of emulsifiers and 75.5 parts of water
Mutually it is made.
Wherein, oil phase formula is：Stearic acid (10 parts), hexadecanol (1.5 parts), lanolin (1 part), paraffin oil (5 parts)；
Emulsifiers formula is：Glycerin monostearate (4.26 parts), lauryl sodium sulfate (1.74 parts)；
Water phase formula is：Glycerine (2.5 parts), deionized water (73 parts).
Oil phase, emulsifier and water phase are prepared in proportion, and oil phase and the emulsifier homogeneous at 75 DEG C stir 15-20min, water phase
After sterilizing is down to 80 DEG C, oil phase and emulsifier are slowly added into water phase, emulsification stirring 15-20min when temperature drops to 75 DEG C,
Matrix is obtained, is added thereto when substrate temperature is down to 60 DEG C, then by astaxanthin of the present invention-collagen couplings, mixing, it is cooling
To room temperature to get the product of prevention and treatment skin photoage.
Astaxanthin-collagen the couplings prepared below to the present invention make further effect detection.
Improvement result of the collagen of the present invention-astaxanthin couplings to light aging mice skin.
Experimental method：
Balb/c mouse adaptable fed for a period of time after, be randomly divided into 7 groups, every group 6 by weight.It is respectively normal right
According to group (A), model control group (B), matrix control group (C), astaxanthin group (D), free collagen and astaxanthin group, (E contains
4% free astaxanthin, w/w), collagen of the present invention-astaxanthin couplings group (F) and vitamin E group (G).Every group of mouse is every
Its back shaving, area are 2cm × 3cm.3 UVB lamp sources (emission spectrum 275-320nm, peak value 313nm, 40w), 4 UVA
Lamp source (emission spectrum 320-420nm, peak value 340nm, 40w) is irradiated.Each group mouse is marked and is put into irradiation case, away from
From light source 50cm, pre-irradiation fluorescent tube preheats 15-20min, measures UV intensity and is irradiated after stablizing, carries out UVB respectively
(Normal group (A) is without UVB and UVA treatment with irradiation) is irradiated with UVA.Exposure dose：From minimum erythema dose MED (UVB
0.1J/cm2, UVA is set to 10 times of UVB, i.e. 1J/cm2) start to irradiate, the 1st week be 1 MED, the 2nd week 2 MED, the 3rd week 4
MED, the 4th week to the 6th week is 4 MED, 1 times/day, is irradiated weekly 6 days, totally 6 weeks, UVB accumulated doses were 11.4J/cm2, UVA
Accumulated dose is 114J/cm2.It is administered in UV pre-irradiations 1h, administrations are as follows.
Normal group (A)：It is smeared without any drug；
Model control group (B)：It is smeared without any drug；
Matrix control group (C)：Matrix smearing is given, matrix used is the matrix described in embodiment 4.
Astaxanthin group (D)：Institute's coat is green in addition to the shrimp that collagen of the present invention-astaxanthin couplings group is substituted for equivalent
Plain outer, remaining ingredient and dosage are same as Example 4.
Free collagen and astaxanthin group (E contains 4% free astaxanthin, w/w)：Institute's coat is in addition to by collagen of the present invention
Albumen-astaxanthin couplings group is substituted for outside the free collagen and astaxanthin of equivalent, remaining ingredient and dosage with reality
It is identical to apply example 4.
Collagen of the present invention-astaxanthin couplings group (F)：Smear the product prepared by embodiment 4.
Vitamin E group (G)：That is positive controls.
Interpretation of result：
(1) skin thickness measurement and pathological analysis
Skin thickness measurement result is as shown in Figures 2 and 3, compared to Normal group, model control group and Matrix controls
The skin thickness of group mouse dramatically increases (p<0.001), this shows that excessive UV irradiations can be such that skin thickness increases；With model comparison
Group is compared, matrix control group there was no significant difference (p>0.05), show that matrix will not reduce skin thickness caused by light aging and increase
Add, matrix is to the noiseless effect of other administration groups；Compared with model control group, the mouse skin degree of impairment of each administration group obtains
To improvement, cuticula and skin layer thickness are obviously reduced, and skin corium collagenous fibres and the netted structure of elastomer are restored, fine
Dimensional tissue phenomenon of rupture is less；Basal cell damage situations are lighter.The mouse skin of astaxanthin group is in apparent orange, and is not easy to disappear
It moves back；Free collagen and astaxanthin group (E groups) experiment mice skin are in micro- orange；Couplings group skin of the present invention is in normal fresh
Red, with control group indifference.Compared to model control group, astaxanthin group (p<0.01), free collagen and astaxanthin group
(p<And couplings group (p 0.05)<0.001) mouse skin thickness significantly reduces.
The above results illustrate astaxanthin-collagen couplings specific ionization collagen and astaxanthin group prepared by the present invention
Function and effect are more notable, have more preferably inoxidizability, and do not have coloring, had more in the practical application of light aging prevention
There is applicability.
(2) mice skin tissue skin biochemical indicator detects
The back baring skin tissue of the above-mentioned experiment mice of clip removes subcutaneous tissue, pre-cooled physiological saline rinsing, filter
Paper is wiped dry, weighs rapidly, is fitted into 5mL EP pipes, by tissue weight and physiological saline 1:9(m:V) respective volume is added in ratio
Pre- cold saline, in -80 DEG C preservation.Progress skin histology homogenate under condition of ice bath, low-temperature centrifugation (3500r/min, 4 DEG C,
15min), supernatant is taken to dispense, -80 DEG C of preservations, for malonaldehyde (MAD, extent of peroxidation index), superoxide dismutase
(SOD) and the measurement of glutathione oxidase (GSH-Px).
As shown in figure 4, compared with Normal group, the MDA contents of model control group and matrix control group dramatically increase (p<
0.001), show that the skin lipid peroxidization of model control group and matrix control group mouse is more serious；With model comparison
Group is compared, and matrix control group is without significant difference (p>0.05), show matrix to the noiseless effect of other administration groups MDA contents.With
Model control group is compared, astaxanthin group (p<0.001), dissociate collagen and astaxanthin group (p<0.05), couplings of the present invention
Group (p<0.001) MDA contents are decreased obviously.
The above results illustrate that couplings group specific ionization collagen of the present invention and astaxanthin group are to caused by improvement UV irradiations
Skin lipid peroxidization effect becomes apparent from, and is more advantageous to the decline of MDA contents.
As shown in figure 5, compared with Normal group, SOD the and GSH-Px vigor of model control group and matrix control group is aobvious
Writing reduces (p<0.001), show that oxidative stress pressure significantly rises in model control group and matrix control group mice skin tissue；
Matrix control group and model control group are without significant difference (p>0.05), show matrix to this Testing index of other administration groups without
Interference effect.Compared with model control group, astaxanthin group, free collagen and astaxanthin group, couplings group of the present invention SOD
(p is significantly increased with GSH-Px vigor<0.05).
The above results illustrate that astaxanthin of the present invention-collagen couplings have green not less than free collagen and shrimp
The ability for improving SOD and GSH-Px antioxidase activities in Mice Body of element group, can effectively weaken ultra-oxygen anion free radical pair
The damaging action of skin histology.
The above embodiment is a preferred embodiment of the present invention, but embodiments of the present invention are not by above-described embodiment
Limitation, it is other it is any without departing from the spirit and principles of the present invention made by changes, modifications, substitutions, combinations, simplifications,
Equivalent substitute mode is should be, is included within the scope of the present invention.
Claims (10)
1. a kind of preparation method of astaxanthin-collagen couplings, which is characterized in that include the following steps：
1) raw material that will be enriched in astaxanthin is mixed with water-miscible organic solvent, removes insoluble composition；By collagen with water-soluble
Solution；
2) above two solution is added dropwise under 4~60 DEG C of temperature, acid condition and is mixed, collagen and astaxanthin is made to react
It is dissolved in liquid, and is protected from light and is stirred to react；
3) astaxanthin generated in above-mentioned reaction solution-collagen couplings are isolated and purified, obtains astaxanthin-collagen coupling
Close object.
2. according to the method described in claim 1, it is characterized in that, in step 2), astaxanthin adds with collagen in reaction solution
The molar ratio for entering amount is 1:1~10:1.
3. according to the method described in claim 1, it is characterized in that, in step 2), water-miscible organic solvent and water in reaction solution
Volume ratio be 0.5:1~4:1.
4. method according to claim 1 or 3, which is characterized in that the water-miscible organic solvent be selected from ethyl alcohol, acetone,
Methanol, ethylene glycol, dimethyl sulfoxide (DMSO), tetrahydrofuran.
5. according to claims 1 to 3 any one of them method, which is characterized in that the raw material Prawn rich in astaxanthin is green
The content of element is no less than 1%w/w.
6. astaxanthin-collagen couplings prepared by any one of Claims 1 to 5 method.
7. astaxanthin-collagen couplings described in claim 6 are in the product for preparing prevention and treatment skin photoage
Application.
8. a kind of product of prevention and treatment skin photoage, which is characterized in that contain the shrimp described in claim 6 in the product
Green element-collagen couplings.
9. it is according to claim 8 it is a kind of prevention and treatment skin photoage product, which is characterized in that the product by
Astaxanthin-collagen couplings, 16~19 parts of oil phases, 5~7 parts of emulsifiers described in 0.5~2.0 part of claim 6,74~
77 parts of water phases are made.
10. a kind of product of prevention and treatment skin photoage according to claim 9, which is characterized in that the oil phase
By 8~12 parts of stearic acid, 1~2 part of hexadecanol, 0.8~1.2 part of lanolin, 4~6 parts of paraffin groups at；
The emulsifier is made of 4~5 parts of glycerin monostearates, 1~2 part of lauryl sodium sulfate；
The water phase is made of 2~3 parts of glycerine, 70~75 parts of water.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201810494864.1A CN108543079B (en) | 2018-05-22 | 2018-05-22 | Astaxanthin-collagen coupling compound and preparation method and application thereof |
Applications Claiming Priority (1)
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| CN113349373A (en) * | 2021-07-01 | 2021-09-07 | 海南三元星生物科技股份有限公司 | Astaxanthin-collagen peptide oral liquid and preparation method thereof |
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