CN103816054B - Chitose base self-assembly nano micellar solution of a kind of load beta-carotene and preparation method thereof - Google Patents
Chitose base self-assembly nano micellar solution of a kind of load beta-carotene and preparation method thereof Download PDFInfo
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Abstract
The invention discloses chitose base self-assembly nano micellar solution of a kind of load beta-carotene and preparation method thereof.The present invention uses glyoxaline ion liquid as the active solvent of chitosan, is grafted on chitosan macromolecular chain is obtained chitosan grafted polylactic acid by the ring-opening polymerisation of lactide under catalyst action; Then chitosan grafted polylactic acid self assembly behavior is in aqueous utilized to realize effective embedding of hydrophobicity beta-carotene.The present invention can effectively improve beta-carotene water solublity and non-oxidizability, and preparation technology is simple, mild condition, the nano micellar solution prepared has good stability, is expected to for cosmetic field or functional food field provide a kind of natural effective stable carrier and Aqueous dispersions agent.
Description
Technical field
The invention belongs to nano-carrier technical field, relate to natural and biodegradable chitosan for raw material carries out the method for hydrophobic modification, in particular to a kind of preparation method and application thereof of beta-carotene nano-micelle carrier, for cosmetic industry and functional food industry provide a kind of natural effective stable carrier and Aqueous dispersions agent.
Background technology
Beta-carotene is at the most ubiquitous natural pigment of occurring in nature, is to safeguard the indispensable nutrient of health.Simultaneously as a kind of effective antioxidant, it effectively can be removed human body and to dissociate free radical, prevents skin aging and tissue injury, is therefore day by day subject to extensive concern at cosmetics and field of food.But beta-carotene is water insoluble, bioavailability is low, and the conjugated double bond structures be rich in makes it comparatively responsive to the extraneous factor such as light, heat, poor stability.At present, find suitable method effectively to improve the water solublity of beta-carotene and stability and become the focus that people pay close attention to.
In recent years, as novel pharmaceutical carrier, polymer nano micelle receives much concern because it has good physicochemical property.Polymer micelle is formed by the self assembly in water of amphipathic polymeric material, has homogeneous nano-scale and spherical core-shell type structure.Its hydrophobic cores effectively can be wrapped and be carried the medicine of slightly solubility, and hydrophilic shell can strengthen its stability in an aqueous medium and dispersibility.Particularly chitosan, has the features such as good biodegradability, biocompatibility, antibiotic property and avirulence due to it, be widely used in the fields such as biology, medicine, food, agricultural.But, because the crystallinity of chitosan is high, poorly soluble, greatly limit the application of chitosan.Therefore, hydrophobic modification is carried out to chitosan, improve its dissolubility, expand the important directions that its application is chitosan research.
At present, most chitosan hydrophobically modified carries out in dilute acidic solution or organic solvent, about then less as the research of solvent report using ionic liquid.Polylactic acid a kind ofly fat-solublely has good biodegradability and the polymer of biocompatibility, is by the Green Polymer Material of food and drug administration (FDA) certification.
Summary of the invention
The object of the present invention is to provide a kind of preparation method using chitosan grafted polylactic acid nano-micelle load beta-carotene.The method embeds hydrophobic dye beta-carotene with self-assembled nano micelle, utilizes microfacies extraction, hydrophobic dyestuff is enriched in micelle inner core.The nano-micelle prepared by the inventive method, effectively can strengthen water solublity and the chemical stability of beta-carotene, and can effectively keep even strengthening beta-carotene antioxidant effect, be a kind of good carrier material.
Another object of the present invention is to provide the nano micellar solution prepared by the inventive method, and this micellar solution can keep the non-oxidizability of beta-carotene itself, provides described as antioxidation, and the cosmetics that protection is old and feeble or functional food adjuvant use.
Object of the present invention is achieved by the following technical programs:
A preparation method for the chitose base self-assembly nano micellar solution of load beta-carotene, comprises the following steps:
(1) synthesis of chitosan grafted polylactic acid: chitosan is dissolved in glyoxaline ion liquid; Lactide and catalyst is added, 100 ~ 130 DEG C of reaction 12 ~ 24h under nitrogen protection in above-mentioned solution; Repeated washing after alcohol settling, extracting 24 ~ 48h; Vacuum drying obtains chitosan grafted polylactic acid; Described catalyst is stannous octoate or DMAP (DMAP); Wherein the mol ratio of chitosan and lactide, catalyst is 1:(1 ~ 4): (0.00001 ~ 0.1);
(2) preparation of pesticide-carrying nano micellar solution: chitosan grafted polylactic acid prepared by step (1) is dissolved in ultra-pure water, slowly drips beta-carotene/tetrahydrofuran solution under magnetic agitation, obtain the mixed liquor of chitosan grafted polylactic acid; Then by mixed liquor probe sonication 0.5 ~ 2h, rotary evaporation goes out oxolane, adds water and is settled to micro-pore-film filtration, i.e. the chitosan self-assembled nano micelle solution of obtained load beta-carotene after initial micellar solution volume.
In the mixed liquor of step (2) described chitosan grafted polylactic acid, the concentration of beta-carotene is 0.05 ~ 2.0mg/mL.
The aperture of step (2) described microporous membrane is 0.22 ~ 0.45 μm.
Chitosan grafted polylactic acid concentration of aqueous solution described in step (2) is 0.5 ~ 2mg/mL.
Described in step (2), ultrasound condition is: output 30 ~ 400W, pulse width 2.0s, intermittent time 2.0s, time 0.5 ~ 2h.
Rotary evaporation described in step (2) carries out according to following condition: after ultrasonic end, mixed liquor is placed in Rotary Evaporators backspin and steams oxolane, preferred temperature 35 DEG C, time 10 ~ 20min.
The molecular weight of the chitosan described in step (1) is 50 ~ 200kDa, and deacetylation is 85 ~ 99%.
Glyoxaline ion liquid described in step (1) is chlorination-1-pi-allyl-3-Methylimidazole. (AmimCl) or chlorination 1-butyl-3-Methylimidazole. (BmimCl).
Described in step (1), vacuum drying condition is at 45 ~ 55 DEG C, dry 24 ~ 48h.
Inventive principle of the present invention is: the present invention proposes to utilize the chitosan-based nano-micelle of self assembly to carry the carrier of beta-carotene as bag, the micelle of this self assembly is using hydrophilic chitosan skeleton as shell, and hydrophobic polylactic acid side chain is as kernel, the bag for beta-carotene carries.The present invention effectively can solve the water solublity of beta-carotene and poor chemical stability, problem that bioavailability is low, improves the antioxidant properties of beta-carotene simultaneously.The chitose base self-assembly nano micellar solution of load beta-carotene prepared by the present invention and high-end cosmetics and functional food field be can be applicable to the bag support method of beta-carotene.
The present invention has following advantage and effect relative to prior art:
(1) the present invention uses glyoxaline ion liquid as the active solvent of chitosan, react with the hydroxyl of chitosan or amino after forming polylactic acid intermediate by lactide ring-opening polymerisation under stannous octoate or DMAP catalysis, the chitosan grafted polylactic acid obtained; Product has good biodegradability, avirulence and biocompatibility.
(2) chitosan derivatives that prepared by the present invention self assembly can form nano-micelle in water.Form hydrophobic inner core by the hydrophobic interaction of polylactic acid, the hydrophilic skeleton of chitosan then forms hydrophilic outer shell in the outside of hydrophobic inner core, greatly strengthens its water solublity.
(3) dewatering medicament can be enriched in hydrophobic inner core by the nano-micelle of what the present invention prepared have unique core-shell type spherical structure, thus increase the dissolubility of dewatering medicament, envelop rate and drug loading higher, for hydrophobicity beta-carotene provides excellent carrier, its optimization of easily extensible and application.
(4) the chitose base self-assembly nano micellar solution of load beta-carotene for preparing of the present invention, preparation technology is simple, mild condition, and has good stability.
Accompanying drawing explanation
The infrared spectrogram of Fig. 1 to be the infrared spectrogram of chitose graft copolymer in embodiment 1: a be CS, b is the infrared spectrogram of CS-g-PLA.
The nucleus magnetic hydrogen spectrum figure of Fig. 2 to be nucleus magnetic hydrogen spectrum figure: a of chitose graft copolymer in embodiment 1 be CS, b is the nucleus magnetic hydrogen spectrum figure of CS-g-PLA.
Fig. 3 is the result figure that in embodiment 1, DPPH method measures non-oxidizability.
Fig. 4 is the result figure that in embodiment 1, FRAP method measures non-oxidizability.
Fig. 5 is the result figure that in embodiment 2, DPPH method measures non-oxidizability.
Fig. 6 is the result figure that in embodiment 2, FRAP method measures non-oxidizability.
Detailed description of the invention
Below in conjunction with specific embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited thereto.
Embodiment 1
(1) preparation of chitosan grafted polylactic acid (CS-g-PLA): take 10g chlorination 1-pi-allyl-3-Methylimidazole. in 25mL there-necked flask, 80 DEG C of oil baths add 1g chitosan (CS after dissolving, molecular weight 50kDa, deacetylation 90%), magnetic agitation 4h is to being uniformly dispersed; Slowly add 1.8g lactide and 100 μ L stannous octoates again, under nitrogen protection, be warming up to 130 DEG C of reaction 24h; After reaction terminates, use dehydrated alcohol precipitation, centrifugal rear abandoning supernatant, the precipitation of collection continues to use washing with alcohol 4 times; Then in Soxhlet extractor, acetone extraction 24h is used; Finally by the vacuum drying 24h at 45 DEG C of the product after extracting, obtain CS-g-PLA, its reaction equation is:
The discriminating of CS-g-PLA: in infrared spectrogram, at 1743cm
-1there is new absworption peak in place, at 2930cm
-1and 2880cm
-1place is respectively the C-H stretching vibration absworption peak of methyl and methylene, and its intensity, apparently higher than CS, proves that CS and polylactic acid (PLA) there occurs graft reaction; In CS-g-PLA nucleus magnetic hydrogen spectrum, the characteristic peak of chemical shift 1.29 and 1.05 corresponds to the methyl proton peak on position, polylactic acid end and on repetitive, again demonstrates the success that CS grafting PLA reacts.
(2) preparation of pesticide-carrying nano micellar solution: chitosan grafted polylactic acid prepared by step (1) is dissolved in ultra-pure water; Take 5mg beta-carotene to dissolve in 2mL oxolane, slowly drop in 10mL1mg/mL CS-g-PLA aqueous solution under magnetic agitation; Ultrasonic 2h(output 75W, pulse width 2.0s, intermittent time 2.0s) after, at 35 DEG C, rotary evaporation 15min removes oxolane, and adds water and be settled to 10mL; Remove the beta-carotene do not embedded with 0.45 μm of filtering with microporous membrane, obtain the nano micellar solution of beta-carotene load.
Ultraviolet spectrometer (HP8453) 457nm place measures the absorbance of beta-carotene micellar solution, the envelop rate calculating beta-carotene according to the standard curve of beta-carotene is 42.1%, drug loading is 20.5%, and in nano-micelle, the concentration of beta-carotene is 205 μ g/mL.Go out its particle diameter with Malvern particle size analyzer determination and be respectively 139.4nm.
(3) DPPH method measures non-oxidizability: compound concentration is 205 μ g/mL beta-carotene alcoholic solution 10mL; Getting beta-carotene/micelle in the above-mentioned isocyatic beta-carotene/ethanol of 2mL or step (2) respectively adds in 2mL40mg/mL DPPH solution, lucifuge reaction under room temperature, uses ultraviolet spectrometer (HP8453) 517nm place to measure the absorbance of mixed solution at set intervals.The clearance rate of DPPH free radical the results are shown in Figure 3.As can be seen from the figure, along with the change of time, beta-carotene/ethanol and beta-carotene/micelle have the trend of similar removing DPPH free radical.After reaction 40min, the free radical scavenging activity of beta-carotene/micelle can reach 99%, and the clearance rate of beta-carotene/ethanol is about 30%.Illustrate that the beta-carotene that nano-micelle bag carries maintains original antioxidant properties.
(4) FRAP method measures non-oxidizability: take 0.31g sodium acetate in volumetric flask, be dissolved in water, then add 1.6mL glacial acetic acid, adding water after mixing is settled to 100mL, obtains 0.3mol/L sodium acetate buffer solution; Take 2,4,6-TPTZ (TPTZ) 31.233mg, after being dissolved in 10mL40mmol/L HCl solution, add 10mL20mmol/L FeCl
3aqueous solution and 100mL0.3mol/L sodium acetate buffer solution, obtain FRAP working solution after mix homogeneously; Compound concentration is 205 μ g/mL beta-carotene alcoholic solution 10mL; Get beta-carotene/micelle in the above-mentioned beta-carotene/ethanol of 150 μ L and step (3) respectively, add in 4.5mL FRAP working solution, lucifuge reaction at 37 DEG C, uses ultraviolet spectrometer (HP8453) 593nm place to measure the absorbance of mixed solution at set intervals.FRAP method non-oxidizability the results are shown in Figure 4.As seen from the figure, beta-carotene ethanol system FRAP value increases gradually along with the change of time, and beta-carotene/micelle also has similar variation tendency, but its FRAP value is a little more than the former.The beta-carotene that sufficient proof nano-micelle bag carries can keep original non-oxidizability.
Embodiment 2
(1) preparation of CS-g-PLA: take 10g chlorination 1-pi-allyl-3-Methylimidazole. in 25mL there-necked flask, 80 DEG C of oil baths add 1g CS(molecular weight 50kDa, deacetylation 90% after dissolving), magnetic agitation 4h is to being uniformly dispersed; Slowly add 1.8g lactide and 100 μ L stannous octoates again, under nitrogen protection, be warming up to 130 DEG C of reaction 24h; After reaction terminates, use dehydrated alcohol precipitation and repeated washing; Then acetone extraction 24h is used; Finally by the vacuum drying 24h at 45 DEG C of the product after extracting.
(2) preparation of pesticide-carrying nano micellar solution: chitosan grafted polylactic acid prepared by step (1) is dissolved in ultra-pure water; Take 10mg beta-carotene to dissolve in 2mL oxolane, slowly drop in 10mL1mg/mL CS-g-PLA aqueous solution under magnetic agitation; Ultrasonic 2h(output 75W, pulse width 2.0s, intermittent time 2.0s) after, rotary evaporation 15min at 35 DEG C, and add water and be settled to 10mL; After 0.45 μm of filtering with microporous membrane, obtain the nano micellar solution of load beta-carotene.
Ultraviolet spectrometer (HP8453) 457nm place measures the absorbance of beta-carotene micellar solution, the envelop rate calculating beta-carotene according to the standard curve of beta-carotene is 41.1%, drug loading is 41.1%, and in nano-micelle, the concentration of beta-carotene is 411 μ g/mL.Go out its particle diameter with Malvern particle size analyzer determination and be respectively 144.4nm, this micellar solution 4 DEG C is preserved 8 days, and its particle diameter remains unchanged substantially, thus has good stability.
(3) DPPH method measures non-oxidizability: compound concentration is 411 μ g/mL beta-carotene alcoholic solution 10mL; Getting beta-carotene/micelle in the isocyatic beta-carotene/ethanol of 2mL or step (2) respectively, in test tube, adds in 2mL40mg/mL DPPH solution, lucifuge reaction under room temperature.Ultraviolet spectrometer (HP8453) 517nm place is used to measure the absorbance of mixed solution at set intervals.The clearance rate of DPPH free radical the results are shown in Figure 5.As can be seen from the figure, along with the change of time, beta-carotene/ethanol and beta-carotene/micelle have the trend of similar removing DPPH free radical.After reaction 10min, the free radical scavenging activity of beta-carotene/micelle almost can reach 100%, and the clearance rate of beta-carotene/ethanol is less than 60%.Illustrate that the beta-carotene that nano-micelle bag carries keeps even enhancing original antioxidant properties.
(4) FRAP method measures non-oxidizability: take after 2,4,6-TPTZ (TPTZ) 31.233mg is dissolved in 10mL40mmol/L HCl solution, add 10mL20mmol/L FeCl
3aqueous solution and 100mL0.3mol/L sodium acetate buffer solution, obtain FRAP working solution after mix homogeneously; Compound concentration is beta-carotene alcoholic solution 10mL; Getting beta-carotene/micelle in 150 μ L411ug/mL beta-carotene/ethanol and step (2) respectively adds in 4.5mL FRAP working solution, lucifuge reaction at 37 DEG C, uses ultraviolet spectrometer (HP8453) 593nm place to measure the absorbance of mixed solution at set intervals.FRAP method non-oxidizability the results are shown in Figure 6.As seen from the figure, the FRAP value of beta-carotene/ethanol and beta-carotene/micellar solution is all increase gradually along with the change of time, but the FRAP value of beta-carotene/micelle apparently higher than.The beta-carotene that sufficient proof nano-micelle bag carries can effectively keep even strengthening original non-oxidizability.
Embodiment 3
(1) preparation of CS-g-PLA: take 10g chlorination 1-butyl-3-Methylimidazole. in 25mL there-necked flask, 80 DEG C of oil baths add 1g CS(molecular weight 100KDa, deacetylation 85% after dissolving), magnetic agitation 4h is to being uniformly dispersed; Slowly add 1.8g lactide and 0.758g4-dimethylamino naphthyridine again, under nitrogen protection, be warming up to 130 DEG C of reaction 24h; After reaction terminates, use dehydrated alcohol precipitation, centrifugal rear abandoning supernatant, the precipitation of collection continues to use washing with alcohol 4 times; Then acetone extraction 24h is used; Finally by the vacuum drying 24h at 45 DEG C of the product after extracting.
(2) preparation of pesticide-carrying nano micellar solution: chitosan grafted polylactic acid prepared by step (1) is dissolved in ultra-pure water; Take 0.6mg beta-carotene to dissolve in 2mL oxolane, slowly drop in 10mL1mg/mL CS-g-PLA aqueous solution under magnetic agitation; Ultrasonic 2h(output 90W, pulse width 2.0s, intermittent time 2.0s) after, at 35 DEG C after rotary evaporation 15min, add water and be settled to 10mL; After 0.45 μm of filtering with microporous membrane, obtain the nano micellar solution of load beta-carotene.
Ultraviolet spectrometer (HP8453) 457nm place measures the absorbance of beta-carotene micellar solution, the envelop rate calculating beta-carotene according to the standard curve of beta-carotene is 59.17%, drug loading is 2.96%, and in nano micellar solution, the concentration of beta-carotene is 29.6 μ g/mL.Go out its particle diameter with Malvern particle size analyzer determination and be respectively 64.72nm.
Above-described embodiment is some embodiments of the present invention; but embodiments of the present invention are not restricted to the described embodiments; change, the modification done under other any does not deviate from spirit of the present invention and principle, substitute, combine, simplify; all should be the substitute mode of equivalence, be included within protection scope of the present invention.
Claims (10)
1. a preparation method for the chitose base self-assembly nano micellar solution of load beta-carotene, is characterized in that, comprise the following steps:
(1) synthesis of chitosan grafted polylactic acid: chitosan is dissolved in glyoxaline ion liquid; Lactide and catalyst is added, 100 ~ 130 DEG C of reaction 12 ~ 24h under nitrogen protection in above-mentioned solution; Repeated washing after alcohol settling, extracting 24 ~ 48h; Vacuum drying obtains chitosan grafted polylactic acid; Described catalyst is stannous octoate or DMAP; Wherein the mol ratio of chitosan and lactide, catalyst is 1:(1 ~ 4): (0.00001 ~ 0.1);
(2) preparation of pesticide-carrying nano micellar solution: chitosan grafted polylactic acid prepared by step (1) is dissolved in ultra-pure water, slowly drips beta-carotene/tetrahydrofuran solution under magnetic agitation, obtain the mixed liquor of chitosan grafted polylactic acid; Then by mixed liquor probe sonication 0.5 ~ 2h, rotary evaporation goes out oxolane, adds water and is settled to micro-pore-film filtration, i.e. the chitosan self-assembled nano micelle solution of obtained load beta-carotene after initial micellar solution volume.
2. preparation method according to claim 1, is characterized in that, in the mixed liquor of step (2) described chitosan grafted polylactic acid, the concentration of beta-carotene is 0.05 ~ 2.0mg/mL.
3. preparation method according to claim 1, is characterized in that, the aperture of step (2) described microporous membrane is 0.22 ~ 0.45 μm.
4. method according to claim 1, is characterized in that, the chitosan grafted polylactic acid concentration of aqueous solution described in step (2) is 0.5 ~ 2mg/mL.
5. method according to claim 1, is characterized in that, described in step (2), ultrasound condition is: output 30 ~ 400W, pulse width 2.0s, intermittent time 2.0s, time 0.5 ~ 2h.
6. method according to claim 1, is characterized in that, the condition of the rotary evaporation described in step (2) is: temperature 35 DEG C, time 10 ~ 20min.
7. method according to claim 1, is characterized in that, the molecular weight of the chitosan described in step (1) is 50 ~ 200kDa, and deacetylation is 85 ~ 99%.
8. method according to claim 1, is characterized in that, the glyoxaline ion liquid described in step (1) is chlorination-1-pi-allyl-3-Methylimidazole. or chlorination-1-butyl-3-Methylimidazole..
9. the method according to claim 1 ~ 8 any one, is characterized in that, described in step (1), vacuum drying condition is at 45 ~ 55 DEG C, dry 24 ~ 48h.
10. a chitose base self-assembly nano micellar solution for load beta-carotene, is characterized in that, is prepared by the method described in any one of claim 1 ~ 9.
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| CN104225614B (en) * | 2014-09-22 | 2016-11-30 | 北京航空航天大学 | With chitosan grafted polylactic acid complex microsphere carrying hydrophobe biomolecule and preparation method thereof |
| CN105732965A (en) * | 2016-02-23 | 2016-07-06 | 山东华铂凯盛生物科技有限公司 | Preparing method and application of segmented copolymer based on nonlinearity |
| CN107348507A (en) * | 2017-07-06 | 2017-11-17 | 天津工业大学 | Carry the preparation of bata-carotene PLA (PLA) nanoparticle |
| CN108929387B (en) * | 2018-08-08 | 2019-08-23 | 烟台浩忆生物科技有限公司 | A kind of preparation method of chitosan-g- antibacterial peptide polymer |
| CN110387142B (en) * | 2019-08-14 | 2021-08-17 | 桂林理工大学 | Preparation method of peach gum polysaccharide nanospheres loaded with fat-soluble pigment |
| CN111019099B (en) * | 2019-12-02 | 2021-12-21 | 华南理工大学 | Chitosan grafted polylactic acid copolymer and preparation method and application thereof |
| CN113633781A (en) * | 2021-08-19 | 2021-11-12 | 青岛科技大学 | Astaxanthin-chitosan self-assembly nano compound and preparation method and application thereof |
| CN115363212B (en) * | 2022-07-27 | 2024-04-05 | 海南师范大学 | Carotenoid-loaded alginic acid derivative micelle, preparation method and application thereof |
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