CN103816054A - Chitosan-based self-assembled nano micelle solution loaded with beta-carotene and preparation method thereof - Google Patents
Chitosan-based self-assembled nano micelle solution loaded with beta-carotene and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a chitosan-based self-assembled nano micelle solution loaded with beta-carotene and a preparation method thereof. An imidazoles ionic liquid is used as an effective solvent of chitosan, and under the action of a catalyst, lactide is subjected to ring opening polymerization and is grafted to a chitosan macromolecular chain to obtain a chitosan-grafted polylactic acid; then a self assembly action of the chitosan-grafted polylactic acid in an aqueous solution is utilized to achieve effective embedding of hydrophobic beta-carotene. The water solubility and the oxidation resistance of beta-carotene can be effectively improved, moreover, the preparation process is simple, and conditions are mild; and the prepared nano micelle solution has good stability, and is expected to provide a natural and effective stable carrier and a water-phase dispersant for the cosmetic field or the functional food field.
Description
Technical field
The invention belongs to nano-carrier technical field, relate to the method for carrying out hydrophobic modification take natural and biodegradable chitosan as raw material, be particularly related 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 water dispersant.
Background technology
Beta-carotene is at the most ubiquitous natural pigment of occurring in nature, is to safeguard the indispensable nutrient of health.As a kind of effectively antioxidant, it can remove the free free radical of human body effectively, prevents skin aging and tissue injury, is therefore day by day subject to extensive concern at cosmetics and field of food simultaneously.But beta-carotene is water insoluble, bioavailability is low, and the conjugated double bond structures being rich in makes it comparatively responsive to the extraneous factor such as light, heat, poor stability.At present, find that suitable method effectively improves the water solublity of beta-carotene and stability becomes 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 to be formed by the self assembly in water of amphipathic polymeric material, has the nano-scale of homogeneous and spherical core-shell type structure.Its hydrophobic cores can effectively be wrapped the medicine that carries slightly solubility, and hydrophilic shell can strengthen its stability and dispersibility in aqueous medium.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, chitosan is carried out to hydrophobic modification, improve its dissolubility, expanding its application is an important directions of chitosan research.
At present, most chitosan hydrophobically modified carries out in rare acid solution or organic solvent, about the research using ionic liquid as solvent is reported less.Polylactic acid is a kind of fat-soluble have good biodegradability and polymer of biocompatibility, is the Green Polymer Material by food and drug administration (FDA) authentication.
Summary of the invention
The object of the present invention is to provide a kind of preparation method that uses chitosan grafted polylactic acid nano-micelle load beta-carotene.The method is, with self-assembled nano micelle, hydrophobic dye beta-carotene is carried out to embedding, utilizes microfacies extraction, and hydrophobic dyestuff is enriched in to micelle kernel.The nano-micelle of being prepared by the inventive method, can effectively 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 of being prepared by the inventive method, and this micellar solution can keep the non-oxidizability of beta-carotene itself, provides described as antioxidation, protects old and feeble cosmetics or functional food adjuvant and uses.
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) chitosan grafted polylactic acid is synthetic: chitosan is dissolved in glyoxaline ion liquid; In above-mentioned solution, add lactide and catalyst, 100～130 ℃ of reaction 12～24h under nitrogen protection; Repeated washing after ethanol precipitation, 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 ultrasonic mixed liquor probe 0.5～2h, rotary evaporation is gone out oxolane, adds water and is settled to micro-pore-film filtration after initial micellar solution volume, makes the chitosan self-assembled nano micelle solution of load beta-carotene.
In the mixed liquor of the described chitosan grafted polylactic acid of step (2), the concentration of beta-carotene is 0.05～2.0mg/mL.
The aperture of the described microporous membrane of step (2) is 0.22～0.45 μ m.
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 to Rotary Evaporators backspin and steams oxolane, 35 ℃ of preferred temperature, 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 ℃, 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, carry for the bag of beta-carotene.The present invention can effectively solve the water solublity of beta-carotene and poor chemical stability, problem that bioavailability is low, has improved 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 the bag support method of beta-carotene be can be applicable to high-end cosmetics and functional food field.
The present invention has following advantage and effect with respect to prior art:
(1) the present invention uses the active solvent of glyoxaline ion liquid as chitosan, after forming polylactic acid intermediate by lactide ring-opening polymerisation under stannous octoate or DMAP catalysis, react the chitosan grafted polylactic acid obtaining with hydroxyl or the amino of chitosan; Product has good biodegradability, avirulence and biocompatibility.
(2) chitosan derivatives that prepared by the present invention can self assembly form nano-micelle in water.Hydrophobic interaction by polylactic acid forms hydrophobic inner core, and the hydrophilic skeleton of chitosan forms hydrophilic outer shell in the outside of hydrophobic inner core, greatly strengthens its water solublity.
(3) nano-micelle of what the present invention prepared have unique core-shell type spherical structure can be enriched in dewatering medicament in hydrophobic inner core, thereby increase the dissolubility of dewatering medicament, envelop rate and drug loading are higher, for hydrophobicity beta-carotene provides good carrier, can expand its optimization and application.
(4) the chitose base self-assembly nano micellar solution of the load beta-carotene that the present invention prepares, preparation technology is simple, mild condition, and there is good stability.
Accompanying drawing explanation
Fig. 1 is that the infrared spectrogram of chitose graft copolymer in embodiment 1: a is the infrared spectrogram of CS, the infrared spectrogram that b is CS-g-PLA.
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of chitose graft copolymer in embodiment 1: the nucleus magnetic hydrogen spectrum figure that a is CS, the nucleus magnetic hydrogen spectrum figure that b is CS-g-PLA.
Fig. 3 is the result figure that in embodiment 1, DPPH method is measured non-oxidizability.
Fig. 4 is the result figure that in embodiment 1, FRAP method is measured non-oxidizability.
Fig. 5 is the result figure that in embodiment 2, DPPH method is measured non-oxidizability.
Fig. 6 is the result figure that in embodiment 2, FRAP method is measured non-oxidizability.
The specific embodiment
Below in conjunction with specific embodiment, the present invention is described in further detail, but embodiments of the present invention are not limited to this.
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 ℃ of oil baths add 1g chitosan (CS after dissolving, molecular weight 50kDa, deacetylation 90%), magnetic agitation 4h is to being uniformly dispersed; Slowly add again 1.8g lactide and 100 μ L stannous octoates, under nitrogen protection, be warming up to 130 ℃ of reaction 24h; After reaction finishes, use dehydrated alcohol precipitation, centrifugal rear abandoning supernatant, the precipitation of collection continues to use washing with alcohol 4 times; Then in Soxhlet extractor, use acetone extracting 24h; Finally, by the vacuum drying 24h at 45 ℃ 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 graft reaction has occurred for CS and polylactic acid (PLA); In CS-g-PLA nucleus magnetic hydrogen spectrum, the characteristic peak of chemical shift 1.29 and 1.05 is the methyl proton peak on upper and repetitive corresponding to polylactic acid end position, proving again the CS grafting PLA success of reacting.
(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 and dissolve in 2mL oxolane, under magnetic agitation, slowly drop in 10mL1mg/mL CS-g-PLA aqueous solution; Ultrasonic 2h(output 75W, pulse width 2.0s, intermittent time 2.0s) after, rotary evaporation 15min removes oxolane at 35 ℃, and adds water and be settled to 10mL; Remove the beta-carotene of not embedding with 0.45 μ m 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 that calculates 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 is measured non-oxidizability: compound concentration is 205 μ g/mL beta-carotene alcoholic solution 10mL; Getting respectively beta-carotene/micelle in the above-mentioned isocyatic beta-carotene/ethanol of 2mL or step (2) 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 variation 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 in 30% left and right.Illustrate that the beta-carotene that nano-micelle bag carries has kept original antioxidant properties.
(4) FRAP method is measured non-oxidizability: take 0.31g sodium acetate in volumetric flask, be dissolved in water, then add 1.6mL glacial acetic acid, add water and be settled to 100mL after mixing, obtain 0.3mol/L sodium acetate buffer solution; Take 2,4,6-TPTZ (TPTZ) 31.233mg, be dissolved in after 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 respectively beta-carotene/micelle in the above-mentioned beta-carotene/ethanol of 150 μ L and step (3), add in 4.5mL FRAP working solution, lucifuge reaction at 37 ℃, 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 variation of time, and beta-carotene/micelle also has similar variation tendency, but its FRAP value is a little more than the former.Fully prove that the beta-carotene that nano-micelle bag carries can keep original non-oxidizability.
(1) preparation of CS-g-PLA: take 10g chlorination 1-pi-allyl-3-Methylimidazole. in 25mL there-necked flask, 80 ℃ of oil baths add 1g CS(molecular weight 50kDa, deacetylation 90% after dissolving), magnetic agitation 4h is to being uniformly dispersed; Slowly add again 1.8g lactide and 100 μ L stannous octoates, under nitrogen protection, be warming up to 130 ℃ of reaction 24h; After reaction finishes, use dehydrated alcohol precipitation repeated washing; Then use acetone extracting 24h; Finally by the vacuum drying 24h at 45 ℃ 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 and dissolve in 2mL oxolane, under magnetic agitation, slowly drop in 10mL1mg/mL CS-g-PLA aqueous solution; Ultrasonic 2h(output 75W, pulse width 2.0s, intermittent time 2.0s) after, rotary evaporation 15min at 35 ℃, and add water and be settled to 10mL; With after 0.45 μ m 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 that calculates 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, 4 ℃ of preservations of this micellar solution 8 days, its particle diameter remains unchanged substantially, thereby has good stability.
(3) DPPH method is measured non-oxidizability: compound concentration is 411 μ g/mL beta-carotene alcoholic solution 10mL; Get respectively beta-carotene/micelle in the isocyatic beta-carotene/ethanol of 2mL or step (2) and, in test tube, add in 2mL40mg/mL DPPH solution, lucifuge reaction under room temperature.Use at set intervals ultraviolet spectrometer (HP8453) 517nm place to measure the absorbance of mixed solution.The clearance rate of DPPH free radical the results are shown in Figure 5.As can be seen from the figure,, along with the variation 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 having strengthened original antioxidant properties.
(4) FRAP method is measured non-oxidizability: take 2,4,6-TPTZ (TPTZ) 31.233mg and be dissolved in after 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 respectively beta-carotene/micelle in 150 μ L411ug/mL beta-carotene/ethanol and step (2) adds in 4.5mL FRAP working solution, lucifuge reaction at 37 ℃, 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 be all along with the variation of time gradually increase, but the FRAP value of beta-carotene/micelle apparently higher than.Fully prove that the beta-carotene that nano-micelle bag carries can effectively keep even strengthening original non-oxidizability.
(1) preparation of CS-g-PLA: take 10g chlorination 1-butyl-3-Methylimidazole. in 25mL there-necked flask, 80 ℃ of oil baths add 1g CS(molecular weight 100KDa, deacetylation 85% after dissolving), magnetic agitation 4h is to being uniformly dispersed; Slowly add again 1.8g lactide and 0.758g4-dimethylamino naphthyridine, under nitrogen protection, be warming up to 130 ℃ of reaction 24h; After reaction finishes, use dehydrated alcohol precipitation, centrifugal rear abandoning supernatant, the precipitation of collection continues to use washing with alcohol 4 times; Then use acetone extracting 24h; Finally by the vacuum drying 24h at 45 ℃ 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 and dissolve in 2mL oxolane, under magnetic agitation, slowly drop in 10mL1mg/mL CS-g-PLA aqueous solution; Ultrasonic 2h(output 90W, pulse width 2.0s, intermittent time 2.0s) after, after rotary evaporation 15min, add water and be settled to 10mL at 35 ℃; With after 0.45 μ m 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 that calculates 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; other any do not deviate from change, the modification done under spirit of the present invention and principle, substitutes, combination, simplify; all should be equivalent substitute mode, within being included in 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, comprises the following steps:
(1) chitosan grafted polylactic acid is synthetic: chitosan is dissolved in glyoxaline ion liquid; In above-mentioned solution, add lactide and catalyst, 100～130 ℃ of reaction 12～24h under nitrogen protection; Repeated washing after ethanol precipitation, 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 ultrasonic mixed liquor probe 0.5～2h, rotary evaporation is gone out oxolane, adds water and is settled to micro-pore-film filtration after initial micellar solution volume, makes the chitosan self-assembled nano micelle solution of load beta-carotene.
2. preparation method according to claim 1, is characterized in that, in the mixed liquor of the described chitosan grafted polylactic acid of step (2), 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 the described microporous membrane of step (2) is 0.22～0.45 μ m.
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: 35 ℃ of temperature, 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. according to the method described in claim 1～8 any one, it is characterized in that, described in step (1), vacuum drying condition is at 45～55 ℃, 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 claim 1～9 any one.
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| CN115363212A (en) * | 2022-07-27 | 2022-11-22 | 海南师范大学 | Carotenoid-loaded alginic acid derivative micelle, and preparation method and application thereof |
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