CN111035579A - Composite liposome/chitosan antioxidant preparation and preparation method thereof - Google Patents
Composite liposome/chitosan antioxidant preparation and preparation method thereof Download PDFInfo
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- 229920001661 Chitosan Polymers 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 50
- 230000003078 antioxidant effect Effects 0.000 title claims abstract description 46
- 239000003963 antioxidant agent Substances 0.000 title claims abstract description 35
- 239000002131 composite material Substances 0.000 title claims abstract description 17
- QAIPRVGONGVQAS-DUXPYHPUSA-N trans-caffeic acid Chemical compound OC(=O)\C=C\C1=CC=C(O)C(O)=C1 QAIPRVGONGVQAS-DUXPYHPUSA-N 0.000 claims abstract description 148
- RWSXRVCMGQZWBV-WDSKDSINSA-N glutathione Chemical compound OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O RWSXRVCMGQZWBV-WDSKDSINSA-N 0.000 claims abstract description 126
- ACEAELOMUCBPJP-UHFFFAOYSA-N (E)-3,4,5-trihydroxycinnamic acid Natural products OC(=O)C=CC1=CC(O)=C(O)C(O)=C1 ACEAELOMUCBPJP-UHFFFAOYSA-N 0.000 claims abstract description 74
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- 235000004883 caffeic acid Nutrition 0.000 claims abstract description 74
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- JQWAHKMIYCERGA-UHFFFAOYSA-N (2-nonanoyloxy-3-octadeca-9,12-dienoyloxypropoxy)-[2-(trimethylazaniumyl)ethyl]phosphinate Chemical compound CCCCCCCCC(=O)OC(COP([O-])(=O)CC[N+](C)(C)C)COC(=O)CCCCCCCC=CCC=CCCCCC JQWAHKMIYCERGA-UHFFFAOYSA-N 0.000 claims description 2
- HYGNFQCEZIWBNB-GEMLJDPKSA-N (2s)-2-amino-5-[[(2r)-1-(carboxymethylamino)-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoic acid;phosphoric acid Chemical compound OP(O)(O)=O.OC(=O)[C@@H](N)CCC(=O)N[C@@H](CS)C(=O)NCC(O)=O HYGNFQCEZIWBNB-GEMLJDPKSA-N 0.000 claims description 2
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Abstract
The invention discloses a composite liposome/chitosan antioxidant preparation and a preparation method thereof. Aims to provide an antioxidant liposome which has the functions of protecting and cooperating with antioxidation, uniform particle size, good water solubility and higher stability. The composite antioxidant takes caffeic acid and glutathione as objects, takes soybean lecithin and cholesterol as lipid bilayer matrixes, and embeds the two together to prepare liposome; and then mixing the liposome with a chitosan solution to prepare the liposome/chitosan antioxidant preparation. The caffeic acid and glutathione embedded liposome/chitosan antioxidant preparation can be used for food preservation, and can also be prepared into skin care cosmetic products such as cream, emulsion, essence, sunscreen cream and the like according to a conventional method according to requirements.
Description
Technical Field
The invention relates to a preparation method of liposome, in particular to a liposome/chitosan antioxidant for embedding caffeic acid and glutathione and a preparation method thereof.
Background
Glutathione as a natural antioxidant can be used in medicines, can also be used as a base material of functional foods, and is widely applied to the functional foods for delaying senility, enhancing immunity, resisting tumors and the like. But because the glutathione is extremely easy to oxidize, the further wide application of the glutathione is limited, the glutathione can be embedded and protected by an excellent carrier, and the glutathione is prevented from being interfered by the outside world.
Caffeic acid is a natural phenolic compound, widely exists in fruits and vegetables, and has biological effects of resisting toxicity, oxidation, virus and the like. Polyphenolic compounds have been widely used in the food and medical fields as antioxidants, for example: food antiseptic, food natural colorant, pigment, cosmetic, etc. However, the caffeic acid has poor water solubility, which greatly limits the application of the caffeic acid in water-soluble systems. The liposome can improve the water solubility of insoluble substances and improve the bioavailability thereof.
The liposome is a bilayer microcapsule composed of phospholipid and cholesterol, and has the characteristics of amphipathy and no toxicity. The active substance is embedded by liposome technology, so that the damage of the environment to the active substance can be reduced, and the stability of the active substance is improved. However, the main membrane material phospholipid of the liposome is easy to be oxidized, decomposed and reduced, and the oxidation stability of the existing liposome product is still to be improved.
Chitosan is a non-toxic, degradable, biocompatible polymer material with good film-forming properties, and is often used as a wall material of microcapsules.
Disclosure of Invention
The invention aims to overcome the defects of the function and the technology of the existing liposome product, and prepares a composite liposome preparation simultaneously embedding glutathione and caffeic acid, and on one hand, the preparation can provide barrier protection for the glutathione and the caffeic acid and improve the utilization rate of the glutathione and the caffeic acid; on the other hand, the antioxidant effect of the two can be comprehensively utilized, and a high-efficiency antioxidant compound liposome preparation is provided.
The invention also aims to provide a preparation method of the composite liposome/chitosan antioxidant preparation for embedding glutathione and caffeic acid. The preparation method adopts natural phospholipid and cholesterol as lipid bilayer matrixes to prepare the antioxidant liposome embedded with glutathione and caffeic acid; then the liposome is mixed with chitosan solution to prepare the liposome/chitosan antioxidant preparation embedded with glutathione and caffeic acid.
The purpose of the invention is realized by the following technical scheme.
A preparation method of a glutathione and caffeic acid embedded composite liposome/chitosan antioxidant preparation comprises the following steps of preparing glutathione and caffeic acid composite liposome by using phospholipid and cholesterol, mixing with a chitosan solution, and preparing the chitosan-based liposome preparation with antibacterial and antioxidant activities, wherein the preparation method comprises the following steps:
a preparation method of a glutathione and caffeic acid embedded composite liposome/chitosan antioxidant preparation is characterized by comprising the following steps:
(1) under the condition of stirring, adding caffeic acid, phospholipid and cholesterol into absolute ethyl alcohol, and fully dissolving to form an oil phase; adding glutathione phosphate buffer solution with the volume of one half of the oil phase, stirring at high speed and mixing uniformly to form a water/oil system; adding phosphate buffer solution with the same volume as the internal water phase to form a water/oil/water three-phase system, and removing the solvent to obtain the primary liposome.
(2) And (3) performing ice-bath low-frequency ultrasonic treatment on the primary liposome for 5 min, sequentially passing through 0.45 mu m and 0.2 mu m microporous filter membranes, and repeating the steps for 3 times to obtain the liposome embedded with caffeic acid and glutathione.
(3) And adding chitosan into the acetic acid solution, fully dissolving, mixing with the liposome embedded with the caffeic acid and the glutathione, and uniformly stirring by magnetic force to obtain the liposome/chitosan antioxidant embedded with the caffeic acid and the glutathione.
Further, in the step (1), the phospholipid is one or a mixture of more than two of soybean lecithin and egg yolk lecithin.
Further, in the step (1), the concentration of the phospholipid solution is 0.1-10 g/L.
Further, in the step (1), the mass ratio of the cholesterol to the phospholipid is 1:2-1: 10.
Further, in the step (1), the ratio of the addition amount of the glutathione to the total mass of the phospholipid and the cholesterol is 1:2-1: 20.
Further, in the step (1), the concentration of the caffeic acid is 0.1-2 g/L.
Further, in the step (1), the mass ratio of the caffeic acid to the glutathione is 2:1-1: 15.
Further, in the step (1), the ratio of the internal water phase to the oil phase is 1:1-1: 10.
Further, in the step (1), the ratio of the phosphate buffer solution to the internal water phase is 2:1-1: 10.
Further, in the step (3), the volume fraction of acetic acid in the chitosan acetic acid solution is 0.5-10%.
Further, in the step (3), the mass fraction of the chitosan is 0.1-5%.
Further, in the step (3), the volume ratio of the liposome to the chitosan solution is 1:1-1: 10.
Further, in the step (3), the rotation speed of the magnetic stirring is 100-.
Further, in the step (3), the stirring time is 5-60 min.
The liposome preparation obtained by the invention has uniform particle size, good water solubility and high stability. After 10 weeks of storage, the retention of the antioxidant activity was 30% -90%.
The liposome/chitosan antioxidant preparation embedded with glutathione and caffeic acid prepared by the preparation method has good antioxidant activity.
The invention utilizes liposome to embed glutathione and caffeic acid with antioxidant effect in the internal water phase to form a composite liposome structure with antioxidant activity, thereby solving the problems of poor stability of glutathione, poor solubility of caffeic acid, low bioavailability and the like, improving the stability of the composite liposome, and promoting the durability of the antioxidant activity. The liposome/chitosan composite antioxidant preparation has excellent and lasting antioxidant activity, and the application of chitosan in the fields of food preservation and the like is expanded.
Compared with the prior art, the invention has the following advantages and beneficial effects:
(1) the liposome adopted by the invention is taken as an ideal encapsulating material of glutathione and caffeic acid, so that the degradation rate of the liposome can be slowed down, and the stability is improved; the high-efficiency antioxidant preparation is obtained by utilizing the synergistic antioxidant capacity of glutathione and caffeic acid;
(2) according to the invention, the specificity of liposome preparation is utilized, the caffeic acid which is difficult to dissolve in water is introduced, the hydrophilicity of the caffeic acid is improved, and the encapsulation of the caffeic acid by the liposome is facilitated;
(3) the preparation method is simple, wide in raw material source and low in energy consumption, and is beneficial to large-scale industrial production;
(4) the lipidosome/chitosan antioxidant preparation embedded with the glutathione and the caffeic acid has good antioxidant effect and lasting activity, and is beneficial to being applied to cosmetic products for food packaging and skin care.
Drawings
FIG. 1 is a graph of DPPH radical clearance of liposomes prepared in example 1 of the present invention: G-Lip: glutathione liposome; C-Lip: a caffeic acid liposome; G-C-Lip: glutathione and caffeic acid complex liposomes; CS-G-C-Lip: liposome/chitosan formulation entrapping glutathione and caffeic acid.
FIG. 2 shows the DPPH scavenging activity retention rate during storage of liposomes obtained in example 1 of the present invention with a mixed solution of glutathione and caffeic acid: G-C-Lip: glutathione and caffeic acid complex liposomes; CS-G-C-Lip: liposome/chitosan formulation entrapping glutathione and caffeic acid.
Detailed description of the invention
The technical solution of the present invention is further described in detail below with reference to specific embodiments and drawings, but the embodiments and the protection scope of the present invention are not limited thereto.
Example 1
The preparation method of the glutathione and caffeic acid embedded composite liposome/chitosan antioxidant preparation comprises the following specific steps:
(1) under the condition of stirring, adding caffeic acid, phospholipid and cholesterol into absolute ethyl alcohol, and fully dissolving to form an oil phase, wherein the concentration of the caffeic acid is 0.2 g/L, the concentration of the phospholipid is 0.5 g/L, and the ratio of the cholesterol to the phospholipid is 1: 5; dissolving glutathione with the mass ratio of caffeic acid of 1:5 in phosphoric acid buffer solution with the volume ratio of oil phase of 1:2, adding the oil phase, stirring at high speed and mixing uniformly to form a water/oil system; adding phosphate buffer solution with the volume ratio of the phosphate buffer solution to the internal water phase being 1:2 to form a water/oil/water three-phase system, and removing the solvent to obtain the primary liposome.
(2) And (3) carrying out ice bath on the primary liposome, carrying out low-frequency ultrasonic treatment for 5 min, sequentially passing through 0.45 mu m and 0.2 mu m microporous filter membranes, and repeating the steps for 3 times to obtain the liposome embedded with caffeic acid and glutathione.
(3) Preparing 0.2% chitosan acetic acid solution (the volume fraction of acetic acid is 1%), mixing with the embedded liposome according to the volume of 1:1, and magnetically stirring for 20 min at 500 r/min to obtain the caffeic acid and glutathione embedded liposome/chitosan antioxidant preparation.
Example 2
The preparation method of the glutathione and caffeic acid embedded composite liposome/chitosan antioxidant preparation comprises the following specific steps:
(1) under the condition of stirring, adding caffeic acid, phospholipid and cholesterol into absolute ethyl alcohol, and fully dissolving to form an oil phase, wherein the concentration of the caffeic acid is 0.5 g/L, the concentration of the phospholipid is 1 g/L, and the ratio of the cholesterol to the phospholipid is 1: 6; dissolving glutathione with the mass ratio of caffeic acid of 1:8 in phosphoric acid buffer solution with the volume ratio of oil phase of 1:5, adding the oil phase, stirring at high speed and mixing uniformly to form a water/oil system; adding phosphate buffer solution with the volume ratio of the phosphate buffer solution to the internal water phase being 1:5 to form a water/oil/water three-phase system, and removing the solvent to obtain the primary liposome.
(2) And (3) carrying out ice bath on the primary liposome, carrying out low-frequency ultrasonic treatment for 5 min, sequentially passing through 0.45 mu m and 0.2 mu m microporous filter membranes, and repeating the steps for 3 times to obtain the liposome embedded with caffeic acid and glutathione.
(3) Preparing 0.5% chitosan acetic acid solution (the volume fraction of acetic acid is 2%), mixing with the embedded liposome according to the volume of 1:2, and magnetically stirring for 30 min at 800 r/min to obtain the caffeic acid and glutathione embedded liposome/chitosan antioxidant preparation.
The DPPH clearance rate of the prepared liposome is shown in figure 1, and as can be seen from figure 1, the DPPH clearance capacity of the liposome in which glutathione and caffeic acid are embedded simultaneously is far greater than that of the liposome embedded separately, which indicates that the combined action of glutathione and caffeic acid has synergistic antioxidation effect. The liposome/chitosan preparation had the strongest DPPH free radical scavenging activity, 59.3%, indicating that chitosan provided antioxidant activity in addition to further protecting the liposomes.
The retention rate of DPPH scavenging activity of the prepared liposome during storage with the mixed solution of glutathione and caffeic acid is shown in FIG. 2, and it can be seen from FIG. 2 that DPPH radical scavenging activity of the liposome is reduced more slowly than that of the mixed solution of non-embedded glutathione and caffeic acid, indicating that the liposome can protect the antioxidant activity of glutathione and caffeic acid. After 70 days, the DPPH free radical retention rate of the liposome/chitosan preparation is the highest and is 56.1 percent of the initial activity, which shows that the liposome/chitosan can well protect the activities of glutathione and caffeic acid, so that the product has more durable antioxidant activity.
Example 3
The preparation method of the glutathione and caffeic acid embedded composite liposome/chitosan antioxidant preparation comprises the following specific steps:
(1) under the condition of stirring, adding caffeic acid, phospholipid and cholesterol into absolute ethyl alcohol, and fully dissolving to form an oil phase, wherein the concentration of the caffeic acid is 1 g/L, the concentration of the phospholipid is 2 g/L, and the ratio of the cholesterol to the phospholipid is 1: 8; dissolving glutathione with the mass ratio of caffeic acid of 1:10 in phosphoric acid buffer solution with the volume ratio of oil phase of 1:8, adding the oil phase, stirring at high speed and mixing uniformly to form a water/oil system; adding phosphate buffer solution with the volume ratio of the phosphate buffer solution to the internal water phase being 1:8 to form a water/oil/water three-phase system, and removing the solvent to obtain the primary liposome.
(2) And (3) carrying out ice bath on the primary liposome, carrying out low-frequency ultrasonic treatment for 5 min, sequentially passing through 0.45 mu m and 0.2 mu m microporous filter membranes, and repeating the steps for 3 times to obtain the liposome embedded with caffeic acid and glutathione.
(3) Preparing 1% chitosan acetic acid solution (the volume fraction of acetic acid is 5%), mixing with the embedded liposome according to the volume of 1:5, and magnetically stirring for 40 min at 1000 r/min to obtain the caffeic acid and glutathione embedded liposome/chitosan antioxidant preparation.
Example 4
The preparation method of the liposome/chitosan antioxidant preparation for embedding the glutathione and the caffeic acid comprises the following specific steps:
(1) under the condition of stirring, adding caffeic acid, phospholipid and cholesterol into absolute ethyl alcohol, and fully dissolving to form an oil phase, wherein the concentration of the caffeic acid is 2 g/L, the concentration of the phospholipid is 5 g/L, and the ratio of the cholesterol to the phospholipid is 1: 15; dissolving glutathione with the mass ratio of caffeic acid of 1:10 into phosphoric acid buffer solution with the volume ratio of oil phase of 1:10, adding the oil phase, stirring at high speed and mixing uniformly to form a water/oil system; adding phosphate buffer solution with the volume ratio of the phosphate buffer solution to the internal water phase being 1:10 to form a water/oil/water three-phase system, and removing the solvent to obtain the primary liposome.
(2) And (3) carrying out ice bath on the primary liposome, carrying out low-frequency ultrasonic treatment for 5 min, sequentially passing through 0.45 mu m and 0.2 mu m microporous filter membranes, and repeating the steps for 3 times to obtain the liposome embedded with caffeic acid and glutathione.
(3) Preparing 2% chitosan acetic acid solution (the volume fraction of acetic acid is 10%), mixing with the embedded liposome according to the volume of 1:10, and magnetically stirring for 60 min at 1200 r/min to obtain the caffeic acid and glutathione embedded liposome/chitosan antioxidant preparation.
The above examples are only preferred embodiments of the present invention, which are intended to be illustrative and not limiting, and all changes, substitutions, modifications, etc. that do not depart from the spirit of the present invention are intended to be included within the scope of the present invention.
Claims (6)
1. A preparation method of a composite liposome/chitosan antioxidant preparation is characterized by comprising the following steps:
(1) under the condition of stirring, adding caffeic acid, phospholipid and cholesterol into absolute ethyl alcohol, and fully dissolving to form an oil phase; adding glutathione phosphate buffer solution serving as an internal water phase into an oil phase, and stirring and mixing uniformly at a high speed to form a water/oil system; adding phosphate buffer solution to form a water/oil/water three-phase system, and removing the solvent to obtain a primary liposome; (2) carrying out ice bath on the primary liposome, carrying out low-frequency ultrasonic treatment for 5 minutes, sequentially passing through 0.45 mu m and 0.2 mu m microporous filter membranes, and repeating for 3 times respectively to obtain a liposome embedded with caffeic acid and glutathione; (3) adding chitosan into acetic acid solution, fully dissolving, mixing with the liposome embedded with caffeic acid and glutathione, and magnetically stirring to obtain the composite liposome/chitosan antioxidant preparation embedded with caffeic acid and glutathione.
2. The method according to claim 1, wherein in the step (1), the phospholipid is a mixture of one or more of soybean lecithin and egg yolk lecithin.
3. The method according to claim 1, wherein in the step (1), the concentration of the phospholipid solution is 0.1 to 10 g/L; the mass ratio of the cholesterol to the phospholipid is 1:2-1: 20; the ratio of the addition amount of the glutathione to the total mass of the phospholipid and the cholesterol is 1:2-1: 10; the concentration of the caffeic acid is 0.1-2 g/L; the mass ratio of the caffeic acid to the glutathione is 2:1-1: 15; the ratio of the internal water phase to the oil phase is 1:1-1: 10; the ratio of the phosphate buffer solution to the internal water phase is 2:1-1: 10.
4. The preparation method according to claim 1, wherein in the step (3), the volume fraction of acetic acid in the chitosan acetic acid solution is 0.5-10%; the mass fraction of the chitosan is 0.1-1%; the volume ratio of the liposome to the chitosan solution is 1:1-1: 10; the magnetic stirring speed is 100-; the stirring time is 5-60 min.
5. The caffeic acid and glutathione embedded complex liposome/chitosan antioxidant prepared by the preparation method of claims 1-4, characterized in that the retention of the activity of the antioxidant after 10 weeks of storage is 30% -90%.
6. The use of the complex liposome/chitosan antioxidant embedded with caffeic acid and glutathione according to claim 5 in cosmetic products for food preservation and skin care.
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