CN113679050B - Fat-soluble tea polyphenol copper assembled nanoflower controlled release carrier and preparation method thereof - Google Patents
Fat-soluble tea polyphenol copper assembled nanoflower controlled release carrier and preparation method thereof Download PDFInfo
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Abstract
The invention provides a liposoluble tea polyphenol copper assembled nanoflower controlled release carrier and a preparation method thereof. The preparation method comprises the following steps: and (3) carrying out polymerization reaction on the fat-soluble tea polyphenol monomer in a solvent, and adding copper ions into the reaction solution after the reaction is finished, and carrying out coordination self-assembly to form the nanoflower controlled release carrier. According to the preparation method, the polymerized fat-soluble tea polyphenol and copper ions are coordinated and self-assembled to form the nano material with good morphology by utilizing the metal chelating capability of the tea polyphenol. The preparation process is simple, and the biodegradable fat-soluble tea polyphenol raw material is used, so that the nano material of the reaction end product is biodegradable, and has good safety and good pH controlled release characteristic.
Description
Technical Field
The invention belongs to the technical field of food, medicine and material science, and particularly relates to a liposoluble tea polyphenol copper assembled nanoflower controlled release carrier and a preparation method thereof.
Background
Tea polyphenols are the general name of polyphenols in tea, have good biocompatibility and health beneficial effects, account for about 30% of dry weight of tea, mainly include flavanones, anthocyanidins, flavonols and anthocyanidins, and phenolic acid and depsipelas 6 class compounds. Wherein, the flavanone (mainly catechin compounds) is the most important, accounting for 60 to 80 percent of the total amount of tea polyphenol, and has various physiological activities of antioxidation, radiation protection, aging resistance, blood fat reduction, blood sugar reduction, bacteriostasis, enzyme inhibition and the like. In the food industry, it is used as an antioxidant, a food preservative, a food color retention agent, a food deodorant, etc.
With the development of discipline crossing, the construction of biological nano materials by using natural biomass as a reactant or a directional structure has become a very hot subject, and tea polyphenols are converted from direct application as functional molecules to the field of materials. In recent years, tea polyphenol has been increasingly applied to the field of materials, such as being combined with macromolecules or being directly polymerized and then deposited on the surface of an object, and the like, and due to the strong metal chelating capability, the research on tea polyphenol and metal coordination materials is also layered out, lin et al coordinate tannic acid and copper into nano-enzymes, and the nano-enzymes have superoxide dismutase-like activity, catalase-like activity and hydroxyl radical scavenging capability, and the synergistic antioxidant capability makes the tea polyphenol and the metal coordination materials become a very promising candidate material for a commercial cigarette filter tip; liu et al coordinates procyanidins and ferric ions on the basis of a first network composed of physically combined gluten molecules to form a second network, and the novel double-network hydrogel shows strong and rapid rheological property recovery under the repeated shearing deformation-compression cycle effect and has good application prospects. In addition, tea polyphenol coordination materials play a role in many fields.
However, the application of tea polyphenol on a controlled release carrier is still rarely reported, and the application of the tea polyphenol in the field is limited.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a preparation method of a liposoluble tea polyphenol copper assembled nanoflower controlled release carrier, which has the advantages of simple and convenient preparation process, safety and good applicability.
A preparation method of a liposoluble tea polyphenol copper assembled nanoflower controlled release carrier comprises the following steps:
and (3) carrying out polymerization reaction on the fat-soluble tea polyphenol monomer in a solvent, and adding copper ions into the reaction solution after the reaction is finished, and carrying out coordination self-assembly to form the nanoflower controlled release carrier.
According to the preparation method, the polymerized fat-soluble tea polyphenol and copper ions are coordinated and self-assembled by utilizing the metal chelating capacity of the tea polyphenol to form the nano flower material with good morphology. The biodegradable fat-soluble tea polyphenol monomer is used, so that the nano flower material as a reaction final product can be biodegradable, has good safety and good pH controlled release characteristic, and is simple in preparation process and environment-friendly.
Preferably, the fat-soluble tea polyphenol monomer is one of tea polyphenol palmitate, tea polyphenol oleate and tea polyphenol laurate; further preferred is tea polyphenol palmitate.
Preferably, the concentration of the fat-soluble tea polyphenol monomer is 1.5-2.0 mg/mL. As a further preference, the concentration of the fat-soluble tea polyphenol monomer is 1.5mg/mL.
Preferably, the solvent is an alkaline buffer. The alkaline buffer solution has the function of providing an alkaline environment for the polymerization reaction and promoting the polymerization of the fat-soluble tea polyphenol monomer. As a further preferred aspect, the alkaline buffer is an alkaline phosphate buffer.
More preferably, the pH of the buffer is 7.5 to 10. As still further preferred, the pH of the buffer is 7.5 to 9; further preferably 8.5.
Preferably, the solvent contains ethanol, and the concentration of the ethanol is 20-30%; the addition of a small amount of ethanol in the solvent of the polymerization reaction can promote the dissolution of the fat-soluble tea polyphenol and improve the efficiency. As a further preferred aspect, the concentration of ethanol in the solvent is 20% to prevent the high concentration ethanol from damaging the self-assembled nanoflower while ensuring biosafety.
Preferably, the reaction temperature of the polymerization reaction is 60-80 ℃ and the reaction time is 3-5 h. More preferably, the reaction temperature is 60 to 70℃and the reaction time is 3 to 4 hours.
Preferably, the fat-soluble tea polyphenol monomer is subjected to oscillation polymerization at the rotating speed of 800-1300 rpm; further preferably, the rotational speed of the vibration polymerization is 1000rpm.
Preferably, the concentration of the copper ions in the reaction solution is 40 to 60mM. As a further preference, the concentration of copper ions is 40mM.
Preferably, the copper ions may be provided by copper salts such as copper sulfate, copper chloride, copper nitrate, and the like.
As a specific preferred, the preparation method of the liposoluble tea polyphenol copper assembled nanoflower controlled release carrier comprises the following steps:
(1) Dissolving fat-soluble tea polyphenol monomer in solvent, and performing polymerization reaction under oscillation state;
(2) And after the polymerization reaction is finished, cooling, adding copper ions into the reaction solution, uniformly stirring, performing coordination self-assembly, and standing to form the nanoflower controlled release carrier.
In the step (2), after the self-assembly reaction is finished, the standing time is 2 to 3 days.
The invention also provides a liposoluble tea polyphenol copper assembled nanoflower controlled release carrier prepared by the preparation method according to any one of the technical schemes. The liposoluble tea polyphenol copper assembled nanoflower controlled release carrier has good safety, biodegradability, simple preparation process, green preparation raw materials and less pollution in the preparation process.
Compared with the prior art, the invention has the beneficial effects that:
(1) The nano flower material is simple to prepare and less in pollution in the preparation process;
(2) The nano flower material has good safety and can be biodegraded;
(3) The nanoflower material is formed by self-assembly of oligomeric tea polyphenol ester and copper ions, and has good pH controlled release characteristic.
According to the preparation method, the polymerized fat-soluble tea polyphenol and copper ions are coordinated and self-assembled to form the nano flower material with good morphology by utilizing the metal chelating capability of the tea polyphenol. The preparation process is simple, and the biodegradable fat-soluble tea polyphenol raw material is used, so that the nano flower material serving as a reaction end product is biodegradable, and has good safety and good pH controlled release characteristic.
Drawings
FIG. 1 is a scanning electron microscope image of the nanoflower controlled release carrier prepared in example 1 of the present invention;
FIG. 2 is a scanning electron microscope image of the nanoflower controlled release carrier prepared in example 2 of the present invention;
FIG. 3 is a scanning electron microscope image of the nanoflower controlled release carrier prepared in example 3 of the present invention.
Detailed Description
The present invention will be described in further detail with reference to examples, but embodiments of the present invention are not limited thereto.
Example 1
The tea polyphenol palmitate is dissolved in a phosphoric acid buffer solution (pH value is 8.5) containing 20% ethanol, a sample solution with the concentration of the tea polyphenol palmitate of 1.5mg/mL is prepared, and the sample solution is subjected to vibration polymerization for 3 hours at the temperature of 60 ℃ at the rotating speed of 1000rpm.
After the reaction is finished, the reaction solution is cooled to room temperature, copper sulfate is added into the reaction solution to ensure that the concentration of copper ions in the reaction solution reaches 40mM, the reaction solution is stirred uniformly, self-assembly is carried out, then the reaction solution is kept stand for 3 days, and then the nano flower controlled release carrier with good form is formed in the reaction solution and is marked as No. 1.
Example 2
The tea polyphenol palmitate was dissolved in a phosphate buffer solution (pH 8.5) containing 20% ethanol to prepare a sample solution having a tea polyphenol palmitate concentration of 1.5mg/mL, and the sample solution was subjected to shaking polymerization at 70℃and a rotational speed of 1000rpm for 3 hours.
After the reaction is finished, the reaction solution is cooled to room temperature, copper sulfate is added into the reaction solution to ensure that the concentration of copper ions in the reaction solution reaches 40mM, the reaction solution is stirred uniformly, self-assembly is carried out, then the reaction solution is kept stand for 3 days, and then the nano flower controlled release carrier with good form is formed in the reaction solution and is marked as No. 2.
Example 3
The tea polyphenol palmitate was dissolved in a phosphate buffer solution (pH 8.5) containing 20% ethanol to prepare a sample solution having a tea polyphenol palmitate concentration of 1.5mg/mL, and the sample solution was subjected to shaking polymerization at 60℃for 3 hours at a rotation speed of 1000rpm.
After the reaction is finished, the reaction solution is cooled to room temperature, copper sulfate is added to the reaction solution to ensure that the concentration of copper ions in the reaction solution reaches 60mM, the reaction solution is stirred uniformly, self-assembly is carried out, then the reaction solution is kept stand for 3 days, and then the nano flower controlled release carrier with good form is formed in the reaction solution and is marked as No. 3.
The formed nanoflower controlled release carriers (No. 1, no. 2 and No. 3) prepared in examples 1-3 were characterized and studied in nature by using a scanning electron microscope, and the results are shown in FIGS. 1-3. As can be seen from fig. 1 to 3, the nanoflower controlled release carriers prepared in examples 1 to 3 all have good nanoflower morphology; and as can be seen by comparing fig. 1 to 3, the controlled release carrier of the 1# nanoflower prepared in the embodiment 1 has relatively good nanoflower morphology. Application of nanoflower controlled release carrier in carrying active ingredient:
because the raw material assembled into the nanoflower controlled release carrier is hydrophobic oligomeric tea polyphenol palmitate, the fat-soluble active ingredient curcumin is selected as a carrier ingredient for carrying.
Determining embedding balance time experiment:
taking 100 microliters of the reaction solution containing the nanoflower controlled release carrier prepared in the example 1, centrifuging, washing for 3 times, adding 25mL of saturated curcumin 20% ethanol water solution into the washed nanoflower controlled release carrier, vibrating and embedding at a rotating speed of 1000rpm, respectively sucking the sample solution when embedding time is 0min, 1min, 10min, 30min, 60min, 120min, 180min and 270min, centrifuging, taking supernatant to dilute by a proper multiple, measuring absorbance, and respectively measuring the absorbance of 0.481, 0.391, 0.354, 0.333, 0.314, 0.293, 0.278 and 0.273.
Determining the maximum embedding amount experiment:
then 5, 15, 25, 35 and 55mL of saturated curcumin 20% ethanol aqueous solution are added into five groups of nanoflower controlled release carriers one by one (obtained by centrifuging five groups of reaction solutions containing the nanoflower controlled release carriers prepared in example 1 in 100 microliters respectively and washing 3 times), shaking is carried out for 3 hours at a rotating speed of 1000rpm for embedding, absorbance of five groups of sample solutions at 425nm is measured respectively, the absorbance is converted into concentration according to a standard curve and divided by the mass of the used nanoflower, and the embedding amount per unit mass is obtained, wherein the results are respectively: 15.8%, 48.6%, 58.7%, 59.9%, 61.7%, and thus it was found that the maximum embedding amount was 61.7% by weight, since the embedding amount per unit mass was almost unchanged with the increase in the curcumin volume.
pH controlled release characteristics test:
the carried nanoflower is controlled to be released by an acidic phosphate buffer solution:
the release rate of curcumin was tested by adding 0.5mL of phosphate buffer (pH 2.8) and 0.5mL of water to 1mg of a controlled release carrier of nanoflower embedded with curcumin (wherein, the controlled release carrier of nanoflower 1#, the embedded amount of curcumin was 0.5 wt%) respectively, and placing it at 37 degrees celsius, counting the number of complete nanoflower in the selected area with a cell counter plate.
The test results are: the release rate of the experimental group (phosphate buffer solution and nano flower controlled release carrier) can reach 92% after 1 hour, and 98% after 8 hours, and the release rate of the control group (water and nano flower controlled release carrier) is close to 0%. The result shows that the nanoflower controlled release carrier provided by the invention has good pH controlled release characteristics.
Carrying uv stability study:
selecting 405nm and 20w ultraviolet light source for irradiation, wherein the irradiation distance is 20cm, and the control group is 1mL of saturated curcumin 20% ethanol water solution; the experimental group is 1mL of saturated curcumin 20% ethanol water solution embedded by 2mg of nanoflower controlled release carrier (wherein, the embedding amount of the nanoflower controlled release carrier 1#, curcumin is 0.5 wt%). The absorbance of the curcumin solution was measured by extraction with ethanol at the time of irradiation for 2 hours. The results showed that under uv damage, the experimental group had curcumin at 95.6% of the initial amount, while the control group had curcumin at only 6.6% of the initial amount. The nano flower has good protective effect on curcumin.
Carrying heat stability study:
heating at 70deg.C was selected, and 0.5mg/mL AAPH (azobisisobutylaminamide hydrochloride) was added to each sample for acceleration test. The control group is 1mL of saturated curcumin 20% ethanol water solution, and the experimental group is 1mL of saturated curcumin 20% ethanol water solution embedded by 2mg of the nanoflower controlled release carrier (wherein, the embedding amount of the nanoflower controlled release carrier 1#, curcumin is 0.5 wt%). After heating at 70 degrees celsius for 2 hours, the measurement of absorbance of the curcumin solution was performed by extraction with ethanol, and the result showed that the curcumin in the experimental group was 28.0% of the initial amount and the curcumin in the control group was only 6.1% of the initial amount in the presence of AAPH at 70 degrees celsius. The nano flower has good protective effect on curcumin.
Claims (6)
1. The preparation method of the liposoluble tea polyphenol copper assembled nanoflower controlled release carrier is characterized by comprising the following steps of:
performing polymerization reaction on the fat-soluble tea polyphenol monomer in an alkaline buffer solution containing ethanol, adding copper ions into the reaction solution after the reaction is finished, and performing coordination self-assembly to form the nanoflower controlled release carrier;
the fat-soluble tea polyphenol monomer is one of tea polyphenol palmitate, tea polyphenol oleate and tea polyphenol laurate;
the concentration of the fat-soluble tea polyphenol monomer is 1.5-2.0 mg/mL;
the concentration of copper ions is 40-60 mM.
2. The method according to claim 1, wherein the buffer has a pH of 7.5 to 10.
3. The preparation method of claim 1, wherein the concentration of ethanol in the alkaline buffer is 20-30%.
4. The preparation method according to claim 1, wherein the reaction temperature of the polymerization reaction is 60-80 ℃ and the reaction time is 3-5 h.
5. The method according to claim 1, wherein the fat-soluble tea polyphenol monomer is subjected to vibration polymerization at a rotation speed of 800-1300 rpm.
6. A liposoluble tea polyphenol copper assembled nanoflower controlled release carrier, characterized in that the carrier is prepared by the preparation method of any one of claims 1-5.
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| CN104194460A (en) * | 2014-08-12 | 2014-12-10 | 西南交通大学 | Preparation method of chelate coating with copper ions capable of controllably catalyzing release of nitrogen monoxide and polyphenol complex |
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| CN104194460A (en) * | 2014-08-12 | 2014-12-10 | 西南交通大学 | Preparation method of chelate coating with copper ions capable of controllably catalyzing release of nitrogen monoxide and polyphenol complex |
| CN104225672A (en) * | 2014-08-12 | 2014-12-24 | 西南交通大学 | Preparation method for copper ion-polyphenol coordination compound chelate material with controllable nitrogen monoxide catalytic release function |
| CN109232905A (en) * | 2018-09-13 | 2019-01-18 | 西安交通大学 | A kind of metal-plant polyphenol complex crystal material and preparation method |
| CN110075083A (en) * | 2019-04-25 | 2019-08-02 | 中国医学科学院生物医学工程研究所 | Metal polyphenol microcapsule carrier and preparation method with ROS responsiveness and metal ion slow-release function |
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