CN112773728A - Compound of nano-encapsulated resveratrol, preparation method and application thereof - Google Patents
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Abstract
The invention belongs to the technical field of nanometer, and provides a compound of nanometer encapsulated resveratrol, a preparation method and application thereof. The preparation method of the nano-encapsulated resveratrol compound provided by the invention comprises the following steps: (1) mixing a lecithin solution and a resveratrol solution to obtain a first mixed solution; (2) adding the first mixed solution into water to obtain a second mixed solution; (3) and purifying the second mixed solution to obtain the compound of the nano-encapsulated resveratrol. According to the invention, the resveratrol is wrapped in the lecithin nanoparticles, so that the effect of continuously and slowly releasing antioxidant ingredients and the good effect of promoting transdermal penetration of antioxidant are achieved, the retention time of the resveratrol on the skin is prolonged, and the bioavailability of the resveratrol is improved.
Description
Technical Field
The invention relates to the technical field of nanometer, in particular to a compound of nanometer encapsulated resveratrol and a preparation method and application thereof.
Background
Resveratrol (RSV), also known as resveratrol, is a natural polyphenolic flavone compound found in the seeds and skins of grapes (red wine), mulberries, peanuts, rhubarb, etc., and has antioxidant and anti-radical effects. Resveratrol contains cis and trans isomers, the latter being considered to be biologically active and most abundant. Resveratrol is used as a natural antioxidant, has the most prominent functions of eliminating free radicals or inhibiting the formation of free radicals, delaying the aging process of skin cells, inhibiting lipid peroxidation and the activity of tyrosinase, reducing the formation of melanin, and achieving the skin care effects of whitening, fading spots, moisturizing and the like. Resveratrol was metabolized in liver and intestinal epithelial cells to a conjugate of glucuronic acid and sulfated phenol groups rapidly (in less than 2 hours) after intravenous injection, and the gene conjugate was then eliminated. The low bioavailability of resveratrol also limits its application in biology and pharmacology. Meanwhile, resveratrol is poorly water soluble and chemically unstable, and is isomerically degraded when exposed to high temperature, pH change, ultraviolet light, or enzymes.
At present, nano-encapsulated polyethylene glycol in cosmetics is a synthetic polymer and can encapsulate most of small molecules into spherical nanoparticles. Polyethylene glycol has good water solubility, and is widely used in cosmetics as a thickener, a lubricating agent, a solvent, a softener, and a humectant. Polyethylene glycol is commonly used as a cosmetic skin base cream. However, there are reports of risks and adverse effects associated with the use of polyethylene glycol and its derivatives in cosmetics. The use of polyethylene glycol on damaged skin causes irritation and systemic toxicity, and industry groups reviewing the safety of cosmetic ingredients concluded that some polyethylene glycol compounds are unsafe for use on damaged skin (although evaluations generally approve the use of these chemicals in cosmetics). In addition, polyethylene glycol acts as a permeation enhancer to increase skin permeability for more product absorption, which also includes harmful ingredients.
Lecithin (LC) is one of choline and is an important nutrient. The lecithin can enhance brain activity, eliminate brain fatigue, enhance memory, improve learning and working efficiency, repair damaged brain cells and prevent senile dementia; lecithin is also a natural antidote that breaks down toxins in the body. By adding the heme, sufficient water and oxygen are provided for the skin, so that the skin becomes smooth and soft; if a human body lacks lecithin, the regeneration capacity of skin cells is reduced, so that rough and wrinkled skin is caused, if the lecithin is properly taken, the regeneration activity of the skin can be ensured, the skin can be shinier, and the lecithin has good hydrophilicity and lipophilicity and is beneficial to osmosis. In addition, inositol contained in lecithin contains a main nutrient for hair, and can inhibit alopecia and gradually blacken white hair. Therefore, the lecithin as a natural nano carrier is safer and has better biological activity. And provides a completely natural, safe and harmless cosmetic additive for consumers, and also has a huge market.
Disclosure of Invention
The invention aims to provide a pure natural, safe and harmless resveratrol additive and a preparation method thereof, so that the resveratrol additive has stable quality and better biological activity and utilization efficiency.
In order to achieve the above purpose, the invention provides the following technical scheme:
the invention provides a preparation method of a nano-encapsulated resveratrol compound, which comprises the following steps:
(1) mixing a lecithin solution and a resveratrol solution to obtain a first mixed solution;
(2) adding the first mixed solution into water to obtain a second mixed solution;
(3) and purifying the second mixed solution to obtain the compound of the nano-encapsulated resveratrol.
Preferably, the concentration of the lecithin solution is 10-40 mg/mL, and the concentration of the resveratrol solution is 10-40 mg/mL.
Preferably, the mass ratio of the resveratrol to the lecithin is 1: 1-10.
Preferably, the volume ratio of the water to the first mixture in the step (2) is 4-6: 0.045.
Preferably, the purification in step (3) is performed by subjecting the second mixed solution to ultrafiltration.
The invention also provides a compound of nano-encapsulated resveratrol.
The invention also provides application of the compound of nano-encapsulated resveratrol as a cosmetic additive.
Preferably, the cosmetic is a mask, lotion or cream.
According to the invention, the resveratrol is wrapped in the lecithin to form a compound of nano-encapsulated resveratrol, which has the effects of continuously and slowly releasing antioxidant ingredients and promoting the good effect of transdermal penetration of antioxidant, so that the retention time of the compound on the skin is prolonged, and the bioavailability of the resveratrol is improved; the developed compound of nano-encapsulated resveratrol has stable quality, the shape and the particle size of the compound are not obviously changed after the compound is maintained for 3 months at 4 ℃, the shape and the particle size of the compound are not obviously changed after the compound is maintained for 25 days at 38 ℃, and the stability is good. But also can realize better and higher biological activity of the resveratrol. The resveratrol nanoparticle provided by the invention can be used in cosmetics.
Drawings
FIG. 1 is a statistical graph of cell viability of lecithin nanocarriers in example 6;
fig. 2 is a graph of the change in dimensions of resveratrol nanoparticles placed at 38 ℃ for 24 days in example 10;
FIG. 3 shows the resveratrol nanoparticle solution of example 10 after being left at 38 deg.C for 24 days;
fig. 4 is a release kinetic curve of resveratrol nanoparticles of example 11.
Detailed Description
The invention provides a compound of nano-encapsulated resveratrol and a preparation method thereof, and the prepared resveratrol nanoparticle product has stable quality, slow release, better biological activity and higher utilization efficiency.
The lecithin provided by the invention is purchased from Shanghai Taiwei pharmaceutical industry Co., Ltd, the resveratrol is purchased from ChemMedExpress, and the raw materials and reagents used in the specification of the invention are all purchased commercially without special description.
The invention provides a preparation method of a nano-encapsulated resveratrol compound, which comprises the following steps:
(1) mixing a lecithin solution and a resveratrol solution to obtain a first mixed solution;
(2) adding the first mixed solution into water to obtain a second mixed solution;
(3) and purifying the second mixed solution to obtain the compound of the nano-encapsulated resveratrol.
When the nano-encapsulated resveratrol compound is prepared, a lecithin solution and a resveratrol solution are mixed to obtain a first mixed solution.
In the invention, the lecithin solution and the resveratrol solution are obtained by solubilization of dimethyl sulfoxide.
In the invention, the concentration of the lecithin solution is preferably 10-40 mg/mL, and more preferably 20 mg/mL; the concentration of the resveratrol solution is preferably 10-40 mg/mL, and more preferably 20 mg/mL.
In the invention, the mass ratio of the resveratrol to the lecithin is preferably 1: 1-10, more preferably 1: 1-5, and still more preferably 1: 1.25.
And after the first mixed solution is prepared, adding the first mixed solution into water to obtain a second mixed solution.
In the present invention, the volume ratio of the water to the first mixed solution is preferably 4 to 6:0.045, and more preferably 5: 0.045.
In the present invention, the first mixture is preferably added dropwise to water under stirring.
In the present invention, the water is preferably purified water.
In the present invention, the stirring rate is preferably 1000 to 5000rpm, and more preferably 2000 to 3000 rpm.
And after preparing a second mixed solution, purifying the second mixed solution to obtain the compound of the nano-encapsulated resveratrol.
In the present invention, the purification is preferably ultrafiltration.
Ultrafiltration using amicon filter (100KDa) is preferred in the present invention to remove dimethyl sulfoxide and unencapsulated resveratrol. And centrifuging the second mixed solution for 7 minutes at a rotation speed of 1000-3000 r/min preferably, and further preferably at 2000 r/min, intermittently washing to remove all organic solvents in the nanoparticles, centrifuging, and collecting residues to obtain the lecithin-coated resveratrol nanoparticle-coated resveratrol compound.
The invention also provides a compound of nano-encapsulated resveratrol.
The invention also provides application of the compound of nano-encapsulated resveratrol as a cosmetic additive.
In the present invention, the cosmetic is preferably a mask, a lotion or a cream.
The technical solutions provided by the present invention are described in detail below with reference to examples, but they should not be construed as limiting the scope of the present invention.
Example 1
(1) Dissolving 100mg of lecithin in 10mL of DMSO to obtain a lecithin solution of 10 mg/mL; dissolving 100mg of resveratrol in 10mL of DMSO to obtain a 10mg/mL resveratrol solution;
(2) mixing 25 mu L of lecithin solution and 20 mu L of resveratrol solution to obtain a first mixed solution;
(3) in a second vessel, 5mL of purified water was stirred at 3000 rpm;
(4) dropwise adding the first mixed solution into the purified water under stirring to obtain a second mixed solution;
(5) and purifying the second mixed solution by using an amicon Filter (100KDa), removing DMSO and unencapsulated RSV, centrifuging the solution at the rotating speed of 3000 r/min for 7 min, washing intermittently to remove all organic solvents in the nanoparticles, centrifuging, and collecting residues to obtain a nano-encapsulated resveratrol compound, namely the resveratrol nanoparticles.
Example 2
(1) Dissolving 200mg of lecithin in 10mL of DMSO to obtain a lecithin solution of 20 mg/mL; dissolving 200mg of resveratrol in 10mL of DMSO to obtain a resveratrol solution of 20 mg/mL;
(2) mixing 25 mu L of lecithin and 20 mu L of resveratrol to obtain a first mixed solution;
(3) in a second vessel, 5mL of purified water was stirred at 2000 rpm;
(4) dropwise adding the first mixed solution into the purified water under stirring to obtain a second mixed solution;
(5) and purifying the second mixed solution by using an amicon Filter (100KDa), removing DMSO and unencapsulated RSV, centrifuging the solution at the rotating speed of 2000 r/min for 7 min, washing intermittently to remove all organic solvents in the nanoparticles, centrifuging, and collecting the residual LC (RSV) to obtain a nano-encapsulated resveratrol compound, namely the resveratrol nanoparticles.
Example 3
(1) Dissolving 400mg of lecithin in 10mL of DMSO to obtain a lecithin solution of 40 mg/mL; dissolving 400mg of resveratrol in 10mL of DMSO to obtain 40mg/mL of resveratrol solution;
(2) mixing 25 mu L of lecithin and 20 mu L of resveratrol to obtain a first mixed solution;
(3) in a second vessel, 5mL of purified water was stirred at 1000 rpm;
(4) dropwise adding the first mixed solution into the purified water under stirring to obtain a second mixed solution;
(5) purifying the solution containing LC (RSV) by using amicon Filter (100KDa), removing DMSO and unencapsulated RSV, centrifuging the solution for 7 minutes at the rotating speed of 1000 r/min, intermittently washing to remove all organic solvents in the nanoparticles, centrifuging, and collecting the residual LC (RSV) to obtain a nano-encapsulated resveratrol compound, namely the resveratrol nanoparticles.
Example 4
(1) Dissolving 400mg of lecithin in 10mL of DMSO to obtain a lecithin solution of 40 mg/mL; dissolving 100mg of resveratrol in 10mL of DMSO to obtain a 10mg/mL resveratrol solution;
(2) mixing 25 mu L of lecithin solution and 20 mu L of resveratrol solution to obtain a first mixed solution;
(3) in a second vessel, 5mL of purified water was stirred at 3000 rpm;
(4) dropwise adding the first mixed solution into the purified water under stirring to obtain a second mixed solution;
(5) and purifying the second mixed solution by using an amicon Filter (100KDa), removing DMSO and unencapsulated RSV, centrifuging the solution at the rotating speed of 3000 r/min for 7 min, washing intermittently to remove all organic solvents in the nanoparticles, centrifuging, and collecting residues to obtain a nano-encapsulated resveratrol compound, namely the resveratrol nanoparticles.
Example 5
(1) Dissolving 400mg of lecithin in 10mL of DMSO to obtain a lecithin solution of 40 mg/mL; dissolving 50mg of resveratrol in 10mL of DMSO to obtain a resveratrol solution of 5 mg/mL;
(2) mixing 25 mu L of lecithin solution and 20 mu L of resveratrol solution to obtain a first mixed solution;
(3) in a second vessel, 5mL of purified water was stirred at 3000 rpm;
(4) dropwise adding the first mixed solution into the purified water under stirring to obtain a second mixed solution;
(5) and purifying the second mixed solution by using an amicon Filter (100KDa), removing DMSO and unencapsulated RSV, centrifuging the solution at the rotating speed of 3000 r/min for 7 min, washing intermittently to remove all organic solvents in the nanoparticles, centrifuging, and collecting residues to obtain a nano-encapsulated resveratrol compound, namely the resveratrol nanoparticles.
Example 6 toxicity testing of lecithin nanocarriers
To ensure the safety of lecithin, we first tested the cytotoxicity of lecithin in vitro. The specific test method for the cytotoxicity of lecithin is as follows: in vitro lecithin assay proliferation assay on normal human epithelial cells. The lecithin was divided into nine groups at concentrations ranging from 8. mu.M to 1000. mu.M, and the degree of epithelial cell proliferation was examined by the cck8 method.
As can be seen from fig. 1, lecithin is not toxic to cells even at high micromolar concentrations (1000 μ M), indicating that lecithin is not only natural, but also safe and available for human use or consumption.
Example 7 toxicity testing of resveratrol nanoparticles
This example tests with resveratrol nanoparticles prepared in example 1 as a sample: skin phototoxicity test of animal model guinea pigs, skin allergy test of animal model guinea pigs-local closed skin coating test, acute skin irritation test of animal model rabbits, acute eye irritation/corrosivity test of animal model rabbits, and multiple skin irritation test of animal model rabbits.
(1) The specific test method for the skin phototoxicity test of the animal model guinea pigs comprises the following steps:
the skin on two sides of the spine of the animal is unhaired 18-24 h before the experiment, and the skin on the experimental part needs to be intact without injuring the abnormality. A total of 4 depilatory regions were prepared, each of which was approximately 2cm by 2 cm. Animals were fixed and 0.2mL of resveratrol nanoparticle liquid was applied to the depilated areas 1 and 2 of the animals. After 30min, the left side (depilated areas 1 and 3) was covered with aluminum foil, taped and the right side (depilated areas 2 and 4) was irradiated with UVA. Light intensity (mW/cm) was measured by setting 6 points on the back irradiation area of the experimental animal using a radiometer2) In average values. And calculating the irradiation time according to a correlation formula. The formula: irradiation time (sec) is an irradiation dose (10000 mJ/cm)2) Light intensity of/2 a (mJ/cm)2Sec). The results show that the resveratrol nanoparticles have no phototoxicity.
In the test, the wavelength of the UVA light source is 365nm, and the average value of the light intensity is 3.6mW/cm2The irradiation dose is 10000mJ/cm2The irradiation time was 2778 s. White guinea pig of experimental animal, provided by breeding farm of experimental animal built in the city of Yuyao, production license number: SCXK (Zhe) 2017-; 6/male/female half; feeding environment, common environment guinea pig house, use license number: SYXK (Zhe) 2018-; the room temperature is 21.0-23.6 ℃, and the relative humidity is 54.7-68.8%.
(2) Skin allergy test of animal model guinea pig-local closed coating test the specific test method is as follows:
the guinea pigs were depilated 24h prior to the trial, with a depilating range of 2cm x 3cm on the left side of the back. And (3) induction contact: 0.2mL of sample (positive control with 0.6% 2, 4-dinitrochlorobenzene solution) was applied to the skin of the hair-removed area of the experimental animals in the test group, covered with two layers of gauze and a layer of cellophane, and sealed and fixed with a non-irritating adhesive plaster for 6 hours. The same procedure was repeated on day 7 and day 14. And (3) exciting contact: 14 days after the last induction, 0.2mL of sample (positive control with 0.3% 2, 4-dinitrochlorobenzene solution) was applied to the right depilated area of the back of the test and negative control guinea pigs, depilated 24 hours before contact, covered with two layers of gauze and a layer of cellophane, and fixed with a non-irritating adhesive tape for 6 hours. And (3) animal observation: skin reactions were observed 24 hours and 48 hours after challenge contact. The experimental group is 20, and the control group is 16/male/female unlimited. White guinea pig of experimental animal, provided by breeding farm of experimental animal built in the city of Yuyao, production license number: SCXK (Zhe) 2017-; feeding environment, common environment guinea pig house, use license number: SYXK (Zhe) 2018-; the room temperature is 21.0-23.6 ℃, and the relative humidity is 54.7-68.8%. According to the grading of the skin sensitization intensity level, the resveratrol nanoparticles have no skin allergy.
(3) The specific test method of the acute skin irritation test of the animal model rabbit comprises the following steps:
the hair on both sides of the spine of the experimental animal is removed 24 hours before the experiment, and the hair removing range is respectively 3cm multiplied by 3 cm. 0.5mL of the sample was applied to one side of the skin and the other side of the skin as a control, and after 2 hours the dressing was removed and the contact site was rinsed with warm water. Observation time was 1 hour, 24 hours, 48 hours, 72 hours after dressing removal. Grading according to skin irritation intensity grade, and observing the irritation condition of the resveratrol nanoparticles wrapped by lecithin to rabbits. The experimental animal is a new Zealand white rabbit, is provided by the Tongxiang silver sea rabbit industry, and has the production license number: SCXK (Zhe) 2018-; 4 male and female are not limited; feeding environment, common environment guinea pig house, use license number: SYXK (Zhe) 2018-; the room temperature is 21.1-23.9 ℃, and the relative humidity is 53.1-69.3%. The resveratrol nanoparticles are graded according to skin irritation strength, and have no irritation to rabbit skin irritation strength.
(4) The specific test method for the acute eye irritation/corrosivity test of the animal model rabbit comprises the following steps:
0.1mL of the sample is dripped into the conjunctival sac of one eye of the rabbit, and the other eye of the rabbit is used as a normal control. Observation times were 1h, 24h, 48h, 72h, 4d, 7 d. The integral mean values of cornea, iris, conjunctival congestion and conjunctival edema were all observed to be 0 for each animal.
The experimental animals are new zealand white rabbits, 3 males and females are unlimited, the experimental animals are provided by the silver hare industry in Tongxiang, and the production permission number is as follows: SCXK (Zhe) 2018-; feeding environment, common environment guinea pig house, use license number: SYXK (Zhe) 2018-; the room temperature is 21.1-23.9 ℃, and the relative humidity is 53.1-69.3%.
(5) The specific test method of the multiple skin irritation test of the animal model rabbit comprises the following steps:
and (3) removing hair on two sides of the spine of the experimental animal 24h before the experiment, wherein the hair removing range is 3cm multiplied by 3cm respectively. 0.5mL of the original sample was applied to one side of the skin and the other side of the skin was used as a control, and the results were observed after 1 h. Applied once daily for 14 consecutive days. The irritation of the sample to the rabbit skin is a nonirritant sample according to the grading of skin irritation intensity. The experimental animal is a new Zealand white rabbit, is provided by the Tongxiang silver sea rabbit industry, and has the production license number: SCXK (Zhe) 2018-; 4 male and female are not limited; feeding environment, common environment guinea pig house, use license number: SYXK (Zhe) 2018-; the room temperature is 21.1-23.9 ℃, and the relative humidity is 53.1-69.3%. The resveratrol nanoparticles are graded according to skin irritation strength, and have no irritation to rabbit skin irritation strength.
Example 8 measurement of particle size of resveratrol nanoparticles
To determine the size of resveratrol nanoparticles, we performed particle size analysis by Dynamic Light Scattering (DLS). As shown in table 1, resveratrol did not show the formation of nanoparticles, and resveratrol formed large aggregates in solution. Lecithin can form nanoparticles with an average particle size of about 150nm, while the nanoparticle size of resveratrol nanoparticles is about 100nm, which indicates that there is charge/electrostatic interaction between resveratrol and lecithin, resulting in densification of lecithin nanoparticles.
Table 1: particle size before and after coating of resveratrol and lecithin
| Substance(s) | Run1 | Run2 | Run3 | Average particle diameter (nm) |
| Resveratrol | 1103 | 716.7 | 1030 | 949 |
| Lecithin | 115.1 | 159 | 159.5 | 144 |
| Tribuli alcohol nanoparticles | 98.45 | 100.5 | 100.1 | 99 |
Example 9 encapsulation efficiency and drug load determination of resveratrol nanoparticles
The resveratrol has unique ultraviolet absorbance at 330nm, and can be used for determination of resveratrol concentration. To determine the encapsulation efficiency of resveratrol, we calculated the encapsulated amount of resveratrol in lecithin using the following formula and compared it with the amount of resveratrol originally used:
the encapsulation rate value of resveratrol can be estimated to be about 92.5% by the equation.
The drug loading of resveratrol was calculated to be about 18.5 wt.% according to this equation.
Example 10 stability of resveratrol nanoparticles
The resveratrol nanoparticles have good stability after being kept for 24 days at the room temperature of 38 ℃, and the encapsulation quality of the nanoparticles is evaluated from the encapsulation rate, the drug loading rate, the form, the particle size, the surface electrical property, the leakage rate, the oxidation degree of phospholipid and the like. The resveratrol nanoparticles are kept at 38 ℃ for 24 days, as shown in figure 2, the size of the resveratrol nanoparticles is not obviously changed, and the stability of the resveratrol nanoparticles is proved to be good. As can be seen from the combination of FIG. 3, no aggregation or cloud fog was observed in the solution, further indicating that the stability of the resveratrol nanoparticles is good.
Example 11 Release kinetics of resveratrol nanoparticles
We determined the release kinetics of resveratrol nanoparticles. As shown in fig. 4, free RSV released 70% after 15 minutes, while the resveratrol nanoparticles of the invention released less than 50% after 12 hours, indicating that lecithin successfully protected the premature release of resveratrol from the nanoparticles.
The foregoing is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, various modifications and decorations can be made without departing from the principle of the present invention, and these modifications and decorations should also be regarded as the protection scope of the present invention.
Claims (8)
1. A preparation method of a nano-encapsulated resveratrol compound is characterized by comprising the following steps:
(1) mixing a lecithin solution and a resveratrol solution to obtain a first mixed solution;
(2) adding the first mixed solution into water to obtain a second mixed solution;
(3) and purifying the second mixed solution to obtain the compound of the nano-encapsulated resveratrol.
2. The method for preparing a nano-encapsulated resveratrol complex according to claim 1, wherein the concentration of the lecithin solution is 10-40 mg/mL, and the concentration of the resveratrol solution is 10-40 mg/mL.
3. The method for preparing a nano-encapsulated resveratrol complex as claimed in claim 1 or 2, wherein the mass ratio of resveratrol to lecithin in step (1) is 1: 1-10.
4. The method for preparing a nano-encapsulated resveratrol complex according to claim 1, wherein the volume ratio of the water to the first mixture in step (2) is 4-6: 0.045.
5. The method of claim 1, wherein the purifying step (3) comprises subjecting the second mixture to ultrafiltration.
6. The compound of nano-encapsulated resveratrol prepared by the preparation method of any one of claims 1-5.
7. Use of the nano-encapsulated resveratrol complex of claim 6 as a cosmetic additive.
8. Use according to claim 7, wherein the cosmetic product is a mask, lotion or cream.
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