CN110538094B - Pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability and preparation method thereof - Google Patents
Pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability and preparation method thereof Download PDFInfo
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Abstract
The invention discloses a pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability and a preparation method thereof, wherein the inclusion compound comprises the following components: pterostilbene, cyclodextrin, organic acid and polyvinylpyrrolidone. The water-soluble pterostilbene @ cyclodextrin inclusion compound prepared by the invention is transparent and colorless when dissolved in water, and can be used in water-based cosmetics to form various cosmetics together with sodium hyaluronate, xanthan gum, carbomer and the like. The invention solves the application problems of poor water solubility, unstable spatial structure, poor compatibility and the like of pterostilbene in water-based cosmetics, and improves the multi-dimensional stability of pterostilbene in water-based cosmetics, wherein the multi-dimensional stability comprises phase stability, light stability and compatibility stability.
Description
Technical Field
The invention relates to the technical field of efficacy cosmetics, and particularly relates to a pterostilbene @ cyclodextrin inclusion compound which is homogeneous, hydrophilic and multi-dimensionally stable, and a preparation method thereof.
Background
Pterostilbene is a methylated derivative of resveratrol as a trans-stilbene compound. Pterostilbene was originally isolated from sandalwood and was later found in fruits such as blueberry, grapes, and the like. Modern pharmacological research shows that pterostilbene has various pharmacological activities of resveratrol, such as antitumor, anti-inflammatory, antioxidant, anti-aging and cardiovascular protection. The antioxidant activity of the composition can be combined with moisturizing essence, moisturizing mask and the like, and the effects of resisting oxidation, moistening, moisturizing, delaying senescence and the like are achieved. Therefore, pterostilbene has great development potential in the field of skin care.
However, pterostilbene also has many defects, which limits the development and utilization of pterostilbene:
1. the water solubility is poor. Pterostilbene has low solubility at room temperature, about 11.49 μ g/ml, and if added to a water-based cosmetic, forms a turbid suspension.
2. The spatial structure is unstable. Pterostilbene is a trans-stilbene compound, and the trans structure of pterostilbene is very easy to be converted into a homeostatic structure under ultraviolet irradiation, so that the pterostilbene is inactivated.
3. The compatibility is poor. Pterostilbene is lipophilic to aid penetration through the skin, but it can only be mixed with polyols or polar oils and needs to be dissolved by heating, and has poor compatibility with other cosmetic materials.
At present, the existing literature indicates that the pterocarpus santalinus has no high stability (including phase stability, light stability, compatibility stability and oxidation stability) in water-based cosmetics. At present, the method for improving the water solubility of pterostilbene is very limited, and an invention patent (201810282857.5) "a high-stability pterostilbene soluble compound providing a weak acid micelle microenvironment and a preparation method thereof" discloses a compound containing pterostilbene, rebaudioside a and glycyrrhizic acid to improve the water solubility of pterostilbene, wherein the solubility of pterostilbene can reach 13 mg/ml. However, the method utilizes a weak acid environment to enhance the stability of pterostilbene, and limits the application of pterostilbene in neutral and weak alkaline cosmetics. The invention patent (201410640407.0) Pterostilbene submicron lipid particle and its preparation method, which is to use lipid and emulsifier to coat Pterostilbene to enhance the water solubility of Pterostilbene. However, this method also has major drawbacks: excessive use of emulsifiers can cause a burden on the skin; the emulsifiers have large mutual influence; the inclusion of lipids can result in a sticky skin feel.
Inclusion techniques refer to techniques in which one molecule is entrapped within the hole structure of another molecule and forms an inclusion compound. The water-insoluble medicine is taken as an object and is wrapped by the carrier, and then is dispersed in the material of the carrier, so that the water-insoluble medicine has high dispersibility. Meanwhile, the inclusion compound has good wettability and hydrophilicity by adding a hydrophilic carrier. In addition, the carrier material coated with the medicine can realize the slow release function of the medicine and slow down the release speed of the medicine.
Since PVP has extremely low toxicity and physiological inertia, it is non-irritating to the skin and eyes, and has been recorded for long-term use in the medical field, it is safe for use in cosmetics and the like. In daily cosmetics, PVP and the copolymer have good dispersibility and film forming property, and the PVP has the function of a protective colloid in emulsion.
Disclosure of Invention
Aiming at the problems that pterostilbene is difficult to dissolve in water and is unstable in the application process, the invention provides a pterostilbene @ cyclodextrin inclusion compound with light stability, phase stability and compatibility stability and a preparation method thereof. The cyclodextrin has a cage structure, and after the pterostilbene molecule enters the cage structure, the spatial turnover is limited, so that the light stability can be enhanced. The hydrophobic structure inside the cyclodextrin and the hydrophilic structure outside the cyclodextrin can enhance the water solubility of the pterostilbene, so that the pterostilbene forms a stable single phase in a water phase, and the phase stability is enhanced. The coordination of the organic acid and the cyclodextrin can enhance the ionization degree of the inclusion compound and enhance the illumination stability of the inclusion compound. The polyvinylpyrrolidone and the cyclodextrin have a synergistic effect, so that the use cost of the cyclodextrin can be reduced, and the compatibility stability is enhanced.
The invention at least achieves the above purpose through one of the following technical schemes.
A homogeneous hydrophilic and multi-dimensionally stable pterostilbene @ cyclodextrin inclusion compound comprises pterostilbene, cyclodextrin and polyvinylpyrrolidone.
Furthermore, the pterostilbene @ cyclodextrin inclusion compound consists of pterostilbene, cyclodextrin and polyvinylpyrrolidone.
Further preferably, the clathrate compound comprises the following components in percentage by mass: 4-6% of pterostilbene, 80-85% of cyclodextrin and 10-15% of polyvinylpyrrolidone.
Further, the pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability is composed of pterostilbene, cyclodextrin, organic acid and polyvinylpyrrolidone.
Further preferably, the clathrate compound comprises the following components in percentage by mass: 4-6% of pterostilbene, 70-80% of cyclodextrin, 1-2% of organic acid and 13-15% of polyvinylpyrrolidone.
Further, the cyclodextrin contains at least one compound or a combination of compounds of: 2-hydroxymethyl-beta-cyclodextrin, carboxymethyl-beta-cyclodextrin, (2-hydroxypropyl) -gamma-cyclodextrin and hepta (2,3, 6-tri-o-methyl) -beta-cyclodextrin.
Further, the organic acid contains at least one compound or a combination of compounds as follows: tartaric acid, oxalic acid, citric acid, ascorbic acid, malic acid and salicylic acid.
The preparation method of the pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability comprises the following steps:
(1) under the condition of keeping out of the sun, fully mixing and grinding pterostilbene, cyclodextrin, organic acid and polyvinylpyrrolidone, dropwise adding an ethanol water solution, and grinding into paste;
(2) placing the mixture obtained in the step (1) at room temperature in a dark place;
(3) and (3) carrying out liquid nitrogen freeze drying on the block powder obtained in the step (2).
Further, the concentration of ethanol in the ethanol aqueous solution in the step (1) is 40-50%.
Further, the concentration of ethanol in the ethanol aqueous solution is 40%.
Compared with the prior art, the invention has the following advantages and beneficial effects:
1. compared with pterostilbene liposome, the invention does not use any emulsifier and does not cause burden to skin. The cyclodextrin used by the invention is composed of glucose units, has good biocompatibility, and is natural and nontoxic.
2. The method utilizes the cyclodextrin inclusion technology, utilizes the naturally existing cage-like structure of the cyclodextrin to include the pterostilbene, does not need to prepare an additional spherical structure, has simple preparation process, is beneficial to industrial production, requires small production energy, and is green and environment-friendly.
3. The method can efficiently improve the water solubility of the pterostilbene and improve the light stability of the pterostilbene. The pterostilbene compound only realizes the water solubility of pterostilbene, but the cyclodextrin and the pvp are compounded, the space size of an inner cavity of the compound is similar to the size of a pterostilbene molecule, and the pterostilbene molecule can be completely included and the overturning of the molecular space structure is hindered.
4. The pterostilbene @ cyclodextrin inclusion compound can be compounded with various cosmetic raw materials, and shows good formula stability.
5. The pterostilbene @ cyclodextrin inclusion compound disclosed by the invention has a slow release effect, the release speed of pterostilbene is reduced, the oxidation effect of a product is not influenced, and the irritation of an effective component to the skin is reduced.
Drawings
FIG. 1 is a transmission electron micrograph of the pterostilbene @ cyclodextrin inclusion compound powder prepared in example 1.
Fig. 2 is a plot of standard concentrations of aqueous solutions of pterostilbene used in examples 1, 2 and 3.
Fig. 3 is a graph showing the ultraviolet absorbance change of characteristic peaks of pterostilbene when the raw material pterostilbene and the pterostilbene @ cyclodextrin inclusion compound prepared in example 1 are irradiated under an ultraviolet lamp for 0-30 minutes.
Fig. 4 is a graph showing the change of uv absorbance of characteristic peaks of pterostilbene when the raw material pterostilbene and the pterostilbene @ cyclodextrin inclusion compound prepared in example 2 are irradiated under an ultraviolet lamp for 0-30 minutes.
Fig. 5 is a graph showing the change of uv absorbance of characteristic peaks of pterostilbene when the raw material pterostilbene and the pterostilbene @ cyclodextrin inclusion compound prepared in example 3 are irradiated under an ultraviolet lamp for 0-30 minutes.
Detailed Description
The following examples and drawings further illustrate specific embodiments of the present invention, but the present invention is not limited to the following embodiments.
Example 1:
the multi-dimensional stable pterostilbene @ cyclodextrin inclusion compound comprises 5% of pterostilbene, 85% of hydroxypropyl beta cyclodextrin and 10% of polyvinylpyrrolidone by weight percent of the total weight of the inclusion compound.
The multi-dimensional stable pterostilbene @ cyclodextrin inclusion compound comprises the following preparation steps:
(1) accurately weighing 0.5g of pterostilbene, 8.5g of hydroxypropyl beta cyclodextrin and 1.0g of polyvinylpyrrolidone. (2) 5ml of an aqueous ethanol solution (ethanol concentration 40%) were prepared. (3) And (2) sufficiently grinding the mixture obtained in the step (1) in a mortar under the condition of keeping out of the light, dropwise adding an ethanol water solution, grinding into paste, stirring for 1 hour, and standing for 24 hours at room temperature in the condition of keeping out of the light. (4) Freezing the block powder obtained in the step (3) for 12 hours, and then carrying out freeze drying. (5) After drying, the resulting fluffy cake was crushed in a mortar and passed through a 120 mesh sieve. (6) The powder was dissolved in water in a ratio of 1: 5.
The pterostilbene @ cyclodextrin inclusion compound prepared by the embodiment is strong in hydrophilicity, is colorless and transparent when dissolved in water, can be added into a facial mask solution without heating, does not affect the stability of a facial mask, and has phase stability, light stability and compatibility stability.
And (3) carrying out transmission electron microscope shooting on the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), wherein a transmission electron microscope picture is shown in figure 1.
Respectively carrying out solubility test on the pterostilbene powder and the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), wherein the test steps are as follows:
respectively putting excessive pterostilbene and pterostilbene @ cyclodextrin inclusion compound powder into 10ml of ultrapure water, performing ultrasonic treatment at 60 ℃ for 30 minutes, filtering suspension by using a needle filter, enabling suspension liquid to penetrate through a water-phase filtering membrane with the pore diameter of 5 mu m, and taking filtrate to perform ultraviolet spectrophotometric spectrum detection. And substituting the obtained spectrophotometry into a pterostilbene standard concentration curve to calculate the concentration of the pterostilbene dissolved in the water. The standard concentration curve of pterostilbene is shown in fig. 2.
The test results were as follows:
before the pterostilbene is wrapped, the solubility in water is as follows: 11.49ug/ml, the solubility in water after formation of pterostilbene clathrate was: 38.97mg/ml, the water solubility of the pterostilbene inclusion compound is increased by 3392 times compared with the water solubility of pterostilbene.
Phase stability test is carried out on the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), the viscosity of the mask liquid before and after adding the pterostilbene @ cyclodextrin inclusion compound is shown in the following table 1, no difference change exists, and good compatibility stability is proved; no separation after centrifugation proved to have good phase stability.
TABLE 1
And (3) carrying out a light stability test on the pterostilbene raw material obtained in the step (5) and the pterostilbene @ cyclodextrin inclusion compound powder, wherein the test result is shown in figure 3, and the light stability of the pterostilbene @ cyclodextrin inclusion compound is enhanced relative to the pterostilbene raw material under the irradiation of an ultraviolet lamp.
Example 2:
the multi-dimensional stable pterostilbene @ cyclodextrin inclusion compound comprises 4% of pterostilbene, 80% of hydroxypropyl gamma cyclodextrin, 1% of malic acid and 15% of polyvinylpyrrolidone in percentage by weight of the total weight of the inclusion compound.
The multi-dimensional stable pterostilbene @ cyclodextrin inclusion compound comprises the following preparation steps:
(1) accurately weighing 0.4g of pterostilbene, 8g of hydroxypropyl gamma cyclodextrin, 1.5g of polyvinylpyrrolidone and 0.1g of malic acid. (2) 5ml of an aqueous ethanol solution (ethanol concentration 50%) were prepared. (3) And (2) sufficiently grinding the mixture obtained in the step (1) in a mortar under the condition of keeping out of the light, dropwise adding an ethanol water solution, grinding into paste, stirring for 1 hour, and standing for 24 hours at room temperature in the condition of keeping out of the light. (4) Freezing the block powder obtained in the step (3) for 12 hours, and then carrying out freeze drying. (5) After drying, the resulting fluffy cake was crushed in a mortar and passed through a 120 mesh sieve. (6) The powder was dissolved in water in a ratio of 1: 3.
The pterostilbene @ cyclodextrin inclusion compound prepared by the embodiment is strong in hydrophilicity, colorless and transparent when dissolved in water, and can be mixed with any proportion of toner to form a transparent product, a centrifugal test shows that the product has good phase stability, and an ultraviolet illumination experiment shows that the product has good light stability.
Respectively carrying out solubility test on the pterostilbene powder and the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), wherein the test results are as follows:
before the pterostilbene is wrapped, the solubility in water is as follows: 11.49ug/ml, the solubility in water after formation of pterostilbene clathrate was: 40.06mg/ml, the water solubility of the pterostilbene inclusion compound is increased by 3487 times compared with the water solubility of the pterostilbene.
Phase stability test is carried out on the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), the viscosity of the toner before and after adding the pterostilbene @ cyclodextrin inclusion compound is shown in the following table 2, and no difference change exists, so that the pterostilbene @ cyclodextrin inclusion compound powder is proved to have good compatibility stability; no separation after centrifugation proved to have good phase stability.
TABLE 2
And (3) performing a light stability test on the pterostilbene raw material and the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), wherein the test result is shown in fig. 4, the pterostilbene activity of the pterostilbene @ cyclodextrin inclusion compound is greatly reduced under the irradiation of an ultraviolet lamp relative to the pterostilbene raw material, and the activity of the pterostilbene @ cyclodextrin inclusion compound is slowly reduced, so that the pterostilbene @ cyclodextrin inclusion compound is proved to well enhance the light stability of pterostilbene.
Example 3:
the multi-dimensional stable pterostilbene @ cyclodextrin inclusion compound comprises 4% of pterostilbene, 80% of hydroxypropyl beta cyclodextrin, 2% of ascorbic acid and 14% of polyvinylpyrrolidone in percentage by weight of the total weight of the inclusion compound.
The multi-dimensional stable pterostilbene @ cyclodextrin inclusion compound comprises the following preparation steps:
(1) accurately weighing 0.4g of pterostilbene, 8g of hydroxypropyl beta cyclodextrin, 1.4g of polyvinylpyrrolidone and 0.2g of ascorbic acid. (2) 5ml of an aqueous ethanol solution (ethanol concentration 40%) were prepared. (3) And (2) sufficiently grinding the mixture obtained in the step (1) in a mortar under the condition of keeping out of the light, dropwise adding an ethanol water solution, grinding into paste, stirring for 1 hour, and standing for 24 hours at room temperature in the condition of keeping out of the light. (4) Freezing the block powder obtained in the step (3) for 12 hours, and then carrying out freeze drying. (5) After drying, the resulting fluffy cake was crushed in a mortar and passed through a 120 mesh sieve. (6) Storing the powder at normal temperature in dark.
The raw material cyclodextrin and the pterostilbene @ cyclodextrin inclusion compound powder obtained in this example were subjected to desorption adsorption experiments, respectively. The raw material cyclodextrin is shown as mesoporous adsorption to nitrogen, and the pterostilbene @ cyclodextrin inclusion compound is shown as microporous adsorption to nitrogen. The pterostilbene enters the cavity of the cyclodextrin to form the pterostilbene cyclodextrin inclusion compound, and the aperture of the cyclodextrin is reduced. From the analysis of pore volume and pore space, the average hollow diameter of the cyclodextrin raw material is 20.9150nm, and the average hollow diameter of the desorption (cylindrical pore model) by the BJH method is 10 nm; the average pore diameter of the pterostilbene cyclodextrin inclusion compound is 5.4995nm, and the average pore diameter of the BJH desorption (cylindrical pore model) is 5.52 nm. Indicating that the pterostilbene enters the cavity of the cyclodextrin to form the pterostilbene cyclodextrin inclusion compound.
Respectively carrying out solubility test on the pterostilbene powder and the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), wherein the test results are as follows:
before the pterostilbene is wrapped, the solubility in water is as follows: 11.49ug/ml, the solubility in water after formation of pterostilbene clathrate was: 43.1mg/ml, the water solubility of the pterostilbene inclusion compound is increased by 3751 times compared with the water solubility of pterostilbene.
Phase stability test is carried out on the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), the viscosity of the mask liquid before and after adding the pterostilbene @ cyclodextrin inclusion compound is shown in the following table 3, no difference change exists, and good compatibility stability is proved; no separation after centrifugation proved to have good phase stability.
TABLE 3
And (3) performing a light stability test on the pterostilbene raw material and the pterostilbene @ cyclodextrin inclusion compound powder obtained in the step (5), wherein the test result is shown in fig. 5, the pterostilbene activity of the pterostilbene @ cyclodextrin inclusion compound is greatly reduced under the irradiation of an ultraviolet lamp relative to the pterostilbene raw material, and the activity of the pterostilbene @ cyclodextrin inclusion compound is slowly reduced, so that the pterostilbene @ cyclodextrin inclusion compound is proved to well enhance the light stability of pterostilbene.
The above embodiments are preferred embodiments of the present invention, but the present invention is not limited to the above embodiments, and any other changes, modifications, substitutions, combinations, and simplifications which do not depart from the spirit and principle of the present invention should be construed as equivalents thereof, and all such changes, modifications, substitutions, combinations, and simplifications are intended to be included in the scope of the present invention.
Claims (3)
1. The pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability is characterized by comprising the following components in percentage by mass: 4-6% of pterostilbene, 70-80% of cyclodextrin, 1-2% of organic acid and 13-15% of polyvinylpyrrolidone;
the cyclodextrin comprises at least one compound or a combination of compounds of: 2-hydroxymethyl- β -cyclodextrin, carboxymethyl- β -cyclodextrin, (2-hydroxypropyl) - γ -cyclodextrin, and hepta (2,3, 6-tri-o-methyl) - β -cyclodextrin;
the organic acid contains at least one compound or a combination of compounds of the following types: tartaric acid, oxalic acid, citric acid, ascorbic acid, malic acid and salicylic acid;
the preparation method of the pterostilbene @ cyclodextrin inclusion compound with homogeneous hydrophilicity and multi-dimensional stability comprises the following steps:
(1) under the condition of keeping out of the sun, fully mixing and grinding pterostilbene, cyclodextrin, organic acid and polyvinylpyrrolidone, dropwise adding an ethanol water solution, and grinding into paste;
(2) placing the mixture obtained in the step (1) at room temperature in a dark place;
(3) carrying out liquid nitrogen freeze drying on the block powder obtained in the step (2);
the concentration of the ethanol in the ethanol aqueous solution in the step (1) is 40-50%.
2. A process for the preparation of the homogeneous hydrophilic and multi-dimensionally stable pterostilbene @ cyclodextrin inclusion complex of claim 1, comprising the steps of:
(1) under the condition of keeping out of the sun, fully mixing and grinding pterostilbene, cyclodextrin, organic acid and polyvinylpyrrolidone, dropwise adding an ethanol water solution, and grinding into paste;
(2) placing the mixture obtained in the step (1) at room temperature in a dark place;
(3) carrying out liquid nitrogen freeze drying on the block powder obtained in the step (2);
the concentration of the ethanol in the ethanol aqueous solution in the step (1) is 40-50%.
3. The method according to claim 2, wherein the concentration of ethanol in the aqueous ethanol solution is 40%.
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| CN1258220A (en) * | 1997-06-05 | 2000-06-28 | 詹森药业有限公司 | Pharmaceutical compositions comprising cyclodextrins |
| CN110251421A (en) * | 2019-07-24 | 2019-09-20 | 上海家化联合股份有限公司 | Activating agent-cyclodextrin inclusion compound and its preparation and application containing nucleoprotamine |
| US10842805B2 (en) * | 2012-11-16 | 2020-11-24 | Song Gao | Compositions containing enriched natural crocin and/or crocetin, and their therapeutic or nutraceutical uses |
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| CN108403633A (en) * | 2018-04-02 | 2018-08-17 | 青岛科技大学 | It is a kind of that there is the high stable type pterostilbene soluble type compound and preparation method thereof for providing faintly acid Micellar Microenvironment |
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| CN1258220A (en) * | 1997-06-05 | 2000-06-28 | 詹森药业有限公司 | Pharmaceutical compositions comprising cyclodextrins |
| US10842805B2 (en) * | 2012-11-16 | 2020-11-24 | Song Gao | Compositions containing enriched natural crocin and/or crocetin, and their therapeutic or nutraceutical uses |
| CN110251421A (en) * | 2019-07-24 | 2019-09-20 | 上海家化联合股份有限公司 | Activating agent-cyclodextrin inclusion compound and its preparation and application containing nucleoprotamine |
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