Cyclodextrin-sanshool supramolecular assembly material as well as preparation method and application thereof

Abstract

The invention relates to the technical field of biomedical functional materials, and discloses a cyclodextrin-sanshool supramolecular assembly material as well as a preparation method and application thereof. The preparation method comprises the following steps: dissolving cyclodextrin in an organic solvent to prepare a solution A; dissolving sanshool in an organic solvent to prepare a solution B; slowly adding the solution B into the solution A, uniformly stirring, and evaporating to remove the organic solvent to obtain a crude product; dissolving the crude product in deionized water, filtering and collecting filtrate; and freezing the filtrate, and carrying out freeze-drying treatment to obtain the cyclodextrin-sanshool supramolecular assembly material. According to the invention, through interaction of host and guest supermolecules, sanshool molecules are encapsulated into hydrophobic cavities of cyclodextrin to form a compound supermolecule system, and the nanoscale cyclodextrin-sanshool supermolecule assembly material is obtained and has high stability, good biocompatibility and high solubility; in addition, good ultraviolet absorption capability and good free radical scavenging capability are realized.

Description

Technical Field

[0001] This application relates to the technical field of biomedical functional materials, and particularly relates to a cyclodextrin-piperine supramolecular assembly material, a preparation method thereof, and an application thereof. Background Art

[0002] The skin is the largest organ of the human body and is the first barrier to protect the body from external stress. Skin photo-damage refers to acute and chronic skin damage directly or indirectly caused by ultraviolet rays, including phototoxic reactions, photoallergy, photoaging, and photocarcinogenesis, which can lead to local tissue damage, imbalance of oxidation and antioxidant systems, activation of the immune system, etc. Among them, oxidative stress plays an important role in skin photo-damage. The reactive oxygen species generated by ultraviolet rays cause a hierarchical chain reaction, resulting in DNA damage, inflammatory reactions, and immunosuppression, disrupting the chain reaction of biomolecules, promoting the expression of matrix metalloproteinases, etc. Eventually, the skin appears wrinkled and dull, affecting the skin's aesthetics and threatening human health and mental state. Therefore, effective light protection materials or measures are needed to reduce the harm caused by photo-damage, especially light protection materials with light protection and antioxidant stress capabilities.

[0003] At present, for the prevention and repair of skin photo-damage caused by ultraviolet rays, there are sunscreen, DNA damage repair enzymes, chemical and physical exfoliation methods, injection filling, use of antioxidants, and use of plant active substances, etc. However, conventional light protection materials on the market have a certain degree of phototoxicity and are prone to causing skin sensitivity. Common anti-photoaging drugs such as vitamin E have a long treatment cycle, and exfoliation and injection treatments have potential risks; there are certain safety problems with the risk of ultraviolet filters in sunscreen leaking into the blood. Developing safe and efficient materials with free radical scavenging ability and light protection ability, and good biocompatibility and stability is very important for the treatment of skin photo-damage.

[0004] Using natural molecules from plants as biological light protection materials to prevent photo-induced skin damage has attracted great interest. Piperine is an amide substance naturally present in Chinese prickly ash, with a characteristic long conjugated chain structure, providing good ultraviolet absorption and free radical scavenging ability. However, its stability is poor and its compatibility is low. Improving the stability of piperine through host-guest complexation technology is a valuable method.

[0005] The host-guest complexation technology refers to that the host material can recognize the guest mutually in solution by virtue of its hydrophobic cavity. Under the action of van der Waals force, hydrogen bond and hydrophobic force, the guest molecules are dynamically encapsulated into the cavity of the host material to form a composite supramolecular system, thereby improving the stability and water solubility of the guest molecules. Cyclodextrins (CDs), as a commonly used material in the host-guest complexation technology, are cyclic macromolecules composed of multiple α-D-glucopyranose units linked by α-1,4-glycosidic bonds. They have a hydrophilic outer surface and a hydrophobic inner cavity, and the hydrophobic cavity allows CDs to complex various low-water-solubility guest molecules through a variety of non-covalent interactions.

[0006] Based on this, developing a cyclodextrin-piperine assembly material to improve the stability and biocompatibility of piperine has broad application prospects. Summary of the Invention

[0007] This application provides a cyclodextrin-piperine supramolecular assembly material, its preparation method and application, aiming to solve the problems of low stability and poor biocompatibility existing in the existing biological photoprotective materials.

[0008] To achieve the above object, this application adopts the following technical solutions.

[0009] In the first aspect of this application, a preparation method of a cyclodextrin-piperine supramolecular assembly material is provided, including:

[0010] S1, dissolving cyclodextrin in an organic solvent to prepare solution A; dissolving piperine in an organic solvent to prepare solution B;

[0011] S2, slowly adding solution B to solution A, stirring evenly, and evaporating to remove the organic solvent to obtain a crude product;

[0012] S3, dissolving the crude product in deionized water, filtering to collect the filtrate; freezing the filtrate and then performing freeze-drying treatment to obtain the cyclodextrin-piperine supramolecular assembly material.

[0013] In some embodiments, the cyclodextrin includes at least one of methyl-β-cyclodextrin, dimethyl-β-cyclodextrin or hydroxypropyl-β-cyclodextrin.

[0014] In some embodiments, the organic solvent is methanol or ethanol.

[0015] In some embodiments, the molar ratio of piperine to cyclodextrin is 1:(0.75 - 1.25).

[0016] In some embodiments, in solution A, the molar concentration of cyclodextrin is 0.015 - 0.025 mmol / mL.

[0017] In some embodiments, in the solution B, the molar concentration of sanshool is 0.1 mmol / mL.

[0018] In some embodiments, in step S3, the filtration is carried out using a 220 nm microporous membrane.

[0019] In the second aspect of the present application, there is provided a cyclodextrin-sanshool supramolecular assembly material prepared by the above preparation method.

[0020] In the third aspect of the present application, there is provided the use of the above cyclodextrin-sanshool supramolecular assembly material as an antioxidant material or a light protection material.

[0021] In the fourth aspect of the present application, there is provided the use of the above cyclodextrin-sanshool supramolecular assembly material in skin care products.

[0022] Compared with the prior art, the beneficial effects of the present application are as follows:

[0023] In the present application, through host-guest supramolecular interaction, sanshool molecules are included in the hydrophobic cavity of cyclodextrin to form a complex supramolecular system, and a nanoscale cyclodextrin-sanshool supramolecular assembly material is obtained, which has high stability, good biocompatibility and high solubility.

[0024] The cyclodextrin-sanshool supramolecular assembly material prepared in the present application has good ultraviolet absorption ability, can effectively resist the invasion of ultraviolet rays; is not easily inactivated, and can provide long-term and stable light protection; has good free radical scavenging ability and can regulate the oxidation state of the microenvironment. Description of the Drawings

[0025] In order to more clearly illustrate the technical solutions of the embodiments of the present application, the following will briefly introduce the drawings required for the description of the embodiments. Obviously, the drawings in the following description are only some embodiments recorded in the present application. For those of ordinary skill in the art, without creative efforts, other drawings can also be obtained based on these drawings.

[0026] Figure 1 It is the SEM image of the cyclodextrin-sanshool supramolecular assembly material of the present application;

[0027] Figure 2 It is the Zeta potential diagram of the cyclodextrin-sanshool supramolecular assembly material of the present application;

[0028] Figure 3 It is the ultraviolet absorption spectrum of the cyclodextrin-sanshool supramolecular assembly material of the present application;

[0029] Figure 4 It is the 1H NMR spectrum of the methyl-β-cyclodextrin-sanshool supramolecular assembly material Me-S2 and methyl-β-cyclodextrin;

[0030] Figure 5 Photostability test chart of methyl-β-cyclodextrin-sanshool supramolecular assembly material Me-S1;

[0031] Figure 6 Photostability test chart of methyl-β-cyclodextrin-sanshool supramolecular assembly material Me-S2;

[0032] Figure 7 Photostability test chart of methyl-β-cyclodextrin-sanshool supramolecular assembly material Me-S3;

[0033] Figure 8 Photostability test chart of sanshool;

[0034] Figure 9 Antioxidant property test chart of methyl-β-cyclodextrin-sanshool supramolecular assembly material. Specific implementation manners

[0035] The technical solutions in the embodiments of the present application will be clearly and completely described below with reference to the accompanying drawings in the embodiments of the present application. Obviously, the described embodiments are only a part of the embodiments of the present application, rather than all the embodiments. All other embodiments obtained by those of ordinary skill in the art based on the embodiments of the present application without creative efforts shall fall within the protection scope of the present application.

[0036] In the following description of this embodiment, the terms "include", "comprise", "have" and "contain" are all open-ended terms, that is, they are meant to include but not be limited to.

[0037] In the following description of this embodiment, the term "and / or" is used to describe the association relationship of associated objects, indicating that there can be three relationships. For example, A and / or B can represent: A exists alone, B exists alone, and both A and B exist simultaneously. Where A and B can be singular or plural. The character " / " generally represents that the associated objects before and after are an "or" relationship.

[0038] In the following description of this embodiment, the term "at least one" means one or more, and "a plurality" means two or more. "At least one of the following items" or its similar expression refers to any combination of these items, including any combination of single item or plural items. For example, "at least one of a, b or c", or, "at least one of a, b and c" can all represent: a, b, c, a - b (that is, a and b), a - c, b - c, or a - b - c, where a, b, and c can be single or multiple respectively.

[0039] The terms used in the embodiments of the present application are for the purpose of describing specific embodiments only and are not intended to limit the present application. The singular forms "a" and "the" used in the embodiments of the present application and the appended claims are also intended to include the plural forms unless the context clearly indicates otherwise.

[0040] Those skilled in the art should understand that in the following description of the embodiments of the present application, the sequence numbers do not mean the order of execution, and some or all steps can be executed in parallel or successively. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation to the implementation process of the embodiments of the present application.

[0041] Those skilled in the art should understand that the numerical ranges in the embodiments of the present application should be understood as specifically disclosing each intermediate value between the upper and lower limits of the range. Each intermediate value within any stated value or stated range, as well as each smaller range between any other stated value or intermediate value within the stated range, is also included in the present application. The upper and lower limits of these smaller ranges can be independently included or excluded from the range.

[0042] Unless otherwise specified, the technical / scientific terms used herein have the same meaning as commonly understood by those of ordinary skill in the art to which this application belongs. Although this application only describes preferred methods and materials, any methods and materials similar or equivalent to those described herein can also be used in the implementation or testing of this application. All documents mentioned in this specification are incorporated by reference to disclose and describe the methods and / or materials related to the documents. In case of conflict with any incorporated document, the content of this specification shall prevail.

[0043] In a first aspect, the present application provides a method for preparing a cyclodextrin-sanshool supramolecular assembly material. Through host-guest supramolecular interaction, sanshool molecules are included in the hydrophobic cavity of cyclodextrin to form a complex supramolecular system, and a nanoscale cyclodextrin-sanshool supramolecular assembly material is obtained. Specifically, it includes:

[0044] S1, dissolve cyclodextrin in an organic solvent to prepare solution A; dissolve sanshool in an organic solvent to prepare solution B;

[0045] In the present application, cyclodextrin can be any one of methyl-β-cyclodextrin, dimethyl-β-cyclodextrin or hydroxypropyl-β-cyclodextrin, or a mixture of two or more. The organic solvent is used to dissolve cyclodextrin or sanshool. In the present application, the organic solvent can be selected from methanol or ethanol.

[0046] In the present application, the molar ratio of sanshool to cyclodextrin is preferably 1:(0.75 - 1.25), such as 1:0.75, 1:1, 1:1.25 or any ratio within the given ratio range.

[0047] Among them, in solution A, the molar concentration of cyclodextrin is preferably 0.015 - 0.025 mmol / mL; in solution B, the molar concentration of sanshool is preferably 0.1 mmol / mL.

[0048] S2, slowly add solution B to solution A, stir evenly, and evaporate to remove the organic solvent to obtain a crude product;

[0049] In this application, solution B is added to solution A dropwise, and stirred thoroughly for 3 - 5 h to allow the assembly reaction of sanshool and cyclodextrin. Then, the organic solvent is evaporated by rotary evaporation to obtain a crude product containing the sanshool-cyclodextrin assembly material.

[0050] S3, dissolve the crude product in deionized water, filter and collect the filtrate; freeze the filtrate and then perform freeze-drying to obtain the cyclodextrin-sanshool supramolecular assembly material.

[0051] Specifically, dissolve the crude product in deionized water to obtain an aqueous solution, filter the aqueous solution with a filter equipped with a 220 nm microporous membrane to remove impurities; freeze the filtrate at -80 °C, and then dry it under vacuum to less than 10 Pa to obtain the cyclodextrin-sanshool supramolecular assembly material.

[0052] The preparation method of this application can quickly and effectively assemble sanshool and cyclodextrin to form a nanomaterial. Its process is simple, the cost is low, and it has good controllability and universality.

[0053] The cyclodextrin-sanshool supramolecular assembly material prepared in this application has high stability, good biocompatibility and high solubility compared with sanshool, and has broad application prospects.

[0054] The cyclodextrin-sanshool supramolecular assembly material prepared in this application has good ultraviolet absorption ability, can effectively resist the invasion of ultraviolet rays; has good photostability, is not easy to inactivate, and can provide long-term and stable light protection; has good free radical scavenging ability, can regulate the oxidation state of the microenvironment; can be used as an antioxidant material or a light protection material, or for the preparation of skin care products.

[0055] The following further illustrates this application through examples.

[0056] Example 1

[0057] This example provides a preparation method of a methyl-β-cyclodextrin-sanshool supramolecular assembly material, including:

[0058] Weigh 0.15 mmol of methyl-β-cyclodextrin, dissolve it in 10 mL of absolute ethanol, and maintain gentle stirring at room temperature to obtain solution A;

[0059] Weigh 0.2 mmol of sanshool, dissolve it in 2 mL of absolute ethanol to obtain a light yellow clear solution B.

[0060] Slowly add solution B dropwise to solution A, and stir well for 4 h; evaporate the ethanol from the resulting solution at room temperature to obtain a crude product;

[0061] Dissolve the crude product in deionized water, remove the insoluble matter with a 220 nm filter, freeze the filtrate at -80 °C, and then dry it under vacuum to less than 10 Pa to obtain a nanomaterial of supramolecular assembly of methyl-β-cyclodextrin and sanshool, denoted as Me-S1.

[0062] Example 2

[0063] This example provides a preparation method of a supramolecular assembly material of methyl-β-cyclodextrin-sanshool, including:

[0064] Weigh 0.2 mmol of methyl-β-cyclodextrin, dissolve it in 10 mL of absolute ethanol, and maintain gentle stirring at room temperature to obtain solution A;

[0065] Weigh 0.2 mmol of sanshool, dissolve it in 2 mL of absolute ethanol to obtain a light yellow clear solution B.

[0066] Slowly add solution B dropwise to solution A, and stir well for 4 h; evaporate the ethanol from the resulting solution at room temperature to obtain a crude product;

[0067] Dissolve the crude product in deionized water, remove the insoluble matter with a 220 nm filter, freeze the filtrate at -80 °C, and then dry it under vacuum to less than 10 Pa to obtain a nanomaterial of supramolecular assembly of methyl-β-cyclodextrin and sanshool, denoted as Me-S2.

[0068] Example 3

[0069] This example provides a preparation method of a supramolecular assembly material of methyl-β-cyclodextrin-sanshool, including:

[0070] Weigh 0.25 mmol of methyl-β-cyclodextrin, dissolve it in 10 mL of absolute ethanol, and maintain gentle stirring at room temperature to obtain solution A;

[0071] Weigh 0.2 mmol of sanshool, dissolve it in 2 mL of absolute ethanol to obtain a light yellow clear solution B.

[0072] Slowly add solution B dropwise to solution A, and stir well for 4 h; evaporate the ethanol from the resulting solution at room temperature to obtain a crude product;

[0073] Dissolve the crude product in deionized water, remove the insoluble matter with a 220 nm filter, freeze the filtrate at -80 °C, and then dry it under vacuum to less than 10 Pa to obtain the nanomaterial of supramolecular assembly of methyl-β-cyclodextrin and sanshool, denoted as Me-S3.

[0074] Example 4

[0075] This example provides a method for preparing a dimethyl-β-cyclodextrin-sanshool supramolecular assembly material.

[0076] The difference between Example 4 and Example 2 is that methyl-β-cyclodextrin is replaced by dimethyl-β-cyclodextrin, and the rest are the same as in Example 2. The nanomaterial of supramolecular assembly of dimethyl-β-cyclodextrin and sanshool obtained in Example 4 is denoted as DM-S2.

[0077] Example 5

[0078] This example provides a method for preparing a hydroxypropyl-β-cyclodextrin-sanshool supramolecular assembly material.

[0079] The difference between Example 5 and Example 2 is that methyl-β-cyclodextrin is replaced by hydroxypropyl-β-cyclodextrin, and the rest are the same as in Example 2. The nanomaterial of supramolecular assembly of hydroxypropyl-β-cyclodextrin and sanshool obtained in Example 4 is denoted as HP-S2.

[0080] Perform performance evaluation on the cyclodextrin-sanshool supramolecular assembly materials prepared in Examples 1-5, specifically including:

[0081] 1. Morphology test

[0082] Take the cyclodextrin-sanshool supramolecular assembly materials Me-S2, DM-S2 and HP-S2, respectively prepare aqueous solutions with a concentration of 1 mg / mL, spin-coat them on the surface of a smooth mica sheet, and observe them after drying and gold spraying in sequence. Their scanning electron microscope photos are as Figure 1 shown.

[0083] From Figure 1 it can be seen that sanshool and cyclodextrin are assembled through host-guest interaction to form good nanoassemblies, and spherical nanoparticles can be observed. Further, by statistically analyzing their particle sizes, the particle size of the nanoassembly (Me-S2) assembled from methyl-β-cyclodextrin and sanshool is 101 nm ± 6 nm, the particle size of the nanoassembly (DM-S2) assembled from dimethyl-β-cyclodextrin and sanshool is 102 nm ± 7 nm, and the particle size of the nanoassembly (HP-S2) assembled from hydroxypropyl-β-cyclodextrin and sanshool is 139 nm ± 5 nm. It can be seen that the cyclodextrin-sanshool supramolecular assembly material has a narrow particle size distribution.

[0084] 2. Zeta potential value

[0085] Take the cyclodextrin-sanshool supramolecular assembly materials Me-S2, DM-S2 and HP-S2, respectively prepare aqueous solutions with a concentration of 20 μg / mL, and use a nano particle size and Zeta potential analyzer for testing. The obtained Zeta potential test results are as Figure 2 shown.

[0086] Zeta potential test is to test and statistically analyze the shear plane potential of the particle solution. When the absolute value of the potential obtained by Zeta test is larger, the stability of the corresponding solution is stronger. From Figure 2 it can be seen that the solutions of Me-S2, DM-S2 and HP-S2 all have high negative charges, indicating that they all have high stability.

[0087] 3. Ultraviolet absorption ability test

[0088] Take the cyclodextrin-sanshool supramolecular assembly materials Me-S2, DM-S2 and HP-S2, respectively prepare aqueous solutions with a concentration of 200 μg / mL, and use an ultraviolet-visible spectrophotometer to measure the ultraviolet absorption of the samples in the wavelength range of 200-400 nm, where the slit width is 2 nm. The results are as Figure 3 shown.

[0089] From Figure 3 it can be seen that Me-S2, DM-S2 and HP-S2 all have good absorption in the ultraviolet band, especially in the UVB band, indicating that they all have good ultraviolet absorption ability.

[0090] 4. 1H NMR test

[0091] Use 1H NMR to characterize the structure of the methyl-β-cyclodextrin-sanshool supramolecular assembly material Me-S2, and prove the host-guest interaction between the sanshool molecule and cyclodextrin.

[0092] Sanshool has poor solubility in water, while the cyclodextrin-sanshool assembly greatly increases the solubility of sanshool. Use D 2 2O as the solvent for NMR testing of the Me-S2 material and methyl-β-cyclodextrin respectively. The test results of the one-dimensional proton NMR are as Figure 4 shown, where Figure 4 the upper one is the proton NMR spectrum of methyl-β-cyclodextrin, and the lower one is the proton NMR spectrum of Me-S2.

[0093] By comparing the methyl-β-cyclodextrin and the Me-S2 assembly in D 2From the chemical shift values in O, it can be seen that the chemical shifts of H-3 and H-5 located inside the hydrophobic cavity in the cyclodextrin-sanshool supramolecular assembly shift to a lower field compared with free methyl-β-cyclodextrin. This indicates that a part of the sanshool molecule enters the interior of the hydrophobic cavity of methyl-β-cyclodextrin, inducing changes in the chemical shifts of H-3 and H-5 of methyl-β-cyclodextrin, which confirms the formation of the host-guest inclusion complex of sanshool and cyclodextrin.

[0094] 5. Stability test

[0095] Take the cyclodextrin-sanshool supramolecular assembly materials Me-S1, Me-S2 and Me-S3, respectively prepare aqueous solutions with a concentration of 200 μg / mL, and use a UV-visible spectrophotometer to measure the UV absorption of the samples at a wavelength of 271 nm, where the slit width is 2 nm. Then irradiate the aqueous solutions of Me-S1, Me-S2 and Me-S3 under the condition of simulated sunlight (2 W) for 2 h, and measure their UV absorption values at a wavelength of 271 nm again. The test results are as follows Figures 5-7 shown, where Figure 5 is the test result of Me-S1, Figure 6 is the test result of Me-S2, Figure 7 is the test result of Me-S3.

[0096] As a comparison, take sanshool and prepare an ethanol solution with a concentration of 30 μg / mL, and test its UV absorption before and after 2 hours of light irradiation. The test results are as Figure 8 shown.

[0097] From Figures 5-8 it can be seen that for the cyclodextrin-sanshool supramolecular assembly materials Me-S1, Me-S2 and Me-S3 prepared in this application, their absorbance values only decrease slightly before and after light irradiation, and they have high photo-stability; while for sanshool, its absorbance value decreases significantly before and after light irradiation. The photo-stability of the cyclodextrin-sanshool supramolecular assembly materials prepared in this application is much higher than that of sanshool.

[0098] 6. Free radical scavenging ability

[0099] The 2,2-diphenyl-1-picrylhydrazyl (DPPH) method is used to evaluate the in vitro DPPH free radical scavenging ability of the cyclodextrin-sanshool supramolecular assembly materials Me-S1, Me-S2 and Me-S3 prepared in this application, as well as sanshool. The specific method is as follows:

[0100] Respectively dissolve Me-S1, Me-S2, Me-S3 and sanshool in ethanol to prepare sample solutions with a concentration of 5 mg / mL; another ethanol solution of DPPH with a concentration of 0.1 mmol / L is prepared.

[0101] Take 2300 μL of ethanol, add 200 μL of DPPH ethanol solution, and then add 500 μL of the sample solution. At the 30th minute, 60th minute, and 120th minute after mixing, use a UV-visible spectrophotometer to measure the absorbance of the mixed solution at 517 nm; take 2800 μL of ethanol, add 200 μL of DPPH ethanol solution, and at the 30th minute, 60th minute, and 120th minute after mixing, use a UV-visible spectrophotometer to measure the absorbance of the mixed solution at 517 nm; obtain the radical scavenging rate of the material from the two absorbances at the same time point, and evaluate the antioxidant capacity of the ethanol phase of each group of samples. The test results are as Figure 9 shown.

[0102] From Figure 9 it can be seen that capsaicin itself has strong radical scavenging ability. After assembling capsaicin and cyclodextrin through host-guest interaction, the cyclodextrin-capsaicin supramolecular assembly material prepared in this application also has strong antioxidant performance.

[0103] Although this application has been described in detail in this specification with general descriptions and specific implementation examples, based on this application, some modifications or improvements can be made, which are obvious to those skilled in the art. Therefore, these modifications or improvements made without departing from the spirit of this application all fall within the scope of protection required by this application.

Claims

1. A method for preparing a cyclodextrin-sanshool supramolecular assembly material, characterized in that: include: S1, dissolving cyclodextrin in an organic solvent to prepare solution A; Dissolve sanshool in an organic solvent to prepare solution B; S2, slowly adding solution B into solution A, stirring evenly, and evaporating to remove the organic solvent to obtain a crude product; S3, dissolving the crude product in deionized water, filtering and collecting the filtrate; freezing the filtrate and then freeze-drying it to obtain a cyclodextrin-sanshool supramolecular assembly material.

2. The preparation method according to claim 1, characterized in that: The cyclodextrin includes at least one of methyl-β-cyclodextrin, dimethyl-β-cyclodextrin or hydroxypropyl-β-cyclodextrin.

3. The preparation method according to claim 1, characterized in that: The organic solvent is methanol or ethanol.

4. The preparation method according to claim 1, characterized in that: The molar ratio of the sanshool to the cyclodextrin is 1:(0.75-1.25).

5. The preparation method according to claim 1, characterized in that: In the solution A, the molar concentration of cyclodextrin is 0.015-0.025 mmol / mL.

6. The preparation method according to claim 1, characterized in that: In the solution B, the molar concentration of sanshool is 0.1 mmol / mL.

7. The preparation method according to claim 1, characterized in that: In step S3, the filtration uses a 220 nm microporous filter membrane.

8. The cyclodextrin-sanshool supramolecular assembly material prepared by the preparation method according to any one of claims 1 to 7.

9. Use of the cyclodextrin-sanshool supramolecular assembly material according to claim 8 as an antioxidant material or a light protection material.

10. Use of the cyclodextrin-sanshool supramolecular assembly material according to claim 8 in skin care products.

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