A cyclodextrin-sanshool supramolecular assembly material and a preparation method and application thereof

Abstract

The application relates to the technical field of biomedical functional materials, and discloses a cyclodextrin-sanshool supramolecular assembly material and a preparation method and application thereof. The preparation method comprises the following steps: dissolving cyclodextrin in an organic solvent to prepare solution A; dissolving sanshool in an organic solvent to prepare solution B; slowly adding solution B into solution A, uniformly stirring, and evaporating and removing the organic solvent to obtain a crude product; dissolving the crude product in deionized water, filtering and collecting the filtrate; and performing freeze-drying treatment on the filtrate after freezing to obtain the cyclodextrin-sanshool supramolecular assembly material. The application forms a complex supramolecular system by encapsulating the sanshool molecules into the hydrophobic cavity of the cyclodextrin through host-guest supramolecular interaction, and obtains the nanoscale cyclodextrin-sanshool supramolecular assembly material which has high stability, good biocompatibility and high solubility, and also has good ultraviolet absorption capacity and good free radical scavenging capacity.

Description

Technical Field

[0001] This application relates to the field of biomedical functional materials technology, and in particular to a cyclodextrin-piperidine supramolecular assembly material, its preparation method and application. Background Technology

[0002] The skin, the largest organ in the human body, serves as the first line of defense against external stressors. Photodamage refers to acute and chronic skin damage caused directly or indirectly by ultraviolet (UV) radiation, including phototoxic reactions, photosensitivity, photoaging, and photocarcinogenic effects. It leads to local tissue damage, imbalances in the oxidative and antioxidant systems, and activation of the immune system. Oxidative stress plays a crucial role in photodamage; reactive oxygen species generated by UV radiation trigger a cascading reaction, causing DNA damage, inflammation, and immunosuppression. It also disrupts chain reactions of biomolecules and promotes the expression of matrix metalloproteinases, ultimately resulting in wrinkles, dullness, and other skin impairing appearance and threatening human health and mental well-being. Therefore, effective photoprotective materials and measures are needed to reduce the harm caused by photodamage, especially those with photoprotective and antioxidant properties.

[0003] Currently, methods for preventing and repairing UV-induced photodamage to the skin include sun protection, DNA damage repair enzymes, chemical and physical exfoliation, injectable fillers, the use of antioxidants, and the use of plant-based active substances. However, conventional photoprotective materials on the market have a certain degree of phototoxicity and can easily cause skin sensitivity. Common anti-photoaging drugs, such as vitamin E, have long treatment cycles, and exfoliation and injection treatments carry potential risks; the risk of UV filters in sunscreens leaking into the bloodstream poses certain safety concerns. Developing safe and efficient materials with free radical scavenging and photoprotective capabilities, as well as good biocompatibility and stability, is crucial for the treatment of photodamage to the skin.

[0004] The use of natural plant-derived molecules as bio-photoprotective materials to prevent photo-induced skin damage has attracted considerable interest. Sanshocaprin, an amide naturally found in Sichuan pepper, possesses a characteristic long conjugated chain structure, providing excellent UV absorption and free radical scavenging capabilities; however, it exhibits poor stability and low biocompatibility. Improving the stability of sanshocaprin through host-guest complexation technology is a valuable approach.

[0005] Host-guest complexation technology refers to the process by which a host material, through its hydrophobic cavity, can recognize and interact with a guest molecule in solution. Under the influence of van der Waals forces, hydrogen bonds, and hydrophobic forces, the guest molecule is dynamically incorporated into the cavity of the host material, forming a supramolecular complex system. This enhances the stability and water solubility of the guest molecule. Cyclodextrins (CDs), commonly used in host-guest complexation, are cyclic macromolecules composed of multiple α-D-glucopyranose molecules linked by α-1,4-glycosidic bonds. They possess a hydrophilic outer surface and a hydrophobic internal cavity. The hydrophobic cavity allows CDs to complex various low-water-soluble guest molecules through multiple non-covalent interactions.

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

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

[0008] To achieve the above objectives, the present application adopts the following technical solution.

[0009] The first aspect of this application provides a method for preparing a cyclodextrin-piperidine supramolecular assembly material, comprising:

[0010] S1. Dissolve cyclodextrin in an organic solvent to prepare solution A; dissolve sorbitol in an organic solvent to prepare solution B;

[0011] S2, slowly add solution B to solution A, stir until homogeneous, evaporate to remove organic solvent, and obtain crude product;

[0012] S3, the crude product was dissolved in deionized water, filtered and the filtrate was collected; the filtrate was frozen and then freeze-dried to obtain cyclodextrin-sanshool 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 sanshool to cyclodextrin is 1:(0.75 to 1.25).

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

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

[0018] In some implementations, in step S3, the filtration uses a 220nm microporous membrane.

[0019] A second aspect of this application provides a cyclodextrin-piperidine supramolecular assembly material prepared by the above-described preparation method.

[0020] A third aspect of this application provides the application of the above-mentioned cyclodextrin-piperidine supramolecular assembly material as an antioxidant or photoprotective material.

[0021] A fourth aspect of this application provides the application of the above-mentioned cyclodextrin-piperidine supramolecular assembly material in skin care products.

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

[0023] This application utilizes host-guest supramolecular interactions to encapsulate sanshool molecules into the hydrophobic cavity of cyclodextrin, forming a complex supramolecular system to obtain nanoscale cyclodextrin-sanshool supramolecular assembled materials, which exhibit high stability, good biocompatibility, and high solubility.

[0024] The cyclodextrin-sanshool supramolecular assembly material prepared in this application has good ultraviolet absorption capacity, which can effectively resist the attack of ultraviolet rays; it is not easily deactivated and can provide long-term and stable photoprotection; it has good free radical scavenging ability and can regulate the oxidation state of the microenvironment. Attached Figure Description

[0025] To more clearly illustrate the technical solutions of the embodiments of this application, the accompanying drawings used in the description of the embodiments will be briefly introduced below. Obviously, the accompanying drawings described below are only some embodiments recorded in this application. For those skilled in the art, other drawings can be obtained based on these drawings without creative effort.

[0026] Figure 1 Here is a SEM image of the cyclodextrin-piperidine supramolecular assembly material of this application;

[0027] Figure 2 This is a Zeta potential diagram of the cyclodextrin-piperidine supramolecular assembly material of this application;

[0028] Figure 3 This is the ultraviolet absorption spectrum of the cyclodextrin-piperidine supramolecular assembly material of this application;

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

[0030] Figure 5 Photostability test results for Me-S1, a supramolecular assembly material of methyl-β-cyclodextrin-sanshool;

[0031] Figure 6 Photostability test results for Me-S2, a supramolecular assembly material of methyl-β-cyclodextrin-sanshool;

[0032] Figure 7 Photostability test results for Me-S3, a supramolecular assembly material of methyl-β-cyclodextrin-sanshool;

[0033] Figure 8 The graph shows the photostability test results for sorbitan;

[0034] Figure 9 This is a graph showing the antioxidant properties of the methyl-β-cyclodextrin-sanshool supramolecular assembly material. Detailed Implementation

[0035] The technical solutions of the embodiments of this application will be clearly and completely described below with reference to the accompanying drawings. Obviously, the described embodiments are only some, not all, of the embodiments of this application. All other embodiments obtained by those skilled in the art based on the embodiments of this application without creative effort are within the scope of protection of this application.

[0036] In the following description of this embodiment, the terms "including", "comprising", "having", and "containing" are all open-ended terms, meaning that they include but are not limited to.

[0037] In the following description of this embodiment, the term "and / or" is used to describe the association relationship between related objects, indicating that three relationships can exist. For example, A and / or B can represent: A existing alone, B existing alone, and A and B existing simultaneously. A and B can be singular or plural. The character " / " generally indicates that the preceding and following related objects have an "or" relationship.

[0038] In the following description of this embodiment, the term "at least one" means one or more, and "more than one" means two or more. "At least one of the following" or similar expressions refer to any combination of these items, including any combination of single or multiple items. For example, "at least one of a, b, or c", or "at least one of a, b, and c", can both mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0039] The terminology used in the embodiments of this application is for the purpose of describing particular embodiments only and is not intended to be limiting of this application. The singular forms "a" and "the" as used in the embodiments of this 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 this application, the sequence of numbers does not imply the order of execution. Some or all steps may be executed in parallel or sequentially. The execution order of each process should be determined by its function and internal logic, and should not constitute any limitation on the implementation process of the embodiments of this application.

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

[0042] Unless otherwise stated, the technical / scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this application pertains. While this application describes only preferred methods and materials, any methods and materials similar or equivalent to those described herein may be used in the implementation or testing of this application. All references to this specification are incorporated by way of citation to disclose and describe methods and / or materials associated with those references. In the event of any conflict with any incorporated reference, the content of this specification shall prevail.

[0043] Firstly, this application provides a method for preparing cyclodextrin-sanshool supramolecular assembled materials. Through host-guest supramolecular interactions, sanshool molecules are incorporated into the hydrophobic cavities of cyclodextrin to form a complex supramolecular system, resulting in nanoscale cyclodextrin-sanshool supramolecular assembled materials. Specifically, this includes:

[0044] S1. Dissolve cyclodextrin in an organic solvent to prepare solution A; dissolve sorbitol in an organic solvent to prepare solution B;

[0045] In this application, the cyclodextrin may be any one of methyl-β-cyclodextrin, dimethyl-β-cyclodextrin, or hydroxypropyl-β-cyclodextrin, or a mixture of two or more thereof. An organic solvent is used to dissolve the cyclodextrin or sorbitol; in this application, methanol or ethanol may be used as the organic solvent.

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

[0047] In solution A, the preferred molar concentration of cyclodextrin is 0.015–0.025 mmol / mL; in solution B, the preferred molar concentration of sorbitol is 0.1 mmol / mL.

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

[0049] In this application, solution B is added dropwise to solution A, and the mixture is stirred thoroughly for 3-5 hours to allow the sorbitan and cyclodextrin to undergo an assembly reaction. The organic solvent is then evaporated by rotary evaporation to obtain a crude product containing the sorbitan-cyclodextrin assembled material.

[0050] S3, the crude product was dissolved in deionized water, filtered and the filtrate was collected; the filtrate was frozen and then freeze-dried to obtain cyclodextrin-sanshool supramolecular assembly material.

[0051] Specifically, the crude product was dissolved in deionized water to obtain an aqueous solution, which was then filtered using a 220nm microporous membrane to remove impurities. The filtrate was then frozen at -80℃ and dried under vacuum to less than 10Pa to obtain the cyclodextrin-sanshool supramolecular assembly material.

[0052] The preparation method of this application can rapidly and effectively assemble sorbitan and cyclodextrin into nanomaterials. The process is simple, low-cost, and has good controllability and versatility.

[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-piperidine supramolecular assembly material prepared in this application has good ultraviolet absorption capacity, which can effectively resist the attack of ultraviolet rays; it has good photostability, is not easily deactivated, and can provide long-term and stable photoprotection; it has good free radical scavenging ability, which can regulate the oxidation state of the microenvironment; it can be used as an antioxidant or photoprotective material, or for the preparation of skin care products.

[0055] The present application will be further illustrated by the following examples.

[0056] Example 1

[0057] This embodiment provides a method for preparing a methyl-β-cyclodextrin-piperidine supramolecular assembly material, including:

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

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

[0060] Solution B was slowly added dropwise to solution A, and the mixture was stirred thoroughly for 4 hours. The resulting solution was then evaporated at room temperature to remove the ethanol, yielding the crude product.

[0061] The crude product was dissolved in deionized water, and insoluble matter was removed using a 220 nm filter. The filtrate was frozen at -80 °C and then dried under vacuum to less than 10 Pa to obtain nanomaterials assembled from methyl-β-cyclodextrin and sorbitol, denoted as Me-S1.

[0062] Example 2

[0063] This embodiment provides a method for preparing a methyl-β-cyclodextrin-piperidine supramolecular assembly material, including:

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

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

[0066] Solution B was slowly added dropwise to solution A, and the mixture was stirred thoroughly for 4 hours. The resulting solution was then evaporated at room temperature to remove the ethanol, yielding the crude product.

[0067] The crude product was dissolved in deionized water, and insoluble matter was removed using a 220 nm filter. The filtrate was frozen at -80 °C and then dried under vacuum to less than 10 Pa to obtain nanomaterials assembled from methyl-β-cyclodextrin and sanshool, denoted as Me-S2.

[0068] Example 3

[0069] This embodiment provides a method for preparing a methyl-β-cyclodextrin-piperidine supramolecular assembly material, including:

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

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

[0072] Solution B was slowly added dropwise to solution A, and the mixture was stirred thoroughly for 4 hours. The resulting solution was then evaporated at room temperature to remove the ethanol, yielding the crude product.

[0073] The crude product was dissolved in deionized water, and insoluble matter was removed using a 220 nm filter. The filtrate was frozen at -80 °C and then dried under vacuum to less than 10 Pa to obtain nanomaterials assembled from methyl-β-cyclodextrin and sorbitol, denoted as Me-S3.

[0074] Example 4

[0075] This embodiment 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 was replaced with dimethyl-β-cyclodextrin; all other aspects were the same as in Example 2. The nanomaterial assembled from dimethyl-β-cyclodextrin and sorbitan obtained in Example 4 is designated DM-S2.

[0077] Example 5

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

[0079] The difference between Example 5 and Example 2 is that methyl-β-cyclodextrin was replaced with hydroxypropyl-β-cyclodextrin; otherwise, they were the same as in Example 2. The nanomaterial assembled from hydroxypropyl-β-cyclodextrin and sorbitan obtained in Example 4 is designated HP-S2.

[0080] The performance of the cyclodextrin-piperidine supramolecular assembly materials prepared in Examples 1-5 was evaluated, specifically including:

[0081] 1. Morphological testing

[0082] Cyclodextrin-piperidine supramolecular assembly materials Me-S2, DM-S2, and HP-S2 were prepared into 1 mg / mL aqueous solutions, spin-coated onto the surface of smooth mica sheets, and then dried and sputter-coated with gold before observation. The resulting scanning electron microscope (SEM) images are shown below. Figure 1 As shown.

[0083] from Figure 1 It can be seen that sorbitan and cyclodextrin, through host-guest interactions, both formed well-formed nanoassemblies, and spherical nanoparticles could be observed. Furthermore, statistical analysis of their particle sizes revealed that the nanoassembly obtained by methyl-β-cyclodextrin and sorbitan (Me-S2) had a particle size of 101 nm ± 6 nm, the nanoassembly obtained by dimethyl-β-cyclodextrin and sorbitan (DM-S2) had a particle size of 102 nm ± 7 nm, and the nanoassembly obtained by hydroxypropyl-β-cyclodextrin and sorbitan (HP-S2) had a particle size of 139 nm ± 5 nm. This indicates that the cyclodextrin-sorbitan supramolecular assembly materials have a relatively narrow particle size distribution.

[0084] 2. Zeta potential value

[0085] Cyclodextrin-piperidine supramolecular assembly materials Me-S2, DM-S2, and HP-S2 were prepared into aqueous solutions with a concentration of 20 μg / mL. The solutions were then tested using a nanoparticle size analyzer and a Zeta potential analyzer. The Zeta potential test results are as follows: Figure 2 As shown.

[0086] The zeta potential test measures and statistically analyzes the shear surface potential of a particle solution. A larger absolute value of the zeta potential indicates greater stability of the solution. Figure 2 It can be seen that the solutions of Me-S2, DM-S2 and HP-S2 all have high negative charge, indicating that they all have high stability.

[0087] 3. Ultraviolet absorption capacity test

[0088] Cyclodextrin-sanshool supramolecular assembly materials Me-S2, DM-S2, and HP-S2 were prepared into aqueous solutions with a concentration of 200 μg / mL. The UV absorption of the samples in the wavelength range of 200–400 nm was measured using a UV-Vis spectrophotometer, with a slit width of 2 nm. The results are as follows: Figure 3 As 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 capabilities.

[0090] 4. Proton NMR spectroscopy

[0091] The structure of the methyl-β-cyclodextrin-sanshool supramolecular assembly material Me-S2 was characterized by 1H NMR, demonstrating the host-guest interaction between sanshool molecules and cyclodextrin.

[0092] Sanshocaprin has poor solubility in water, while the cyclodextrin-sanshocaprin assembly significantly increases its solubility. NMR spectroscopy was performed on the Me-S2 material and methyl-β-cyclodextrin using heavy water (D2O) as the solvent. The one-dimensional 1H NMR results are shown below. Figure 4 As shown, where Figure 4 The upper middle section shows the 1H NMR spectrum of methyl-β-cyclodextrin, and the lower section shows the 1H NMR spectrum of Me-S2.

[0093] By comparing the chemical shift values ​​of the methyl-β-cyclodextrin and Me-S2 assembly in heavy water D2O, 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 to free methyl-β-cyclodextrin. This indicates that a portion 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, thus confirming the formation of a host-guest inclusion complex between sanshool and cyclodextrin.

[0094] 5. Stability Test

[0095] Cyclodextrin-piperidine supramolecular assembly materials Me-S1, Me-S2, and Me-S3 were prepared into aqueous solutions with a concentration of 200 μg / mL. The UV-Vis absorbance of the samples at 271 nm was measured using a UV-Vis spectrophotometer, with a slit width of 2 nm. The aqueous solutions of Me-S1, Me-S2, and Me-S3 were then irradiated under simulated sunlight (2W) for 2 h, and their UV absorbance at 271 nm was measured again. The test results are as follows. Figure 5-7 As shown, where Figure 5 For the test results of Me-S1, Figure 6 For the test results of Me-S2, Figure 7 The results are for the Me-S3 test.

[0096] For comparison, a 30 μg / mL ethanol solution of sanshool was prepared, and its UV absorption was tested before and after 2 hours of light exposure. The test results are as follows: Figure 8 As shown.

[0097] from Figure 5-8 It is evident that the cyclodextrin-sanshool supramolecular assembly materials Me-S1, Me-S2, and Me-S3 prepared in this application exhibit only a slight decrease in absorbance before and after light exposure, demonstrating high photostability; while sanshool shows a significant decrease in absorbance before and after light exposure. The photostability of the cyclodextrin-sanshool supramolecular assembly materials prepared in this application is far superior to that of sanshool.

[0098] 6. Free radical scavenging ability

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

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

[0101] 2300 μL of ethanol was added to 200 μL of DPPH ethanol solution, followed by 500 μL of sample solution. The absorbance of the mixed solution at 517 nm was measured using a UV-Vis spectrophotometer at 30 min, 60 min, and 120 min after mixing. Similarly, 2800 μL of ethanol was added to 200 μL of DPPH ethanol solution, and the absorbance of the mixed solution at 517 nm was measured using a UV-Vis spectrophotometer at 30 min, 60 min, and 120 min after mixing. The free radical scavenging rate of the material was obtained from the two absorbance readings at the same time point, and the antioxidant capacity of the ethanol phase in each group of samples was evaluated. The test results are as follows: Figure 9 As shown.

[0102] from Figure 9 It is known that sorbitan itself has a strong free radical scavenging ability. After assembling sorbitan and cyclodextrin through host-guest interaction, the cyclodextrin-sorbitan supramolecular assembly materials prepared in this application also have strong antioxidant properties.

[0103] Although this application has been described in detail in this specification with general descriptions and specific embodiments, some modifications or improvements can be made to it, which will be obvious to those skilled in the art. Therefore, such modifications or improvements made without departing from the spirit of this application are all within the scope of protection claimed in this application.

Claims

1. A method for preparing a cyclodextrin-piperidine supramolecular assembly material, characterized in that, include: S1, Dissolve cyclodextrin in an organic solvent to prepare solution A; Dissolve the sorbitol in an organic solvent to prepare solution B; The cyclodextrin includes at least one of methyl-β-cyclodextrin, dimethyl-β-cyclodextrin, or hydroxypropyl-β-cyclodextrin; S2, slowly add solution B to solution A, stir until homogeneous, evaporate to remove organic solvent, and obtain crude product; wherein, the molar ratio of sanshool to cyclodextrin is 1:(0.75~1.25); S3, the crude product was dissolved in deionized water, filtered and the filtrate was collected; the filtrate was frozen and then freeze-dried to obtain cyclodextrin-sanshool supramolecular assembly material.

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

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

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

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

6. The cyclodextrin-piperidine supramolecular assembly material prepared by the preparation method according to any one of claims 1-5.

7. The application of the cyclodextrin-piperidine supramolecular assembly material as an antioxidant or photoprotective material in the diagnosis and treatment of diseases.

8. The application of the cyclodextrin-piperidine supramolecular assembly material according to claim 7 in the preparation of skin care products.

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