Preparation method of water-soluble urolithin compound powder

Abstract

The invention discloses a preparation method of water-soluble urolithin compound powder, and belongs to the technical field of material modification. The preparation method comprises the following steps: adding cyclodextrin and potassium ions into a urolithin compound solution, further adsorbing at room temperature and environmental pressure so that the urolithin compound is loaded into a compound of the cyclodextrin and the potassium ions, and then washing and drying to obtain water-soluble urolithin compound powder. According to the invention, the water solubility of the urolithin compound is improved, the urolithin compound stably exists in water and does not aggregate, and the transparent aqueous solution is formed after the water-soluble urolithin compound powder is dissolved in water, so that the problem that the transparent urolithin compound solution cannot be obtained in the existing technology for improving the extremely low water solubility of the urolithin compound is solved.

Description

Technical Field

[0001] The invention relates to the technical field of material modification, and in particular to a method for preparing water-soluble urolithin compound powder. Background Art

[0002] Urolithin compounds are widely used in cosmetics, functional foods, health products, medicines and other fields. Improving their low water solubility can promote the wider and deeper application of urolithin compounds.

[0003] Urolithin compounds are a kind of fermentation product of intestinal flora. Urolithin compounds can enhance mitochondrial function, repair damaged nerve cells, and have the functions of anti-oxidation and scavenging free radicals. They are indispensable nutrients for human growth and are increasingly attracting attention in the fields of cosmetics, functional foods, health products, and medicine. Urolithin compounds have obtained the Generally Recognized as Safe (GRAS) certification from the US Food and Drug Administration (US Food and Drug Administration), namely: GRAS Notice No. 791, Urolithin A, and can be added as raw materials to cosmetics and dietary supplements. According to literature reports, urolithin compounds can effectively improve mitochondrial function and have a positive effect on the treatment of cancer, muscle dysfunction, obesity and neurodegeneration. Urolithin compounds have extremely low solubility in water, resulting in poor bioavailability, and simple urolithin compounds themselves are not alkali-resistant.

[0004] In order to improve the extremely low water solubility of urolithin compounds, existing methods usually include emulsion encapsulation, liposome vesicle encapsulation, etc., but the currently reported technologies for improving the extremely low water solubility of urolithin compounds cannot obtain a transparent urolithin compound solution.

[0005] Therefore, it is necessary to provide a method for preparing water-soluble urolithin compound powder. Summary of the invention

[0006] The object of the present invention is to provide a method for preparing a water-soluble urolithin compound powder, so as to solve the problem that a transparent urolithin compound solution cannot be obtained in the existing technology for improving the extremely low water solubility of urolithin compounds.

[0007] In order to achieve the above object, the present invention adopts the following technical solutions:

[0008] A method for preparing a water-soluble urolithin compound powder is as follows:

[0009] Cyclodextrin and potassium ions are added to the urolithin compound solution, and further adsorbed at room temperature and ambient pressure so that the urolithin compound is loaded into the complex of the cyclodextrin and the potassium ions, followed by washing and drying to obtain a water-soluble urolithin compound powder.

[0010] Furthermore, the cyclodextrin is one of α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin.

[0011] Furthermore, the urolithin compound is one or more of urolithin A, urolithin AR, urolithin B, urolithin C, urolithin CR, urolithin D, urolithin E, urolithin G, urolithin M0, urolithin M5, urolithin M6, urolithin M6R, urolithin M7, urolithin M7R, urolithin MA, urolithin MB, and isourolitin A.

[0012] Furthermore, the potassium ion is one or more of potassium hydroxide, potassium chloride, potassium nitrate, potassium sulfate, potassium carbonate, potassium tartrate, potassium acetate, and potassium citrate.

[0013] Furthermore, the molar ratio of the cyclodextrin to the potassium ion is 1:(0.01-10).

[0014] Furthermore, the molar ratio of the added amount of the cyclodextrin and the potassium ion complex to the urolithin compound is 1:(0.01-10).

[0015] Furthermore, during the adsorption process, the adsorption pressure is ambient pressure, the temperature is 1° C. to 60° C., and the time is 1 h to 72 h.

[0016] Furthermore, the washing process includes: washing several times with 0.1 mL to 100 mL of organic solvent respectively.

[0017] Furthermore, the drying method includes: one or more of spray drying, freeze drying, oven drying, and room temperature vacuum drying.

[0018] The present invention has the following beneficial effects:

[0019] 1. In the present invention, a water-soluble urolithin compound powder is prepared by loading a urolithin compound with a cyclodextrin and a potassium ion complex. After the prepared water-soluble urolithin compound powder is dissolved in water, the cyclodextrin and the potassium ion complex are dissociated, but the hydrophobic internal cavity of the cyclodextrin still has a protective effect on the urolithin compound, thereby improving the water solubility of the urolithin compound, making it stably exist in water without aggregation. After the water-soluble urolithin compound powder is dissolved in water, a transparent aqueous solution is formed, which solves the problem that a transparent urolithin compound solution cannot be obtained in the existing technology for improving the extremely low water solubility of urolithin compounds.

[0020] 2. The cyclodextrin, potassium ion complex and urolithin compounds used in the production of the present invention are all food-grade raw materials, so the produced water-soluble hydrophobic bioactive substance powder has biocompatibility.

[0021] 3. The process flow of the present invention is simple, does not involve complicated equipment, the working parameters are easy to control, and can be fully automated with high production efficiency.

[0022] 4. The preparation process of each component in the process of preparing the water-soluble urolithin compound powder in the present invention is simple, no wastewater is discharged, and damage to the environment is avoided. BRIEF DESCRIPTION OF THE DRAWINGS

[0023] Figure 1 is an image of the water-soluble urolithin compound powder in this example;

[0024] Figure 2 This is an image comparison of saturated solutions formed after 1 mg / mL of water-soluble urolithin A powder and 0.05 mg / mL of urolithin A powder are dissolved in water in a neutral aqueous solution in this example;

[0025] Figure 3 The high performance liquid chromatography (HPLC) diagram of 1 mg / mL water-soluble urolithin A powder in this example stored in an aqueous solution at room temperature for 0 days and 50 days. DETAILED DESCRIPTION

[0026] The technical solutions in the embodiments of the present invention will be described clearly and completely below in conjunction with the accompanying drawings in the embodiments of the present invention.

[0027] The present invention provides a method for preparing water-soluble urolithin compound powder, which is specifically as follows:

[0028] Cyclodextrin and potassium ions are added to the urolithin compound solution, and further adsorbed at room temperature and ambient pressure so that the urolithin compound is loaded into the complex of cyclodextrin and potassium ions, followed by washing to remove unadsorbed urolithin compounds and residual organic solvent, etc., and drying to obtain water-soluble urolithin compound powder.

[0029] In the present invention, water-soluble urolithin compound powder is prepared by loading urolithin compounds with cyclodextrin and potassium ion complexes. After the prepared water-soluble urolithin compound powder is dissolved in water, the cyclodextrin and potassium ion complexes are dissociated, but the hydrophobic internal cavity of the cyclodextrin still has a protective effect on the urolithin compound, thereby improving the water solubility of the urolithin compound, making it stably exist in water without aggregation. After the water-soluble urolithin compound powder is dissolved in water, a transparent aqueous solution is formed, which solves the problem that a transparent urolithin compound solution cannot be obtained in the existing technology for improving the extremely low water solubility of urolithin compounds.

[0030] After the cyclodextrin and potassium ion complex are loaded with urolithin compounds, the prepared water-soluble urolithin compound powder significantly improves the water solubility of the urolithin compound. The process conditions in the reaction process of the present invention, such as the amount of raw material added, adsorption, etc., are the optimal conditions obtained through experimental exploration. If it is not within the range of process conditions defined by the present invention, it will lead to a reduction in the output of the water-soluble urolithin compound powder of the present invention or the inability to form the water-soluble urolithin compound powder of the present invention.

[0031] Compared with simple urolithin compounds, the water solubility of the present invention is significantly improved, and can be applied to the fields of cosmetics, functional foods, health products, dietary nutritional supplements, medicines, etc.

[0032] The cyclodextrin is one of α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin.

[0033] The urolithin compounds are one or more of urolithin A, urolithin AR, urolithin B, urolithin C, urolithin CR, urolithin D, urolithin E, urolithin G, urolithin M0, urolithin M5, urolithin M6, urolithin M6R, urolithin M7, urolithin M7R, urolithin MA, urolithin MB, and isourolitin A.

[0034] The potassium ion is one or more of potassium hydroxide, potassium chloride, potassium nitrate, potassium sulfate, potassium carbonate, potassium tartrate, potassium acetate, and potassium citrate.

[0035] The molar ratio of cyclodextrin to potassium ion is 1:(0.01-10).

[0036] The molar ratio of the added amount of the cyclodextrin and potassium ion complex to the urolithin compound is 1:

[0037] (0.01~10).

[0038] The adsorption pressure is ambient pressure, the temperature is 1°C to 60°C, and the time is 1h to 72h.

[0039] The washing process is: washing several times with 0.1mL to 100mL of organic solvent respectively.

[0040] The drying method includes: one or more of spray drying, freeze drying, oven drying, and room temperature vacuum drying.

[0041] In the following examples, urolithin A was purchased from Beijing Inokai Reagent Co., Ltd. (Beijing, China), potassium hydroxide (KOH) was purchased from Beijing Inokai Reagent Co., Ltd. (Beijing, China), γ-cyclodextrin (γ-CD) was purchased from Beijing Inokai Reagent Co., Ltd. (Beijing, China), anhydrous ethanol was purchased from Aladdin Reagent (Shanghai) Co., Ltd. (Shanghai, China), and N,N-dimethylformamide (DMF) was purchased from Aladdin Reagent (Shanghai) Co., Ltd. (Shanghai, China).

[0042] If there is no special description of raw materials or processing techniques, it means that they are all conventional commercially available raw materials or conventional processing techniques in the art.

[0043] Example 1

[0044] This embodiment provides a method for preparing a water-soluble urolithin compound powder, and the specific process is as follows:

[0045] 100 mg of cyclodextrin and potassium hydroxide complex was added to the DMF solution of urolithin A (30 mg PQQ / 5 mL DMF). The urolithin A was loaded into the cyclodextrin and potassium hydroxide complex by further adsorption at room temperature and ambient pressure for 24 hours; the urolithin A was washed 3 times with 30 mL of anhydrous ethanol and dried under vacuum at room temperature for 12 hours to obtain a water-soluble urolithin A powder (such as Figure 1 ).

[0046] The images of pure urolithin A and the prepared water-soluble urolithin A powder dissolved in water in neutral water (such as Figure 2 ) comparison shows that the solubility of the prepared water-soluble urolithin A powder in water is greater than the solubility of urolithin A, indicating that urolithin A has significantly improved water solubility.

[0047] After the aqueous solution of water-soluble urolithin A powder was stored at room temperature for 0 days and 50 days, high performance liquid chromatography was performed (eg Figure 3 ), the results showed that the prepared water-soluble urolithin A powder had good chemical stability in neutral aqueous solution.

[0048] In summary, the equipment required by the present invention is simple, the production efficiency is high, and the cost is saved. The obtained water-soluble urolithin compound powder has high stability, high quality, and good safety, can meet the actual production and life needs, and is suitable for large-scale industrial production.

[0049] The embodiments described above are only descriptions of the preferred modes of the present invention, and are not intended to limit the scope of the present invention. Without departing from the design spirit of the present invention, various modifications and improvements made to the technical solutions of the present invention by ordinary technicians in this field should all fall within the protection scope determined by the claims of the present invention.

Claims

1. A method for preparing a water-soluble urolithin compound powder, characterized in that: The details are as follows: Cyclodextrin and potassium ions are added to the urolithin compound solution, and further adsorbed at room temperature and ambient pressure so that the urolithin compound is loaded into the complex of the cyclodextrin and the potassium ions, followed by washing and drying to obtain a water-soluble urolithin compound powder.

2. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The cyclodextrin is one of α-cyclodextrin, β-cyclodextrin and γ-cyclodextrin.

3. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The urolithin compound is one or more of urolithin A, urolithin AR, urolithin B, urolithin C, urolithin CR, urolithin D, urolithin E, urolithin G, urolithin M0, urolithin M5, urolithin M6, urolithin M6R, urolithin M7, urolithin M7R, urolithin MA, urolithin MB, and isourolitin A.

4. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The potassium ion is one or more of potassium hydroxide, potassium chloride, potassium nitrate, potassium sulfate, potassium carbonate, potassium tartrate, potassium acetate, and potassium citrate.

5. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The molar ratio of the cyclodextrin to the potassium ion is 1:(0.01-10).

6. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The molar ratio of the added amount of the cyclodextrin and the potassium ion complex to the urolithin compound is 1:(0.01-10).

7. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: During the adsorption process, the adsorption pressure is the ambient pressure, the temperature is 1° C. to 60° C., and the time is 1 h to 72 h.

8. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The washing process comprises: washing several times with 0.1 mL to 100 mL of organic solvent.

9. The method for preparing the water-soluble urolithin compound powder according to claim 1, characterized in that: The drying method includes: one or more of spray drying, freeze drying, oven drying, and room temperature vacuum drying.

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