A compound of quercetin derived from blueberry tree and probenecid, as well as its preparation method and application

Abstract

The present invention discloses a compound comprising quercetin and probenecid derived from the Japanese blueberry tree, as well as its preparation method and application. The compound comprising quercetin and probenecid derived from the Japanese blueberry tree of the present invention has a structural formula as shown in Formula (I): #imgabs0# The compound comprising quercetin and probenecid derived from the Japanese blueberry tree of the present invention is synthesized through a series of chemical reaction steps, including solvent dissolution, heating and stirring, vacuum concentration, extraction, and silica gel column chromatography. The derivative of the quercetin and probenecid derived from the Japanese blueberry tree of the present invention exhibits enhanced biological activity and therapeutic effects through structural modification. The compound of the present invention has a significant effect on lowering blood uric acid, blood sugar, and serum total cholesterol, and increasing serum total protein levels in experimental mice.

Description

Technical Field

[0001] The present invention relates to the technical field of chemistry, and in particular to a compound of quercetin derived from blueberry tree and probenecid, and a preparation method and application thereof. Background Art

[0002] Uric acid is the end product of purine catabolism and is physiologically excreted in the urine. Endogenously produced uric acid accounts for approximately 80% of total serum uric acid (SUA), with the remainder derived from dietary purines. Most bacteria and mammals metabolize uric acid through uricase-mediated metabolism to produce the water-soluble allantoin. However, humans lack uricase, and uric acid is primarily excreted through the kidneys. Consequently, excessive uric acid secretion or insufficient renal excretion leads to hyperuricemia, typically defined as a serum uric acid level >6.8 mg / dL. Hyperuricemia may be asymptomatic, but when total serum uric acid concentrations exceed 6.8 mg / dL, monosodium urate crystallizes and deposits in joints or surrounding tissues—the cause of gout, a serious disease affecting millions worldwide, particularly adult men. Hyperuricemia is also associated with a range of chronic diseases, including hypertension, diabetes, metabolic syndrome, and renal and cardiovascular disease. Obesity and excessive intake of meat and alcoholic beverages are considered causative factors for hyperuricemia and / or gout. 98% of uric acid in the body is in the form of sodium salt. Gouty arthritis is caused by the accumulation of monosodium urate (MSU) crystals in joints and other tissues, leading to pathological changes and inflammation. In gout, excessive uric acid deposits in the joints are consumed by macrophages, leading to the release of inflammatory factors, which in turn cause acute synovitis and articular cartilage destruction. Therefore, it is important to control the occurrence of local inflammatory reactions.

[0003] Vaccinium bracteatum Thunb., a perennial shrub belonging to the genus Vaccinium in the Ericaceae family, is widely distributed across East Asia. It is famous for its fruit, the black rice seed, which is not only unique in color and high in nutritional value, but also has a long history of use in traditional medicine. The leaves, bark, and fruit of the black rice tree are rich in various bioactive components, including significant amounts of quercetin. Quercetin is a polyphenolic flavonol compound with significant biological activities, including anti-inflammatory, antioxidant, anti-tumor, and blood pressure-lowering properties.

[0004] Quercetin, molecular formula C 15 H 10O7 is a flavonoid compound widely found in the plant kingdom. It is found in a variety of vegetables, fruits, and herbs, with particularly high concentrations in onions, apples, tea leaves, and blueberry trees. Quercetin has attracted considerable attention for its potent antioxidant properties, which can scavenge free radicals in the body and reduce oxidative stress, thereby protecting cells from damage. Quercetin also has anti-inflammatory effects, inhibiting the release of inflammatory mediators and alleviating inflammatory responses. Studies have shown that quercetin can lower blood pressure through multiple mechanisms, including blocking angiotensin-converting enzyme (ACE) and relaxing vascular smooth muscle.

[0005] The abundant quercetin content in the Japanese blueberry tree makes it a medicinal plant resource with development potential. Through modern extraction and purification techniques, highly purified quercetin can be obtained from the Japanese blueberry tree, and then a medicine with the treatment of various diseases can be developed. The present invention is based on these characteristics of quercetin in the Japanese blueberry tree. Through a chemical synthesis method, it is combined with probenecid to prepare a new compound. This compound not only retains the biological activity of quercetin, but also, through structural modification, enhances its therapeutic effect, particularly showing a significant effect in reducing blood uric acid, blood sugar and serum total cholesterol.

[0006] In the treatment of hyperuricemia, traditional therapeutic drugs often have problems such as large side effects and poor patient compliance.

[0007] Currently, there is a lack of a compound of quercetin derived from blueberry tree and probenecid with fewer side effects, as well as a preparation method and application thereof. Summary of the Invention

[0008] The present invention aims to provide a compound of quercetin derived from blueberry tree and probenecid with small side effects, as well as a preparation method and application thereof.

[0009] In order to solve the problems of the prior art, the present invention provides the following technical solutions: In a first aspect, the present application provides a compound of quercetin derived from the blueberry tree and probenecid;

[0010] In a second aspect, the present application provides a method for preparing a compound of quercetin derived from the blueberry tree and probenecid.

[0011] In a third aspect, the present application provides a pharmaceutical composition for treating hyperuricemia, comprising a compound of quercetin derived from the blueberry tree and probenecid.

[0012] In a fourth aspect, the present application provides a use of a compound of quercetin derived from B. chinensis and probenecid in the preparation of a pharmaceutical composition for treating hyperuricemia.

[0013] The present invention provides a compound of quercetin derived from blueberry and probenecid, the structural formula of the compound of quercetin derived from blueberry and probenecid is shown in formula (I): (Molecular formula: C28 H 27 NO9S):

[0014]

[0015] The present invention provides a method for preparing a compound of quercetin derived from B. chinensis and probenecid, comprising the following steps:

[0016]

[0017] (1) Compound 2, probenecid, was dissolved in 1,4-dioxane, thionyl chloride was added dropwise, and the mixed solution was stirred at 95° C. for 4-8 hours;

[0018] (2) concentrating the stirred mixed solution in vacuo, dissolving the concentrated solid in a certain amount of 1,4-dioxane and adding compound 1 quercetin;

[0019] (3) stirring the mixed solution at 100° C. for 12-24 hours, and cooling to room temperature after the reaction is completed by TLC detection;

[0020] (4) adding triethylamine and water to the mixed solution after stirring and stirring at room temperature for 3-5 hours;

[0021] (5) After the stirring is completed, the mixed solution is concentrated under vacuum, and the concentrated solid is extracted 2-3 times with ethyl acetate and water, and the ethyl acetate is separated and excess water is removed with anhydrous sodium sulfate;

[0022] (6) Compound 3, a compound of quercetin derived from the blueberry tree and probenecid, was obtained by silica gel column chromatography.

[0023] Furthermore, in step (1), the molar volume ratio of compound 2 probenecid to 1,4-dioxane is 0.4:10, and the volume ratio of dichlorothionyl to 1,4-dioxane is 4.5:10.

[0024] Furthermore, in step (2), the molar ratio of quercetin to compound 2 is 1:0.8.

[0025] Furthermore, in step (4), the volume ratio of triethylamine to water is 1:1.

[0026] Furthermore, in step (5), the volume ratio of ethyl acetate to water is 4:1.

[0027] Furthermore, in step (1), the amount of compound 2 probenecid used is 114 mg, 0.4 mmol, the amount of dichlorothionyl used is 4.5 mL, and the amount of 1,4-dioxane used is 10 mL.

[0028] Furthermore, in step (2), the amount of compound 1 quercetin used is 0.5 mmol, and in step (3), the amounts of triethylamine and water used are 4 mL respectively.

[0029] The invention discloses a pharmaceutical composition for treating hyperuricemia, comprising a compound of quercetin derived from blueberry tree and probenecid.

[0030] The invention discloses an application of a compound of quercetin derived from the blueberry tree and probenecid in preparing a pharmaceutical composition for treating hyperuricemia.

[0031] H NMR spectrum of compound 3: 1H NMR (500 MHz, Chloroform-d) δ 8.25–8.19 (m, 2H), 7.90–7.83 (m, 2H), 7.46–7.40 (m, 2H), 7.15 (s, 1H), 6.95 (s, 1H), 6.91–6.86 (m, 2H), 6.73 (d, J = 2.2 Hz, 1H), 6.48 (s, 1H), 3.97 (s, 1H), 3.03 (t, J = 7.4 Hz, 4H), 1.55 (p, J = 7.6 Hz, 4H), 0.90 (t, J = 7.6 Hz, 6H).

[0032] Beneficial Effects: The quercetin-probenecid compound of the present invention improves patient compliance due to its natural plant origin, minimal side effects, and significant therapeutic efficacy. The quercetin-probenecid derivative of the present invention, derived from the Japanese blueberry tree, has enhanced biological activity and therapeutic efficacy through structural modification.

[0033] Compared with the prior art, the present invention has the following advantages: (1) Uric acid-lowering properties: Quercetin derivatives have demonstrated the ability to lower serum uric acid levels, which is helpful in treating hyperuricemia and preventing diseases such as gout. The compounds of the present invention have a significant effect on lowering blood uric acid, blood sugar, serum total cholesterol, and increasing serum total protein levels in experimental mice.

[0034] (3) Anti-inflammatory effect: Since quercetin has anti-inflammatory properties, combining it with probenecid may further enhance this effect. This may help alleviate the inflammation and pain symptoms caused by hyperuricemia such as gout. In addition, quercetin's antioxidant and anti-inflammatory properties also provide potential application prospects for this compound in the treatment of chronic diseases such as cardiovascular disease and diabetes.

[0035] (2) Antioxidant properties: Quercetin, as a polyphenolic flavonol, has antioxidant properties. The structurally modified compound 3 may retain this property, helping to reduce oxidative stress and protect cells from damage.

[0036] (3) Pleiotropic effects: Since humans lack uricase, uric acid is mainly excreted through the kidneys. Compound 3 may promote uric acid excretion, lower serum uric acid levels, thereby reducing uric acid crystals and deposition, and preventing gout attacks.

[0037] (4) Safety: Animal experiments showed no significant side effects during administration of compound 3, demonstrating a favorable safety profile. This provides important preliminary data support for its potential as a drug candidate. The method is reproducible and operable, facilitating the large-scale production of the compound.

[0038] (5) Potential clinical applications: Since compound 3 showed the effects of lowering uric acid, blood glucose and total cholesterol in animal models, it suggests that it may have broad clinical application prospects, especially in the treatment of metabolic syndrome and cardiovascular diseases. DETAILED DESCRIPTION

[0039] In order to make the technical problems, technical solutions and beneficial effects to be solved by this application more clearly understood, the present application is further described in detail below in conjunction with the embodiments. It should be understood that the specific embodiments described herein are only used to explain this application and are not intended to limit this application.

[0040] In this application, the term "and / or" describes the relationship between associated objects, indicating that three possible relationships exist. For example, A and / or B can represent: A exists alone, A and B exist simultaneously, and B exists alone. A and B can be singular or plural. The character " / " generally indicates that the associated objects are in an "or" relationship.

[0041] In this application, "at least one" means one or more, and "more than one" means two or more. "At least one of the following" or similar expressions refers to any combination of these items, including any combination of single items or plural items. For example, "at least one of a, b, or c", or "at least one of a, b, and c" can all mean: a, b, c, ab (i.e., a and b), ac, bc, or abc, where a, b, and c can be single or multiple.

[0042] It should be understood that in the various embodiments of the present application, the size of the serial numbers of the above-mentioned processes does not mean the order of execution. Some or all of the steps can 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 the present application.

[0043] 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", "an", "the" and "the" used in the embodiments of the present application and the appended claims are also intended to include plural forms unless the context clearly indicates otherwise.

[0044] The weights of the relevant components mentioned in the examples of this application may not only refer to the specific content of each component, but also represent the weight ratio between the components. Therefore, as long as the content of the relevant components is proportionally enlarged or reduced according to the examples of this application, it is within the scope disclosed in the examples of this application. Specifically, the mass described in the examples of this application may be a mass unit known in the chemical industry, such as μg, mg, g, kg, etc.

[0045] The terms "first" and "second" are used solely for descriptive purposes to distinguish objects, such as substances, from one another and should not be construed as indicating or implying relative importance or implicitly specifying the quantity of the technical features being referred to. For example, a first XX could also be referred to as a second XX, and similarly, a second XX could also be referred to as a first XX, without departing from the scope of the embodiments of this application. Thus, features defined as "first" or "second" may explicitly or implicitly include one or more of such features.

[0046] Example 1

[0047] The first aspect of the present invention is to provide a compound of quercetin derived from blueberry tree and probenecid, the structural formula of the compound of quercetin derived from blueberry tree and probenecid is shown in formula (I): (Molecular formula: C 28 H 27 NO9S):

[0048]

[0049] The second aspect of the present invention is to provide a method for preparing a compound of quercetin derived from B. chinensis and probenecid, comprising the following steps:

[0050]

[0051] (1) Compound 2 was dissolved in 1,4-dioxane, thionyl chloride was added dropwise, and the mixed solution was stirred at 95°C for 4 hours; the molar volume ratio of compound 2 probenecid to 1,4-dioxane was 0.4:10, and the volume ratio of thionyl chloride to 1,4-dioxane was 4.5:10.

[0052] (2) The stirred mixed solution was concentrated in vacuo, and the concentrated solid was dissolved in a certain amount of 1,4-dioxane and quercetin was added; the molar ratio of quercetin to compound 2 was 1:0.8.

[0053] (3) The mixed solution was stirred at 100°C for 19 hours and cooled to room temperature after the reaction was completed by TLC detection;

[0054] (4) Add triethylamine and water to the mixed solution after stirring, and stir at room temperature for 4 hours; the volume ratio of triethylamine to water is 1:1.

[0055] (5) After stirring, the mixed solution was concentrated under vacuum, and the concentrated solid was extracted 2-3 times with ethyl acetate and water, and the ethyl acetate was separated and excess water was removed with anhydrous sodium sulfate; the volume ratio of ethyl acetate to water was 4:1.

[0056] (6) Compound 3, a compound of quercetin derived from the blueberry tree and probenecid, was obtained by silica gel column chromatography.

[0057] In some embodiments, in step (1), Compound 2 probenecid is dissolved in 1,4-dioxane, thionyl chloride is added dropwise, and the mixed solution is stirred at 95° C. for 5 hours.

[0058] In some embodiments, Compound 2 probenecid is dissolved in 1,4-dioxane, thionyl chloride is added dropwise, and the mixed solution is stirred at 95° C. for 8 hours.

[0059] In some embodiments, in step (3), the mixed solution is stirred at 100° C. for 24 hours, and cooled to room temperature after the reaction is completed as detected by TLC.

[0060] In some embodiments, in step (3), the mixed solution is stirred at 100° C. for 12 hours, and cooled to room temperature after the reaction is completed as detected by TLC.

[0061] In some embodiments, in step (4), triethylamine and water are added to the mixed solution after stirring, and then stirred at room temperature for 5 hours; the volume ratio of triethylamine to water is 1:1.

[0062] In some embodiments, in step (4), triethylamine and water are added to the mixed solution after stirring, and then stirred at room temperature for 3 hours; the volume ratio of triethylamine to water is 1:1.

[0063] In some embodiments, in step (1), the amount of compound 2 probenecid used is 114 mg, 0.4 mmol, the amount of dichlorothionyl used is 4.5 mL, and the amount of 1,4-dioxane used is 10 mL.

[0064] In some embodiments, in step (2), the amount of compound 1 quercetin used is 0.5 mmol, and in step (3), the amount of triethylamine and water used is 4 mL respectively.

[0065] The third aspect of the present invention is to provide a pharmaceutical composition for treating hyperuricemia, comprising a compound of quercetin derived from the blueberry tree and probenecid.

[0066] The fourth aspect of the present invention is to provide a use of a compound of quercetin derived from B. chinensis and probenecid in the preparation of a pharmaceutical composition for treating hyperuricemia.

[0067] H NMR spectrum of compound 3: 1H NMR (500 MHz, Chloroform-d) δ 8.25–8.19 (m, 2H), 7.90–7.83 (m, 2H), 7.46–7.40 (m, 2H), 7.15 (s, 1H), 6.95 (s, 1H), 6.91–6.86 (m, 2H), 6.73 (d, J = 2.2 Hz, 1H), 6.48 (s, 1H), 3.97 (s, 1H), 3.03 (t, J = 7.4 Hz, 4H), 1.55 (p, J = 7.6 Hz, 4H), 0.90 (t, J = 7.6 Hz, 6H).

[0068] Example 1

[0069] The present invention provides a compound of quercetin derived from blueberry and probenecid, the structural formula of the compound of quercetin derived from blueberry and probenecid is shown in formula (I): (Molecular formula: C 28 H 27 NO9S):

[0070]

[0071] The present invention provides a method for preparing a compound of quercetin derived from B. chinensis and probenecid, comprising the following steps:

[0072]

[0073] (1) Compound 2 (114 mg, 0.4 mmol) was dissolved in 1,4-dioxane (10 mL), and 4.5 mL of thionyl chloride was added dropwise. The mixed solution was stirred at 95° C. for 4 hours, and the stirred mixed solution was concentrated in vacuo;

[0074] (2) The concentrated solid was dissolved in 10 mL of 1,4-dioxane and compound 1 quercetin (143 mg, 0.5 mmol) was added. The mixed solution was stirred at 100° C. for 24 hours. After the reaction was completed by TLC, the mixture was cooled to room temperature. 4 mL of triethylamine and 4 mL of water were added to the mixed solution after stirring, and the mixture was stirred at room temperature for 4 hours.

[0075] (3) After stirring, the mixed solution was concentrated in vacuo, and the concentrated solid was extracted 2-3 times with ethyl acetate (200 mL) and water (50 mL). The ethyl acetate was separated and the excess water was removed with anhydrous sodium sulfate. After silica gel column chromatography, compound 3 (183 mg, 82%) of quercetin derived from blueberry tree and probenecid was obtained.

[0076] H NMR spectrum of compound 3: 1H NMR (500 MHz, Chloroform-d) δ 8.25–8.19 (m, 2H), 7.90–7.83 (m, 2H), 7.46–7.40 (m, 2H), 7.15 (s, 1H), 6.95 (s, 1H), 6.91–6.86 (m, 2H), 6.73 (d, J = 2.2 Hz, 1H), 6.48 (s, 1H), 3.97 (s, 1H), 3.03 (t, J = 7.4 Hz, 4H), 1.55 (p, J = 7.6 Hz, 4H), 0.90 (t, J = 7.6 Hz, 6H).

[0077] Example 2

[0078] The difference between Example 2 and Example 1 is that:

[0079] The present invention provides a method for preparing a compound of quercetin derived from B. chinensis and probenecid, comprising the following steps:

[0080]

[0081] In step (1), compound 2 probenecid (114 mg, 0.4 mmol) was dissolved in 1,4-dioxane (10 mL), 4.5 mL of thionyl chloride was added dropwise, and the mixed solution was stirred at 95° C. for 8 hours, and the stirred mixed solution was concentrated in vacuo;

[0082] In step (2), the concentrated solid was dissolved in 10 mL of 1,4-dioxane and compound 1 quercetin (143 mg, 0.5 mmol) was added. The mixed solution was stirred at 100° C. for 12 hours. After the reaction was completed by TLC, the mixture was cooled to room temperature. 4 mL of triethylamine and 4 mL of water were added to the mixed solution after stirring, and then stirred at room temperature for 5 hours.

[0083] Example 3

[0084] The difference between Example 3 and Example 1 is that:

[0085] The present invention provides a method for preparing a compound of quercetin derived from B. chinensis and probenecid, comprising the following steps:

[0086]

[0087] In step (1), compound 2 probenecid (114 mg, 0.4 mmol) was dissolved in 1,4-dioxane (10 mL), 4.5 mL of thionyl chloride was added dropwise, and the mixed solution was stirred at 95° C. for 6 hours, and the stirred mixed solution was concentrated in vacuo;

[0088] In step (2), the concentrated solid was dissolved in 10 mL of 1,4-dioxane and compound 1 quercetin (143 mg, 0.5 mmol) was added. The mixed solution was stirred at 100° C. for 20 hours. After the reaction was completed by TLC, the mixture was cooled to room temperature. 4 mL of triethylamine and 4 mL of water were added to the mixed solution after stirring, and then stirred at room temperature for 3 hours.

[0089] Test Example 1

[0090] Results of blood uric acid determination in experimental mice

[0091] Sixty male rats were randomly divided into 6 groups, 10 rats in each group: positive group (benzbromarone), normal saline group, CMC model group, high, medium and low dose groups of compound 3, and control group.

[0092] Reagent preparation:

[0093] (1) Preparation of CMC-Na solution (0.8%): Weigh 2.4 g of CMC-Na, first adjust it to a lake with a small amount of purified water, then dilute it to 300 ml with purified water, pour it into a beaker and boil it to completely dissolve it, then pour it into a volumetric flask and make up to 300 ml with purified water.

[0094] (2) Preparation of 50 mg / ml hypoxanthine: Weigh 1 g hypoxanthine and dissolve it in 20 ml CMC-Na solution.

[0095] (3) Preparation of 0.5 mg / ml benzbromarone: Weigh 20 mg of benzbromarone and dissolve it in 40 ml of CMC-Na solution to a concentration of 0.5 mg / ml.

[0096] (4) Preparation of the pseudo-positive drug compound 3: Compound 3 (1 g) was accurately weighed and prepared into 0.5 mg / mL, 1.0 mg / mL, and 2.0 mg / mL dose test solutions using the above CMC-Na solution. Each group of test animals was administered once a day (weighed before administration each day) for 7 consecutive days. The experimental method for each animal group was as follows: Animals in groups 1, 3, 4, 5, 6, and 7 were administered intragastrically (ig), and CMC-Na was administered intragastrically (ig) to the model group 2. The specific results are as follows: The blood uric acid levels of the different administration groups are shown in Table 1:

[0097] Table 1

[0098]

[0099] In the experimental mouse model, compound 3 demonstrated the ability to significantly reduce blood uric acid levels. Different doses of compound 3 significantly reduced blood uric acid levels in the model group, and the uric acid-lowering effect became more pronounced with increasing doses.

[0100] Test Example 2

[0101] Blood glucose test results of experimental mice

[0102] The test showed that low, medium and high doses of compound 3 all had different degrees of effect on reducing the blood glucose levels of hyperuricemia mice, while the positive control benzbromarone group had no significant effect (Table 2). The blood glucose levels of different dosing groups are shown in Table 2:

[0103] Table 2

[0104]

[0105] Hyperuricemia is associated with a variety of chronic diseases. Compound 3 can lower blood uric acid levels by regulating blood uric acid levels, which may help improve or prevent complications such as hypertension, diabetes, metabolic syndrome, and kidney and cardiovascular diseases associated with hyperuricemia.

[0106] Test Example 3

[0107] Results of total cholesterol determination in experimental mice

[0108] After testing, low, medium and high doses of compound 3 all had different degrees of effect on reducing the serum total cholesterol level of hyperuricemia mice (Table 3). The serum total cholesterol levels of different dosing groups are shown in Table 3:

[0109] Table 3

[0110]

[0111]

[0112] The experimental results showed that compound 3 could have a positive effect on blood glucose and serum total cholesterol levels, showing a potential therapeutic effect on metabolic syndrome.

[0113] Test Example 4

[0114] Results of total protein determination in experimental mice

[0115] The test showed that the total serum protein level in hyperuricemia mice decreased significantly. Low, medium, and high doses of compound 3 all had varying degrees of effect on the elevated serum total protein level in hyperuricemia mice. The serum total protein level in the experimental group was very close to the normal level of the saline group (Table 4). The serum total protein levels in different dosing groups are shown in Table 4:

[0116] Table 4

[0117]

[0118]

[0119] As can be seen from Tables 1 to 4, high doses of Compound 3 can significantly reduce blood uric acid levels. Low and medium doses of Compound 3 are more effective in treating hyperuricemia than the existing hyperuricemia treatment drug benzbromarone. Furthermore, Compound 3 is superior to benzbromarone in lowering blood sugar and cholesterol. In summary, Compound 3 has a certain therapeutic effect on hyperuricemia.

[0120] The basic principles, main features and advantages of the present invention are shown and described above. It should be understood by those skilled in the art that the present invention is not limited to the above embodiments. The above embodiments and descriptions are merely illustrative of the principles of the present invention. Various changes and improvements may be made to the present invention without departing from the spirit and scope of the present invention. The scope of protection claimed in the present invention is defined by the appended claims, the description and their equivalents.

Claims

1. A compound of quercetin derived from B. chinensis and probenecid, characterized in that: The structural formula of the compound of quercetin derived from the blueberry tree and probenecid is shown in formula (I):

2. The method for preparing the compound of quercetin from the blueberry tree and probenecid according to claim 1, wherein The steps include: (1) Compound 2, probenecid, was dissolved in 1,4-dioxane, thionyl chloride was added dropwise, and the mixed solution was stirred at 95° C. for 4-8 hours; (2) concentrating the stirred mixed solution in vacuo, dissolving the concentrated solid in 1,4-dioxane, and adding compound 1 quercetin; (3) stirring the mixed solution at 100° C. for 12-24 hours, and cooling to room temperature after the reaction is completed by TLC detection; (4) adding triethylamine and water to the mixed solution after stirring and stirring at room temperature for 3-5 hours; (5) After the stirring is completed, the mixed solution is concentrated under vacuum, and the concentrated solid is extracted 2-3 times with ethyl acetate and water, and the ethyl acetate is separated and excess water is removed with anhydrous sodium sulfate; (6) Compound 3, a compound of quercetin derived from the blueberry tree and probenecid, was obtained by silica gel column chromatography.

3. The method for preparing a compound of quercetin from Japanese blueberry tree with probenecid according to claim 2, wherein: In step (1), the molar volume ratio of the compound 2, probenecid, to 1,4-dioxane is 0.4:10, and the volume ratio of thionyl chloride to 1,4-dioxane is 4.5:

10.

4. The method for preparing a compound of quercetin from Japanese blueberry tree with probenecid according to claim 2, wherein: In step (2), the molar ratio of quercetin to compound 2 probenecid is 1:0.

8.

5. The method for preparing a compound of quercetin from Japanese blueberry tree with probenecid according to claim 2, wherein: In step (4), the volume ratio of triethylamine to water is 1:

1.

6. The method for preparing the compound of quercetin from B. chinensis L. and probenecid according to claim 2, wherein: In step (5), the volume ratio of ethyl acetate to water is 4:

1.

7. The method for preparing a compound of quercetin from B. chinensis L. and probenecid according to claim 2, wherein: In step (1), the amount of compound 2, probenecid, is 114 mg, 0.4 mmol, the amount of thionyl chloride is 4.5 mL, and the amount of 1,4-dioxane is 10 mL.

8. The method for preparing the compound of quercetin derived from B. chinensis and probenecid according to claim 2, wherein: In step (2), the amount of compound 1 quercetin used is 0.5 mmol, and in step (3), the amounts of triethylamine and water used are 4 mL respectively.

9. A pharmaceutical composition for treating hyperuricemia, characterized in that A compound comprising the quercetin derived from the blueberry tree according to claim 1 and probenecid.

10. Use of the compound of quercetin derived from B. chinensis and probenecid according to claim 1 in preparing a pharmaceutical composition for treating hyperuricemia.

Images