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Method for improving water solubility and bioavailability of hesperidin

A hesperidin and water-soluble technology, which is applied in the field of improving the water-solubility and bioavailability of hesperidin, can solve the problems of unsuitable preparation process, difficulty in cyclodextrin embedding, and inability to remove the solvent, so as to overcome the inability to remove the solvent , Improve oral bioavailability and avoid the use of toxic reagents

Active Publication Date: 2021-03-19
GUANGZHOU HANFANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since hesperidin is almost insoluble in water and also insoluble in conventional organic solvents, it brings difficulties for cyclodextrin embedding
The research results show that hesperidin dissolves best in dimethyl sulfoxide (DMSO), pyridine, and N,N-dimethylformamide (DNF). However, the above three solvents can dissolve hesperidin The preparation of cyclodextrin embeddings, however, has serious defects that the solvent cannot be removed, and DMSO, DMF, and pyridine are highly toxic, and are not suitable for the preparation process of drug development
[0005] In addition, studies have shown that hesperidin is easily soluble in alkaline solutions, and sodium hydroxide solution was used to prepare hesperidin cyclodextrin embeddings. However, the dissolution of hesperidin in alkaline environments is due to the formation of The by-product of its ring opening, the structure is destroyed
After consulting the published technical literature reports, there is no similar technical report on using cyclodextrin to encapsulate hesperidin without destroying the structure of hesperidin

Method used

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  • Method for improving water solubility and bioavailability of hesperidin
  • Method for improving water solubility and bioavailability of hesperidin
  • Method for improving water solubility and bioavailability of hesperidin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Weigh 10g of β-cyclodextrin, add 100mL of purified water, heat and stir at 50°C to completely dissolve the cyclodextrin, adjust the pH to 11.5 with triethylamine, add 5g of hesperidin raw material (such as figure 1 shown), maintain 50°C and continue stirring to completely dissolve the hesperidin. Stirring was continued at 50°C for 3 hours for full embedding. After the embedding was completed, it was dried under reduced pressure to remove part of triethylamine, and then spray-dried to obtain a hesperidin-β-cyclodextrin sample. Finally, 14.74 g of the product was obtained with a yield of 98.27%. The solubility of hesperidin before and after embedding was measured, and its solubility in water, pH 1.2, pH 4.5, and pH 6.8 was measured. Determine its water partition coefficient. The results showed that the solubility of hesperidin in water increased from 0.0165 mg / mL before inclusion to 5.9533 mg / mL after inclusion by cyclodextrin.

[0044] Table 1 Example 1 Hesperidin bef...

Embodiment 2

[0047] Weigh 25g of HP-β-cyclodextrin, add 200mL of purified water, heat and stir at 60°C to completely dissolve the cyclodextrin, adjust the pH to 11.8 with diethylamine, add 10g of hesperidin raw material (such as figure 1shown), maintain 60°C and continue stirring to completely dissolve the hesperidin. And continue stirring at 60° C. for 2 hours to fully embed. After the embedding is completed, spray-dry to obtain a hesperidin-β-cyclodextrin sample. Finally, 34.12 g of the product was obtained with a yield of 97.49%. The solubility of hesperidin before and after embedding was measured, and its solubility in water, pH 1.2, pH 4.5, and pH 6.8 was measured (37°C, shaking for 24 hours). Determine its water partition coefficient. The results showed that the solubility of hesperidin in water increased from 0.0165mg / mL before inclusion to 6.3327mg / mL after inclusion by HP-β-cyclodextrin.

[0048] Table 2 Example 2 Hesperidin before and after embedding solubility and oil-water p...

Embodiment 3

[0051] Weigh 30g of α-cyclodextrin, add 500mL of purified water, heat and stir at 40°C to completely dissolve the cyclodextrin, adjust the pH to 11.96 with ethylenediamine, add 6g of hesperidin raw material (such as figure 1 shown), maintain 40°C and continue stirring to completely dissolve the hesperidin. And continue to stir at 40°C for 6 hours to fully embed. After the embedding is completed, part of the ethylenediamine is removed by drying under reduced pressure, and then the loose hesperidin-α-cyclodextrin inclusion complex is obtained by freeze-drying. Finally, 44.27 g of the product was obtained with a yield of 98.38%. The solubility of hesperidin before and after embedding was measured, and its solubility in water, pH 1.2, pH 4.5, and pH 6.8 was measured (37°C, shaking for 24 hours). Determine its water partition coefficient. The results showed that after α-cyclodextrin inclusion, the solubility of hesperidin in water increased from 0.0165 mg / mL before inclusion to 4...

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Abstract

The invention belongs to the field of pharmaceutical preparations, and discloses a method for improving the water solubility and bioavailability of hesperidin. A cyclodextrin embedding method is adopted, an alkalic system is used for solubilization, and the hesperidin is embedded in an inner cavity of cyclodextrin to prepare a hesperidin-cyclodextrin embedded object, so that the water solubility of the hesperidin is obviously improved, meanwhile the side reaction of hesperidin ring opening caused by the conventional technical means is avoided, the structural integrity of the hesperidin is ensured, and the oral bioavailability of the hesperidin is remarkably improved.

Description

technical field [0001] The invention belongs to the field of pharmaceutical preparations, and in particular relates to a method for improving the water solubility and bioavailability of hesperidin. Background technique [0002] Hesperidin, also known as hesperidin and hesperidin, is a glycoside formed by hesperetin and rutinose, and is a dihydroflavone derivative. It is widely found in legumes, Labiatae, Disciformes, and Rutaceae citrus plants. It has the functions of maintaining normal osmotic pressure of blood vessels, reducing vascular fragility, enhancing capillary toughness, and shortening bleeding time. Hesperidin not only has the effect of lowering cholesterol in the human body, but also has the effect of anti-virus and improving immunity. [0003] Hesperidin has poor water solubility, which greatly limits its clinical application. The structural formula of hesperidin is as figure 1 shown. In order to improve its solubility in water, some scholars have used glycos...

Claims

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Application Information

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IPC IPC(8): A61K47/69A61K47/18A61K31/7048A61P3/06A61P31/12A61P37/04A61P29/00A61P39/06A61P31/04A61P31/10A61P35/00A61P39/00A61P9/00A61P7/04A61P9/14
CPCA61K47/6951A61K47/18A61K31/7048A61P3/06A61P31/12A61P37/04A61P29/00A61P39/06A61P31/04A61P31/10A61P35/00A61P39/00A61P9/00A61P7/04A61P9/14
Inventor 袁诚许文东牛亚伟唐顺之蔡鸿飞杨阳李松涛毛禹康李咏华李遥傅玉萍牟肖男
Owner GUANGZHOU HANFANG PHARMA
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