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Preparation of hesperetin derivative for strengthening bones

A technology of hesperetin and derivatives, which is applied in the field of preparation of hesperetin derivatives, can solve the problems of insignificant effect, low bioavailability and low solubility of hesperidin, and achieve poor solubility and improve bioavailability , high biological activity effect

Inactive Publication Date: 2020-06-05
张才来
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low solubility of hesperidin in water and buffer solution, the bioavailability of hesperidin is low and the effect is not obvious

Method used

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  • Preparation of hesperetin derivative for strengthening bones
  • Preparation of hesperetin derivative for strengthening bones
  • Preparation of hesperetin derivative for strengthening bones

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 16

[0041] Example 1 6,8-diprenyl substituted hesperetin derivatives (Ⅱ d ) preparation

[0042] 1) React 2g of hesperetin, 2.2 equivalents of acetic anhydride, and 2 to 4 times of piperidine at 100 to 140°C for 8 hours, and the product is II a , the yield is 91.0%;

[0043] 2) will Ⅱ a 2g and 1 to 5 times the amount of thiophenol, 0.4 times the amount of imidazole, using N-methylpyrrolidone as the solvent, reacting at 0°C for 5-10 hours, the product is II b , the yield is 85.9%;

[0044] 3) will Ⅱ b And 4 to 5 times of (2-methylbut-3-en-2-yl) isobutyl carbonate, triphenylphosphine as a catalyst, in THF solution, react at -4 to 0°C for 12h to obtain II c , the yield is 83.0%;

[0045] 4) will Ⅱ c Add 2 times the equivalent of acetic anhydride and 8 times the ammonium acetate to 2 g, and reflux in methanol for 20 hours to obtain the product 6,8-diprenyl substituted hesperetin derivative II d , the yield was 91.3%.

[0046] The structural formula of the step of its reacti...

Embodiment 2

[0048] Glycosylation of Example 2 Hesperetin Derivatives

[0049] Using 6,8-diprenyl substituted hesperetin derivatives as raw materials, the reaction buffer is dipotassium hydrogen phosphate-potassium citrate buffer with a mass fraction of 0.05%, the pH of the buffer is 8, and the reaction temperature is 60°C, the reaction time is controlled for 18-24 hours. Add glucosyltransferase to the reaction system, the mass fraction of the enzyme is 25-30% of the input 6,8-diprenyl substituted hesperetin derivatives to obtain hesperetin derivatives, in the reaction system , the molar yield of hesperetin derivatives is 94.1%. After the reaction is completed, the hesperetin derivatives are dried by suction filtration, and the HPLC of hesperetin derivatives is shown in image 3 .

Embodiment 3

[0050] Embodiment 3 Solubility determination of hesperetin derivatives

[0051] Then add excess hesperetin derivatives into 2mL of water phase, place it on a 25±1°C constant temperature shaker for 72h, take it out, transfer it to a centrifuge tube, centrifuge at 8000r / min for 15min, and take the supernatant with 0.45 The μm microporous membrane was filtered, and diluted with methanol to within the linear range, and the solubility of hesperetin derivatives in water was determined by HPLC. The result is as figure 1 .

[0052] The results showed that the solubility of hesperetin derivatives was about 230 times that of hesperetin.

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Abstract

The invention provides preparation and application of a hesperetin derivative for strengthening bones and belongs to the field of biomedicines. According to the hesperetin derivative provided by the invention, an isoprenyl group is connected to a mother ring of hesperetin, and then, a glycosyl group is connected by using a bio-enzyme, so that the hesperetin derivative with high purity and high bioavailability can be prepared. The hesperetin derivative provided by the invention has the characteristics of high solubility and high bioactivity; and effects in aspects of controlling and treating osteoporosis and promoting blood circulation are also superior to those of hesperetin.

Description

technical field [0001] The invention relates to the preparation of a hesperetin derivative for bone strengthening, belonging to the field of biomedicine. [0002] technical background [0003] Osteoporosis is a systemic disease characterized by damage to the microstructure of bone tissue, loss of bone mineral composition and bone matrix, bone thinning, decreased number of trabecular bone, increased bone fragility, and increased risk of fracture. Diseases of bone metabolism disorders. When hormone levels in the body decrease, bone resorption increases and bone formation decreases. Therefore, there is currently no effective regimen for treating the symptoms of osteoporosis. [0004] Hesperidin in citrus has anti-cancer effects, treatment of osteoporosis, anti-oxidation, promotion of blood circulation, improvement of cardiovascular and cerebrovascular circulation and sleep improvement, etc., and has high economic and medicinal value. Because of the low solubility of hesperidi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60C12P19/18C07D311/32A61K31/7048A61P19/10A61P9/14
CPCA61K31/7048A61P9/14A61P19/10C07D311/32C12P19/18C12P19/605
Inventor 张才来
Owner 张才来
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