Production of isoquercetin derivative used for scavenging free radicals

A technology of isoquercetin and its derivatives, which is applied in the field of preparation of isoquercetin derivatives, can solve the problems of inconspicuous effect, low solubility of isoquercetin, and low bioavailability of isoquercetin, and increase the Efficacy, increased solubility, improved bioavailability

Inactive Publication Date: 2020-05-29
张才来
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, due to the low solubility of isoquercetin in water and buffer solution, the bioavailability of isoquercetin is low and the effect is not obvious

Method used

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  • Production of isoquercetin derivative used for scavenging free radicals
  • Production of isoquercetin derivative used for scavenging free radicals
  • Production of isoquercetin derivative used for scavenging free radicals

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1 Preparation of 6-prenyl substituted isoquercetin derivatives

[0043] 1) React 2 g of isoquercetin, 3-4 equivalents of acetic anhydride, and 1-2 equivalents of pyridine at 100-140° C. for 15 hours, and the product is IIIa with a yield of 90.5%;

[0044] 2) 2 g of IIIa, 3 times of thiophenol, 0.1-1 times of imidazole, and N-methylpyrrolidone as a solvent were reacted at 0°C for 4-20 hours, and the product was IIIb with a yield of 85.1%;

[0045] 3) React Ⅲb with 2-4 times (2-methylbut-3-en-2-yl) isobutyl carbonate, triphenylphosphine as catalyst, in THF solution at -5-0°C for 12h to obtain Ⅲc The yield is 92.1%;

[0046] 4) 2 g of IIIc was added with 2 times equivalent of acetic anhydride and 10 times of acetic anhydride, and refluxed in methanol for 24 hours to obtain product IIId with a yield of 88.0%.

[0047]

Embodiment 2

[0048] Example 2 Glycosylation of prenylated isoquercetin derivatives

[0049] Using 6-prenyl substituted isoquercetin derivatives as raw materials, the reaction buffer is disodium hydrogen phosphate-sodium citrate buffer with a mass fraction of 0.05%, the pH of the buffer is 8, and the reaction temperature is 65°C , The reaction time is controlled for 18-24 hours. Glucosyltransferase is added into the reaction system, and the mass fraction of the enzyme is 25-30% of the input 6-prenyl substituted isoquercetin derivative to obtain the isoquercetin derivative. In the reaction system, the molar yield of the isoquercetin derivative is 95.8%. After the reaction is completed, the isoquercetin derivative is obtained by suction filtration and drying. HPLC of isoquercetin derivatives see image 3 .

Embodiment 3

[0050] Solubility and dissolution rate determination of embodiment 3 isoquercetin derivatives

[0051] 1. Determination of Solubility

[0052] The solubility of the compound directly affects the application of the drug in the solution system and cell system. Because isoquercetin derivatives are stable in aqueous solution, we use ultraviolet spectrophotometry to determine the solubility value of saturated isoquercetin aqueous solution. In this experiment, 10mg, 50mg, 100mg, 200mg, and 1000mg of phloretin were accurately measured, placed in a 100mL volumetric flask, diluted to the mark with DMSO, and shaken to obtain a series of concentrations of 0.1mg / mL, 0.5mg / mL, 1mg / mL, 2mg / mL, 10mg / mL standard solutions of phloretin were analyzed by HPLC, the characteristic peaks in the 283nm interval were integrated, and the peak areas were recorded. Take the concentration of phloretin as the ordinate, and the peak area as the abscissa to draw a graph, and perform linear regression.

[...

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Abstract

The invention provides production of an isoquercetin derivative used for scavenging free radicals. A production method of the isoquercetin derivative comprises the steps of connecting a 5' position ofisoquercetin with isoprene, and then treating prenylisoquercetin by means of biological enzymes to produce the isoquercetin derivative with high purity, high solubility and high bioavailability. Theisoquercetin derivative has effects, 3-5 times those of isoquercetin, in the aspects of scavenging of free radicals, anti-inflammation and bacteriostasis, and has effects, better than those of the isoquercetin, in the aspects of cardiovascular protection, blood fat reduction and blood pressure reduction.

Description

technical field [0001] The invention relates to the preparation of an isoquercetin derivative used for scavenging free radicals, as well as for scavenging free radicals, cardiovascular protection and lowering blood fat, and belongs to the field of biomedicine. [0002] technical background [0003] Current research shows that isoquercetin can be used as an antioxidant for its specific properties, and it has a wide range of applications in slowing down human aging and disease occurrence. Isoquercetin has higher bioactivity and bioavailability than rutin and quercetin in terms of anti-oxidation, lowering blood pressure, anti-inflammation, anti-cancer and inhibition of platelet aggregation, and is more effective in delaying human aging play an important role in the prevention and control of diseases. The results of relevant pharmacological experiments show that the medicinal value of isoquercetin is extremely high, and its pharmacological activity is much higher than that of ru...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P19/60C07D311/30A61K31/7048A61P39/06A61P29/00A61P31/00A61P3/06A61P9/00A61P9/12A61P9/14A61P9/08
CPCA61K31/7048A61P3/06A61P9/00A61P9/08A61P9/12A61P9/14A61P29/00A61P31/00A61P39/06C07D311/30C12P19/60
Inventor 张才来
Owner 张才来
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