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Method for preparing hesperetin dihydrochalcone glucoside by immobilized enzyme method

A technology of hesperetin dihydrochalcone and hesperidin dihydrochalcone, which is applied in the direction of immobilized enzymes, biochemical equipment and methods, glycosylases, etc., can solve the difficulty of separation and purification of the target product, difficult Realize the problems of industrialized production, HSD hydrolysis by-products, etc., to achieve the effect of low cost, good stability, and reduced energy consumption

Pending Publication Date: 2022-01-04
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned technology has the following problems: (1) the poor water solubility of the substrate HSD affects the efficiency of enzymolysis, and the product after enzymolysis needs to be further separated and purified, and the yield is low; (2) there are many by-products of HSD hydrolysis, including hesperetin, rutinose, Rhamnose, glucose, and HMG make the separation and purification of the target product difficult, and produce a large amount of industrial wastewater that needs to be treated
Therefore, above-mentioned two kinds of methods are all difficult to realize suitability for industrialized production

Method used

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  • Method for preparing hesperetin dihydrochalcone glucoside by immobilized enzyme method
  • Method for preparing hesperetin dihydrochalcone glucoside by immobilized enzyme method
  • Method for preparing hesperetin dihydrochalcone glucoside by immobilized enzyme method

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Experimental program
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Effect test

Embodiment 1

[0049] Such as figure 1 As shown, the immobilized enzymatic conversion method for realizing hesperidin to hesperetin dihydrochalcone glucoside is mainly divided into the following three steps: (1) catalytic hydrogenation of hesperidin; (2) immobilized enzyme Preparation; (3) Enzymatic hydrolysis of the hydrogenation product of hesperidin to synthesize hesperetin dihydrochalcone glucoside. The specific operation is:

[0050] (1) Accurately weigh 10 g of hesperidin, 30 g of sodium hydroxide, and 5 g of Raney nickel. Dissolve in 100mL deionized water, add the solution to the reaction kettle, and pass N 2 , and then evacuate and feed N 2 , and then evacuate and then feed H 2 , repeated into H 2 React for about 1 to 6 hours until the H in the reactor 2When the pressure does not change any more, the reaction is terminated, the solution is transferred to a beaker, and 37% concentrated hydrochloric acid is added to adjust the pH to about 3. Take 1mL of the solution and filter i...

Embodiment 2

[0054] (1) Accurately weigh 50 g of hesperidin, 15 g of sodium hydroxide, and 25 g of Raney nickel. Dissolve in 500mL deionized water, add the solution to the reaction kettle, and pass N 2 , and then evacuate and feed N 2 , and then evacuate and then feed H 2 , repeated into H 2 React for about 1 to 6 hours until the H in the reactor 2 The pressure does not change anymore, the reaction is terminated, the solution is transferred to a beaker, and concentrated hydrochloric acid is added to adjust the pH to about 3. Take 1mL of the solution and filter it with a 0.22μm microporous membrane. Take 20 μL of the filtered sample solution and directly inject it into the HPLC system to analyze the product hesperidin dihydrochalcone.

[0055] (2) Take 100g MIL-101(Cr) and disperse it in water evenly, and add 200g FeCl 3 ·6H 2 O and 100g FeSO 4 ·7H 2 O, after stirring and dissolving, raise the temperature to 85°C and continue to stir for 30 minutes, add ammonia dropwise to adjust t...

Embodiment 3

[0058] (1) Accurately weigh 30 g of hesperidin, 20 g of sodium hydroxide, and 10 g of Raney nickel. Dissolve in 300mL deionized water, add the solution to the reaction kettle, and pass N 2 , and then evacuate and feed N 2 , and then evacuate and then feed H 2 , repeated into H 2 React for about 1 to 6 hours until the H in the reactor 2 The pressure does not change anymore, the reaction is terminated, the solution is transferred to a beaker, and concentrated hydrochloric acid is added to adjust the pH to about 3. Take 1mL of the solution and filter it with a 0.22μm microporous membrane. Take 20 μL of the filtered sample solution and directly inject it into the HPLC system to analyze the product hesperidin dihydrochalcone.

[0059] (2) Disperse 80g MIL-101(Cr) in water evenly, and add 300g FeCl 3 ·6H 2 O and 150gFeSO 4 ·7H 2 O, after stirring and dissolving, raise the temperature to 65°C and continue stirring for 30 minutes, add ammonia water dropwise to adjust the pH t...

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Abstract

The invention discloses a method for preparing hesperetin dihydrochalcone glucoside by an immobilized enzyme method, which comprises the following steps: S1, dissolving hesperidin, sodium hydroxide and a catalyst in water, performing repeated vacuumizing and then introducing N2, performing repeated vacuumizing and then introducing H2, reacting until the pressure of H2 in a reaction kettle is not changed any more, and terminating the reaction, and adjusting the pH value of reaction liquid to 2.5-3.5 to obtain hesperidin dihydrochalcone; S2, mixing a magnetic metal-organic framework, rhamnosidase and a cross-linking agent, and reacting to obtain immobilized rhamnosidase; and S3, taking the hesperidin dihydrochalcone and the immobilized rhamnosidase, adding the hesperidin dihydrochalcone and the immobilized rhamnosidase into a PBS with a pH value of 1-7, and reacting to obtain the hesperetin dihydrochalcone glucoside. The method can be used for efficient and green production of HMGDC, and compared with a traditional method, the method has high conversion rate, has no by-products, is green and environment friendly, has a simple process, is convenient to operate, is efficient and energy-saving and has excellent industrial utilization value.

Description

technical field [0001] The invention relates to the field of food science and engineering, in particular to a method for preparing hesperetin dihydrochalcone glucoside by an immobilized enzyme method. Background technique [0002] Hesperetin dihydrochalcone glucoside (HMGDC, CAS No.: 21940-36-3) is a low-calorie, non-nutritive sweetener whose sweetness is about 300-500 times that of sucrose. Pure, without bitterness and aftertaste, and has a fruity flavor. Pharmacological and metabolic studies have shown that HMGDC does not accumulate in tissues and is a substance that has a therapeutic effect on diabetic patients. In recent years, there have been a large number of reports on the application of HMGDC in the fields of food, medicine, and cosmetics, especially in the United States and Japan. [0003] There are two main methods for the synthesis of HMGDC reported in the research: one is the enzymatic method, that is, hesperidin (HSD, CAS number: 520-26-3) is enzymatically hyd...

Claims

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Application Information

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IPC IPC(8): C12N11/089C12N9/24C12P19/44C12P19/14
CPCC12N11/089C12N9/2402C12P19/44C12P19/14C12Y302/0104
Inventor 朱思明王春庆
Owner SOUTH CHINA UNIV OF TECH
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