Method for preparing genipin

A technology of geniposide and glycoside hydrolase, which is applied in the direction of sustainable manufacturing/processing, immobilized on/in organic carriers, chemical industry, etc., and can solve the problem of industrial production of geniposide, β-glucose, etc. Problems such as high price of glucosidase and high dosage of β-glucosidase achieve the effect of high market price, difficulty in obtaining and reducing the generation of by-products

Inactive Publication Date: 2011-08-10
SHANGHAI UNIV OF T C M
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there are some problems in this method: first, geniposide has poor stability in water, and it is very easy to open the ring to form a dialdehyde structure (as shown in formula 3), and reacting in water for a long time will affect its yield; secondly, Genipogenin also cross-links with amino acids and proteins to generate gardenia blue pigment (as shown in formula 4), and β-glucosidase itself is a protein, so the enzyme will interact with the product during the reacti...

Method used

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  • Method for preparing genipin
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  • Method for preparing genipin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] The reaction of free-glucosidase single-phase system hydrolyzing geniposide, the experimental operation steps are as follows:

[0039] (1) Take 0.5 g of geniposide with a purity of 90%, put it in a round bottom flask, add 50 U of free β-glucosidase, 50 ml of acetic acid-sodium acetate buffer solution (pH 4.5), heat and stir in a water bath at 55°C for 2 hours.

[0040] (2) The reaction solution was extracted three times with 50 ml of ethyl acetate, and the ethyl acetate extracts were combined.

[0041] (3) Add an appropriate amount of anhydrous sodium sulfate to the combined ethyl acetate extracts, dry for 30 minutes, and filter.

[0042] (4) Ethyl acetate was recovered by rotary evaporation under reduced pressure, and concentrated to 5% of the original volume.

[0043] (5) Put the concentrated liquid at 0°C for crystallization, and recover the crystals.

[0044] (6) The crystals were vacuum-dried at 40° C. for 1 h, weighed and stored.

[0045] Experimental results: ...

Embodiment 2

[0047] The reaction of free β-glucanase biphasic system to hydrolyze geniposide, the experimental steps are as follows:

[0048] (1) Take 0.5g of geniposide with a purity of 90%, put it in a round bottom flask, add 45U of free β-glucanase, 50ml of acetic acid-sodium acetate buffer solution (pH 4.2) and 50ml of ethyl acetate, at 50°C Heated and stirred in a water bath for 2h.

[0049] (2) The reaction solution was extracted three times with 50 ml of ethyl acetate, and the ethyl acetate extracts were combined.

[0050] (3) Add an appropriate amount of anhydrous sodium sulfate to the combined ethyl acetate extracts, dry for 30 minutes, and filter.

[0051] (4) Ethyl acetate was recovered by rotary evaporation under reduced pressure, and concentrated to 5% of its original volume.

[0052] (5) Put the concentrated liquid at 0°C for crystallization, and recover the crystals.

[0053] (6) The crystals were vacuum-dried at 40° C. for 1 h, weighed and stored.

[0054] Experimental re...

Embodiment 3

[0056] Immobilized β-glucanase single-phase system hydrolyzes geniposide, and the experimental steps are as follows:

[0057] (1) Weigh 0.6g of sodium alginate and add 20ml of deionized water, heat to dissolve.

[0058] (2) Add 110 U of free β-glucanase in proportion and mix well.

[0059] (3) Then add 0.64 ml of 25% glutaraldehyde aqueous solution, stir and cross-link at room temperature for 2 hours.

[0060] (4) Use a syringe (No. 5 needle) to draw the above solution, drop it into 100ml of calcium chloride solution with a concentration of 0.5% at a height of about 10cm, form a smooth gel ball with a diameter of about 3mm, and let it stand to harden 2h.

[0061] (5) The immobilized enzyme gel particles were filtered out, washed with deionized water, blotted to dry the surface moisture, and stored in a refrigerator at 4°C.

[0062] (6) Take 0.25g of geniposide with a purity of 90%, put it in a round bottom flask, add 5U of immobilized β-glucanase, 25ml of acetic acid-sodium...

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Abstract

The invention discloses a method for preparing genipin. In the invention, sodium alginate serving as a carrier and glutaraldehyde serving as a crosslinking agent to immobilize glycoside hydrolase, the immobilized glycoside hydrolase catalyzes the hydrolysis geniposide in a double-phase system consisting of acetic acid-sodium acetate buffer solution and ethyl acetate to convert the geniposide into the genipin, the ethyl acetate in the reaction solution is separated out, and white genipin crystalsare obtained by concentration and crystallization. In the invention, the glycoside hydrolase is immobilized before an enzymatic reaction, so the side reactions of the enzymatic reaction glycoside hydrolase and the genipin are reduced, the glycoside hydrolase can be recycled repeatedly, and the production cost is reduced; and the double-phase system used in the invention can extract the genipin to the ethyl acetate phase from a water phase in reaction, so the hydrolysis reaction of the genipin and the side reactions of the glycoside hydrolase and the genipin can be reduced, the yield of the genipin can be improved, the reaction is accelerated, and the separation and purification of the product is more easy.

Description

technical field [0001] The invention relates to a method for preparing geniposide; in particular, it relates to a method for preparing geniposide by using immobilized enzymes to convert geniposide in a two-phase system. Background technique [0002] Gardenia is derived from the dried and mature fruit of Gardenia jasminoides Ellis, a plant belonging to the family Rubiaceae. It is cold in nature and bitter in taste. The active ingredients of the traditional Chinese medicine Gardenia are iridoids represented by geniposide. Geniposide (Geniposide, whose structural formula is shown in formula 1), also known as geniposide, is a raw material medicine for treating cardiovascular and cerebrovascular diseases, liver and gallbladder diseases and diabetes, and has high medicinal value. [0003] Studies have shown that geniposide must be metabolized into geniposide in the intestinal tract to exert its curative effect. Geniposide (Genipin, Genipin, structural formula shown in formula 2)...

Claims

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Application Information

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IPC IPC(8): C12P17/06C12N11/10C12N11/04
CPCY02P20/50
Inventor 张彤杨轶舜于筛成丁越玄振玉
Owner SHANGHAI UNIV OF T C M
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