Producing and refining method for high-purity cycloastragenol

A technology for cycloastragaloside and astragaloside IV is applied in the field of high-purity cycloastragaloside production and refining, which can solve the problems of many reaction steps, complicated processes, injury to operators and the like, and achieves the advantages of fewer reaction steps, high operation efficiency and convenient operation. Effect

Inactive Publication Date: 2016-07-06
CHENGDU KING TIGER PHARM CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chinese patent CN1809364B proposes a method of hydrolyzing astragaloside IV with acid and purifying by silica gel column chromatography to obtain cycloastragenol, but practice has proved that the ratio of ring-opening by-product-astragenol is relatively high and the process is complicated, which is difficult for industrial production.
Chinese patent CN103880910B adopts redox method to prepare cycloastragenol, and there are many reaction steps, using strong oxidant periodate, sodium periodate or potassium periodate, strong reducing agent sodium borohydride, potassium borohydride, etc., and the reaction After adding ethylene glycol in the process, a large amount of formaldehyde will be produced, which will cause certain harm to the operator, and does not meet the requirements of green environmental protection

Method used

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  • Producing and refining method for high-purity cycloastragenol
  • Producing and refining method for high-purity cycloastragenol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] A. Two-phase enzymatic hydrolysis

[0025] 1000ml0.02MKH 2 PO 4 - Add 20g of 90% astragaloside IV and 4.0g of β-glucosidase to NaOHPH5.0 buffer solution, stir and suspend, add 1000ml of ethyl acetate, stir slowly, and react at 37°C for 48h;

[0026] B. Extraction

[0027] After the enzymatic hydrolysis reaction is over, let it stand for 1 hour, take the upper layer of ethyl acetate solution; add 500ml of ethyl acetate to the water phase, stir well and then let it stand for 1 hour, after the water phase and the organic phase are completely separated, take the upper layer of ethyl acetate solution Solution; two ethyl acetate solutions were combined, filtered, and the ethyl acetate was recovered to obtain 10.68 g of the crude product of cycloastragenol. The purity of the cycloastragenol crude product detected by HPLC was 83.20%, and the conversion rate was 78.98%;

[0028] C. Recrystallization

[0029] Take 5 g of the crude product of cycloastragenol and add it to 250 ...

Embodiment 2

[0032] A. Two-phase enzymatic hydrolysis

[0033] 800ml0.04MNaH 2 PO 4 - Add 10g of 80% astragaloside IV and 2.0g of helicase to NaOHPH5.5 buffer solution, stir and suspend, add 800ml of dichloromethane, stir slowly, and react at 40°C for 58h;

[0034] B. Extraction

[0035] After the enzymatic hydrolysis reaction, let stand for 1.5h, remove the dichloromethane solution in the lower layer; add 500ml of dichloromethane to the water phase, stir well and then let it stand for 1h, after the water phase and the organic phase are completely separated, remove the dichloromethane solution in the lower layer. Methane solution; two dichloromethane solutions were combined, filtered, and dichloromethane was recovered to obtain 4.25 g of crude product of cycloastragenol, the purity of cycloastragenol crude product detected by HPLC was 78.32%, and the conversion rate was 66.57%;

[0036] C. Recrystallization

[0037] Add 2 g of the crude cycloastragenol to 100 ml of ethyl acetate, add 0...

Embodiment 3

[0039] A. Two-phase enzymatic hydrolysis

[0040] 1500ml0.04MNaH 2 PO 4 -In NaOHPH6.0 buffer solution, add 20g85% astragaloside IV, 3.0g naringinase, 1.0g helicase, stir and suspend, add 1000ml chloroform, stir slowly, and react at 30°C for 60h;

[0041] B. Extraction

[0042] After the enzymatic hydrolysis reaction is over, let stand for 2 hours, take the chloroform solution of the lower layer; add 1000ml of chloroform to the water phase, stir well and then let it stand for 1 hour, after the water phase and the organic phase are completely separated, take the chloroform solution of the lower layer; combine the chloroform twice solution, filtered, reclaimed chloroform to obtain crude product 11.29g of cycloastragenol, the purity of cycloastragenol crude product detected by HPLC was 79.41%, and the conversion rate was 84.38%;

[0043] C. Recrystallization

[0044] Take 5 g of the crude product of cycloastragenol and add it to a mixed solvent of 400 ml of acetone and petrole...

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PUM

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Abstract

The invention relates to a method for producing and refining cycloastragenol with a purity greater than or equal to 95%. Using astragaloside IV as a raw material, through two-phase enzymatic hydrolysis, extraction, and recrystallization, cycloastragenol products with a purity greater than or equal to 95% are obtained. Compared with the existing cycloastragenol production method, the present invention has simple production process, mild reaction conditions, high reaction conversion rate, is more suitable for large-scale production, and solves the problem of astragaloside IV being hydrolyzed under acid-base conditions. The easy ring opening leads to the difficulty of generating astragalol.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a new method for producing and refining high-purity cycloastragenol. Background technique [0002] The active ingredients in Astragalus include flavonoids, saponins, polysaccharides and amino acids. Among them, astragaloside has the effects of strengthening the heart, lowering blood pressure, anti-tumor, lowering blood sugar in diabetic rats, and promoting insulin secretion. Dozens of astragalosides have been isolated and identified from Astragalus root, and astragaloside IV is the main active ingredient of saponins. Cycloastragenol belongs to triterpenoid saponins and is mainly obtained by hydrolysis of astragaloside IV. Its physical properties are odorless and amorphous white powder. Cycloastragenol is a telomerase activator found in Astragalus membranaceus. By increasing telomerase activity and delaying the shortening of telomeres, it is believed to have the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P33/20C07J53/00
CPCC12P33/20C07J53/001
Inventor 陈谨苏俊何云燕刘辉李艾任平海
Owner CHENGDU KING TIGER PHARM CHEM TECH CO LTD
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