Method for preparing sulforaphane by using roquette seed glycosides

A technology of arugin and sulforaphane, which is applied in the field of biochemistry, can solve the problems of complex process, low yield, and many by-products, and achieve the effect of simple process, high yield and low cost

Active Publication Date: 2015-03-04
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The chemical method adopts the method of stereochiral synthesis, which has complex experiments, many reaction steps, many by-products, high toxicity, low yield, high cost of raw materials, difficult separation and other shortcomings, making it difficult to achieve large-scale production
[0005] The natural product extraction method first extracts 4-methyl-R-sulfinylbutyl glucosinolate (R-glucoraphanin) in cruciferous plants such as broccoli seeds, and then uses myrosinase to hydrolyze 4-methyl-R - sulfinyl butyl glucosinolate (R-glucoraphanin) to get R-sulforaphane (4-methyl-R-sulfinyl butyl isothiocyanate), but due to the high cost of broccoli seeds , and the content of 4-methyl-R-sulfinyl butyl glucosinolate is low, the obtained sulforaphane products are few, and can only be produced on a laboratory scale
The Chinese invention patent application with the application number 200910037363.1 discloses a method for extracting multifunctional sulforaphane from broccoli sprouts. This method needs to consider the growth time of the sprouts and pretreat the sprouts. The process is complicated , low yield, high cost

Method used

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  • Method for preparing sulforaphane by using roquette seed glycosides
  • Method for preparing sulforaphane by using roquette seed glycosides
  • Method for preparing sulforaphane by using roquette seed glycosides

Examples

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Effect test

Embodiment 1

[0035] Preparation of arugin: take 100 g of arugula seeds, inactivate enzymes at 100°C for 30 minutes, pulverize, add 1L of phosphate buffer, pH value of 7, and stir under boiling water for 1 hour, and filter with suction. The filtrate was applied to a D261 resin column with a column volume of 100ml, 500ml of deionized water to wash impurities, 500ml of 2M potassium chloride solution to wash the arugin product, 40°C rotary evaporation to remove the solvent, 500ml methanol extraction desalination, 40°C rotary evaporation to remove the solvent to obtain sesame seeds The crude cabbage glycoside is 9.87g.

[0036] Preparation of 4-methyl-R-sulfinyl butyl glucosinolate: dissolve the crude arugin in 500ml phosphate buffer (pH 7), add glucose oxidase 0.0006mmol horseradish peroxide Enzyme 0.0024mmol, sealed with oxygen (1ml / min), controlled temperature at 28°C, and stirred with a magnetic stirrer. After 15 minutes, 1.4 mol glucose was added, and the reaction was stirred for 4 hours. T...

Embodiment 2

[0039] Preparation of arugin: take 100 g of arugula seeds, inactivate enzymes at 100°C for 30 minutes, pulverize, add 1L of phosphate buffer, pH value of 7, and stir under boiling water for 1 hour, and filter with suction. The filtrate was applied to a D261 resin column with a column volume of 100ml, 500ml of deionized water to wash impurities, 500ml of 2M potassium chloride solution to wash the arugin product, 40°C rotary evaporation to remove the solvent, 500ml methanol extraction desalination, 40°C rotary evaporation to remove the solvent to obtain sesame seeds Crude cabbage glycosides 10.12g.

[0040] Preparation of 4-methyl-R-sulfinyl butyl glucosinolate: dissolve the crude arugin in 500ml phosphate buffer (pH 7), add glucose oxidase 0.0006mmol horseradish peroxide Enzyme 0.0024mmol, sealed with oxygen (1ml / min), controlled temperature at 28°C, and stirred with a magnetic stirrer. After 15 minutes, 1.4 mol glucose was added, and the reaction was stirred for 2 hours. The fo...

Embodiment 3

[0043] Preparation of arugin: Take 1000g of arugula seeds, inactivate enzymes at 100°C for 30 minutes, pulverize, add 10L of phosphate buffer, pH value of 7, and stir under boiling water for 1 hour, and filter with suction. The filtrate was applied to a D261 resin column with a column volume of 1000ml, 5000ml of deionized water to wash impurities, 5000ml of 2M potassium chloride solution to wash the arugin product, 40℃ rotary evaporation to remove the solvent, 5000ml methanol extraction desalination, 40℃ rotary evaporation to remove the solvent to obtain sesame seeds The crude cabbage glycoside is 97.28g.

[0044] Preparation of 4-methyl-R-sulfinyl butyl glucosinolate: add arugula glycoside crude product to 500ml phosphate buffer (pH value 7), add glucose oxidase 0.006mmol chloroperoxidase 0.024 mmol, control the temperature at 31°C, use a magnetic stirrer. After 15 minutes, 14 mol glucose was added, and the reaction was stirred for 4 hours. The formation of reactants was detec...

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Abstract

The invention belongs to the field of biological chemistry, and particularly relates to a method for preparing sulforaphane by using roquette seed glycosides. The method comprises the following steps: oxidizing roquette seed glycosides to prepare 4-methyl-R-sulfinyl butyl glucosinolate by using a peroxidase-oxidase reaction system; hydrolyzing 4-methyl-R-sulfinyl butyl glucosinolate to prepare sulforaphane by using myrosinase. The defects of an existing preparation method that the raw material cost is high, the yield of the sulforaphane is low, the process is complicated, and large-scale production is difficult to achieve are overcome. Cheap and available roquette seeds, flowers, stems or leaves are adopted as raw materials; the raw material cost is 1/6 of that when broccoli is adopted as the raw material; the yield of the finally obtained sulforaphane is four times of that when the broccoli is adopted as the raw material; and the sulforaphane is high in purity, low in cost, high in yield, and extremely suitable for large-scale industrial production.

Description

Technical field [0001] The invention belongs to the field of biochemistry, and particularly relates to a method for preparing sulforaphane by using arugin. Background technique [0002] At present, with the improvement of people's living standards, the incidence of cancer has increased significantly, seriously affecting human life and health. Eating large amounts of fruits and vegetables can significantly inhibit or slow down the occurrence of cancer. Vegetables and fruits contain a lot of active ingredients, such as lycopene in tomatoes, soy isoflavones in soybeans, ellagic acid in fruits, and isothiocyanates and indoles in cruciferous vegetables. Proved to have outstanding anti-cancer and anti-cancer effects. [0003] Sulforaphane (sulforaphane, 4-methyl-sulfinyl butyl isothiocyanate) is currently recognized as one of the natural products with the best anti-cancer and anti-cancer effects. It has the strongest ability to induce type II detoxification enzymes in nature. Inducer....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P11/00
Inventor 梁浩周筱袁其朋程立田飞豹
Owner BEIJING UNIV OF CHEM TECH
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