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Method for preparing gram-level high-purity natural thiosulfinate

A thiosulfinate, high-purity technology, applied in the direction of fermentation, etc., can solve the problems of tediousness, reduce production efficiency, increase production cost, etc., and achieve the effect of high reaction yield, simple operation and rapid reaction

Inactive Publication Date: 2014-10-08
JIANGNAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method is cumbersome and needs to extract allinase or immobilize allinase, which greatly increases the production cost and reduces the production efficiency

Method used

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  • Method for preparing gram-level high-purity natural thiosulfinate
  • Method for preparing gram-level high-purity natural thiosulfinate
  • Method for preparing gram-level high-purity natural thiosulfinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] Example 1: Preparation of Diallyl Thiosulfinate (Allicin)

[0060] (1) Weigh 100g of peeled garlic bulbs, mix it with 20mL of deionized water at room temperature, crush the garlic tissue into a homogenate with a mechanical mixer or crusher at 0°C, and beat for 5 minutes to make a tissue homogenate.

[0061] (2) Incubate the garlic tissue homogenate obtained in step (1) at room temperature for 1 hour, filter it with roving cloth, and take the filtrate. At room temperature, the filtrate was washed twice with an equal amount of dichloromethane for 20 min each time to ensure complete extraction. The washed filtrate has sufficient enzymatic activity to catalyze the conversion of exogenous ACSO to thiosulfinate. The washing process can adopt centrifugation or ionization accelerated phase separation process.

[0062] (3) Dissolve 4 g of exogenous allyl cysteine ​​sulfoxide ((±) 2-PeCSO) in 40 mL of deionized water to prepare an ACSO solution. Add the 2-PeCSO solution into t...

Embodiment 2

[0065] Embodiment 2: Preparation of diethyl thiosulfinate

[0066] (1) Weigh 100 g of peeled garlic bulbs, mix it with 90 mL of deionized water at room temperature, and crush the garlic tissue into a homogenate with a mechanical mixer or crusher at 4°C, and beat for 5 minutes to make a tissue homogenate.

[0067] (2) Incubate the garlic tissue homogenate obtained in step (1) at room temperature for 1 hour, filter it with roving cloth, and take the filtrate. At room temperature, wash the filtrate twice with 100 mL of dichloromethane for 15 min each time to ensure complete extraction. The washed filtrate has sufficient enzymatic activity to catalyze the conversion of exogenous ACSO to thiosulfinate. The washing process can adopt centrifugation or ionization accelerated phase separation process.

[0068] (3) Dissolve 3.6 g of exogenous S-ethyl-L-cysteine ​​sulfoxide ((±) ECSO) in 30 mL of deionized water to prepare an ECSO solution. Add the ECSO solution to the aqueous extract...

Embodiment 3

[0071] Example 3: Preparation of Dipropylthiosulfinate (Allicin)

[0072] (1) Weigh 100g of peeled onion bulbs, mix it with 70mL of deionized water at room temperature, crush the garlic tissue into a homogenate with a mechanical mixer or crusher at 0°C, and beat for 10 minutes to make a tissue homogenate.

[0073] (2) Incubate the onion tissue homogenate obtained in step (1) at room temperature for 1 hour, filter it with roving cloth, and take the filtrate. At room temperature, wash the filtrate twice with 100 mL of dichloromethane for 20 min each time to ensure complete extraction. The washed filtrate has sufficient enzymatic activity to catalyze the conversion of exogenous ACSO to thiosulfinate. The washing process can adopt centrifugation or ionization accelerated phase separation process.

[0074] (3) Dissolve 2 g of exogenous S-propyl-L-cysteine ​​sulfoxide ((±) PCSO) in 20 mL of deionized water to make a PCSO solution. The PCSO solution was added to the aqueous extrac...

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Abstract

The invention relates to a method for preparing gram-level high-purity natural thiosulfinate, belonging to the technical field of compound preparation. The method comprises the following steps: preparing an allium tissue homogenate containing active alliinase, keeping the temperature, washing off endogenous thiosulfinate generated in the tissue homogenate with an organic solvent, preparing exogenous ACSO into a solution, adding the solution into the tissue homogenate, keeping the temperature to generate single thiosulfinate or mixed thiosulfinates, and finally, purifying to obtain the product. The method has the advantages of mild reaction conditions, high product purity, high reaction yield, high cleanness and environmental protection, is simple to operate, and conforms to green technological requirements. The purity of the prepared pure thiosulfinate is sufficient for manufacturing drugs and especially diallyl thiosulfinate (garlicin). The research indicates that the garlicin has the maximum antibacterial, antihypertensive, anticancer, antioxidation and other activities in thiosulfinate.

Description

technical field [0001] The invention relates to a method for preparing gram-level high-purity natural thiosulfinate. The product can be used in food, cosmetics, health care products or medicine, and belongs to the technical field of compound preparation. Background technique [0002] Epidemiological evidence has shown that consumption of plants rich in allium can greatly reduce the risk of many diseases, such as bacterial, fungal, and viral infections. In addition, eating allium plants also has the effects of anti-oxidation, inducing apoptosis of cancer cells, and killing tumor cells. These plants include more than 700 species of Allium liliaceae such as garlic, onion, ginger, and chives. [0003] The health benefits of allium plants have been attributed to a class of substances called thiosulfinates (TS) catalyzed by allinase in Allium genus to form thioalkyl(alkenyl) L-cysteine ​​sulfoxide ACSO. [0004] ACSO includes MCSO, ECSO, PCSO, 2-PeCSO, 1-PeCSO, BCSO, and the spe...

Claims

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Application Information

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IPC IPC(8): C12P11/00
Inventor 孔祥珍陈海桥华欲飞丁秀臻张彩猛
Owner JIANGNAN UNIV
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