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Method for preparing mogrol and 11-O-mogrol by combining enzyme hydrolysis and oxidative cracking

A technology of grosvenorol and oxidative cracking, applied in the direction of fermentation, etc., can solve the problems of not suitable for the preparation of a large number of samples, oxidant consumption, long time, etc., and achieve the effect of retaining chemical integrity, reducing complexity, and less by-products

Active Publication Date: 2016-09-21
GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The methods for preparing saponin aglycone usually include: oxidative cleavage, acid hydrolysis and enzymatic hydrolysis, but the direct application to mogroside has its own shortcomings
The traditional oxidative cracking method (smith method) generates iodide ions after the oxidant sodium periodate reacts with the adjacent hydroxyl group, and iodide ions will undergo complex redox reactions with unreacted sodium periodate to cause a large amount of oxidant consumption, so the reaction It must be carried out at a lower temperature to suppress this side reaction. It takes a very long time to achieve complete reaction for substrates containing long or complex sugar chains, which is not suitable for the preparation of a large number of samples
Using the enzymatic hydrolysis method, because of the solubility of the product, the sugar chain of mogroside can only be partially hydrolyzed, and the purpose of obtaining aglycone cannot be achieved
The acid hydrolysis method is also not suitable for the preparation of mogrogenin because the damage to aglycon is too strong and the yield is too low

Method used

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  • Method for preparing mogrol and 11-O-mogrol by combining enzyme hydrolysis and oxidative cracking
  • Method for preparing mogrol and 11-O-mogrol by combining enzyme hydrolysis and oxidative cracking

Examples

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Embodiment 1

[0038] The enzymatic hydrolysis and oxidative cleavage of the present embodiment are combined to prepare the method for mogrosolic alcohol and 11-oxidative-mogrosolic alcohol, comprising the following steps:

[0039] Step 1: Enzymatic hydrolysis of Mogroside V

[0040] Take 6 g of hydrolase, dissolve it in 600 mL of water, take the supernatant, adjust pH=2 with acetic acid to obtain an enzymatic hydrolysis solution; take 6 g of Mogroside V, dissolve in 50 mL of the above enzymatic hydrolysis solution, react for 24 hours, and add ethanol to terminate the reaction, After filtration, 150 mL of mixed saponin solution was obtained;

[0041] Step 2: smith degradation

[0042] (1) Sodium Periodate Oxidative Cracking

[0043] In the mixed saponin solution obtained in step 1, 1 mL of acetic acid was added, and 50 mL of sodium periodate solution was slowly stirred under stirring, and the reaction was stirred at 20° C. in the dark to obtain a reaction solution after sodium periodate ox...

Embodiment 2

[0049] The enzymatic hydrolysis and oxidative cleavage of the present embodiment are combined to prepare the method for mogrosolic alcohol and 11-oxidative-mogrosolic alcohol, comprising the following steps:

[0050] Step 1: Enzymatic hydrolysis of Mogroside V

[0051] Take 10 g of hydrolase, dissolve it in 1000 mL of water, take the supernatant, adjust pH=4 with citric acid to obtain an enzymatic hydrolysis solution; take 100 g of commercial Mogroside V (50% content), use 1000 mL of the above enzymatic hydrolysis solution to dissolve, and react 18h, add ethanol to stop the reaction, after filtration, 2000mL mixed saponin solution was obtained;

[0052] Step 2: smith degradation

[0053] (1) Sodium Periodate Oxidative Cracking

[0054] In the mixed saponin solution obtained in step 1, 20 mL of acetic acid was added, and 400 mL of sodium periodate solution was slowly stirred under stirring, and the reaction was stirred at 50° C. in the dark to obtain a reaction solution after s...

Embodiment 3

[0060] The enzymatic hydrolysis and oxidative cleavage of the present embodiment are combined to prepare the method for mogrosolic alcohol and 11-oxidative-mogrosolic alcohol, comprising the following steps:

[0061] Step 1: Enzymatic hydrolysis of Mogroside V

[0062] Take 30 g of hydrolase, dissolve it in 3000 mL of water, take the supernatant, adjust pH=6 with phosphoric acid to obtain an enzymatic hydrolysis solution; take 500 g of commercial Mogroside V (50% content), dissolve it with 3000 mL of the above enzymatic hydrolysis solution, and react for 12 hours , adding ethanol to terminate the reaction, after filtration, to obtain 5000 mL of mixed saponin solution, the relative content of Mogroside V in the solution was found to be 38% by HPLC, the solvent was evaporated to dryness, and the reaction was dissolved with 3000 mL of enzymatic hydrolysis solution for 8 hours again, and ethanol was added to terminate the reaction, After filtration, 6000 mL of mixed saponin soluti...

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Abstract

The invention discloses a method for preparing mogrol and 11-O-mogrol by combining enzyme hydrolysis and oxidative cracking, belonging to the technical field of prodrugs or health care products. The method comprises the following steps: 1, carrying out enzyme hydrolysis on mogroside V; 2, carrying out smith degradation: (1) carrying out oxidative cracking on sodium periodate; (2) reducing sodium borohydride; (3) carrying out hydrolysis. The method combines the enzyme hydrolysis and the oxidative cracking for use, firstly removes part of sugar residues of the mogroside V by utilizing the enzyme hydrolysis so as to reduce the complexity of a sugar chain, and then uses the oxidative cracking method to finally obtain the two momordica grosvenori sapogenins i.e., the mogrol and the 11-O-mogrol. The method is suitable for preparing a great deal of samples, is high in yield, and can be used for obtaining the two sapogenins i.e., the mogrol and the 11-O-mogrol at the same time.

Description

technical field [0001] The invention relates to a method for preparing mogrosideol and 11-oxidation-mogrosolic alcohol by combining enzymatic hydrolysis and oxidative cleavage, and belongs to the technical field of drug precursors or health-care products. Background technique [0002] Luo Han Guo is the fruit of the cucurbit vine Siraitia grosvenorii, which has the effect of clearing away heat and moistening the lungs, soothing the throat, and relaxing the bowels. The main active ingredient of Luo Han Guo is mogroside, and mature Luo Han Guo is mainly rich in Mogroside V (Mogroside V), which is a five-sugar aglycone linked, and its sweetness is more than 300 times that of sucrose, and the calories are almost zero. Japanese scholars have reported that Mogroside V has anti-cancer effects and can be used as a chemopreventive agent for cancer. Its aglycones are cucurbitane-type tetracyclic triterpene mogrol (mogrol) and 11-oxidation-mogrol (11-O-mogrol), and the structural form...

Claims

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Application Information

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IPC IPC(8): C12P33/00
CPCC12P33/00
Inventor 王磊李炳辰羊学荣符毓夏李典鹏
Owner GUANGXI INST OF BOTANY THE CHINESE ACAD OF SCI
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