CN109134579A - Hypoglycemic low polarity triterpene glucoside group and preparation method thereof - Google Patents
Hypoglycemic low polarity triterpene glucoside group and preparation method thereof Download PDFInfo
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Abstract
A kind of hypoglycemic low polarity triterpene glucoside group and preparation method thereof, obtains saponin(e crude extract first with Siraitia grosvenorii sour water solution, then is further purified to obtain low polarity triterpene glucoside group using macroreticular resin and polyamide column chromatography.The present invention is directed to the low polarity saponin group of active component-Siraitia grosvenorii of Siraitia grosvenorii hypoglycemic, and using acid hydrolysis process beam system for low polarity triterpene glucoside, obtained active component has the effect for being substantially reduced type-2 diabetes mellitus blood glucose.
Description
Technical field
The present invention relates to a kind of technology of medical medicine preparation field, specifically a kind of hypoglycemic low polarity arhat
Fruit saponin(e group and preparation method thereof.
Background technique
Siraitia grosvenorii is cucurbitaceous plant Siraitia grosvenorii [Siraitia grosvenorii (Swingle) C.Jeffery ex Lu
Et Z.Y.Zhang] dry mature fruit, saponin extract has and significantly reduces diabetic model rats, mouse blood sugar
Effect.Fresh fructus momordicae saponin extract has apparent inhibiting effect to the generation of normal mouse postprandial blood sugar.
But it recent studies have shown that, Siraitia grosvenorii triterpenoid saponin is metabolized through diabetes source of people enterobacteriaceae occurs desugar reaction, metabolism
At siamenoside Ⅰ, mogroside IV E, Momordia grosvenori aglycone II, I A of Momordia grosvenori aglycone1With I E of Momordia grosvenori aglycone1Equal products, to be lower than 4 glycosyls
Low polarity triterpenoid saponins based on.Also metabolism generates the low pole of 1-3 glycosyl to momordica grosvenori glycoside V in diabetes rat body
Property triterpenoid saponins.Therefore, carrying out preparation and activity research to the low polarity triterpenoid saponins of 1-3 glycosyl has
Significance.However, the content in Siraitia grosvenorii medicinal material of the saponin(e containing 1~3 glycosyl is extremely low, it is only about Mogroside V content
8%, it is difficult to scale preparation.
Summary of the invention
The present invention In view of the above shortcomings of the prior art, propose a kind of hypoglycemic low polarity triterpene glucoside group and
Preparation method, for the low polarity saponin group of active component-Siraitia grosvenorii of Siraitia grosvenorii hypoglycemic, using acid hydrolysis process beam system
Standby low polarity triterpene glucoside, obtained active component have the effect for being substantially reduced type-2 diabetes mellitus blood glucose.
The present invention is achieved by the following technical solutions:
The present invention relates to the industrial production process of low polarity triterpene glucoside group a kind of, are obtained first with Siraitia grosvenorii sour water solution
Then saponin(e crude extract is further purified to obtain low polarity triterpene glucoside group using macroreticular resin and the comprehensive absorption of polyamide.
The sour water solution, it is concentrated to obtain after dry extract through sulfuric acid and/or salt using drying and ripening Siraitia grosvenorii as raw material
Sour water solution prepares saponin(e crude extract.
Ethyl alcohol is added by choosing Siraitia grosvenorii in the dry extract after crushing, and filtering and concentrating obtains after heated reflux.
Described is referred to by sulfuric acid and/or hydrochloric acid hydrolysis: sulfuric acid and/or hydrochloric acid being added after dry extract is diluted and heats
It is incubated for, is concentrated to get after then extracting hydrolysis supernatant by organic reagent.
The organic reagent includes ethyl acetate and n-butanol.
The comprehensive absorption refers to: after taking AB-8 macroporous absorbent resin and polyamide to be impregnated with ethyl alcohol, column is filled, with distillation
It is washed to no alcohol taste, then with distilled water flushing to neutrality after soda acid rinses；Then supernatant solution is taken after water dissolves, be splined on
After the macroporous resin column absorption pre-processed, after removing water-solubility impurity with water and ethyl alcohol respectively, then with ethyl alcohol 5~27 are carried out
Column volume elution obtains the ethanol eluate containing low polarity triterpene glucoside group, and concentration, low-temperature reduced-pressure are dry, obtain dried powder；
Dried powder is finally splined on to the polyamide column pre-processed with dry method, removes water-solubility impurity with water, then carry out 5 with ethyl alcohol
A column volume elution, obtains the ethanol eluate of the low polarity saponin group containing Siraitia grosvenorii, is concentrated, and low-temperature reduced-pressure is dry, obtains low
Polarity triterpene glucoside group.
The low polarity triterpene glucoside group measures the content of low polarity triterpene glucoside group using UPLC, calculates total
Content.UPLC testing conditions are as follows: C18 chromatographic column is used, with water (A)-acetonitrile (B) gradient elution, gradient elution program are as follows: 0~
30min 20%~50%B, 30~32min 50%~20%B, 20%B 32~33min, Detection wavelength 205nm, flow velocity
For 0.6mL/min.
The present invention relates to the low polarity triterpene glucoside groups that the above method is prepared, and include mogroside Ⅲ, Siraitia grosvenorii
III A of glycosides1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Mixture, in which: mogroside Ⅲ, Momordia grosvenori aglycone
ⅢA1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Content be respectively 0.5%~5%, 0.5%~5%,
1%~20%, 1%~20%, 2%~40%, total content is greater than 60%.
The present invention relates to the applications of above-mentioned low polarity triterpene glucoside group, are used for the medicine of preparation treatment type-2 diabetes mellitus
Object.
The application specially prepares the drug for significantly reducing type-2 diabetes mellitus blood glucose.
Technical effect
Compared with prior art, the present invention is low for low polarity saponin content in Siraitia grosvenorii, directly extracts from medicinal material
The problems such as rate is low, cumbersome, using acid hydrolysis process beam system for low polarity triterpene glucoside.This method has operation letter
Just, (its effect for reducing diabetes B rat blood sugar is obvious by force for yield high (more than 5%), (more than 60%) with high purity, activity
Better than Fructus Monordicae extract and the total glycosides of Siraitia grosvenorii) the advantages that.
Specific embodiment
Embodiment 1
The present embodiment the following steps are included:
Step 1) Siraitia grosvenorii 100g is crushed, and is added for 1:6 into raw material according to raw material weight (kg) than solvent volume (L)
50% ethyl alcohol, 80 DEG C refluxing extraction 1 time, extract 0.5h every time, extracting solution filtered, merge, concentration, be dried under reduced pressure, obtain dry
Medicinal extract.
Water is added according to the ratio of mass ratio 1:3 to the dry extract in step 1) in step 2), is sufficiently stirred, 2500r/min
Centrifugation, takes supernatant.It is the aqueous hydrochloric acid solution that 1:0.5 concentration is 0.5M that volume ratio, which is added, is incubated for 0.5h, water in 70 DEG C of water-baths
Liquid centrifugation is solved, supernatant is taken.
Hydrolyzate supernatant in step 2) is that 1:1 is extracted 2 times with volume ratio with ethyl acetate by step 3), merges extraction
Extract liquor is adjusted to neutrality by liquid, and concentration is dried under reduced pressure, obtains saponin(e crude extract.
The saponin(e crude extract that step 4) obtains step 3) is dissolved for the water of 1:3 with mass ratio, takes supernatant solution, loading
5 columns are carried out with water, 10% ethyl alcohol and 50% ethyl alcohol respectively after adsorbing 2h in the AB-8 large pore resin absorption column pre-processed
Volume elution, 50% ethanol eluate is concentrated, and low-temperature reduced-pressure is dry, obtains dried powder.
50% alcohol elution dried powder in step 4), dry method are splined on the polyamide pre-processed by step 5)
Column carries out 5 column volume elutions with water and 10% ethyl alcohol respectively, 10% ethanol eluate is concentrated, low temperature drying is at powder
Obtain low polarity triterpene glucoside group 5.7g.
The low polarity triterpene glucoside group that the present embodiment is prepared based on the above process is through UPLC detection level, wherein sieve
Chinese fruit glycosides III, mogroside Ⅲ A1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Mass percent be respectively
5%, 5%, 19%, 20%, 14%, total content 63%.
Ingredient chemical structure is as follows:
The present embodiment technical effect evaluation method is as follows:
I) bibliography [Shi Hong, etc., modeling mode of the induction building most similar to people type-2 diabetes mellitus rat, Chinese Clinical
Rehabilitation, 2005,9 (39), 69-71] building endomorphy type type-2 diabetes mellitus rat model；
Ii) low polarity sieve obtained in isolation and purification method (3) is given to the successful type-2 diabetes mellitus rat oral gavage of modeling
Chinese fruit saponin(e group's aqueous solution, after two weeks, tail vein needle adopts blood, measures type-2 diabetes mellitus rat fasting blood-glucose with blood glucose meter
(FBG, mmol/L) value, the low polarity triterpene glucoside group that the present embodiment is prepared can make type-2 diabetes mellitus rat fasting blood-glucose
Value reduces by 31%, and antidiabetic effect is significantly better than Fructus Monordicae extract (blood glucose value reduces by 21%) and the total glycosides (blood of Siraitia grosvenorii
25%) sugar value reduces.
Embodiment 2
The present embodiment the following steps are included:
Step 1) Siraitia grosvenorii 50g is crushed, and is added for 1:10 into raw material according to raw material weight (kg) than solvent volume (L)
50% ethyl alcohol, 90 DEG C refluxing extraction 2 times, extract 1h every time, extracting solution filtered, merge, concentration, be dried under reduced pressure, obtain dry leaching
Cream.
Water is added according to the ratio of mass ratio 1:5 to the dry extract in step 1) in step 2), is sufficiently stirred, 2500r/min
Centrifugation, takes supernatant.It is the aqueous hydrochloric acid solution that 1:1 concentration is 1M that volume ratio, which is added, 2h is incubated in 75 DEG C of water-baths, by hydrolyzate
Centrifugation, takes supernatant.
Hydrolyzate supernatant in step 2) is that 1:1 is extracted 2 times with volume ratio with n-butanol by step 3), combining extraction liquid,
Extract liquor is adjusted to neutrality, is concentrated, is dried under reduced pressure, obtains saponin(e crude extract.
The saponin(e crude extract that step 4) obtains step 3) is dissolved for the water of 1:5 with mass ratio, takes supernatant solution, loading
15 columns are carried out with water, 20% ethyl alcohol and 60% ethyl alcohol respectively after adsorbing 4h in the AB-8 large pore resin absorption column pre-processed
Volume elution, 60% ethanol eluate is concentrated, and low-temperature reduced-pressure is dry, obtains dried powder.
60% alcohol elution dried powder in step 4), dry method are splined on the polyamide pre-processed by step 5)
Column carries out 5 column volume elutions with water and 20% ethyl alcohol respectively, 20% ethanol eluate is concentrated, low temperature drying is at powder
Obtain low polarity triterpene glucoside group 2.8g.
The low polarity triterpene glucoside group that the present embodiment is prepared based on the above process is through UPLC detection level, wherein sieve
Chinese fruit glycosides III, mogroside Ⅲ A1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Content be respectively 3%,
3%, 13%, 13%, 29%, total content 61%.
The low polarity triterpene glucoside group that the present embodiment is obtained is evaluated and tested using method same as Example 1, can make II type
Diabetes rat fasting blood sugar reduces by 43%, and antidiabetic effect significant (P < 0.05) is better than Fructus Monordicae extract (blood glucose
21%) and the total glycosides of Siraitia grosvenorii (blood glucose value reduce by 25%) value reduces.
Embodiment 3
The present embodiment the following steps are included:
Step 1) Siraitia grosvenorii 80g is crushed, and is added for 1:12 into raw material according to raw material weight (kg) than solvent volume (L)
50% ethyl alcohol, 100 DEG C refluxing extraction 2 times, extract 3h every time, extracting solution filtered, merge, concentration, be dried under reduced pressure, obtain dry leaching
Cream.
Water is added according to the ratio of mass ratio 1:12 to the dry extract in step 1) in step 2), is sufficiently stirred, 2500r/min
Centrifugation, takes supernatant.It is the aqueous sulfuric acid that 1:3 concentration is 0.5M that volume ratio, which is added, is incubated for 3h in 85 DEG C of water-baths, will hydrolyze
Liquid centrifugation, takes supernatant.
Hydrolyzate supernatant in step 2) is that 1:1 is extracted 3 times with volume ratio with n-butanol by step 3), combining extraction liquid,
Extract liquor is adjusted to neutrality, is concentrated, is dried under reduced pressure, obtains saponin(e crude extract.
The saponin(e crude extract that step 4) obtains step 3) is dissolved for the water of 1:5 with mass ratio, takes supernatant solution, loading
20 are carried out with water, 30% ethyl alcohol and 60% ethyl alcohol respectively after adsorbing 2.5h in the AB-8 large pore resin absorption column pre-processed
Column volume elution, 60% ethanol eluate is concentrated, and low-temperature reduced-pressure is dry, obtains dried powder.
60% alcohol elution dried powder in step 4), dry method are splined on the polyamide pre-processed by step 5)
Column carries out 5 column volume elutions with water and 15% ethyl alcohol respectively, 15% ethanol eluate is concentrated, low temperature drying is at powder
Obtain low polarity triterpene glucoside group 4.5g.
The low polarity triterpene glucoside group that the present embodiment is prepared based on the above process is through UPLC detection level, wherein sieve
Chinese fruit glycosides III, mogroside Ⅲ A1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Mass percent be respectively
4%, 5%, 14%, 14%, 22.5%, total content 59.5%.
The low polarity triterpene glucoside group that the present embodiment is obtained is evaluated and tested using method same as Example 1, can make II type
Diabetes rat fasting blood sugar reduces by 37%, and antidiabetic effect is significantly better than Fructus Monordicae extract, and (blood glucose value reduces
And the total glycosides of Siraitia grosvenorii (blood glucose value reduce by 25%) 21%).
Above-mentioned specific implementation can by those skilled in the art under the premise of without departing substantially from the principle of the invention and objective with difference
Mode carry out local directed complete set to it, protection scope of the present invention is subject to claims and not by above-mentioned specific implementation institute
Limit, each implementation within its scope is by the constraint of the present invention.
Claims (10)
1. a kind of industrial production process of low polarity triterpene glucoside group, which is characterized in that obtained first with Siraitia grosvenorii sour water solution
Then saponin(e crude extract is further purified to obtain low polarity triterpene glucoside group using macroreticular resin and the comprehensive absorption of polyamide.
2. according to the method described in claim 1, it is characterized in that, the sour water solution, using drying and ripening Siraitia grosvenorii as raw material, warp
It is concentrated to get after dry extract and saponin(e crude extract is prepared by sulfuric acid and/or hydrochloric acid hydrolysis.
3. according to the method described in claim 1, it is characterized in that, the dry extract, by choose Siraitia grosvenorii add after crushing
Enter ethyl alcohol, filtering and concentrating obtains after heated reflux.
4. according to the method described in claim 1, it is characterized in that, it is described by sulfuric acid and/or hydrochloric acid hydrolysis refer to: by dry leaching
Sulfuric acid and/or hydrochloric acid and incubation with heat is added after cream dilution, is concentrated to get after then extracting hydrolysis supernatant by organic reagent.
5. according to the method described in claim 1, it is characterized in that, the organic reagent includes ethyl acetate and n-butanol.
6. according to the method described in claim 1, it is characterized in that, the described comprehensive absorption refers to: taking AB-8 macroporous absorbent resin
After being impregnated with polyamide with ethyl alcohol, column is filled, is rushed with distilled water to no alcohol taste, then rushed with distilled water to neutrality after soda acid rinses；
Then supernatant solution is taken after water dissolves, after being splined on the macroporous resin column absorption pre-processed, is removed respectively with water and ethyl alcohol
After water-solubility impurity, then 5~27 column volumes are carried out with ethyl alcohol and are eluted, obtain the ethanol elution containing low polarity triterpene glucoside group
Liquid, concentration, low-temperature reduced-pressure are dry, obtain dried powder；Dried powder is finally splined on to the polyamide column pre-processed with dry method,
Water-solubility impurity is removed with water, then carries out 5 column volume elutions with ethyl alcohol, the ethyl alcohol for obtaining the low polarity saponin group containing Siraitia grosvenorii is washed
De- liquid, is concentrated, and low-temperature reduced-pressure is dry, obtains low polarity triterpene glucoside group.
7. according to the method described in claim 1, it is characterized in that, the low polarity triterpene glucoside group is measured using UPLC
The content of low polarity triterpene glucoside group calculates total content.UPLC testing conditions are as follows: C18 chromatographic column is used, with water (A)-acetonitrile
(B) gradient elution, gradient elution program are as follows: 0~30min 20%~50%B, 30~32min 50%~20%B, 20%B
32~33min, Detection wavelength 205nm, flow velocity 0.6mL/min.
8. a kind of low polarity triterpene glucoside group being prepared based on any of the above-described claim the method, feature are existed
In comprising mogroside Ⅲ, mogroside Ⅲ A1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Mixture,
Wherein: mogroside Ⅲ, mogroside Ⅲ A1, mogroside ⅡE, II A of Momordia grosvenori aglycone1With I A of Momordia grosvenori aglycone1Content be respectively
0.5%~5%, 0.5%~5%, 1%~20%, 1%~20%, 2%~40%, total content is greater than 60%, chemical structure
Specifically:
9. a kind of application of polarity triterpene glucoside group low according to any of the above-described claim, which is characterized in that used
In the drug of preparation treatment type-2 diabetes mellitus.
10. application according to claim 9, characterized in that specially prepare the medicine for significantly reducing type-2 diabetes mellitus blood glucose
Object.
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| CN110669094A (en) * | 2019-10-14 | 2020-01-10 | 上海交通大学 | New mogroside and its prepn |
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