CN101967505A - Method for preparing dihydro quercetin - Google Patents
Method for preparing dihydro quercetin Download PDFInfo
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- CN101967505A CN101967505A CN2010102107471A CN201010210747A CN101967505A CN 101967505 A CN101967505 A CN 101967505A CN 2010102107471 A CN2010102107471 A CN 2010102107471A CN 201010210747 A CN201010210747 A CN 201010210747A CN 101967505 A CN101967505 A CN 101967505A
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- ethanol
- dihydroquercetin
- water
- enzymolysis
- gradient elution
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Abstract
The invention relates to a method for preparing dihydro quercetin, which comprises the following steps of: pulverizing engelhardia roxburghiana wall leaves serving as raw materials, adding acidulous water for wetting, adding naringinase and keeping the temperature constant for enzymolysis; performing refluxing extraction in ethanol; adding polyamide resin into concentrated solution for adsorbing, performing gradient elution in ethanol and the water, and concentrating eluent for crystallizing; and performing recrystallization by using the water and 70 percent ethanol, and performing vacuum drying at the low temperature to obtain dihydro quercetin. In process, reagents have no toxic properties, and the process flow is simple; and the dihydro quercetin produced by the process can be used as raw materials of health-care products and medicines directly.
Description
Technical field:
The present invention relates to a kind of preparation method of dihydroquercetin, especially a kind of method for preparing dihydroquercetin with the Folium Engelhardia roxburghina for the raw material biological enzymolysis.
Background technology:
Dihydroquercetin different name Taxifolin, taxifolin, flavonoid compound, molecular formula: C
15H
12O
7, molecular weight: 304.256, colourless needle crystal (50% ethanol), fusing point 240-240 ℃.Be soluble in ethanol, acetate, boiling water, be dissolved in cold water slightly, be dissolved in benzene hardly.
Pharmacological action:
1. anticancer: P388 has activity to mouse leukemia, 150 and the increase in life span of 100mg/kg be respectively 40% and 37%.
2. antibiotic: that streptococcus aureus, intestinal bacteria, dysentery bacterium and Corynebacterium diphtheriae are had stronger bacteriostatic action.
American Pharmacopeia and Russian pharmacopeia have all been included dihydroquercetin.
Existing natural extract dihydroquercetin has two kinds of approach: a kind of is directly to extract from the Pseudotsuga menziesii (Mirbel) Franco skin, and second kind is that the astilbin acid hydrolysis is arranged.
Pseudotsuga menziesii (Mirbel) Franco bark dihydroquercetin content is about 7%, but the Pseudotsuga menziesii (Mirbel) Franco resource-constrained, and content is not high in other tamarackes.Limited the output of dihydroquercetin.
As patent (application number 200610035280) " a kind of method of from tamarack, extracting dihydroquercetin ", the method of this patent disclosure is to be extraction agent with water, the larch in Xinanlin area that contains dihydroquercetin is extracted, aqueous extraction liquor to gained is that extraction agent carries out liquid-liquid extraction with the methyl tertiary butyl ether, adopt gac or atlapulgite the methyl tertiary butyl ether extraction liquid is carried out adsorption bleaching, the back methyl tertiary butyl ether extraction liquid that decolours is carried out removing of solvent under vacuum condition, the paste water that removes behind the solvent carries out crystallization purifying.
Patent (application number 200610035752) " a kind of method that adopts absorption method from tamarack, to extract dihydroquercetin " for another example, disclosed method is that water is extraction agent, the larch in Xinanlin area that contains dihydroquercetin is extracted, adopt gac or atlapulgite that extracting solution is decoloured, thereafter, aqueous extraction liquor to gained is that sorbent material adsorbs with polyamide powder earlier, carry out desorb with desorption solvent again, the gained stripping liquid carries out solvent removal under vacuum condition, water carries out recrystallization purifying, just obtains the dihydroquercetin highly finished product.
Astilbin content is about 6% in the Folium Engelhardia roxburghina, and Folium Engelhardia roxburghina also is a waste, produces astilbin and does not also damage trees.
The astilbin astilbin, another name dihydroquercetin-3-O-α-L-pyrans rhamnoside, molecular formula: C
21H
22O
11Molecular weight: 450.39.
The astilbin dihydroquercetin
There is astilbin to be hydrolyzed to dihydroquercetin again.
As patent (application number 200710105982) method of extraction separation dihydroquercetin " a kind of from Folium Engelhardia roxburghina ", this patented method is to be raw material with the Folium Engelhardia roxburghina, by extract, concentrate, operations such as macroporous resin column chromatography, crystallization, acid hydrolysis.
People such as Wang Ping " extraction of dihydroquercetin in the thorn rose rose stem " delivered for another example, it is raw material that document adopts with Flos Rosae Davuricae rose stem, organic reagent extracts acid hydrolysis, extract dihydroquercetin.
As mentioned above, with existing explained hereafter dihydroquercetin, there is following problem:
1) directly extract from the Pseudotsuga menziesii (Mirbel) Franco bark, raw material is expensive and short.
2) the astilbin acid hydrolysis is arranged, reaction process is violent, and is seriously polluted.
Summary of the invention:
The technical problem to be solved in the present invention provides a kind of preparation method of dihydroquercetin, and this method adopts biological enzymolysis, the process gentleness, the products obtained therefrom quality better, solved raw material shortage and can not scale operation.
In order to solve the problems of the technologies described above, extractive technique scheme of the present invention is as follows:
A kind of preparation method of dihydroquercetin is characterized in that comprising following steps:
1) pulverizes enzymolysis: Folium Engelhardia roxburghina is pulverized the 20-80 order, add the acidic aqueous solution of 10-20%ph4-6, mix thoroughly and add naringinase again, 35-5 ℃ of insulation enzymolysis;
2) extract: above-mentioned enzymolysis raw material was added the 6-15BV50-90% alcohol reflux 1-5 hour, extracts 1-3 time, merge extracting solution;
3) polyamide resin purifying: ethanol is reclaimed in the pressurization of said extracted liquid, adds polyamide column absorption, and the water-ethanol gradient elution is collected the dihydroquercetin flow point, and decompression recycling ethanol is placed crystallization;
4) recrystallization: leach crystallisate, use deionized water, 70% alcohol reflux crystallization successively, leach low-temperature vacuum drying and promptly get dihydroquercetin.
Described step 1) is pulverized enzymatic hydrolysis condition: sour optional organic acid or mineral acid, enzyme addition 1-5 ‰, enzymolysis time were not less than 28 hours.
The optional 100-200 order of polymeric amide polymeric amide in the described step 3).
Described step 3) water-ethanol gradient elution is: use 10-15BV water → 4-7BV20-40% ethanol → 5-8BV60-80% ethanol gradient elution successively.
There is following advantage in the present invention:
1) present method employing Folium Engelhardia roxburghina is a raw material, solves the shortage of raw material resources.
2) biological enzymolysis, process operations is simple.
3) production process agents useful for same kind is few, does not have toxic agent, and product meets the food and medicine requirement.
Further specify the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
Embodiment:
Embodiment 1:
20 orders are pulverized in the Folium Engelhardia roxburghina impurity elimination, get 1kg, the aqueous hydrochloric acid that adds 200mlph4 is wetting, getting the adding of 1g naringinase again stirs, be placed in 35 ℃ the thermostat container enzymolysis 48 hours, taking-up drops into and adds 6L90% alcohol reflux extraction in 1 hour 3 times in the flask, and the extracting solution Rotary Evaporators reclaims ethanol, adds polyamide resin column while hot and adsorbs, use 15BV water → 4BV40% ethanol → 8BV60% ethanol gradient elution then successively, collect 60% ethanol eluate, decompression recycling ethanol is placed crystallization, leaches crystallization, use deionized water again, 70% alcohol reflux dissolving-recrystallization, crystallisate leaches vacuum dehydrating at lower temperature, gets dihydroquercetin 32g, content 99%.
Embodiment 2:
80 orders are pulverized in the Folium Engelhardia roxburghina impurity elimination, get 1kg, the aqueous hydrochloric acid that adds 100mlph5 is wetting, getting the adding of 3g naringinase again stirs, be placed in 35 ℃ the thermostat container enzymolysis 36 hours, taking-up drops into and adds 6L50% alcohol reflux extraction in 1 hour 3 times in the flask, and the extracting solution Rotary Evaporators reclaims ethanol, adds polyamide resin column while hot and adsorbs, use 10BV water → 7BV20% ethanol → 5BV80% ethanol gradient elution then successively, collect 80% ethanol eluate, decompression recycling ethanol is placed crystallization, leaches crystallization, use deionized water again, 70% alcohol reflux dissolving-recrystallization, crystallisate leaches vacuum dehydrating at lower temperature, gets dihydroquercetin 37g, content 98%.
Embodiment 3:
40 orders are pulverized in the Folium Engelhardia roxburghina impurity elimination, get 1kg, the aqueous hydrochloric acid that adds 150mlph5 is wetting, getting the adding of 5g naringinase again stirs, be placed in 35 ℃ the thermostat container enzymolysis 28 hours, taking-up drops into and adds 15L70% alcohol reflux extraction in 5 hours 1 time in the flask, and the extracting solution Rotary Evaporators reclaims ethanol, adds polyamide resin column while hot and adsorbs, use 13BV water → 7BV30% ethanol → 6BV75% ethanol gradient elution then successively, collect 75% ethanol eluate, decompression recycling ethanol is placed crystallization, leaches crystallization, use deionized water again, 70% alcohol reflux dissolving-recrystallization, crystallisate leaches vacuum dehydrating at lower temperature, gets dihydroquercetin 36g, content 98%.
Embodiment 4:
60 orders are pulverized in the Folium Engelhardia roxburghina impurity elimination, get 2kg, the aqueous hydrochloric acid that adds 400mlph6 is wetting, getting the adding of 7g naringinase again stirs, be placed in 35 ℃ the thermostat container enzymolysis 48 hours, taking-up drops into and adds 15L70% alcohol reflux extraction in 3 hours 2 times in the flask, and the extracting solution Rotary Evaporators reclaims ethanol, adds polyamide resin column while hot and adsorbs, use 10BV water → 8BV30% ethanol → 7BV70% ethanol gradient elution then successively, collect 70% ethanol eluate, decompression recycling ethanol is placed crystallization, leaches crystallization, use deionized water again, 70% alcohol reflux dissolving-recrystallization, crystallisate leaches vacuum dehydrating at lower temperature, gets dihydroquercetin 71g, content 98%.
Claims (4)
1. the preparation method of a dihydroquercetin is characterized in that comprising following steps:
1) pulverizes enzymolysis: Folium Engelhardia roxburghina is pulverized the 20-80 order, add the acidic aqueous solution of 10-20%ph4-6, mix thoroughly and add naringinase again, 35-55 ℃ of insulation enzymolysis;
2) extract: above-mentioned enzymolysis raw material was added the 6-15BV50-90% alcohol reflux 1-5 hour, extracts 1-3 time, merge extracting solution;
3) polyamide resin purifying: ethanol is reclaimed in the pressurization of said extracted liquid, adds polyamide column absorption, and the water-ethanol gradient elution is collected the dihydroquercetin flow point, and decompression recycling ethanol is placed crystallization;
4) recrystallization: leach crystallisate, use deionized water, 70% alcohol reflux crystallization successively, leach low-temperature vacuum drying and promptly get dihydroquercetin.
Such as claim 1 the preparation method of dihydroquercetin, it is characterized in that described step 1) pulverizes enzymatic hydrolysis condition and be: sour optional organic acid or mineral acid, enzyme addition 1-5 ‰, enzymolysis time were not less than 28 hours.
3. the preparation method of dihydroquercetin according to claim 1 is characterized in that the optional 100-200 order of polymeric amide polymeric amide in the described step 3).
4. the preparation method of dihydroquercetin according to claim 1 is characterized in that described step 3) water-ethanol gradient elution is: use 10-15BV water → 4-7BV20-40% ethanol → 5-8BV60-80% ethanol gradient elution successively.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102107471A CN101967505A (en) | 2010-06-28 | 2010-06-28 | Method for preparing dihydro quercetin |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102107471A CN101967505A (en) | 2010-06-28 | 2010-06-28 | Method for preparing dihydro quercetin |
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| CN101967505A true CN101967505A (en) | 2011-02-09 |
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740778A (en) * | 2014-01-06 | 2014-04-23 | 桂林莱茵生物科技股份有限公司 | Method for extracting dihydroquercetin and rhamnose from engelhardtia leaves |
| CN105175378A (en) * | 2015-07-16 | 2015-12-23 | 苏州禾研生物技术有限公司 | Preparation method of taxifolin |
| CN106924187A (en) * | 2017-02-22 | 2017-07-07 | 吉速利（上海）健康科技股份有限公司 | Nutrition Co-Q10 powder and preparation method thereof |
| CN108524313A (en) * | 2018-07-02 | 2018-09-14 | 吉林农业科技学院 | Dihydroquercetin skin care skin-lightening cosmetic |
-
2010
- 2010-06-28 CN CN2010102107471A patent/CN101967505A/en active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103740778A (en) * | 2014-01-06 | 2014-04-23 | 桂林莱茵生物科技股份有限公司 | Method for extracting dihydroquercetin and rhamnose from engelhardtia leaves |
| CN103740778B (en) * | 2014-01-06 | 2016-03-23 | 桂林莱茵生物科技股份有限公司 | The method of dihydroquercetin and rhamnosyl is extracted from Folium Engelhardia roxburghina |
| CN105175378A (en) * | 2015-07-16 | 2015-12-23 | 苏州禾研生物技术有限公司 | Preparation method of taxifolin |
| CN106924187A (en) * | 2017-02-22 | 2017-07-07 | 吉速利（上海）健康科技股份有限公司 | Nutrition Co-Q10 powder and preparation method thereof |
| CN108524313A (en) * | 2018-07-02 | 2018-09-14 | 吉林农业科技学院 | Dihydroquercetin skin care skin-lightening cosmetic |
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Application publication date: 20110209 |