CN101054369A - Method of extracting and separating dihydroquercetin from roxburgh engelhardtia leaf - Google Patents
Method of extracting and separating dihydroquercetin from roxburgh engelhardtia leaf Download PDFInfo
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Abstract
The present invention discloses a method for extracting and separating dihydroquercetin from wolfberry leaf, in which dihydroquercetin is prepared from wolfberry leaf through extracting, concentrating, column chromatography, crystallizing and hydrolyzing to generate an acicular crystal white dihydroquercetin, wherein the content of dihydroquercetin more than 95%(HPLC test). The present invention can extract astilbin, quercetin and dihydroquercetin from wolfberry leaf simultaneously, which has advantages of high yield and ripe technology, and it is suitable for industrialization and continuous production.
Description
Technical field
The present invention relates to that extraction separation has the active dihydroquercetin of antioxidation biology from plant, be specifically related to extraction separation dihydroquercetin from Folium Engelhardia roxburghina.
Background technology
Yellow Qi (Engelhardia Roxburghiana Wall Leaf) is the wild evergreen arbor of walnut section of SOUTHERN CHINA Guangdong and Guangxi two provinces, and leaf uses as the health tea of heat-clearing, detoxifcation and fat-reducing usefulness since ancient times.Folium Engelhardia roxburghina: have certain promoting blood circulation and removing blood stasis, reducing blood-fat, the hypoglycemic and effect that improves immunologic function; Multiple physiological activities such as effect with antioxygenation, inhibition obesity action, antianaphylaxis effect and preventing cancer; Not only type i allergic reaction diseases such as pathergy rhinitis, allergic dermatitis and bronchitis there is result of treatment, but also effective in cure to type iv allergic reaction diseases such as contact atopic dermatitis.
Dihydroquercetin (Taxifolin, i.e. Dihydroquercetin:
2-(3,4-dihydroxypheny 1)-2,3-dihydro-3,5,7-trihydroxy-4H-benzopyran-4-one) be a kind of of Vitamin P complex, chemical molecular formula: C
15H
12O
7, structural formula is as follows:
Dihydroquercetin has antioxygenation efficiently as one of Vitamin P complex, keeping the immunizing power that can effectively improve body aspect the human recycle system, improves erythrocytic activity, and it is aging to delay human body; Dihydroquercetin is natural vitamer P class material, is the biologically active agent of widespread use, belongs to vitamin PP family; Have characteristics such as the capillary permeability of reduction and brittleness, anti-inflammatory, protection stomach, it is twin to eliminate the unstriated muscle convulsion, strengthens the function of liver, has radiation-resistant provide protection; Be free radical aceeptor, so can close the antioxidant of acid esters, butterfat, lard etc. as insatiable hunger; Have radioprotective and oxidation resistant characteristics, can make, add in the food such as milk powder, chocolate, can prolong the storage life of food, and can make food have precious pharmaceutical use as foodstuff additive.
Through the patent inquiry, there is not to find the patent of extraction separation dihydroquercetin from Folium Engelhardia roxburghina.Now, generally all be from tamarack, to extract dihydroquercetin, such as number of patent application " 200610035752.7 1 kinds of methods that adopt absorption method from tamarack, to extract dihydroquercetin ", this invention provides a kind of method that adopts absorption method to extract dihydroquercetin from tamarack, with 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, the white or the little yellow powdered dihydroquercetin raw product that obtain, resulting dihydroquercetin raw product water carries out recrystallization purifying, just obtains the dihydroquercetin highly finished product.Number of patent application " 200610035280.5 1 kinds of methods of from tamarack, extracting dihydroquercetins " for another example, this invention provides a kind of method of extracting dihydroquercetin from tamarack, with water is extraction agent, 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, back methyl tertiary butyl ether extraction liquid carries out removing of solvent under vacuum condition to decolouring, removing paste water behind the solvent carries out crystallization purifying and makes the dihydroquercetin raw product, resulting dihydroquercetin raw product water carries out recrystallization purifying, just obtains the dihydroquercetin highly finished product.Above patent, in purification procedures, just simple employing polyamide column or liquid-liquid extraction, the recrystallization by crude product comes purifying again, so the yield of product is very low.
Summary of the invention
The objective of the invention is to be to provide a kind of from Folium Engelhardia roxburghina the method for extraction separation dihydroquercetin.
In order to achieve the above object, the present invention adopts following technical measures:
(1) raw material is handled: with the raw material impurity elimination, be cut into the segment of 3-5cm;
(2) extract, concentrate: the raw material of handling well is dropped in the multi-function extractor, add the ethanol of 6 times of amounts 80% for the first time, refluxing extraction 2 hours is collected extracting solution; The ethanol that adds for the second time 5 times of amounts 80%, refluxing extraction 2 hours is collected extracting solution; Residual residue reclaimed ethanol about 2 hours; Merge the extracting solution that obtains for twice, being evaporated to does not have the alcohol flavor, the centrifugal precipitation of going;
(3) column chromatography: the soup after centrifugal is crossed polymeric adsorbent adsorb, clean resin to colourless with purified water, the ethanol elution with 70%, colourless to effluent liquid, collect the merging elutriant, with the elutriant concentrating under reduced pressure, reclaim ethanol;
(4) crystallization: elutriant is evaporated to no ethanol, places, separate out faint yellow precipitation, the leaching precipitation, behind 50% dissolve with ethanol, concentrating part ethanol, recrystallization, leaching crystallization, vacuum-drying;
(5) hydrolysis: faint yellow crystallization is added hydrochloric acid hydrolysis, and flowing water is cooled to room temperature, separates out yellow powdery precipitation, and leaching should precipitate, and was washed to neutrality, added rare pure recrystallization then, got Quercetin; In addition supernatant liquor was placed 24 hours, separated out off-white color needle crystal, this crystallization of leaching is washed to neutrality, adds the hot water dissolving then, places recrystallization naturally, obtains product.
Raw material of the present invention is a Folium Engelhardia roxburghina.
Polymeric adsorbent of the present invention is a macroporous resin, and model is selected from: D101, D102, AB-8 type, X-5 type, NKA-II type, HPD400 type, HPD500 type.
Faint yellow crystallization of the present invention is an Astilbin.
In the hydrolysing step of the present invention, the concentration of hydrochloric acid is 0.5-2.5%, and add-on is 15-25 a times of crystallization weight, and hydrolysis temperature is 80-95 ℃, and the time is 1-3 hour, and rare alcohol is the ethanol of 20-30%.
In the product of the present invention off-white color, acicular dihydroquercetin, wherein dihydroquercetin content is greater than 95% (HPLC test).
Advantage of the present invention:
From Folium Engelhardia roxburghina, extract dihydroquercetin; Can obtain simultaneously Astilbin, Quercetin,
Dihydroquercetin; The yield height, technical maturity is suitable for industrialization, continuity production.
Description of drawings
Fig. 1 is the HPLC collection of illustrative plates of dihydroquercetin in the Folium Engelhardia roxburghina extrat.
Embodiment
Embodiment 1
(1) raw material is handled: with the impurity elimination of Folium Engelhardia roxburghina raw material, be cut into the segment of 3-5cm;
(2) extract, concentrate: the raw material of handling well is dropped in the multi-function extractor, add the ethanol of 6 times of amounts 80% for the first time, refluxing extraction 2 hours is collected extracting solution; The ethanol that adds for the second time 5 times of amounts 80%, refluxing extraction 2 hours is collected extracting solution; Residual residue reclaimed ethanol about 2 hours; Merge the extracting solution that obtains for twice, being evaporated to does not have the alcohol flavor, the centrifugal precipitation of going;
(3) column chromatography: it is that the macroporous adsorbent resin of D101 adsorbs that the soup after centrifugal is crossed model, cleans resin to colourless with purified water, and the ethanol elution with 70% is colourless to effluent liquid, collect to merge elutriant, and with the elutriant concentrating under reduced pressure, recovery ethanol;
(4) crystallization: elutriant is evaporated to no ethanol, places, separate out faint yellow precipitation, the leaching precipitation, behind 50% dissolve with ethanol, concentrating part ethanol, recrystallization, the leaching crystallization, vacuum-drying obtains Astilbin;
(5) hydrolysis: crystallization is added 2% hydrochloric acid of 20 times of amounts, 90 degree hydrolysis 2 hours, flowing water is cooled to room temperature, separates out yellow powdery precipitation, leaching should precipitation, is washed to neutrality, uses 20% ethyl alcohol recrystallization then, Quercetin; In addition supernatant liquor was placed 24 hours, separated out off-white color needle crystal, this crystallization of leaching is washed to neutrality, adds the hot water dissolving then, places recrystallization naturally, obtains the needle crystal of dihydroquercetin, content 96.1% (HPLC test).
The HPLC collection of illustrative plates as shown in Figure 1.
Embodiment 2
(1) raw material is handled: with the impurity elimination of Folium Engelhardia roxburghina raw material, be cut into the segment of 3-5cm;
(2) extract, concentrate: the raw material of handling well is dropped in the multi-function extractor, add the ethanol of 6 times of amounts 80% for the first time, refluxing extraction 2 hours is collected extracting solution; The ethanol that adds for the second time 5 times of amounts 80%, refluxing extraction 2 hours is collected extracting solution; Residual residue reclaimed ethanol about 2 hours; Merge the extracting solution that obtains for twice, being evaporated to does not have the alcohol flavor, the centrifugal precipitation of going;
(3) column chromatography: it is that the macroporous adsorbent resin of AB-8 adsorbs that the soup after centrifugal is crossed model, cleans resin to colourless with purified water, and the ethanol elution with 70% is colourless to effluent liquid, collect to merge elutriant, and with the elutriant concentrating under reduced pressure, recovery ethanol;
(4) crystallization: elutriant is evaporated to no ethanol, places, separate out faint yellow precipitation, the leaching precipitation, behind 50% dissolve with ethanol, concentrating part ethanol, recrystallization, the leaching crystallization, vacuum-drying obtains Astilbin;
(5) hydrolysis: crystallization is added 0.5% hydrochloric acid of 15 times of amounts, 80 degree hydrolysis 3 hours, flowing water is cooled to room temperature, separates out yellow powdery precipitation, leaching should precipitation, is washed to neutrality, uses 30% ethyl alcohol recrystallization then, Quercetin; In addition supernatant liquor was placed 24 hours, separated out off-white color needle crystal, this crystallization of leaching is washed to neutrality, adds the hot water dissolving then, places recrystallization naturally, obtains the needle crystal of dihydroquercetin, content 95.7% (HPLC test).
Embodiment 3
(1) raw material is handled: with the impurity elimination of Folium Engelhardia roxburghina raw material, be cut into the segment of 3-5cm;
(2) extract, concentrate: the raw material of handling well is dropped in the multi-function extractor, add the ethanol of 6 times of amounts 80% for the first time, refluxing extraction 2 hours is collected extracting solution; The ethanol that adds for the second time 5 times of amounts 80%, refluxing extraction 2 hours is collected extracting solution; Residual residue reclaimed ethanol about 2 hours; Merge the extracting solution that obtains for twice, being evaporated to does not have the alcohol flavor, the centrifugal precipitation of going;
(3) column chromatography: it is that the macroporous adsorbent resin of NKA-II adsorbs that the soup after centrifugal is crossed model, cleans resin to colourless with purified water, and the ethanol elution with 70% is colourless to effluent liquid, collect to merge elutriant, and with the elutriant concentrating under reduced pressure, recovery ethanol;
(4) crystallization: elutriant is evaporated to no ethanol, places, separate out faint yellow precipitation, the leaching precipitation, behind 50% dissolve with ethanol, concentrating part ethanol, recrystallization, the leaching crystallization, vacuum-drying obtains Astilbin;
(5) hydrolysis: crystallization is added 3% hydrochloric acid of 25 times of amounts, 95 degree hydrolysis 1 hour, flowing water is cooled to room temperature, separates out yellow powdery precipitation, leaching should precipitation, is washed to neutrality, uses 25% ethyl alcohol recrystallization then, Quercetin; In addition supernatant liquor was placed 24 hours, separated out off-white color needle crystal, this crystallization of leaching is washed to neutrality, adds the hot water dissolving then, places recrystallization naturally, obtains the needle crystal of dihydroquercetin, content 96.5% (HPLC test).
Claims (6)
1, a kind of from Folium Engelhardia roxburghina the method for extraction separation dihydroquercetin, comprise the steps:
(1) raw material is handled: with the raw material impurity elimination, be cut into the segment of 3-5cm;
(2) extract, concentrate: the raw material of handling well is dropped in the multi-function extractor, add the ethanol of 6 times of amounts 80% for the first time, refluxing extraction 2 hours is collected extracting solution; The ethanol that adds for the second time 5 times of amounts 80%, refluxing extraction 2 hours is collected extracting solution; Residual residue reclaimed ethanol about 2 hours; Merge the extracting solution that obtains for twice, being evaporated to does not have the alcohol flavor, the centrifugal precipitation of going;
(3) column chromatography: the soup after centrifugal is crossed polymeric adsorbent adsorb, clean resin to colourless with purified water, the ethanol elution with 70%, colourless to effluent liquid, collect the merging elutriant, with the elutriant concentrating under reduced pressure, reclaim ethanol;
(4) crystallization: elutriant is evaporated to no ethanol, places, separate out faint yellow precipitation, the leaching precipitation, behind 50% dissolve with ethanol, concentrating part ethanol, recrystallization, leaching crystallization, vacuum-drying;
(5) hydrolysis: faint yellow crystallization is added hydrochloric acid hydrolysis, and flowing water is cooled to room temperature, separates out yellow powdery precipitation, and leaching should precipitate, and was washed to neutrality, added rare pure recrystallization then, got Quercetin; In addition supernatant liquor was placed 24 hours, separated out off-white color needle crystal, this crystallization of leaching is washed to neutrality, adds the hot water dissolving then, places recrystallization naturally, obtains product.
2, the method for extraction separation dihydroquercetin from Folium Engelhardia roxburghina according to claim 1, it is characterized in that: described raw material is a Folium Engelhardia roxburghina.
3, the method for extraction separation dihydroquercetin from Folium Engelhardia roxburghina according to claim 1, it is characterized in that: described polymeric adsorbent is a macroporous resin, model is selected from D101, D102, AB-8 type, X-5 type, NKA-II type, HPD400 type, HPD500 type.
4, the method for extraction separation dihydroquercetin from Folium Engelhardia roxburghina according to claim 1, it is characterized in that: described faint yellow crystallization is an Astilbin.
5, the method for extraction separation dihydroquercetin from Folium Engelhardia roxburghina according to claim 1, it is characterized in that: in the described hydrolysing step, the concentration of hydrochloric acid is 0.5-2.5%, add-on is 15-25 a times of crystallization weight, hydrolysis temperature is 80-95 ℃, time is 1-3 hour, and rare alcohol is the ethanol of 20-40%.
6, the method for extraction separation dihydroquercetin from Folium Engelhardia roxburghina according to claim 1 is characterized in that: be off-white color in the described product, and acicular dihydroquercetin, wherein dihydroquercetin content is greater than 95% (HPLC test).
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Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010095969A1 (en) * | 2009-02-17 | 2010-08-26 | Закрытое Акционерное Общество "Биoxиmmak Ct" | Method for producing dihydroquercetin |
| CN101851221A (en) * | 2010-05-27 | 2010-10-06 | 东北林业大学 | Method for preparing dihydroquercetin from larches |
| CN101863869A (en) * | 2010-06-03 | 2010-10-20 | 东北林业大学 | Method for extracting dihydroquercetin from larch sheets |
| CN102234300A (en) * | 2010-04-26 | 2011-11-09 | 广州医学院 | Methods for extracting astilbin and dihydroquercetin from engelhardia roxburghiana wall leaves and application of extractives thereof |
| CN102579567A (en) * | 2012-04-10 | 2012-07-18 | 广西壮族自治区中医药研究院 | Medicine for treating diabetes and preparation method thereof |
| CN103044379A (en) * | 2012-12-31 | 2013-04-17 | 李玉山 | Green preparation technology of dihydroquercetin |
| CN103181952A (en) * | 2011-12-31 | 2013-07-03 | 天津药物研究院 | Roxburgh engelhardtia extractive for preventing and treating autoimmune diseases and preparation method thereof |
| CN103183656A (en) * | 2011-12-31 | 2013-07-03 | 天津药物研究院 | Preparation method of high-purity taxifolin monomer |
| 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 |
| CN105237505A (en) * | 2015-10-20 | 2016-01-13 | 北京化工大学 | Method for preparing high-purity taxifolin with saw dust of larix gmelinii in Lesser Khingan mountains as raw material |
| CN105585551A (en) * | 2016-03-01 | 2016-05-18 | 苏州禾研生物技术有限公司 | Hydrolysis method of astilbin |
| CN107893033A (en) * | 2017-11-23 | 2018-04-10 | 浙江工业大学 | Aspergillus fumigatus SQH4 and the application in biotransformation method prepares texifolin |
| CN108675978A (en) * | 2018-05-28 | 2018-10-19 | 江西农业大学 | A method of preparing high-purity texifolin by raw material of smilax |
| CN111440221A (en) * | 2019-12-13 | 2020-07-24 | 湖南甜蔓生物科技有限公司 | Astilbin prepared from Engelhardtia chrysolepis Hance leaf and its preparation method |
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2007
- 2007-06-05 CN CN 200710105982 patent/CN101054369A/en active Pending
Cited By (20)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2010095969A1 (en) * | 2009-02-17 | 2010-08-26 | Закрытое Акционерное Общество "Биoxиmmak Ct" | Method for producing dihydroquercetin |
| CN102234300A (en) * | 2010-04-26 | 2011-11-09 | 广州医学院 | Methods for extracting astilbin and dihydroquercetin from engelhardia roxburghiana wall leaves and application of extractives thereof |
| CN101851221A (en) * | 2010-05-27 | 2010-10-06 | 东北林业大学 | Method for preparing dihydroquercetin from larches |
| CN101851221B (en) * | 2010-05-27 | 2012-09-05 | 东北林业大学 | Method for preparing dihydroquercetin from larches |
| CN101863869A (en) * | 2010-06-03 | 2010-10-20 | 东北林业大学 | Method for extracting dihydroquercetin from larch sheets |
| CN103181952A (en) * | 2011-12-31 | 2013-07-03 | 天津药物研究院 | Roxburgh engelhardtia extractive for preventing and treating autoimmune diseases and preparation method thereof |
| CN103183656A (en) * | 2011-12-31 | 2013-07-03 | 天津药物研究院 | Preparation method of high-purity taxifolin monomer |
| CN102579567A (en) * | 2012-04-10 | 2012-07-18 | 广西壮族自治区中医药研究院 | Medicine for treating diabetes and preparation method thereof |
| CN103044379A (en) * | 2012-12-31 | 2013-04-17 | 李玉山 | Green preparation technology of dihydroquercetin |
| 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 |
| 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 |
| CN105237505A (en) * | 2015-10-20 | 2016-01-13 | 北京化工大学 | Method for preparing high-purity taxifolin with saw dust of larix gmelinii in Lesser Khingan mountains as raw material |
| CN105585551A (en) * | 2016-03-01 | 2016-05-18 | 苏州禾研生物技术有限公司 | Hydrolysis method of astilbin |
| CN105585551B (en) * | 2016-03-01 | 2018-10-02 | 苏州禾研生物技术有限公司 | A kind of method for hydrolysis of astilbin |
| CN107893033A (en) * | 2017-11-23 | 2018-04-10 | 浙江工业大学 | Aspergillus fumigatus SQH4 and the application in biotransformation method prepares texifolin |
| CN107893033B (en) * | 2017-11-23 | 2020-08-21 | 浙江工业大学 | Aspergillus fumigatus SQH4 and application thereof in preparation of taxifolin by biotransformation method |
| CN108675978A (en) * | 2018-05-28 | 2018-10-19 | 江西农业大学 | A method of preparing high-purity texifolin by raw material of smilax |
| CN108675978B (en) * | 2018-05-28 | 2021-06-01 | 江西农业大学 | Method for preparing high-purity taxifolin by taking rhizoma smilacis glabrae as raw material |
| CN111440221A (en) * | 2019-12-13 | 2020-07-24 | 湖南甜蔓生物科技有限公司 | Astilbin prepared from Engelhardtia chrysolepis Hance leaf and its preparation method |
| CN111440221B (en) * | 2019-12-13 | 2021-11-26 | 湖南甜蔓生物科技有限公司 | Astilbin prepared from Engelhardtia chrysolepis Hance leaf and its preparation method |
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