CN114794153A - Method for recovering ginkgolic acid from waste residues in production of ginkgo biloba extract - Google Patents
Method for recovering ginkgolic acid from waste residues in production of ginkgo biloba extract Download PDFInfo
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- YXHVCZZLWZYHSA-FPLPWBNLSA-N Ginkgoic acid Chemical compound CCCCCC\C=C/CCCCCCCC1=CC=CC(O)=C1C(O)=O YXHVCZZLWZYHSA-FPLPWBNLSA-N 0.000 title claims abstract description 61
- YXHVCZZLWZYHSA-UHFFFAOYSA-N (Z)-6-[8-pentadecenyl]salicylic acid Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1C(O)=O YXHVCZZLWZYHSA-UHFFFAOYSA-N 0.000 title claims abstract description 59
- 239000002699 waste material Substances 0.000 title claims abstract description 24
- 239000009429 Ginkgo biloba extract Substances 0.000 title claims abstract description 20
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 title claims abstract description 19
- 235000020686 ginkgo biloba extract Nutrition 0.000 title claims abstract description 18
- 229940068052 ginkgo biloba extract Drugs 0.000 title claims abstract description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 78
- 239000000284 extract Substances 0.000 claims abstract description 32
- 244000194101 Ginkgo biloba Species 0.000 claims abstract description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 23
- 229920005989 resin Polymers 0.000 claims abstract description 23
- 235000008100 Ginkgo biloba Nutrition 0.000 claims abstract description 19
- 235000011201 Ginkgo Nutrition 0.000 claims abstract description 13
- 239000003480 eluent Substances 0.000 claims abstract description 12
- 238000011068 loading method Methods 0.000 claims abstract description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000012535 impurity Substances 0.000 claims abstract description 6
- 238000001179 sorption measurement Methods 0.000 claims abstract description 6
- 238000003756 stirring Methods 0.000 claims abstract description 6
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- 239000003208 petroleum Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 4
- 239000010410 layer Substances 0.000 claims description 3
- 239000012044 organic layer Substances 0.000 claims description 3
- 239000000243 solution Substances 0.000 claims 7
- 241000218628 Ginkgo Species 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- 239000000575 pesticide Substances 0.000 abstract description 11
- 238000012545 processing Methods 0.000 abstract description 4
- 238000011161 development Methods 0.000 abstract description 3
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- 230000007613 environmental effect Effects 0.000 abstract description 2
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- 241000607479 Yersinia pestis Species 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- YLKVIMNNMLKUGJ-FPLPWBNLSA-N (15:1)-Cardanol Chemical compound CCCCCC\C=C/CCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-FPLPWBNLSA-N 0.000 description 5
- YLKVIMNNMLKUGJ-UHFFFAOYSA-N 3-Delta8-pentadecenylphenol Natural products CCCCCCC=CCCCCCCCC1=CC=CC(O)=C1 YLKVIMNNMLKUGJ-UHFFFAOYSA-N 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000000287 crude extract Substances 0.000 description 3
- 231100000053 low toxicity Toxicity 0.000 description 3
- 150000007965 phenolic acids Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- DNTSXRMSSGNLFL-UHFFFAOYSA-N Hydroginkgolinic acid Natural products CCCCCCCCCCCCCCC1=CC=CC(O)=C1C(O)=O DNTSXRMSSGNLFL-UHFFFAOYSA-N 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- ADFWQBGTDJIESE-UHFFFAOYSA-N anacardic acid Chemical compound CCCCCCCCCCCCCCCC1=CC=CC(O)=C1C(O)=O ADFWQBGTDJIESE-UHFFFAOYSA-N 0.000 description 2
- 230000007123 defense Effects 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
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- 238000012360 testing method Methods 0.000 description 2
- 231100000331 toxic Toxicity 0.000 description 2
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- XXMFJKNOJSDQBM-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;hydrate Chemical compound [OH3+].[O-]C(=O)C(F)(F)F XXMFJKNOJSDQBM-UHFFFAOYSA-N 0.000 description 1
- TUGAUFMQYWZJAB-FPLPWBNLSA-N 5-[(8Z)-pentadec-8-enyl]resorcinol Chemical compound CCCCCC\C=C/CCCCCCCC1=CC(O)=CC(O)=C1 TUGAUFMQYWZJAB-FPLPWBNLSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- SRLTUZDQBFYLQI-FPLPWBNLSA-N Bilobol Natural products Oc1c(CCCCCCC/C=C\CCCCCC)ccc(O)c1 SRLTUZDQBFYLQI-FPLPWBNLSA-N 0.000 description 1
- 241000255789 Bombyx mori Species 0.000 description 1
- 241000222199 Colletotrichum Species 0.000 description 1
- 240000003759 Erodium cicutarium Species 0.000 description 1
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- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 208000026935 allergic disease Diseases 0.000 description 1
- 230000007815 allergy Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
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- 239000003337 fertilizer Substances 0.000 description 1
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- 230000000749 insecticidal effect Effects 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 238000013507 mapping Methods 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 230000000607 poisoning effect Effects 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
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- 238000001228 spectrum Methods 0.000 description 1
- 230000001502 supplementing effect Effects 0.000 description 1
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/06—Coniferophyta [gymnosperms], e.g. cypress
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- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Agronomy & Crop Science (AREA)
- Mycology (AREA)
- Plant Pathology (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
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- Environmental Sciences (AREA)
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Abstract
The method for recovering ginkgolic acid from the production waste residue of the ginkgo biloba extract comprises the following steps: (1) extracting folium Ginkgo with ethanol extractive solution, concentrating, removing ethanol, standing, precipitating, dissolving with methanol, centrifuging, extracting the filtrate with the same volume of extractant, adding water, layering, and concentrating the organic liquid layer to obtain extract; (2) dissolving the extract with ethanol solution, stirring, centrifuging, and collecting supernatant; (3) filling the treated resin into an adsorption column to ensure that the resin is uniformly filled without bubbles; loading the supernatant into a resin adsorption column; after the process is finished, removing impurities by using 1-3 BV of ethanol solution; eluting with 1-5 BV of ethanol solution, collecting the eluent, and vacuum concentrating to obtain purified ginkgolic acid extract. The invention promotes the rapid development of gingko planting and processing industry, improves the economic income of people, lays a foundation for increasing a novel biological pesticide in the market, and has obvious economic, environmental and social benefits.
Description
Technical Field
The invention relates to alkylphenol and alkylphenol phenolic acid in organic compounds, in particular to ginkgolic acid; further relates to a method for recovering ginkgolic acid from waste residues in the production of ginkgo biloba extract.
Background
Chinese gingko resources are extremely rich, account for about 80% of the worldwide gingko resources, and the gingko planting amount is large. Ginkgo biloba (Ginkgo biloba L.) is also called gingko, and a high-efficiency defense system evolved by natural selection of the gingko biloba is rarely damaged by diseases and pests in the growth process, and the defense effect is closely related to secondary chemicals of the gingko biloba. It is reported that the reason why ginkgo is rarely damaged by pests is that phenolic acid components of ginkgo leaves play a major role. However, people only pay attention to the effect of ginkgo on the medical value for a long time, and neglect the application in the agricultural pest control. In recent years, although some pest control reports exist, the types of target pests to be researched are few, and most of the target pests are tested by using crude extracts due to the limitation of extraction technology, and the test result of high-purity ginkgolic acid is lacked. The ginkgolic acid is a byproduct in the production and application of the ginkgo biloba extract and the preparation thereof, is abandoned during the extraction and processing of the ginkgo biloba, not only pollutes the environment, but also can cause poisoning of people and livestock.
Ginkgolic acid is alkylphenol and alkylphenol acid substances existing in ginkgo, belongs to long-chain phenol compounds, and comprises ginkgolic acid (ginkgolic acid), hydroginkgolic acid (hydroginkgolic acid), ginkgol (bilobol), ginkgol (ginkgol) and other components, wherein the components can be related to allergy and mutation and are toxic and side effects components in ginkgo biloba extracts. The content of the ginkgolic acid is controlled to be below 5 mug/g under the item of ginkgo leaf extract in the Chinese pharmacopoeia of 2015 edition, and researches show that the content of the ginkgolic acid in the ginkgo leaves in China is 500 to 200 mug/g.
The ginkgoic acid, ginkgol and ginkgol in the ginkgo testa are all insecticidal and antibacterial active substances. In forest flood clearing and the like, methanol and ethanol are used as solvents to obtain a crude extract of ginkgo episperm, and the hypha growth inhibition rate of all the crude extracts on colletotrichum album, solanum solani and fusarium oxysporum is 100%. Indoor and potted plant antibacterial tests of the dupont crowfoot and the like show that the ginkgo episperm extracting solution has 90% of control effect on tomato leaf mold and tomato bacterial wilt after being treated for 10 days. The research of Zhanghongmei finds that the low-concentration ginkgo episperm extract can improve the germination rate and the germination rate of wheat, soybean and corn seeds; promoting the growth of the overground and underground parts of the seedlings. The biological pesticide prepared from the ginkgo exocarp phenolic acid substance has good effect on preventing and treating aphids, cabbage caterpillars and thrips, and has the same effect as the control chemical pesticide; research on the golden dangqin shows that the ginkgolic acid can be degraded quickly after being applied into soil for 5 days. The toxicity experiment of the pesticide prepared from ginkgolic acid by Jiangsu province disease prevention and control center shows that the acute oral LD50 is more than 5000 mg/kg, and the pesticide belongs to a slightly toxic pesticide. The pesticide has low toxicity to bees, birds, fish and silkworms and no influence on the environment, and is a high-efficiency low-toxicity botanical pesticide which can be developed. The documents show that the ginkgolic acid has good potential for developing plant-derived pesticides. The plant disease and insect pest prevention and control method has the characteristics of high efficiency, low toxicity and low residue, and has a good application prospect in the production of green agricultural products.
In the Chinese patent database, only one patent application related to ginkgo leaf extract waste residue is available, namely 291310393164.0 < organic compound fertilizer of ginkgo leaf extract waste residue and preparation method thereof >. So far, no patent application for recovering ginkgolic acid from waste residue in production of ginkgo biloba extract is available.
Disclosure of Invention
The invention aims to provide a method for recovering ginkgolic acid from waste residues generated in the production of a ginkgo biloba extract, so as to improve the comprehensive utilization rate of ginkgo biloba, solve the problem of waste pollution, change waste into valuables, change harm into benefit, increase social wealth and promote economic development.
The method for recovering the ginkgolic acid from the waste residue in the production of the ginkgo biloba extract provided by the inventor comprises the following steps:
(1) extracting folium Ginkgo with ethanol extractive solution, concentrating, removing ethanol, standing, precipitating, dissolving with methanol, centrifuging, extracting with petroleum ether or dichloromethane or ethyl acetate with the same volume as the solution, adding water, layering, and concentrating the organic liquid layer to obtain extract;
(2) dissolving the extract with ethanol solution, stirring, centrifuging, and collecting supernatant;
(3) filling the resin which is processed in advance into an adsorption column to ensure that the resin is uniformly filled without bubbles; loading the supernatant into a resin adsorption column; after the sample loading is finished, removing impurities by using 1-3 BV of ethanol solution; and eluting by using 1-5 BV of ethanol solution, collecting eluent, and concentrating the eluent in vacuum to obtain an extract, namely the purified ginkgolic acid extract.
In the step (1), after centrifugation, water is supplemented until demixing, and a methanol solution with the concentration of 33-75% is prepared.
In the step (2) of the method, the mass fraction of the ethanol solution is 60-70%.
In the step (3), the mass fraction of the ethanol solution used for removing impurities is 60-70%; the mass fraction of the ethanol solution used for elution is 90-95 percent; the purified ginkgolic acid extract is a finished product of ginkgolic acid with the ginkgolic acid content of more than 75 percent.
The determination of the content of the ginkgolic acid in the finished ginkgolic acid product is carried out by adopting a chromatography, and the chromatographic conditions are as follows: a chromatographic column: Supersil-U C18(4.6 mm. times.150 mm, 5 m); mobile phase: acetonitrile (a) -0.1% trifluoroacetic acid water (B); detection wavelength: 310 nm; sample introduction amount: 50 mu l; column temperature: 45 ℃; flow rate: 1 ml/min; analysis time: and (4) 40 min.
The purification of the ginkgolic acid adopts a relatively mature column chromatography method, selects an HPD-5000 macroporous resin column, and screens the concentration of the eluent and the dosage of the eluent. And (3) screening the concentration of the eluent, dissolving 6.32g of the ginkgolic acid extract in 160ml of 70% ethanol, loading the dissolved extract on a column, removing impurities by using 2BV of 70% ethanol, eluting by using 3BV of 75%, 80% and 90% ethanol in sequence, collecting eluates with different concentrations, concentrating to obtain an extract, and determining the content of ginkgolic acid.
The results of different concentrations of column chromatography eluents are shown in table 1, only 4.10mg of ginkgolic acid is eluted from 70% ethanol eluents, a large amount of ginkgolic acid is enriched between 80% and 90% ethanol, and the content of ginkgolic acid respectively reaches 71.35% and 84.31%. Thus, the column chromatography method was determined: dissolving the extract with 70% ethanol, purifying with 70% ethanol, resolving with 4BV 90% ethanol, and concentrating the eluate to obtain final column eluate extract.
TABLE 1 comparison of eluent concentrations
The positive significance of the invention is that: firstly, waste residue generated in the production of the ginkgo biloba extract is used as a raw material, the cost is not required, and comprehensive utilization and harm conversion are realized by extracting the ginkgolic acid; secondly, macroporous resin is adopted to separate effective components, so that the cost is low and the operation is simple; the recovery and utilization of the ginkgolic acid have good prospect of preparing biological bactericide, change waste into valuable and have certain economic value; the invention reduces the environmental pollution of gingko processing and lays a foundation for developing green plant biological pesticide.
The invention promotes the rapid development of the whole gingko planting and processing industry, improves the economic income of local people, lays a foundation for adding a novel plant source biological pesticide to the domestic market, and has obvious economic, environmental and social benefits.
Drawings
FIG. 1 is a HPLC mapping spectrum of a ginkgolic acid control;
FIG. 2 is an HPLC chromatogram of a ginkgolic acid control;
FIG. 3 is an HPLC chromatogram of 77% ginkgolic acid extract separated and purified from waste residue;
Detailed Description
Example 1
Taking 104.8kg of ginkgo biloba extract production waste residue as a raw material, adding 300L of methanol, stirring for dissolving, centrifuging, extracting filtrate with 300L of petroleum ether, replenishing water for 75L, layering, concentrating the petroleum ether layer into paste, dissolving with 150L of 65% ethanol, loading onto a macroporous resin column, washing with 65% ethanol with the volume of 3BV resin, eluting with 90% ethanol with the volume of 5BV resin, and concentrating the eluent to obtain the extract with the ginkgolic acid content of more than 75%. The ginkgolic acid is used as a standard sample, the content of ginkgolic acid is measured by an HPLC method, and the result shows that: extracting 17% of waste residues in the production of the ginkgo biloba extract, concentrating to obtain 31.5kg of extract with the content of the ginkgolic acid of 52.6%, and purifying by using a resin column to obtain 20.3kg of extract with the content of the ginkgolic acid of 78%.
Example 2
Taking 102.4kg of ginkgo biloba extract production waste residue as a raw material, adding 400L of methanol, stirring for dissolving, centrifuging, extracting the filtrate with 400L of dichloromethane, supplementing 135L of water, concentrating the organic layer to paste, dissolving with 150L of 70% ethanol, loading onto a macroporous resin column, eluting with 70% ethanol with the volume of 1.5BV resin, eluting with 95% ethanol with the volume of 3BV resin, and concentrating the eluate to obtain the extract with the ginkgolic acid content of more than 75%. The ginkgolic acid is used as a standard sample, the content of ginkgolic acid is measured by an HPLC method, and the result shows that: extracting 17% of waste residues in the production of the ginkgo biloba extract, concentrating to obtain 32.4kg of extract with the content of the ginkgolic acid of 51.5%, and purifying by using a resin column to obtain 19.5kg of extract with the content of the ginkgolic acid of 79.4%.
Example 3
Taking 107.2kg of ginkgo biloba extract production waste residue as a raw material, adding 500L of methanol, stirring for dissolving, centrifuging, filtering, extracting with 500L of ethyl acetate, replenishing 1000L of water, concentrating an organic layer to obtain an extract, dissolving with 150L of 70% ethanol, introducing into a macroporous resin column, eluting with 70% ethanol with the volume of 2BV resin, eluting with 95% ethanol with the volume of 4BV resin, and concentrating the eluate to obtain an extract with the content of ginkgolic acid more than 75%. The ginkgolic acid is used as a standard sample, the content of ginkgolic acid is measured by an HPLC method, and the result shows that: extracting 17% of waste residues in the production of the ginkgo biloba extract, concentrating to obtain 33.8kg of extract with the content of the ginkgolic acid of 53.1%, and purifying by using a resin column to obtain 22.1kg of extract with the content of the ginkgolic acid of 77.2%.
Claims (4)
1. A method for recovering ginkgolic acid from waste residues generated in the production of ginkgo biloba extract is characterized by comprising the following steps:
(1) extracting folium Ginkgo with ethanol extractive solution, concentrating, removing ethanol, standing, precipitating, dissolving with methanol, centrifuging, extracting with petroleum ether or dichloromethane or ethyl acetate, adding water, layering, and concentrating the organic layer to obtain extract;
(2) dissolving the extract with ethanol solution, stirring, centrifuging, and collecting supernatant;
(3) filling the resin which is processed in advance into an adsorption column to ensure that the resin is uniformly filled without bubbles; loading the supernatant into a resin adsorption column; after the sample loading is finished, removing impurities by using 1-3 BV of ethanol solution; and eluting by using 1-5 BV of ethanol solution, collecting eluent, and concentrating the eluent in vacuum to obtain an extract, namely the purified ginkgolic acid extract.
2. The method for recovering ginkgolic acid from the waste residues generated in the production of ginkgo biloba leaves extract as claimed in claim 1, wherein in the step (1), said step of adding water to separate layers is to prepare a methanol aqueous solution with a concentration of 33% -75%.
3. The method for recovering ginkgolic acid from waste residues generated in the production of ginkgo biloba extract according to claim 1, wherein in the step (2), the mass fraction of the ethanol solution is 60% -70%.
4. The method for recovering ginkgolic acid from waste residues generated in the production of ginkgo biloba leaves extract according to claim 1, wherein in the step (3), the mass fraction of the ethanol solution used for removing impurities is 60% -70%, and the mass fraction of the ethanol solution used for eluting is 90% -95%; the purified ginkgolic acid extract is a finished product of ginkgolic acid with the ginkgolic acid content of more than 75 percent.
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Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1374300A (en) * | 2002-03-26 | 2002-10-16 | 贵州省生化工程中心 | Resin process of eliminating ginkgolic acid from gingko leaf extractive |
| CN101531590A (en) * | 2009-04-21 | 2009-09-16 | 福州大学 | Ginkgoic acid preparation method using macroporous adsorption resin |
| US20150044311A1 (en) * | 2012-04-23 | 2015-02-12 | Chengdu Baiyu Technology Pharmacy Co., Ltd. | Method for extracting and separating ginkgolides |
| CN105477026A (en) * | 2016-02-02 | 2016-04-13 | 武汉理工大学 | Process for extracting ginkgolic acid, flavone, terpene lactones and polysaccharose from gingko exotesta in combined mode |
| US20160367612A1 (en) * | 2014-02-10 | 2016-12-22 | Dr. Willmar Schwabe Gmbh & Co., Kg | Improved method for producing ginko extracts |
| CN106832045A (en) * | 2015-12-02 | 2017-06-13 | 中国科学院大连化学物理研究所 | A kind of method that gingko episperm extracts pectin and phenolic acid compound simultaneously |
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