CN1291989C - Method for separating lycorine from plant extract - Google Patents
Method for separating lycorine from plant extract Download PDFInfo
- Publication number
- CN1291989C CN1291989C CN 200310102276 CN200310102276A CN1291989C CN 1291989 C CN1291989 C CN 1291989C CN 200310102276 CN200310102276 CN 200310102276 CN 200310102276 A CN200310102276 A CN 200310102276A CN 1291989 C CN1291989 C CN 1291989C
- Authority
- CN
- China
- Prior art keywords
- narcissine
- lycorine
- alkali
- solution
- plant extract
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- XGVJWXAYKUHDOO-DANNLKNASA-N lycorine Chemical compound C1CN2CC3=CC=4OCOC=4C=C3[C@H]3[C@H]2C1=C[C@H](O)[C@H]3O XGVJWXAYKUHDOO-DANNLKNASA-N 0.000 title claims abstract description 45
- 238000000034 method Methods 0.000 title claims abstract description 34
- XGVJWXAYKUHDOO-UHFFFAOYSA-N galanthidine Natural products C1CN2CC3=CC=4OCOC=4C=C3C3C2C1=CC(O)C3O XGVJWXAYKUHDOO-UHFFFAOYSA-N 0.000 title abstract description 7
- KQAOMBGKIWRWNA-UHFFFAOYSA-N lycorine Natural products OC1C=C2CCN3C2C(C1O)c4cc5OCOc5cc34 KQAOMBGKIWRWNA-UHFFFAOYSA-N 0.000 title abstract description 7
- 239000000419 plant extract Substances 0.000 title abstract description 6
- 239000003513 alkali Substances 0.000 claims abstract description 31
- 229930013930 alkaloid Natural products 0.000 claims abstract description 13
- 239000012043 crude product Substances 0.000 claims abstract description 11
- 150000003797 alkaloid derivatives Chemical class 0.000 claims abstract description 10
- 241000234270 Amaryllidaceae Species 0.000 claims abstract description 9
- 239000003960 organic solvent Substances 0.000 claims abstract description 9
- 239000000284 extract Substances 0.000 claims description 17
- 235000020245 plant milk Nutrition 0.000 claims description 9
- 241001633628 Lycoris Species 0.000 claims description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 8
- 238000002425 crystallisation Methods 0.000 claims description 8
- 230000008025 crystallization Effects 0.000 claims description 8
- 238000001514 detection method Methods 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 4
- 239000000047 product Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- 230000001476 alcoholic effect Effects 0.000 claims 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000003729 cation exchange resin Substances 0.000 abstract description 2
- 239000013078 crystal Substances 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- 238000010828 elution Methods 0.000 description 7
- 238000004809 thin layer chromatography Methods 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical group CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 230000007704 transition Effects 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 4
- 238000011010 flushing procedure Methods 0.000 description 4
- 239000003456 ion exchange resin Substances 0.000 description 4
- 229920003303 ion-exchange polymer Polymers 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 206010003445 Ascites Diseases 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- DPDMMXDBJGCCQC-UHFFFAOYSA-N [Na].[Cl] Chemical group [Na].[Cl] DPDMMXDBJGCCQC-UHFFFAOYSA-N 0.000 description 2
- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 229920001429 chelating resin Polymers 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- 238000003795 desorption Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 201000007270 liver cancer Diseases 0.000 description 2
- 208000014018 liver neoplasm Diseases 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000002203 pretreatment Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000000452 restraining effect Effects 0.000 description 2
- 239000012745 toughening agent Substances 0.000 description 2
- DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
- 201000009030 Carcinoma Diseases 0.000 description 1
- 241000755719 Crinum Species 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 241001534793 Haemanthus Species 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- 241000234479 Narcissus Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 206010039491 Sarcoma Diseases 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 208000001792 Sarcoma 37 Diseases 0.000 description 1
- 208000009916 Yoshida Sarcoma Diseases 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000006538 anaerobic glycolysis Effects 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000013375 chromatographic separation Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 238000004255 ion exchange chromatography Methods 0.000 description 1
- 210000002751 lymph Anatomy 0.000 description 1
- 208000025036 lymphosarcoma Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- HKIJKEFVQKXWGW-UHFFFAOYSA-N oxylycorine Chemical compound CC([O-])=O.C1=C2C3=CC(O)=CC(CC4)=C3[N+]4=CC2=CC2=C1OCO2 HKIJKEFVQKXWGW-UHFFFAOYSA-N 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 229920003987 resole Polymers 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The present invention relates to a method for separating effective components from plant extracts, particularly to a method from separating lycorine from a plant extract containing amaryllidaceae alkaloid. The method comprises the following technological steps: pretreating a plant extract containing amaryllidaceae alkaloid; absorbing and eluting the treated plant extract by using cation exchange resin; tracking and detecting the eluted flowing component; concentrating and enriching the flowing component in a lycorine section to obtain a crude product of free lycorine alkali; recrystallizing the crude product of the free lycorine alkali with an organic solvent to obtain the crystals of the free lycorine alkali whose purity is about 99%.
Description
(1) technical field
The present invention relates to the extracting method of the effective medicinal ingredients of plant, especially from the plant milk extract that contains amaryllidaceae alkaloid, with narcissine and the isolating method of other numerous alkaloids.
(2) background technology
Narcissine (lycorine) can suppress the anaerobic glycolysis of mouse ascites cancer cells, and mouse lymph sarcoma, sarcoma 37 and rat lymphosarcoma, liver cancer cell are had remarkable restraining effect; Hela cell, sarcoma 180, ehrlich carcinoma, ascites liver cancer and yoshida sarcoma also there is restraining effect.It also is the raw material of preparation cancer therapy drug oxylycorine (AT-1840).
Narcissine structural formula such as figure below.
Narcissine extracts from natural phant.These plants are distributed in fields such as Lycoris, Crinum, Narcissus, Haemanthus.Wherein representative with lycoris plants.The method of prior art separating short-tube lycoris alkali from plant milk extract mainly is an organic solvent extractionprocess.Utilize the lipotropy alkaloid to be dissolved in the lipotropy organic solvent, and the water-soluble character of its salt, and the difference of alkalescence between the various haplont alkali in the total alkaloids, under different pH conditions, separate.
Shortcoming and defect such as the technology of said extracted, separating short-tube lycoris alkali exists that organic solvent consumption is big, be easy to generate emulsion during extraction, influence the separation and Extraction effect, operative employee's duration.
Along with the continuous expansion of ion exchange resin Application Areas, the method for ion-exchange is also adopted in many alkaloidal separation.But above-mentioned patent documentation and non-patent literature there is no the identical record with the method for ion exchange resin absorption, wash-out narcissine of claim relevant and of the present invention.
(3) summary of the invention
Contain and contain tens of kinds of alkaloids such as narcissine, narcissine, narcissine in the amaryllidaceae alkaloid plant milk extract.The invention provides a kind of method by ion-exchange chromatography separating short-tube lycoris alkali, have that yield height, purity are good, an advantage of saving working hour, material saving.
Task of the present invention realizes by following technical scheme.
Contain the amaryllidaceae alkaloid plant milk extract through pre-treatment, according to used resin choice, with sample preparation is acid, neutral or alkaline, with Zeo-karb adsorb, wash-out, tracking detection wash-out stream part, enrichment method narcissine section stream part gets narcissine free alkali crude product, again with the organic solvent recrystallization, purity is about 99% narcissine free alkali crystallization.
The parent of described Zeo-karb is a kind of in SDEB styrene diethylenebenzene, resol, crosslinked polystyrene, the dextran.The functional group of Zeo-karb is a kind of formed strong acid in sulfonic group, methylsulphonic acid base, phosphate, carboxyl and the phenolic group, middle strong acid, weakly acidic cationic exchanger resin.The preferred cation exchange resin is a STREAMLINE SP resin.
Basic technology method of the present invention is as follows:
1. contain the pre-treatment of amaryllidaceae alkaloid plant milk extract: pretreated purpose is absorption or the exchange that helps the plant extract matter sample.Adopt different pretreatment processs according to the chromatographic technique that is adopted.Comprising, regulate the pH value that goes up sample solution with acid or alkali; By filtering or centrifugation method is removed solid particulate in the solution; And with sample through carrying out method such as chromatographic separation after the initial gross separation again.The acid that is used to regulate the pH value does not have specific limited, preferably hydrochloric acid or sulfuric acid, and concentration is 0.1%-10%; The alkali that is used to regulate the pH value does not have specific limited yet, preferably sodium hydroxide or ammoniacal liquor, and concentration is 1%-20%
2. the exchange of sample or absorption: ion exchange resin makes the transition, and is positioned over by any way in the exchange column, sample and ion exchange resin are adsorbed or exchanges.Absorption or exchange can be adopted dynamic method, also can adopt stationary method, and dynamic method preferably.
3. washing: be lower than the washing soln washing Zeo-karb of elute soln ionic strength to be higher than the equalizing and buffering solution ion strength, not combined thing under the wash-out from the Zeo-karb.The washing soln volume is 2-3 a times of column volume, and flow velocity is 2-3ml/min.
4. the wash-out of effective constituent: will adsorb or exchange the effective constituent material that gets on and discharge, and change elute soln again over to.Control elute soln volume, flow velocity 2-3ml/min.Type of elution can adopt dynamic desorption or static wash-out, but dynamic desorption mode preferably.Wash-out can adopt gradient elution or non-gradient elution.
Elute soln can be the salts solution bigger than the ionic strength of balanced solution, and for strengthening organic solvent that the ion elute effect takes as toughener.Preferred salt is sodium-chlor, and concentration is 0.1mol/L-10mol/L, and preferred toughener is an ethanol, and concentration is 10%-20%; Elute soln also can be the buffered soln bigger than balanced solution pH value; Elute soln can also be the mixing solutions of alkali and organic solvent, and preferred alkali is ammonia, and concentration is 1%-20%, and preferred organic is an ethanol, and concentration is 10%-95%.
5. the tracking of wash-out stream part detects and collects: when wash-out stream part, the tracking that should carry out the active substance narcissine detects.Detection method can be used thin-layer chromatography (TLC) method, also can use the method that other are suitable for detecting narcissine.According to detected result, collection, the identical R of merging with narcissine
fStream part of value.
6. flow the enrichment method of narcissine in part: the narcissine in enrichment method wash-out stream part can adopt extraction and/or distill spissated method.
Usually through enrichment method, can obtain the crude product of narcissine free alkali.
7. recrystallization: can use any organic solvent commonly used that narcissine free alkali crude product is carried out recrystallization, preferred solvent is a methyl alcohol.Through recrystallization, obtain the crystallization of pure product narcissine free alkali.Its purity is (HPLC) about 99%.
The method according to this invention can obtain narcissine effectively from vegetable material, be a kind of preparation method of separating short-tube lycoris alkali from the plant milk extract that contains amaryllidaceae alkaloid who is suitable for suitability for industrialized production.Advantage such as have the yield height, purity is good, technological operation is simple, save man-hour, raw materials consumption is few.
(4) embodiment
The following example is used to describe in detail the present invention, but does not limit the scope of the invention.
Embodiment 1
Amrallid extract 10kg adds 1% dissolve with hydrochloric acid solution, adjusting and keeps solution acidic.Remove by filter insoluble particles thing in the solution, the STREAMLINE SP Zeo-karb (2L) good by balance exchanges, and resin water flushing is to neutral, carries out gradient elution with the sodium chloride solution of 1mol/L, follow the tracks of detection with the TLC method, collecting has identical R with narcissine
fStream part of value, alkalize to pH8.7 with saturated sodium carbonate solution, 5 (500ml * 2 of ethyl acetate methanol mixed solvent (9/1V/V) extraction, 250ml * 3), anhydrous sodium sulfate drying, underpressure distillation obtains narcissine free alkali crude product 53.0g to doing, with recrystallizing methanol, content is about 99% narcissine free alkali crystallization 47.1g.
Embodiment 2
Amrallid extract 10kg adds 1% dissolve with hydrochloric acid solution, adjusting and keeps solution acidic.Remove by filter insoluble particles thing in the solution, exchange by the Amberlite CG-120 Zeo-karb (10L) that makes the transition, the flushing of resin water is carried out gradient elution to neutral with 5% ammoniacal liquor/ethanolic soln, follow the tracks of detection with the TLC method, collecting has identical R with narcissine
fStream part of value, ethanol is reclaimed in distillation.Regulator solution is to pH8.7, and chloroform methanol mixed solvent (9/2V/V) extracts 5 times (500ml * 2,250ml * 3), anhydrous sodium sulfate drying, underpressure distillation obtains narcissine free alkali crude product 54.2g to doing, with recrystallizing methanol, content is about 99% narcissine free alkali crystallization 47.6g.
Embodiment 3
Amrallid extract 10kg adds 1% dissolve with hydrochloric acid solution, adjusting and keeps solution acidic.Remove by filter insoluble particles thing in the solution, exchange by the STREAMLINE SP Zeo-karb (2L) that makes the transition, the flushing of resin water is to neutral, carry out wash-out with 0.1mol/L, 0.2mol/L, 0.3mol/L, 0.4mol/L, 0.6mol/L, 0.8mol/L sodium-chlor/20% ethanolic soln respectively, follow the tracks of detection with the TLC method, collecting has identical R with narcissine
fStream part of value, alkalize to pH8.7 with saturated sodium carbonate solution, 5 (500ml * 2 of ethyl acetate methanol mixed solvent (9/1V/V) extraction, 250ml * 3), anhydrous sodium sulfate drying, underpressure distillation obtains narcissine free alkali crude product 49.7g to doing, with recrystallizing methanol, content is about 99% narcissine free alkali crystallization 45.9g.
Embodiment 4
Amrallid extract 10kg adds the dissolving of 1% sodium hydroxide solution, regulates and keeps solution alkalescence.Remove by filter insoluble particles thing in the solution, exchange by the Amberlite IRC-50 Zeo-karb (10L) that makes the transition, the flushing of resin water is to neutral, sodium chloride solution with 0.1mol/L, 0.2mol/L, 0.3mol/L, 0.4mol/L, 0.6mol/L, 0.8mol/L carries out stepwise elution respectively, follow the tracks of detection with the TLC method, collecting has identical R with narcissine
fStream part of value, regulator solution is to pH8.7,5 (500ml * 2 of ethyl acetate methanol mixed solvent (9/1V/V) extraction, 250ml * 3), anhydrous sodium sulfate drying, underpressure distillation obtains narcissine free alkali crude product 50.5g to doing, with recrystallizing methanol, content is about 99% narcissine free alkali crystallization 47.9g.
Embodiment 5
Amrallid extract 10kg adds the dissolving of 1% sodium hydroxide solution, regulates and keeps solution alkalescence.Remove by filter insoluble particles thing in the solution, exchange by the Amberlite IRC-76 Zeo-karb (10L) that makes the transition, resin washes with the buffered soln of pH3.0, carry out stepwise elution with 0.1mol/L, the 0.4mol/L of pH3.0, the sodium chloride solution of 0.8mol/L respectively, follow the tracks of detection with the TLC method, collecting has identical R with narcissine
fStream part of value, alkalize to pH8.7 with saturated sodium carbonate solution, 5 (500ml * 2 of ethyl acetate methanol mixed solvent (9/1V/V) extraction, 250ml * 3), anhydrous sodium sulfate drying, underpressure distillation obtains narcissine free alkali crude product 52.3g to doing, with recrystallizing methanol, content is about 99% narcissine free alkali crystallization 46.6g.
Above embodiment 1～5 used amrallid extract all can use the product that obtains by " extracting the technology of amaryllidaceae alkaloid from natural phant " patent application method.This processing method is the applicant's in addition part invention, and Chinese patent application number is 03153992.0.
Claims (1)
1. the method for a separating short-tube lycoris alkali from contain the amaryllidaceae alkaloid plant milk extract, it is characterized in that, to the pretreated plant milk extract of process, the use Zeo-karb adsorbs, wash-out, tracking detection wash-out stream part, enrichment method narcissine section stream part gets narcissine free alkali crude product, with the organic solvent recrystallization, get the crystallization of pure product narcissine free alkali again; Wherein, described elute soln is, 1. 0.1mol/L-10mol/L sodium chloride solution and 10%-20% alcoholic acid mixing solutions, or 2. than the big buffered soln of balanced solution pH value.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310102276 CN1291989C (en) | 2003-10-30 | 2003-10-30 | Method for separating lycorine from plant extract |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 200310102276 CN1291989C (en) | 2003-10-30 | 2003-10-30 | Method for separating lycorine from plant extract |
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| CN1611504A CN1611504A (en) | 2005-05-04 |
| CN1291989C true CN1291989C (en) | 2006-12-27 |
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| CN 200310102276 Expired - Lifetime CN1291989C (en) | 2003-10-30 | 2003-10-30 | Method for separating lycorine from plant extract |
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Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101698022B (en) * | 2007-05-31 | 2012-02-29 | 北京和润创新医药科技发展有限公司 | Method for separating pepper total alkaloids by ion exchange resin |
| CN101698031B (en) * | 2007-05-31 | 2013-01-23 | 山东中医药大学 | Method for separating short-tube lycoris total alkaloids by ion exchange resin |
| CN101647854B (en) * | 2008-08-13 | 2012-08-29 | 代龙 | Method for separating total alkaloid from sophora flavescens ait by using ion exchange resin |
| CN101451155B (en) * | 2008-12-17 | 2011-08-31 | 华宝食用香精香料（上海）有限公司 | Method for extracting lycorine from Lycoris radiata |
| CN104031056A (en) * | 2014-06-18 | 2014-09-10 | 潘井生 | Production method of lycorine |
| CN104961744B (en) * | 2015-04-27 | 2018-07-17 | 吉首大学 | A method of extracting lycorine from lycoris plants |
| CN109303919B (en) * | 2017-07-26 | 2020-09-04 | 天津中医药大学 | Application of Akt inhibitor in preparation of anti-liver cancer active drug for enhancing lycorine |
| CN109303783B (en) * | 2017-07-26 | 2020-09-04 | 天津中医药大学 | Application of autophagy inhibitor in preparation of medicine for enhancing anti-liver cancer activity of lycorine |
| CN109303920B (en) * | 2017-07-26 | 2020-09-08 | 天津中医药大学 | Application of reagent for reducing expression or activity of LC-3B in preparation of anti-liver cancer active drug for enhancing lycorine |
| CN110128436A (en) * | 2019-06-19 | 2019-08-16 | 成都虹冉生物科技有限公司 | A kind of extracting method of lycorine |
| CN111269828B (en) * | 2020-03-30 | 2023-09-29 | 平顶山市慧鑫源生物科技有限公司 | Process for preparing high-purity lycorine oxide from lycoris by enzyme method |
-
2003
- 2003-10-30 CN CN 200310102276 patent/CN1291989C/en not_active Expired - Lifetime
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| CN1611504A (en) | 2005-05-04 |
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