CN102659866A - Method for preparing cadambine - Google Patents
Method for preparing cadambine Download PDFInfo
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- CN102659866A CN102659866A CN2012101193341A CN201210119334A CN102659866A CN 102659866 A CN102659866 A CN 102659866A CN 2012101193341 A CN2012101193341 A CN 2012101193341A CN 201210119334 A CN201210119334 A CN 201210119334A CN 102659866 A CN102659866 A CN 102659866A
- Authority
- CN
- China
- Prior art keywords
- extraction
- chloroform
- danbin
- cadambine
- temperature
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title abstract description 8
- OVRROYYXOBYCSR-UHFFFAOYSA-N Cadambin Natural products C12C(O3)CN4CCC(C5=CC=CC=C5N5)=C5C43CC2C(C(=O)OC)=COC1OC1OC(CO)C(O)C(O)C1O OVRROYYXOBYCSR-UHFFFAOYSA-N 0.000 title abstract description 6
- OVRROYYXOBYCSR-HBOFMRDYSA-N Cadambine Natural products O=C(OC)C=1[C@@H]2[C@H]([C@H](O[C@H]3[C@@H](O)[C@@H](O)[C@@H](O)[C@H](CO)O3)OC=1)[C@H]1O[C@@]3(N(C1)CCc1c4c([nH]c31)cccc4)C2 OVRROYYXOBYCSR-HBOFMRDYSA-N 0.000 title abstract description 6
- OVRROYYXOBYCSR-OTZSZKQMSA-N cadambine Chemical compound COC(=O)C1=CO[C@@H](OC2OC(CO)C(O)C(O)C2O)[C@@H]2[C@H]3CN4CCc5c([nH]c6ccccc56)[C@]4(C[C@H]12)O3 OVRROYYXOBYCSR-OTZSZKQMSA-N 0.000 title abstract description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000000605 extraction Methods 0.000 claims abstract description 46
- 238000001035 drying Methods 0.000 claims abstract description 11
- 239000000843 powder Substances 0.000 claims abstract description 10
- 239000002994 raw material Substances 0.000 claims abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 claims abstract description 3
- 239000002904 solvent Substances 0.000 claims abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 36
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
- 229910021529 ammonia Inorganic materials 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 8
- 230000005526 G1 to G0 transition Effects 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003513 alkali Substances 0.000 claims description 4
- ONPSRCNNSZSSMH-UHFFFAOYSA-N chloroform;hexane;methanol Chemical compound OC.ClC(Cl)Cl.CCCCCC ONPSRCNNSZSSMH-UHFFFAOYSA-N 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims description 2
- 230000007935 neutral effect Effects 0.000 claims description 2
- 238000011084 recovery Methods 0.000 claims description 2
- 230000001105 regulatory effect Effects 0.000 claims description 2
- 239000012043 crude product Substances 0.000 abstract 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000706 filtrate Substances 0.000 abstract 1
- 238000001914 filtration Methods 0.000 abstract 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 abstract 1
- 238000004064 recycling Methods 0.000 abstract 1
- 238000009736 wetting Methods 0.000 abstract 1
- 238000004090 dissolution Methods 0.000 description 5
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 3
- NGAUATZUWHZXEK-UHFFFAOYSA-N 10-hydroxy-2,2,6b,9,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a,6a-dicarboxylic acid Chemical compound C1CC(O)C(C)(C)C2CCC3(C)C4(C(O)=O)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C NGAUATZUWHZXEK-UHFFFAOYSA-N 0.000 description 2
- MIJYXULNPSFWEK-GTOFXWBISA-N 3beta-hydroxyolean-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CCC(C)(C)C[C@H]5C4=CC[C@@H]3[C@]21C MIJYXULNPSFWEK-GTOFXWBISA-N 0.000 description 2
- 241000288027 Chrysolophus pictus Species 0.000 description 2
- JKLISIRFYWXLQG-UHFFFAOYSA-N Epioleonolsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4CCC3C21C JKLISIRFYWXLQG-UHFFFAOYSA-N 0.000 description 2
- 240000003492 Neolamarckia cadamba Species 0.000 description 2
- YBRJHZPWOMJYKQ-UHFFFAOYSA-N Oleanolic acid Natural products CC1(C)CC2C3=CCC4C5(C)CCC(O)C(C)(C)C5CCC4(C)C3(C)CCC2(C1)C(=O)O YBRJHZPWOMJYKQ-UHFFFAOYSA-N 0.000 description 2
- MIJYXULNPSFWEK-UHFFFAOYSA-N Oleanolinsaeure Natural products C1CC(O)C(C)(C)C2CCC3(C)C4(C)CCC5(C(O)=O)CCC(C)(C)CC5C4=CCC3C21C MIJYXULNPSFWEK-UHFFFAOYSA-N 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000019713 millet Nutrition 0.000 description 2
- 229940100243 oleanolic acid Drugs 0.000 description 2
- HZLWUYJLOIAQFC-UHFFFAOYSA-N prosapogenin PS-A Natural products C12CC(C)(C)CCC2(C(O)=O)CCC(C2(CCC3C4(C)C)C)(C)C1=CCC2C3(C)CCC4OC1OCC(O)C(O)C1O HZLWUYJLOIAQFC-UHFFFAOYSA-N 0.000 description 2
- 239000002023 wood Substances 0.000 description 2
- CFTOTSJVQRFXOF-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole Chemical compound N1C2=CC=CC=C2C2=C1CNCC2 CFTOTSJVQRFXOF-UHFFFAOYSA-N 0.000 description 1
- HNZGKRAKJFZQAY-UHFFFAOYSA-N 3beta-Dihydrocadambine Natural products C1C(C2=C(C3=CC=CC=C3N2)CC2)N2CC(O)C2C1C(C(=O)OC)=COC2OC1OC(CO)C(O)C(O)C1O HNZGKRAKJFZQAY-UHFFFAOYSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 206010020741 Hyperpyrexia Diseases 0.000 description 1
- 201000009053 Neurodermatitis Diseases 0.000 description 1
- 241000123069 Ocyurus chrysurus Species 0.000 description 1
- 241000223960 Plasmodium falciparum Species 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000013738 Sleep Initiation and Maintenance disease Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
- 208000002173 dizziness Diseases 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 206010022437 insomnia Diseases 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- ZXLDQJLIBNPEFJ-UHFFFAOYSA-N tetrahydro-beta-carboline Natural products C1CNC(C)C2=C1C1=CC=C(OC)C=C1N2 ZXLDQJLIBNPEFJ-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Seasonings (AREA)
Abstract
The invention provides a method for preparing cadambine. The method includes the process steps: taking fine powder of flower mission leaf raw materials, adding alkaline alcohol for wetting the fine powder for 2-6 hours, adding the fine powder into an extraction kettle and using supercritical CO2 for extraction; dissolving extract with 3% of hydrochloric acid water solution, filtering the solution, extracting filtrate with chloroform, taking a chloroform layer and recycling and drying the chloroform to obtain a crude product; and taking ammonia water solution with normal hexane-chloroform-methanol-pH=8.5 as a solvent system, separating cadambine from the crude product by the aid of a high-speed counter current chromatograph, collecting target components, and concentrating and drying the target components to obtain the high-content cadambine. Operation is simple, pollution is low, the cadambine prepared by the method is high in purity, and industrial enlargement is easily realized.
Description
Technical field
The present invention relates to the preparation method of a kind of Ka Danbin, particularly relate to a kind of application supercritical CO
2Extraction and high speed adverse current chromatogram prepare the method for Ka Danbin.
Background technology
Group's flower
Anthocephalus chinensis(lam.) A Rich.et Walp. is madder wort Da Ye a variety of millet wood; Another name a variety of millet wood; Be born under small stream side, mountain valley or the shaw, be distributed in Guangdong, Guangxi, Yunnan, be used as medicine with bark, leaf; Have effects such as heat-clearing, cure mainly hyperpyrexia, dizziness, headache, insomnia, neurodermatitis, psoriasis.The anthocephalus chinensis skin contains vegeto-alkali: Ka Danbin (cadambine); 3 α-dihydro Ka Danbin (3 α-dihvdrocadambine); 3 β-dihydro Ka Danbin (3 β-dihydro-cadambine); ((tetrahydro-β-carboline) contains also that to spend acid (cadambagenic acid) with Oleanolic Acid (oleanolic acid) and group be the first saponin of glucoside to 3 β-different dihydro Ka Danbin for 3 β-isodihydrocadarnbine) and tetrahydrochysene-β-Ka Lin; Leaf contains vegeto-alkali: Ka Danbin, golden pheasant peaceful (cinchonine) and dihydro golden pheasant peaceful (di-hydrOcinchonine).
Ka Danbin is a floral leaf main active ingredient, is carboline alkaloid.Ka Danbin has anti-cruel activity, can suppress the growth of plasmodium falciparum.
Through the document retrieval, do not find the relevant report of the industrial extracting and purifying method of Ka Danbin as yet.
Summary of the invention
The technical problem that the present invention will solve provides the preparation method of a kind of Ka Danbin, and this method product yield is high, content is high.
In order to solve the problems of the technologies described above, technical scheme of the present invention is following:
(1) group of getting floral leaf raw material fine powder adds alkaline alcohol and soaked into 2-6 hour, adds in the extraction kettle, adopts supercritical CO
2Extraction;
(2) extract filters with the dissolving of 3% aqueous hydrochloric acid, and filtrating use chloroform extraction, gets chloroform layer, and recovery chloroform drying obtains bullion;
(3) ammonia soln with normal hexane-chloroform-methanol-pH=8.5 is a solvent systems, adopts high-speed counter-current chromatograph to separate the Ka Danbin in the bullion, collects target components, concentrates, is drying to obtain high-content Ka Danbin.
Said step (1) neutral and alkali alcohol is 90-99% methyl alcohol, and ammoniacal liquor is regulated pH8-10.
Supercritical CO in the said step (1)
2Extraction conditions is: extraction temperature is 40-55 ℃, and extracting pressure is 30-40MPa, CO
2Flow is 2-5ml/g crude drug/min, and the extraction time is 2-4h, and separating still I temperature is 40-45 ℃, and pressure is 7-9MPa, and separating still II temperature is 30-40 ℃, and pressure is 4-6MPa.
The ammonia soln volume ratio of normal hexane-chloroform-methanol in the said step (3)-pH=8.5 is 3-5:7-9:4-5:2-4, on be moving phase mutually, time is stationary phase mutually.
Positively effect of the present invention is:
1) adopts supercritical CO
2Extraction, environment friendly and pollution-free, efficient is high, and energy consumption is lower;
2) adopt high speed adverse current chromatogram to separate, preparation amount is big, and sample loss is few, and preparation cycle is short, and product content is high.
To combine embodiment to further specify the present invention below, but the scope that the present invention requires to protect is not limited to following embodiment.
Embodiment
Embodiment 1:
The floral leaf raw material fine powder 1kg of the group of getting, 90% methyl alcohol that adds 300mlpH8 soaked into 2 hours, added in the extraction kettle, carried out supercritical CO
2Extraction, extraction temperature is 45 ℃, extracting pressure is 30MPa, CO
2Flow is 2ml/g crude drug/min, and the extraction time is 4h, and separating still I temperature is 40 ℃; Pressure is 7MPa, and separating still II temperature is 30 ℃, and pressure is 4MPa; Collect and resolve extract, the aqueous hydrochloric acid dissolution extraction thing with 3% filters; Filtrating is used chloroform extraction, gets chloroform layer, reclaims the chloroform drying and obtains bullion; Get the ammonia soln of normal hexane, chloroform, methyl alcohol, pH=8.5, for 3:7:4:4 mixes, leave standstill by volume, tell phase up and down; Below be stationary phase mutually, on be moving phase mutually, open high-speed counter-current chromatograph, regulate speed adjustment 750rpm; Get phased soln bullion injecting chromatograph, the control flow rate of mobile phase is 2ml/min, the red guest's flow point of collector cards; Concentrated, dry De Kadanbin 191mg detect through HPLC, and content is 96.3%.
Embodiment 2:
The floral leaf raw material fine powder 1kg of the group of getting, 95% methyl alcohol that adds 400mlpH9 soaked into 6 hours, added in the extraction kettle, carried out supercritical CO
2Extraction, extraction temperature is 40 ℃, extracting pressure is 30MPa, CO
2Flow is 3ml/g crude drug/min, and the extraction time is 3h, and separating still I temperature is 40 ℃; Pressure is 7MPa, and separating still II temperature is 35 ℃, and pressure is 5MPa; Collect and resolve extract, the aqueous hydrochloric acid dissolution extraction thing with 3% filters; Filtrating is used chloroform extraction, gets chloroform layer, reclaims the chloroform drying and obtains bullion; Get the ammonia soln of normal hexane, chloroform, methyl alcohol, pH=8.5, for 4:9:5:3 mixes, leave standstill by volume, tell phase up and down; Below be stationary phase mutually, on be moving phase mutually, open high-speed counter-current chromatograph, regulate speed adjustment 800rpm; Get phased soln bullion injecting chromatograph, the control flow rate of mobile phase is 2.5ml/min, the red guest's flow point of collector cards; Concentrated, dry De Kadanbin 230mg detect through HPLC, and content is 95.4%.
Embodiment 3:
The floral leaf raw material fine powder 3kg of the group of getting, 99% methyl alcohol that adds 1000mlpH8 soaked into 6 hours, added in the extraction kettle, carried out supercritical CO
2Extraction, extraction temperature is 50 ℃, extracting pressure is 40MPa, CO
2Flow is 4ml/g crude drug/min, and the extraction time is 3h, and separating still I temperature is 45 ℃; Pressure is 8MPa, and separating still II temperature is 30 ℃, and pressure is 4MPa; Collect and resolve extract, the aqueous hydrochloric acid dissolution extraction thing with 3% filters; Filtrating is used chloroform extraction, gets chloroform layer, reclaims the chloroform drying and obtains bullion; Get the ammonia soln of normal hexane, chloroform, methyl alcohol, pH=8.5, for 4:9:4:4 mixes, leave standstill by volume, tell phase up and down; Below be stationary phase mutually, on be moving phase mutually, open high-speed counter-current chromatograph, regulate speed adjustment 700rpm; Get phased soln bullion injecting chromatograph, the control flow rate of mobile phase is 2ml/min, the red guest's flow point of collector cards; Concentrated, dry De Kadanbin 601mg detect through HPLC, and content is 95.7%.
Embodiment 4:
The floral leaf raw material fine powder 5kg of the group of getting, 99% methyl alcohol that adds 1.8LpH10 soaked into 2 hours, added in the extraction kettle, carried out supercritical CO
2Extraction, extraction temperature is 48 ℃, extracting pressure is 32MPa, CO
2Flow is 3.5ml/g crude drug/min, and the extraction time is 4h, and separating still I temperature is 45 ℃; Pressure is 7MPa, and separating still II temperature is 35 ℃, and pressure is 4.5MPa; Collect and resolve extract, the aqueous hydrochloric acid dissolution extraction thing with 3% filters; Filtrating is used chloroform extraction, gets chloroform layer, reclaims the chloroform drying and obtains bullion; Get the ammonia soln of normal hexane, chloroform, methyl alcohol, pH=8.5, for 5:8:5:4 mixes, leave standstill by volume, tell phase up and down; Below be stationary phase mutually, on be moving phase mutually, open high-speed counter-current chromatograph, regulate speed adjustment 900rpm; Get phased soln bullion injecting chromatograph, the control flow rate of mobile phase is 2.5ml/min, the red guest's flow point of collector cards; Concentrated, dry De Kadanbin 897mg detect through HPLC, and content is 98.8%.
Embodiment 5:
The floral leaf raw material fine powder 10kg of the group of getting, 95% methyl alcohol that adds 3LpH8 soaked into 5 hours, added in the extraction kettle, carried out supercritical CO
2Extraction, extraction temperature is 55 ℃, extracting pressure is 40MPa, CO
2Flow is 5ml/g crude drug/min, and the extraction time is 2h, and separating still I temperature is 45 ℃; Pressure is 9MPa, and separating still II temperature is 40 ℃, and pressure is 6MPa; Collect and resolve extract, the aqueous hydrochloric acid dissolution extraction thing with 3% filters; Filtrating is used chloroform extraction, gets chloroform layer, reclaims the chloroform drying and obtains bullion; Get the ammonia soln of normal hexane, chloroform, methyl alcohol, pH=8.5, for 5:9:5:4 mixes, leave standstill by volume, tell phase up and down; Below be stationary phase mutually, on be moving phase mutually, open high-speed counter-current chromatograph, regulate speed adjustment 850rpm; Get phased soln bullion injecting chromatograph, the control flow rate of mobile phase is 3ml/min, the red guest's flow point of collector cards; Concentrated, dry De Kadanbin 2.1g detect through HPLC, and content is 96.3%.
Claims (4)
1. the preparation method of Yi Zhong Ka Danbin is characterized in that may further comprise the steps:
(1) group of getting floral leaf raw material fine powder adds alkaline alcohol and soaked into 2-6 hour, adds in the extraction kettle, adopts supercritical CO
2Extraction;
(2) extract filters with the dissolving of 3% aqueous hydrochloric acid, and filtrating use chloroform extraction, gets chloroform layer, and recovery chloroform drying obtains bullion;
(3) ammonia soln with normal hexane-chloroform-methanol-pH=8.5 is a solvent systems, adopts high-speed counter-current chromatograph to separate the Ka Danbin in the bullion, collects target components, concentrates, is drying to obtain high-content Ka Danbin.
2. according to the preparation method of the said a kind of Ka Danbin of claim 1, it is characterized in that said step (1) neutral and alkali alcohol is 90-99% methyl alcohol, ammoniacal liquor is regulated pH8-10.
3. according to the preparation method of the said a kind of Ka Danbin of claim 1, it is characterized in that supercritical CO in the said step (1)
2Extraction conditions is: extraction temperature is 40-55 ℃, and extracting pressure is 30-40MPa, CO
2Flow is 2-5ml/g crude drug/min, and the extraction time is 2-4h, and separating still I temperature is 40-45 ℃, and pressure is 7-9MPa, and separating still II temperature is 30-40 ℃, and pressure is 4-6MPa.
4. according to the preparation method of the said a kind of Ka Danbin of claim 1, it is characterized in that the ammonia soln volume ratio of normal hexane-chloroform-methanol in the said step (3)-pH=8.5 is 3-5:7-9:4-5:2-4, on be moving phase mutually, time is stationary phase mutually.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101193341A CN102659866A (en) | 2012-04-23 | 2012-04-23 | Method for preparing cadambine |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2012101193341A CN102659866A (en) | 2012-04-23 | 2012-04-23 | Method for preparing cadambine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102659866A true CN102659866A (en) | 2012-09-12 |
Family
ID=46769474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2012101193341A Pending CN102659866A (en) | 2012-04-23 | 2012-04-23 | Method for preparing cadambine |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102659866A (en) |
-
2012
- 2012-04-23 CN CN2012101193341A patent/CN102659866A/en active Pending
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Application publication date: 20120912 |