CN103588774B - Clean technology for extracting tabersonine from Voacanga chalotiana Pierre ex Stapf - Google Patents
Clean technology for extracting tabersonine from Voacanga chalotiana Pierre ex Stapf Download PDFInfo
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- CN103588774B CN103588774B CN201310613225.XA CN201310613225A CN103588774B CN 103588774 B CN103588774 B CN 103588774B CN 201310613225 A CN201310613225 A CN 201310613225A CN 103588774 B CN103588774 B CN 103588774B
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- JSLDLCGKZDUQSH-RTBUJCADSA-N 19-epivindolinine Natural products O=C(OC)[C@H]1[C@@]23[C@H](C)[C@]4([C@@H]5N(CC=C4)CC[C@]25c2c(N3)cccc2)C1 JSLDLCGKZDUQSH-RTBUJCADSA-N 0.000 title claims abstract description 29
- KILNDJCLJBOWAN-UHFFFAOYSA-N Tabersonine Natural products CCC12CC(=C3N(C)c4cc(OC)ccc4C35CCN(CC=C1)C25)C(=O)OC KILNDJCLJBOWAN-UHFFFAOYSA-N 0.000 title claims abstract description 29
- FNGGIPWAZSFKCN-ACRUOGEOSA-N tabersonine Chemical compound N1C2=CC=CC=C2[C@]2([C@H]34)C1=C(C(=O)OC)C[C@]3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-ACRUOGEOSA-N 0.000 title claims abstract description 29
- FNGGIPWAZSFKCN-UHFFFAOYSA-N xi-tabersonine Natural products N1C2=CC=CC=C2C2(C34)C1=C(C(=O)OC)CC3(CC)C=CCN4CC2 FNGGIPWAZSFKCN-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 241001246889 Voacanga Species 0.000 title claims abstract description 26
- 238000005516 engineering process Methods 0.000 title abstract description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 58
- 238000000605 extraction Methods 0.000 claims abstract description 35
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000000243 solution Substances 0.000 claims abstract description 20
- 239000007788 liquid Substances 0.000 claims abstract description 13
- 239000000284 extract Substances 0.000 claims abstract description 10
- 239000000843 powder Substances 0.000 claims abstract description 10
- 238000003756 stirring Methods 0.000 claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 8
- 238000010992 reflux Methods 0.000 claims abstract description 6
- 239000007787 solid Substances 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000012141 concentrate Substances 0.000 claims abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 11
- 238000002955 isolation Methods 0.000 claims description 7
- 238000002425 crystallisation Methods 0.000 claims description 6
- 230000008025 crystallization Effects 0.000 claims description 5
- 238000002203 pretreatment Methods 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 4
- 238000001035 drying Methods 0.000 abstract description 4
- 241000196324 Embryophyta Species 0.000 abstract description 3
- 238000009210 therapy by ultrasound Methods 0.000 abstract 2
- 238000009413 insulation Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 abstract 1
- 239000002253 acid Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical compound [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 4
- 238000004064 recycling Methods 0.000 description 4
- 239000013078 crystal Substances 0.000 description 3
- 238000001514 detection method Methods 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 238000010606 normalization Methods 0.000 description 3
- 238000010298 pulverizing process Methods 0.000 description 3
- 239000003513 alkali Substances 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000004065 wastewater treatment Methods 0.000 description 2
- 241000208328 Catharanthus Species 0.000 description 1
- 206010008190 Cerebrovascular accident Diseases 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- 208000006011 Stroke Diseases 0.000 description 1
- 208000001871 Tachycardia Diseases 0.000 description 1
- DDNCQMVWWZOMLN-IRLDBZIGSA-N Vinpocetine Chemical compound C1=CC=C2C(CCN3CCC4)=C5[C@@H]3[C@]4(CC)C=C(C(=O)OCC)N5C2=C1 DDNCQMVWWZOMLN-IRLDBZIGSA-N 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 150000003797 alkaloid derivatives Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000136 cloud-point extraction Methods 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000035619 diuresis Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003344 environmental pollutant Substances 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 201000009939 hypertensive encephalopathy Diseases 0.000 description 1
- 230000002218 hypoglycaemic effect Effects 0.000 description 1
- 150000002475 indoles Chemical class 0.000 description 1
- 208000028867 ischemia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000011275 oncology therapy Methods 0.000 description 1
- 231100000719 pollutant Toxicity 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 210000000582 semen Anatomy 0.000 description 1
- 235000020238 sunflower seed Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000002137 ultrasound extraction Methods 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/20—Spiro-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
Abstract
The invention relates to the plant extraction field, and aims to provide an efficient and environmentally-friendly technology for extracting tabersonine from Voacanga chalotiana Pierre ex Stapf. The technology comprises the following steps: 1, taking Voacanga chalotiana Pierre ex Stapf, sun-drying, peeling shells, and crushing; 2, micronizing treatment: adding submicron powder obtained in step 1 into ethyl acetate having a volume 1.5-3 times the mass of the submicron powder, and carrying out ultrasonic treatment at normal temperature for 0.5-1h, and centrifuging; 3, carrying out reflux extraction of the filter residue obtained in step 2 for 0.5-2h twice by utilizing ethyl acetate having a volume 2-5 times the mass of the filter residue; 4, mixing the obtained reflux extract liquid with the obtained centrifugate obtained after the ultrasonic treatment, and concentrating until no droplets drop; 5, adding an aqueous solution containing 6-10% of TritonX-114 having a volume 0.5-3 times the volume of the concentrate obtained in step 4, carrying out heat insulation stirring at 35-50DEG C for 0.5-1h, and centrifuging; and 6, adding a proper amount of water to the solid obtained in step 5, stirring for 10-20min, allowing the obtained solution to stand for separating out the upper layer yellow oil, and extracting 1-3 times by using the above same method, wherein the yellow oil is liquid tabersonine. The technology has the advantages of ingenious combination, high total extraction efficiency and less pollution emission.
Description
Technical field
The present invention relates to field of plant extraction, also relate to extraction tabersonine, be specifically related to the cleaning procedure extracting tabersonine from Voacanga seed.
Background technology
Tabersonine has another name called Aspidospermidine-3-carboxylic acid,2,3,6,7-tetradehydro-(5ALPHA,12BETA,19ALPHA)-methylseter, willow leaf tabersonine, is the one list indoles alkaloid in African Voacanga (being called for short: Voacanga), belongs to the yaruru alkaline in catharanthus alkaloid.It has the effects such as step-down, antitumor, hypoglycemic, diuresis, and for the treatment of the various diseases such as apoplexy sequela, ischemia hypertensive encephalopathy, nervosa tachycardia and other plant nervous dysfunction.In addition, Aspidospermidine-3-carboxylic acid,2,3,6,7-tetradehydro-(5ALPHA,12BETA,19ALPHA)-methylseter is also widely used in synthesis cancer therapy drug vinpocetin.
The production mainly chemosynthesis of current tabersonine; Or obtain from Voacanga extraction and isolation, normally the seed in Voacanga shell is dried, fragmentation extracts.Voacanga aboundresources, raw material sources are extensive.This seed is annual one ripe, and can keep biological Sustainable development, and in Voacanga seed, the content of tabersonine is about about 2.65%, content is higher, has industrialization value.Domestic also started introduction and acclimatization Africa Voacanga.
For the concrete technology technology of extraction and isolation tabersonine, the technical publications such as patent CN201010609832.5, CN201210165108.7, CN201010554096.8, CN201010602111.1, CN201110237688.1 all has introduction, but there is following problem:
1. effective component extraction rate is low, and organic solvent consumption is large, causes industrial production cost higher.
2. soda acid usage quantity is large, and require high to equipment is corrosion-resistant, and wastewater treatment capacity is large.
3. various toxic organic solvent usage quantity is large, and recycling difficulty, is also unfavorable for that producers' health and environment is protected.
For technology disclosed in immediate documents CN201010602111.1, soda acid be used to soak, and repeated multiple times adjustment potential of hydrogen, use a large amount of soda acid, operation steps is more; And soda acid consumption is large, equipment corrosion requires high, and wastewater treatment capacity is large.
Summary of the invention
Main purpose of the present invention is to provide a kind of technique extracting tabersonine from Voacanga of efficient, environmental protection.
The technical solution adopted in the present invention is: a kind of technique extracting tabersonine from Voacanga, is characterized in that: step comprises:
Pre-treatment: get Voacanga seed and dry, peel off, pulverize;
Micronizing process: the material after coarse reduction is carried out micronizing;
Extraction and isolation: it is centrifugal after ultrasonic 0.5-1 hour under normal temperature super-fine powder to be added 1.5-3 times amount ethyl acetate (mass volume ratio);
Filter residue 2-5 times amount ethyl acetate (mass volume ratio) refluxing extraction 2 times, each 0.5-2 hour;
Reflux extracting liquid and ultrasonic rear centrifugate are merged concentrated; Concentrated main purpose is recycling design, also reduces the reagent dosage of subsequent disposal, oozes, also can determine an empirical value accordingly, such as, be concentrated to certain volume, simplify the operation so can be concentrated into solvent-free (ethyl acetate) drop;
0.5-3 times amount (volume ratio) the 6%-10%TritonX-114 aqueous solution is added, insulated and stirred 0.5-1 hour at 35 DEG C-50 DEG C in concentrated solution, centrifugal; Add suitable quantity of water in solid, stir 10-20 minute, leave standstill, separate upper strata yellow oil, with method extraction 1-3 time; The tabersonine product that gained yellow oil is namely liquid.
Preferably, described yellow oil adds 5-10 doubly (mass volume ratio) acetic acid ethyl dissolution, then adds hydrochloric acid, and tune pH is 4-5, left at room temperature 4-8 hour crystallization; Through centrifugal, dry tabersonine hydrochloride.Recycling after ethyl acetate reclaims, sour consumption is little, usual centrifugal rear centrifugate process discharge.Concentration of hydrochloric acid is not strict with, and preferably uses concentrated hydrochloric acid, reduces usage quantity.
Preferably, described twice backflow gained extracting solution, primary and ultrasonic rear centrifugate merges and then concentrates, and second time extracting solution is used as next batch Extraction solvent for the first time.
Preferably, after described concentrated solution adds the TritonX-114 aqueous solution, the centrifugate of centrifugal treating and extraction liquid recycle; Because amount seldom, also can process discharge.
Preferably, in described concentration, recovered solvent recycles.
Advantageous Effects of the present invention:
1. extract again after the seed of Voacanga being peeled off pioneeringly, greatly reduce material treatment capacity while ensureing productive rate, greatly reduce solvent usage quantity.And similar devices such as employing existing sunflower seeds, Semen Cucurbitae decorticator etc. of peeling off can realize.
2. adopt micronizing to combine with ultrasonic extraction, improve tabersonine extraction yield, decrease solvent load, shorten extraction time.Supersound process destroys material cell tissue, is beneficial to extraction.
3. purge process introduces Cloud-Point Extraction Technique principle, solves the problems such as traditional technology soda acid uses pollution to environment, product yield is low, purity is low.
4. the ingenious combination of technology characteristics, overall extraction efficiency is high, and disposal of pollutants is few; Zero release liquid tabersonine can be obtained in whole process.The acid & alkali liquid of the processing salify also only little amount of crystallisation process discharge, and this acid & alkali liquid also can be applied mechanically in less demanding occasion.Realize zero release.
Embodiment
There is provided preferred embodiment below, to make those skilled in the art clearly and technical scheme clearly of the present invention and Advantageous Effects.But enforcement of the present invention is not limited in the following example.Simultaneously do not prove that formula of the present invention is unique particular requirement yet, but allow reasonably equivalent replace and industrial production, practical application error.
Embodiment one
Voacanga pre-treatment: by Voacanga seed drying, peel off, pulverize that to be No. 5 sieves for subsequent use.
Micronizing process: the Voacanga after pulverizing is ground into super-fine powder.
Extraction and isolation: get 10Kg super-fine powder, adds 20L ethyl acetate, and the ultrasonic lower effect of 200W 30 minutes under normal temperature, centrifugal, filtrate is for subsequent use;
Filter residue adds 30L ethyl acetate backflow and extracts 2 times, each 1 hour; To extracting solution and ultrasonic rear centrifugate merge for the first time, heating is concentrated into frozen-free drop and oozes, and the condensation product obtained is solvent, recycle; Second time extracting solution is used as next batch first time Extraction solvent;
Add the 1 times amount volume 8%TritionX-114 aqueous solution in gained concentrated solution, stir 1 hour at 45 DEG C, centrifugal, centrifugate is calibration and usage again; Add 0.2L water in solid, stir 10 minutes, leave standstill, separate upper strata yellow oil; Extract again once with method, be total to obtain yellow oil, i.e. tabersonine 0.52Kg; Extraction liquid recycles;
Crystallization: after yellow oil being added 3L acetic acid ethyl dissolution, add concentrated hydrochloric acid again, regulate and make the pH of ethyl acetate layer be 4.5, left at room temperature 8 hours crystallizatioies, crystal obtains tabersonine hydrochloride 0.50Kg through centrifugal, dry, is 99.1% through HPLC normalization method detection level.
Embodiment two
Voacanga pre-treatment: by Voacanga seed drying, peel off, pulverized 80 mesh sieves.
Micronizing process: the powder after pulverizing is carried out micronizing.
Extraction and isolation: get 20Kg powder, adds 50L ethyl acetate, and the ultrasonic lower effect of 200W 45 minutes under normal temperature, centrifugal, filtrate is for subsequent use;
Filter residue adds 40L ethyl acetate backflow and extracts 2 times, each 1 hour; To extracting solution and ultrasonic rear centrifugate merge for the first time, be concentrated into original volume 1/2, the solvent collection that concentration obtains is for subsequent use; The preparation of second time extracting solution is used as next batch first time Extraction solvent;
Add the 1.5 times amount volume 7%TritionX-114 aqueous solution in concentrated solution, stir 0.5 hour at 45 DEG C, centrifugal, add 0.5L water in solid, stir 15 minutes, leave standstill, separate upper strata yellow oil; Extract again once with method, merge to obtain yellow oil, tabersonine 1.02Kg; Centrifugate and extraction liquid process discharge;
Crystallization: yellow oil is added 6L acetic acid ethyl dissolution, then add concentrated hydrochloric acid, regulates and makes the pH=4 of ethyl acetate layer, left at room temperature 6 hours, and crystal is through centrifugal, and dry tabersonine hydrochloride 0.99Kg is 99.4% through HPLC normalization method detection level.
Embodiment three
Voacanga pre-treatment: by Voacanga seed drying, peel off, pulverize and be 50 mesh sieves.
Micronizing process: the Voacanga after pulverizing is ground into super-fine powder.
Extraction and isolation: get 10Kg super-fine powder, adds the ethyl acetate 20L of concentration and recovery in embodiment one, and the ultrasonic lower effect of 200W 30 minutes under normal temperature, centrifugal, filtrate is for subsequent use;
Filter residue adds the ethyl acetate successively refluxing extraction of second time extracting solution and concentration and recovery in 30L embodiment one, each 1 hour; To extracting solution and ultrasonic rear centrifugate merge for the first time, being concentrated into frozen-free drop oozes, and recycling design is for subsequent use; Second time extracting solution prepares as next batch first time Extraction solvent again;
Add the 2 times amount volume 6%TritionX-114 aqueous solution in gained concentrated solution, stir 1 hour at 45 DEG C, centrifugal, centrifugate is calibration and usage again; Add 0.2L water in solid, stir 15 minutes, leave standstill, separate upper strata yellow oil; Extract again once with method, be total to obtain yellow oil, tabersonine 0.53Kg; Extraction liquid recycles;
Crystallization: yellow oil is added 4L acetic acid ethyl dissolution, then add concentrated hydrochloric acid, regulates and makes the pH of ethyl acetate layer be 4.5, left at room temperature 6 hours crystallizatioies, crystal is through centrifugal, and dry tabersonine hydrochloride 0.51Kg is 99.0% through HPLC normalization method detection level.
Claims (5)
1. from Voacanga, extract a technique for tabersonine, it is characterized in that: step comprises:
Pre-treatment: get Voacanga seed and dry, peel off, pulverize;
Micronizing process: the material after coarse reduction is carried out micronizing;
Extraction and isolation: super-fine powder is added 1.5-3 times amount ethyl acetate by mass volume ratio centrifugal after ultrasonic 0.5-1 hour under normal temperature;
Filter residue extracts 2 times, each 0.5-2 hour by mass volume ratio 2-5 times amount ethyl acetate backflow;
Reflux extracting liquid and ultrasonic rear centrifugate are merged concentrated;
Concentrated solution adds the 0.5-3 times amount 6%-10%TritonX-114 aqueous solution by volume, and insulated and stirred 0.5-1 hour at 35 DEG C-50 DEG C is centrifugal; Add suitable quantity of water in solid, stir 10-20 minute, leave standstill, separate upper strata yellow oil; Product is obtained 1-3 time with method extraction.
2. the technique of extraction tabersonine according to claim 1, is characterized in that: described yellow oil by weight volume ratio adds 5-10 times of ethyl acetate, then adds hydrochloric acid, and tune pH is 4-5, left at room temperature 4-8 hour crystallization; Through centrifugal, dry tabersonine hydrochloride.
3. the technique of extraction tabersonine according to claim 2, is characterized in that: described twice backflow gained extracting solution, and primary and ultrasonic rear centrifugate merges and then concentrates, and second time extracting solution is used as next batch Extraction solvent for the first time.
4. the technique of extraction tabersonine according to claim 2, is characterized in that: after described concentrated solution adds the TritonX-114 aqueous solution, the centrifugate of centrifugal treating and extraction liquid recycle.
5. the technique of extraction tabersonine according to claim 2, is characterized in that: in described concentration, recovered solvent recycles.
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| CN201310613225.XA CN103588774B (en) | 2013-11-26 | 2013-11-26 | Clean technology for extracting tabersonine from Voacanga chalotiana Pierre ex Stapf |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN111808103A (en) * | 2020-07-29 | 2020-10-23 | 湖南华诚生物资源股份有限公司 | Clean production method for extracting tabersonine from African voacanga |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106397438B (en) * | 2016-09-23 | 2018-06-01 | 成都合盛生物技术有限公司 | The method that Aspidospermidine-3-carboxylic acid,2,3,6,7-tetradehydro-(5ALPHA,12BETA,19ALPHA)-methylseter is extracted from Voacanga |
| CN106243106B (en) * | 2016-09-23 | 2017-10-31 | 成都合盛生物技术有限公司 | A kind of method that tabersonine is extracted in the health seeds of trees from volt |
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| CN101250188B (en) * | 2008-03-25 | 2011-05-11 | 西安皓天生物工程技术有限责任公司 | Technique for preparing willow leaf tabersonine |
| CN102060856B (en) * | 2010-12-21 | 2012-10-03 | 天医堂(厦门)生物工程有限公司 | Method for extracting tabersonine from voacanga seeds |
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| CN111808103A (en) * | 2020-07-29 | 2020-10-23 | 湖南华诚生物资源股份有限公司 | Clean production method for extracting tabersonine from African voacanga |
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