CN101914053A - Method for preparing indolylacetic acid and abscisic acid from seaweeds - Google Patents
Method for preparing indolylacetic acid and abscisic acid from seaweeds Download PDFInfo
- Publication number
- CN101914053A CN101914053A CN 201010253089 CN201010253089A CN101914053A CN 101914053 A CN101914053 A CN 101914053A CN 201010253089 CN201010253089 CN 201010253089 CN 201010253089 A CN201010253089 A CN 201010253089A CN 101914053 A CN101914053 A CN 101914053A
- Authority
- CN
- China
- Prior art keywords
- dormin
- phase
- indolylacetic acid
- resin
- marine alga
- 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.)
- Granted
Links
Images
Abstract
The invention relates to a method for preparing indolylacetic acid and abscisic acid from seaweeds, aiming to solve the problems of limited bioactivity because the two plant hormones of the indolylacetic acid and the abscisic acid are mostly prepared by chemical synthesis in industry, high plant cost, large solvent consumption, low yield, low purity and the like in the prior art. In the adopted technical scheme for solving the technical problems, the indolylacetic acid and the abscisic acid are prepared through seaweeds soaking, macroporous resin sorption, desorption, concentration, high-speed countercurrent chromatograph purification and crystallization. The method can be used for preparing the indolylacetic acid and the abscisic acid from the seaweeds and has the remarkable advantages of natural biological resource utilization, simplicity, convenience, easy operation, low cost, high yield, good environment protection and the like.
Description
Technical field: the method that the present invention relates to from marine alga, prepare long hormone indolylacetic acid of plant growth-promoting and plant growth hormones dormin.
Background technology: many marine alga bodies contain abundant natural phant growth hormone, because in the unique ecological environment of ocean, marine alga belongs to the weak person who is eaten, marine alga is in order to tackle the eating in a large number to keep the survival and reproduction of self of ocean herbivore, often can produce some special metabolic substds in the body, they can impel self a large amount of breeding fast.As far back as 1940, people just found to contain in the marine alga growth regulator such as plant growth hormones indolylacetic acid, also had dormin.Yet, being subjected to resource and technology limitation, this two kind of plant hormone is obtained by chemosynthesis in industrial major part, and biological activity is restricted.
Indolylacetic acid (indole-3-acetic acid) is as plant growth substance and analytical reagent, and in the natural existence of nature, Britain scientist research thinks that indolylacetic acid has anti-cancer function, is expected to be used to develop the new drug of the multiple cancer of treatment.Experiment shows, indolylacetic acid is being subjected to after illumination activates, effective kill cancer cell, and efficient reaches 99.9%.Be to use the chemical industry synthetic method yet prepare the indolylacetic acid major part at present, the rarely seen report of technology that it obtains from natural product.
Dormin (Abscisic acid) is a kind of endogenous plant hormone with comprehensive physiological function.Up to the present about studies confirm that of dormin physiological function it in plant-growth, brought into play important effect, for example seed development and ripe, important Accommodation is played in replying of the contrary factor of environment.Dormin can promote fruit, cereal, beans and maturation or the like, can greatly improve their productivity and quality, and improve its cold-resistant, the drought-enduring and anti-saline and alkaline function of face.Yet the source of highly purified PBI 58 has been subjected to very big restriction, and the acquisition that can be used for the PBI 58 of plant physiology function research becomes difficult more.Therefore the price of high-purity natural dormin is still high now, and price is up to 230.9 dollars/milligram (Sigma).Because expensive price and the difference on the activity, dormin is not widely used in agriculture production always, and the various countries scientist is seeking the cheap method of producing of natural type dormin.Dormin has two kinds of optical configuration, is (s)-(+)-dormin but have physiological function, be present in the intravital PBI 58 optical configuration of plant, and its structure is:
Summary of the invention: purpose of the present invention is exactly to propose a kind of technical scheme for preparing the method for indolylacetic acid and dormin from marine alga, exist with the solution background technology: this two kind of plant hormone of indolylacetic acid and dormin is obtained by chemosynthesis in industrial major part, and biological activity is restricted; Perhaps plant cost height, problem such as solvent-oil ratio is big, process is loaded down with trivial details, yield is low, purity is low.Solving this technical problem the technical scheme that is adopted is: a kind of method for preparing indolylacetic acid and dormin from marine alga is characterized in that this method finishes according to following steps:
The first step, marine alga is dried, according to getting 1: the weight ratio of 20-30 added the ethanol lixiviate more than 8 days;
Second goes on foot, algae leaching liquor is evaporated, and establishing bath temperature is 55-75 ℃, and evaporate to dryness obtains medicinal extract;
The 3rd the step, medicinal extract is used the 30%-50% dissolve with ethanol, remove insolubles after filtration, pretreated macroporous resin column chromatography on the filtrate;
The 4th goes on foot, uses the ethanol elution of 70%-80%, collects elutriant, is concentrated into dried;
The 5th step, will go up the step and be concentrated into dried material, by being equipped with constant flow pump, Ultraviolet Detector, the high-speed counter-current chromatograph of data collecting system carries out purifying; Promptly at ambient temperature, be equipped with normal hexane-ethyl acetate-methanol-water, its volume ratio is the solvent system of 3-5: 5-6: 5-6: 4-6, and this system is placed fully mixing of separating funnel, uses preceding phase solution up and down separately, supersound process is removed bubble respectively, the speed that with the flow velocity is 8-10ml/min earlier pumps into phase (stationary phase), treats that stationary phase is full of after all pipelines, stops to pump into stationary phase, open high-speed counter-current chromatograph, rotating speed is transferred to 700-900r/min.Open ram pump again, flow velocity is transferred to 1-2ml/min, pumps into down phase (moving phase), when treating that moving phase flows out continuously, uses moving phase to dissolve the above-mentioned dried material that is concentrated into, from last sample mouth sample introduction, fraction collection;
Cut behind the 6th step, the detection high speed adverse current chromatogram purifying obtains natural indolylacetic acid and dormin.
In the aforesaid method, in the 3rd step, the preprocessor of macroporous resin is as follows: get macroporous resin and place triangular flask, earlier allow the resin full of water with the 30%-50% alcohol immersion, resin is fully launched; Change ethanolic soln, the resin after fully launching is placed on the shaking table vibration, more than the shaking table oscillation frequency 200r/min, resin is cleaned repeatedly, be washed till till the limpid nothing muddiness of water outlet, the inclusion-free with clear water; Triangular flask is placed on the shaking table, and the NaOH that adds the 2%-4% of 2 times of above-mentioned resin volumes soaks, and vibration is soaked fully it on shaking table simultaneously, and pure water is washed till neutrality; The HCl solution that adds the 2%-4% of 2 times of volumes of above-mentioned resin again vibrates on shaking table it is soaked fully, blots solution, adds just submergence resin of 2%-4%HCl solution again, and the dress post makes it even with pure water elution chromatography post.In second step, reclaim ethanol, the recycling solvent.In the 4th step, reclaim ethanol.Use high performance liquid chromatography to detect identification indolylacetic acid and dormin in the 6th step.Solvent system after optimizing in the 5th step is normal hexane-ethyl acetate-methanol-water, and its volume ratio is 4: 6: 5.5: 5.The optimization flow velocity of going up phase (stationary phase) in the 5th step is 10ml/min, and following phase (moving phase) is optimized flow velocity 2ml/min, and high-speed counter-current chromatograph is optimized rotating speed 850r/min.
The beneficial effect that the present invention and background technology comparison are had is: owing to adopt technique scheme, utilize marine algae resource, the main scientific method that uses macroporous resin in conjunction with high speed adverse current chromatogram, select the processing parameter of reasonable numerical range, make alcohol concn, solvent system volume ratio, pump into up and down that the parameters such as speed of phase form organic cooperation, solve the background technology problem, realized goal of the invention.Its beneficial effect is summarized as follows: the first, extract plant hormone from marine alga, make full use of marine algae resource, both solved the cost problem, protected environment again.The second, extracting method advantages of simple, feasible, solvent is recyclable, reuses save energy.Three, present method adopts macroporous resin to separate and disposable high-purity indolylacetic acid and the dormin two kind of plant hormones of acquiring from marine alga of high speed adverse current chromatogram purifying, and the purity of indolylacetic acid reaches 98.1%, and the rate of recovery reaches 94.1%; The purity of dormin reaches 99.3%, and the rate of recovery reaches 94.0%.
Description of drawings: Fig. 1 is the schema of the inventive method.
Embodiment:
Embodiment 1: with reference to figure 1, get 10kg drying in the sun sea-tangle, with 20 times to the ethanol lixiviate of sea-tangle weight 10 days, the vat liquor rotary evaporation, establishing bath temperature is 55 ℃, evaporate to dryness obtains medicinal extract, reclaim ethanol, medicinal extract uses 30% dissolve with ethanol, removes insolubles through filter paper filtering, macroporous resin column chromatography on the filtrate.The preprocessor of resin is as follows: get macroporous resin AB-8 1000ml and place the 3000ml triangular flask, pre-treatment earlier allows the resin full of water with 30% alcohol immersion 20h, and resin is fully launched.Change ethanolic soln, the resin after fully launching is placed on shaking table vibration 2h, shaking table oscillation frequency 200r/min cleans resin repeatedly with clear water, is washed till till the limpid nothing muddiness of water outlet, the inclusion-free.Clean resin with ultrapure water, the 2h that vibrates on shaking table changes ultrapure water.Triangular flask is placed on the shaking table, be immersed in the 2h that vibrates on the shaking table, clean to neutral with pure water with 2% NaOH of 2 times of volumes.With 2% HCl solution of the 2 times of volumes 2h that on shaking table, vibrates, blot solution again, add just submergence resin of 4%HCl solution again, standby.The resin of handling is put into beaker, adds less water and stirs, and resin is slowly poured into chromatography column along wall.Ethanol elution with 70%, flow velocity 2ml/min collects the 3000ml elutriant.Be concentrated into driedly, reclaim ethanol.Dried material will be concentrated into, by being equipped with constant flow pump, Ultraviolet Detector, the high-speed counter-current chromatograph of registering instrument and data collecting system carries out purifying, solvent system is normal hexane-ethyl acetate-methanol-water (3: 5: 5: 4), promptly at ambient temperature, organic phase and the water with solvent system places the abundant mixing of separating funnel to spend the night.Use preceding 30 minutes separately and removed bubble in ultrasonic 10 minutes with two phase liquid.。The speed that with the flow velocity is 8ml/min earlier pumps into phase (stationary phase), treats that stationary phase is full of after all pipelines, stops to pump into stationary phase, opens the high-speed counter-current chromatograph rotating speed and is transferred to 700r/min.Open ram pump again, flow velocity is transferred to 1ml/min, pumps into down phase (moving phase), when treating that moving phase flows out continuously, uses moving phase to dissolve the above-mentioned dried material that is concentrated into, from last sample mouth sample introduction, fraction collection; The cut that obtains behind the high speed adverse current chromatogram purifying uses high performance liquid chromatography to detect identification, and obtaining natural indolylacetic acid and dormin altogether is respectively 7.8 grams and 10.6 grams.The purity of indolylacetic acid reaches 97.1%, and the rate of recovery reaches 93.1%; The purity of dormin reaches 98.3%, and the rate of recovery reaches 93.0%.
Embodiment 2: with reference to figure 1, with reference to figure 1, get 10kg drying in the sun sea-tangle, with 30 times to the ethanol lixiviate of sea-tangle weight 12 days, vat liquor rotary evaporation, if bath temperature is 75 ℃, evaporate to dryness obtains medicinal extract, reclaims ethanol, and medicinal extract uses 50% dissolve with ethanol, remove insolubles through filter paper filtering, macroporous resin column chromatography on the filtrate.The preprocessor of resin is as follows: get macroporous resin AB-81000ml and place the 3000ml triangular flask, pre-treatment earlier allows the resin full of water with 50% alcohol immersion 20h, and resin is fully launched.Change ethanolic soln, the resin after fully launching is placed on shaking table vibration 2h, shaking table oscillation frequency 200r/min cleans resin repeatedly with clear water, is washed till till the limpid nothing muddiness of water outlet, the inclusion-free.Clean resin with ultrapure water, the 2h that vibrates on shaking table changes ultrapure water.Triangular flask is placed on the shaking table, be immersed in the 2h that vibrates on the shaking table, clean to neutral with pure water with 4% NaOH of 2 times of volumes.With 4% HCl solution of the 2 times of volumes 2h that on shaking table, vibrates, blot solution again, add just submergence resin of 4%HCl solution again, standby.The resin of handling is put into beaker, adds less water and stirs, and resin is slowly poured into chromatography column along wall.Ethanol elution with 80%, flow velocity 2ml/min collects the 3000ml elutriant.Be concentrated into driedly, reclaim ethanol.Dried material will be concentrated into, by being equipped with constant flow pump, Ultraviolet Detector, the high-speed counter-current chromatograph of registering instrument and data collecting system carries out purifying, solvent system is normal hexane-ethyl acetate-methanol-water (5: 6: 6: 6), promptly at ambient temperature, organic phase and the water with solvent system places the abundant mixing of separating funnel to spend the night.Use preceding 30 minutes separately and removed bubble in ultrasonic 10 minutes with two phase liquid.The speed that with the flow velocity is 9ml/min earlier pumps into phase (stationary phase), treats that stationary phase is full of after all pipelines, stops to pump into stationary phase, opens high-speed counter-current chromatograph, and rotating speed is transferred to 900r/min.Open ram pump again, flow velocity is transferred to 1.5ml/min, pumps into down phase (moving phase), when treating that moving phase flows out continuously, uses moving phase to dissolve the above-mentioned dried material that is concentrated into, from last sample mouth sample introduction, fraction collection; The cut that obtains behind the high speed adverse current chromatogram purifying uses high performance liquid chromatography to detect identification, and obtaining natural indolylacetic acid and dormin altogether is respectively 8.0 grams and 10.4 grams.The purity of indolylacetic acid reaches 97.5%, and the rate of recovery reaches 92.4%; The purity of dormin reaches 98.6%, and the rate of recovery reaches 92.6%.
Embodiment 3: with reference to figure 1, get 10kg drying in the sun sea-tangle, with 25 times to the ethanol lixiviate of sea-tangle weight 10 days, the vat liquor rotary evaporation, establishing bath temperature is 60 ℃, evaporate to dryness obtains medicinal extract, reclaim ethanol, medicinal extract uses 40% dissolve with ethanol, removes insolubles through filter paper filtering, macroporous resin column chromatography on the filtrate.The preprocessor of resin is as follows: get macroporous resin AB-8 1000ml and place the 3000ml triangular flask, pre-treatment earlier allows the resin full of water with 40% alcohol immersion 20h, and resin is fully launched.Change ethanolic soln, the resin after fully launching is placed on shaking table vibration 2h, shaking table oscillation frequency 200r/min cleans resin repeatedly with clear water, is washed till till the limpid nothing muddiness of water outlet, the inclusion-free.Clean resin with ultrapure water, the 2h that vibrates on shaking table changes ultrapure water.Triangular flask is placed on the shaking table, be immersed in the 2h that vibrates on the shaking table, clean to neutral with pure water with 4% NaOH of 2 times of volumes.With 4% HCl solution of the 2 times of volumes 2h that on shaking table, vibrates, blot solution again, add just submergence resin of 4%HCl solution again, standby.The resin of handling is put into beaker, adds less water and stirs, and resin is slowly poured into chromatography column along wall.Ethanol elution with 75%, flow velocity 2ml/min collects the 3000ml elutriant.Be concentrated into driedly, reclaim ethanol.Dried material will be concentrated into, by being equipped with constant flow pump, Ultraviolet Detector, the high-speed counter-current chromatograph of registering instrument and data collecting system carries out purifying, solvent system is normal hexane-ethyl acetate-methanol-water (4: 6: 5.5: 5), promptly at ambient temperature, organic phase and the water with solvent system places the abundant mixing of separating funnel to spend the night.Use preceding 30 minutes separately and removed bubble in ultrasonic 10 minutes with two phase liquid.The speed that with the flow velocity is 10ml/min earlier pumps into phase (stationary phase), treats that stationary phase is full of after all pipelines, stops to pump into stationary phase, opens high-speed counter-current chromatograph, and rotating speed is transferred to 850r/min.Open ram pump again, flow velocity is transferred to 2ml/min, pumps into down phase (moving phase), when treating that moving phase flows out continuously, uses moving phase to dissolve the above-mentioned dried material that is concentrated into, from last sample mouth sample introduction, fraction collection; The cut that obtains behind the high speed adverse current chromatogram purifying uses high performance liquid chromatography to detect identification, and obtaining indolylacetic acid and dormin altogether is respectively 8.1 grams and 11.0 grams.The purity of indolylacetic acid reaches 98.1%, and the rate of recovery reaches 94.1%; The purity of dormin reaches 99.3%, and the rate of recovery reaches 94.0%.
Claims (10)
1. method for preparing indolylacetic acid and dormin from marine alga is characterized in that this method finishes according to following steps:
The first step, marine alga is dried, according to getting 1: the weight ratio of 20-30 added the ethanol lixiviate more than 8 days;
Second goes on foot, algae leaching liquor is evaporated, and establishing bath temperature is 55-75 ℃, and evaporate to dryness obtains medicinal extract;
The 3rd the step, medicinal extract is used the 30%-50% dissolve with ethanol, remove insolubles after filtration, pretreated macroporous resin column chromatography on the filtrate;
The 4th goes on foot, uses the ethanol elution of 70%-80%, collects elutriant, is concentrated into dried;
The 5th step, will go up the step and be concentrated into dried material, by being equipped with constant flow pump, Ultraviolet Detector, the high-speed counter-current chromatograph of data collecting system carries out purifying; Promptly at ambient temperature, be equipped with normal hexane-ethyl acetate-methanol-water, its volume ratio is the solvent system of 3-5: 5-6: 5-6: 4-6, this system is placed fully mixing of separating funnel, use preceding phase solution up and down separately, supersound process is removed bubble respectively, the speed that with the flow velocity is 8-10ml/min earlier pumps into phase (stationary phase), treat that stationary phase is full of after all pipelines, stop to pump into stationary phase, open high-speed counter-current chromatograph, rotating speed is transferred to 700-900r/min, open ram pump again, flow velocity is transferred to 1-2ml/min, pumps into down phase (moving phase), when treating that moving phase flows out continuously, use moving phase to dissolve the above-mentioned dried material that is concentrated into, from last sample mouth sample introduction, fraction collection;
Cut behind the 6th step, the detection high speed adverse current chromatogram purifying obtains natural indolylacetic acid and dormin.
2. state a kind of method that from marine alga, prepares indolylacetic acid and dormin according to claim 1, it is characterized in that in the 3rd step, the preprocessor of macroporous resin is as follows: get macroporous resin and place triangular flask, earlier allow the resin full of water with the 30%-50% alcohol immersion, resin is fully launched; Change ethanolic soln, the resin after fully launching is placed on more than the shaking table vibration 1h, more than the shaking table oscillation frequency 200r/min, resin is cleaned repeatedly, be washed till till the limpid nothing muddiness of water outlet, the inclusion-free with clear water; Triangular flask is placed on the shaking table, and the NaOH that adds the 2%-4% of 2 times of above-mentioned resin volumes soaks, and vibration is soaked fully it on shaking table simultaneously, and pure water is washed till neutrality; The HCl solution that adds the 2%-4% of 2 times of volumes of above-mentioned resin again vibrates on shaking table it is soaked fully, blots solution, adds just submergence resin of 2%-4%HCl solution again, and the dress post makes it even with pure water elution chromatography post;
3. according to claim 1 or 2 described a kind of methods that from marine alga, prepare indolylacetic acid and dormin, it is characterized in that in second step, reclaiming ethanol, the recycling solvent.
4. it is characterized in that in the 4th step, reclaiming ethanol according to claim 1 or 2 described a kind of methods that from marine alga, prepare indolylacetic acid and dormin.
5. according to claim 1 or 2 described a kind of methods that from marine alga, prepare indolylacetic acid and dormin, it is characterized in that using high performance liquid chromatography to detect identification indolylacetic acid and dormin in the 6th step.
6. according to claim 1 or 2 described a kind of methods that prepare indolylacetic acid and dormin from marine alga, the solvent system after it is characterized in that optimizing in the 5th step is normal hexane-ethyl acetate-methanol-water, and its volume ratio is 4: 6: 5.5: 5.
7. according to the described a kind of method for preparing indolylacetic acid and dormin from marine alga of claim 3, the solvent system after it is characterized in that optimizing in the 5th step is normal hexane-ethyl acetate-methanol-water, and its volume ratio is 4: 6: 5.5: 5.
8. according to the described a kind of method for preparing indolylacetic acid and dormin from marine alga of claim 4, the solvent system after it is characterized in that optimizing in the 5th step is normal hexane-ethyl acetate-methanol-water, and its volume ratio is 4: 6: 5.5: 5.
9. according to claim 1 or 2 described a kind of methods that from marine alga, prepare indolylacetic acid and dormin, the optimization flow velocity that it is characterized in that last phase (stationary phase) in the 5th step is 10ml/min, following phase (moving phase) is optimized flow velocity 2ml/min, and high-speed counter-current chromatograph is optimized rotating speed 850r/min.
10. according to the described a kind of method that from marine alga, prepares indolylacetic acid and dormin of claim 3, it is characterized in that the flow velocity of last phase (stationary phase) in the 5th step is 10ml/min, following phase (moving phase) 2ml/min, high-speed counter-current chromatograph rotating speed 850r/min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102530894A CN101914053B (en) | 2010-08-16 | 2010-08-16 | Method for preparing indolylacetic acid and abscisic acid from seaweeds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010102530894A CN101914053B (en) | 2010-08-16 | 2010-08-16 | Method for preparing indolylacetic acid and abscisic acid from seaweeds |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN101914053A true CN101914053A (en) | 2010-12-15 |
| CN101914053B CN101914053B (en) | 2012-06-13 |
Family
ID=43321730
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010102530894A Expired - Fee Related CN101914053B (en) | 2010-08-16 | 2010-08-16 | Method for preparing indolylacetic acid and abscisic acid from seaweeds |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN101914053B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111107864A (en) * | 2017-09-18 | 2020-05-05 | 欧洲地中海股份有限公司 | Method for preparing plant extract of abscisic acid |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56160996A (en) * | 1980-05-15 | 1981-12-11 | Kyowa Hakko Kogyo Co Ltd | Preparation of abscisic acid by fermentation method |
-
2010
- 2010-08-16 CN CN2010102530894A patent/CN101914053B/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS56160996A (en) * | 1980-05-15 | 1981-12-11 | Kyowa Hakko Kogyo Co Ltd | Preparation of abscisic acid by fermentation method |
Non-Patent Citations (1)
| Title |
|---|
| 《Phytochemical Analysis》 20080710 FENG JUAN ZHANG et al. Study on the Extraction, Purification and Quantification of Jasmonic Acid, Abscisic acid and Indole-3-acetic Acid in Plants 560-567 1-10 第19卷, 2 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111107864A (en) * | 2017-09-18 | 2020-05-05 | 欧洲地中海股份有限公司 | Method for preparing plant extract of abscisic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| CN101914053B (en) | 2012-06-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107474088B (en) | Extraction process for industrial mass production of spinosad | |
| CN102491938B (en) | A kind of purification process of S-GI | |
| CN108409539A (en) | A kind of preparation method and purposes of Porphyra yezoensis sesquiterpenoids algistatic activity compound | |
| CN109867663A (en) | A method of with preparation chromatographic isolation chrysomycin A and chrysomycin B | |
| CN105001052A (en) | Method used for extracting cembrenediols from tobacco inflorescence | |
| CN103657593A (en) | Sunflower husk biomass carbon adsorbent, preparation method and method for removing methylene blue from water | |
| CN103274927A (en) | Purification method for nature abscisic acid | |
| CN102863116A (en) | Method and device for repeatedly utilizing ramie biological degumming waste water | |
| CN105331562A (en) | Bacillus amyloliquefaciens Q-426 and lipopeptid separation method thereof | |
| CN102766172A (en) | Industrial production method of rhamnolipid biosurfactant dry powder | |
| CN104119229A (en) | Technology for producing pure chlorogenic acid | |
| CN101914053B (en) | Method for preparing indolylacetic acid and abscisic acid from seaweeds | |
| CN104045725B (en) | D301G resin anion(R.A) is adopted to refine the method for Phaeopoms obliquus Crude polysaccharides | |
| CN102391117B (en) | Method for preparing chlorogenic acid from eucommia leaves | |
| CN102516041A (en) | Method for extracting quebrachitol from natural rubber whey | |
| CN107473979A (en) | A kind of processing method of film extraction theanine | |
| CN105622342B (en) | A kind of method for detaching 2,3- butanediols | |
| CN100513377C (en) | Method for separating and extracting abscisic acid from fermented liquid by ionic exchanging and reversed phase chromatography | |
| CN103664610A (en) | Method for extracting chlorogenic acid from sweet potato leaves | |
| CN1321123C (en) | High purity yolk cephalin preparation method | |
| CN102863433A (en) | Mupirocin purification method | |
| CN101624411B (en) | Method for preparing lincomycin hydrochloride | |
| CN104031159B (en) | 732 resin cation (R.C.)s are adopted to refine the method for Phaeopoms obliquus Crude polysaccharides | |
| CN102816050A (en) | Method for extracting solanesol by activating waste and defective tobacco by enzyme catalysis | |
| CN109609568B (en) | Method for preparing swainsonine by solid fermentation |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20120613 Termination date: 20150816 |
|
| EXPY | Termination of patent right or utility model |