CN1394865A - Method for extracting, separating and purifying linolenic lignan by using linseed cake - Google Patents
Method for extracting, separating and purifying linolenic lignan by using linseed cake Download PDFInfo
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- CN1394865A CN1394865A CN 01120199 CN01120199A CN1394865A CN 1394865 A CN1394865 A CN 1394865A CN 01120199 CN01120199 CN 01120199 CN 01120199 A CN01120199 A CN 01120199A CN 1394865 A CN1394865 A CN 1394865A
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- Prior art keywords
- secoisolariciresinol diglycoside
- alcohol
- produce
- linseed meal
- acid
- 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.)
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- 235000004431 Linum usitatissimum Nutrition 0.000 title claims abstract description 27
- 238000000034 method Methods 0.000 title claims abstract description 25
- 240000006240 Linum usitatissimum Species 0.000 title claims abstract description 22
- 235000004426 flaxseed Nutrition 0.000 title claims abstract description 22
- 229930013686 lignan Natural products 0.000 title claims abstract description 15
- 235000009408 lignans Nutrition 0.000 title claims abstract description 15
- 150000005692 lignans Chemical class 0.000 title claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000007864 aqueous solution Substances 0.000 claims abstract description 16
- 239000000284 extract Substances 0.000 claims abstract description 16
- 239000000243 solution Substances 0.000 claims abstract description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000605 extraction Methods 0.000 claims abstract description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000000741 silica gel Substances 0.000 claims abstract description 7
- 229910002027 silica gel Inorganic materials 0.000 claims abstract description 7
- 238000001179 sorption measurement Methods 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 42
- SBVBJPHMDABKJV-PGCJWIIOSA-N secoisolariciresinol diglucoside Chemical compound C1=C(O)C(OC)=CC(C[C@@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)[C@H](CO[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)O)CC=2C=C(OC)C(O)=CC=2)=C1 SBVBJPHMDABKJV-PGCJWIIOSA-N 0.000 claims description 41
- SBVBJPHMDABKJV-UHFFFAOYSA-N secoisolariciresinol diglycoside Natural products C1=C(O)C(OC)=CC(CC(COC2C(C(O)C(O)C(CO)O2)O)C(COC2C(C(O)C(O)C(CO)O2)O)CC=2C=C(OC)C(O)=CC=2)=C1 SBVBJPHMDABKJV-UHFFFAOYSA-N 0.000 claims description 41
- 235000012054 meals Nutrition 0.000 claims description 20
- 230000007062 hydrolysis Effects 0.000 claims description 19
- 238000006460 hydrolysis reaction Methods 0.000 claims description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 12
- 238000003756 stirring Methods 0.000 claims description 10
- 238000010521 absorption reaction Methods 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 8
- 238000000746 purification Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 241000208202 Linaceae Species 0.000 claims description 5
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 239000000706 filtrate Substances 0.000 claims description 4
- 238000000638 solvent extraction Methods 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 2
- 229960001701 chloroform Drugs 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims description 2
- 238000010025 steaming Methods 0.000 claims description 2
- 239000000413 hydrolysate Substances 0.000 abstract 1
- 150000001851 cinnamic acid derivatives Chemical class 0.000 description 5
- 238000004237 preparative chromatography Methods 0.000 description 4
- 238000013375 chromatographic separation Methods 0.000 description 3
- 235000021388 linseed oil Nutrition 0.000 description 3
- 239000000944 linseed oil Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000790917 Dioxys <bee> Species 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 230000000840 anti-viral effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 235000006708 antioxidants Nutrition 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000011097 chromatography purification Methods 0.000 description 1
- 230000006837 decompression Effects 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 description 1
- 238000011017 operating method Methods 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000000072 sodium resin Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Abstract
The method for extracting, separating and purifying linolenic lignan from linseed cake adopts organic solution extraction and silica gel adsorption instead of preparation chroamtography, and includes the following steps: A. preparing alcohol and water extract; B. preparing hydrolysate aqueous solution; C. separating linolenic lignan and D. purifying linolenic lignan.
Description
Wood invention relates to a kind of method of manufacturing secoisolariciresinol diglycoside, particularly by the method for linseed meal extraction, separation and purification of flax lignan.
Secoisolariciresinol diglycoside (SDG) is owing to have the biological activity of multiple wide spectrum such as antitumor, antiviral and anti-oxidant, thereby causes people's great attention in dietotherapy and healthcare applications.
Secoisolariciresinol diglycoside content in linseed oil is higher.As far back as the 1950's just report by linseed oil with ethanol and six pairs one solvent extractions of dioxy, the method for secoisolariciresinol diglycoside is produced in hydrolysis in anhydrous methanol through sodium methylate or barium methylate again.Be improved to aqueous ethanolic solution later on and extract, the method of water-soluble hydrolysis of sodium hydroxide and resin chromatography purification, the WO96/30468 patent has also been reported with alcohol-water solution and has been extracted alkali catalyzed hydrolysis recently, and resin chromatographic separation and preparative chromatography purifying are produced the method for secoisolariciresinol diglycoside.No matter the sort of method all needs resin chromatographic separation and preparative chromatography purifying, has the extraction cost height and is difficult to the industrial production problem
The purpose of this invention is to provide a kind of method for preparing secoisolariciresinol diglycoside by linseed meal extraction, separation and purifying, it can solve in the prior art owing to causing the problem that cost is high and be difficult to produce in batches with chromatographic technique, separation provided by the invention, purification process, its technology is simple, can reduce cost, and be beneficial to suitability for industrialized production.
Technical scheme of the present invention is as follows, a kind ofly produces the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that it may further comprise the steps:
A, prepare pure water extract,
The linseed meal pulverizing is added in the resin acid alcohol solution, and stirring at room is extracted, and filters, and with filtrate steaming removal solvent, gets extract,
B, the preparation hydrolyzate aqueous solution,
Extract is added in the alkaline aqueous solution, and the stirring at room hydrolysis gets hydrolyzate solution,
The separation of C, secoisolariciresinol diglycoside,
With the hydrolyzed solution organic solvent extraction, separate, get the hurds lignan aqueous solution,
The purifying of D, secoisolariciresinol diglycoside,
The isolating hurds lignan aqueous solution is added the silica gel adsorption of alcohol back,, make secoisolariciresinol diglycoside with acidiferous pure hydrolysis absorption.
Stirring at room extraction time described in the steps A is 22-26 hour, and the stirring at room hydrolysis time described in the step B is 5-7 hour.
The resin acid alcohol that is used to extract secoisolariciresinol diglycoside in the steps A is methyl alcohol or ethanol, and pure water ratio is 0.5～1.5: 1.
Among the step B, the alkali that is used for hydrolysis extract is sodium hydroxide or potassium hydroxide; The concentration of alkali is 1～12%.
Among the step C, the organic solvent that is used for the extracting and separating secoisolariciresinol diglycoside is methylene dichloride, trichloromethane or ethyl acetate.
Described organic solvent is a methylene dichloride.
Among the step D, the alcohol that uses when being used for purification of flax lignan absorption is methyl alcohol or ethanol, and the ratio of pure water is 0.25～0.75: 1; The alcohol that uses during hydrolysis absorption is methyl alcohol or ethanol, and the acid of using is acetic acid or hydrochloric acid or sulfuric acid, and using the ratio of acid is 0.5～1.5%.
The present invention adopts organic extractant solution to separate and the alternative chromatographic separation of the prior art of method of silica gel adsorption purifying and the method for preparative chromatography purifying.Present method is at first extracted the phenolic compound that contains secoisolariciresinol diglycoside and cinnamic acid derivative with pure water from linseed meal.The secoisolariciresinol diglycoside and the cinnamic acid derivative that prepare non-form complexed again with the alkali aqueous solution hydrolysis.Then with organic solvent with the secoisolariciresinol diglycoside extracting and separating, remove cinnamic acid derivative, secoisolariciresinol diglycoside, last, use the methanol-water desorption again with silica gel adsorption, produce secoisolariciresinol diglycoside.
In sum, advantage of the present invention is: owing to the cost height that needs chromatographic technique and preparative chromatography to exist in the separation in the method for prior art being produced secoisolariciresinol diglycoside with linseed oil, the purification procedures, the difficulty that is difficult to produce in batches, adopt organic solvent extraction to separate and the silica gel adsorption purifying, and the method for having set up the recycling of solvent is replaced solving, thereby reduced cost, simplified operating procedure, reduced expensive facility investment, and help producing in batches, reached the purpose of extracting the high purity secoisolariciresinol diglycoside by linseed meal equally.
With embodiment the present invention is specified below.
Embodiment extracts the high purity secoisolariciresinol diglycoside with linseed meal, may further comprise the steps:
A, prepare pure water extract, extract the phenolic compound that contains secoisolariciresinol diglycoside and cinnamic acid derivative:
The 1Kg linseed meal is at room temperature stirred extraction 24 hours with the methanol aqueous solution of 8000ml 50%, filtration, the filter residue methanol aqueous solution washing of 2000ml 50%, filtrate decompression is steamed and is desolventized, and recovery methanol aqueous solution 9000ml gets extract 80g.
B, the preparation hydrolyzate aqueous solution, basic hydrolysis prepares the non-form complexed secoisolariciresinol diglycoside and the cinnamic acid derivative aqueous solution:
Above-mentioned 80g extract is at room temperature stirred hydrolysis 6 hours with the aqueous sodium hydroxide solution of 200ml 5%, transfer PH=7 with acetate then, get hydrolyzed solution.
The separation of C, secoisolariciresinol diglycoside:
Above-mentioned 200ml hydrolyzed solution is got hurds lignan hydrolyzed solution twice with the 200ml dichloromethane extraction, and the 180ml methylene dichloride is reclaimed in the extraction liquid distillation.
The purifying of D, secoisolariciresinol diglycoside
Above-mentioned 200ml hurds lignan hydrolyzed solution is added 100ml methyl alcohol and 50g silica gel, stirring at room was adsorbed in 4 hours, filter then, filter residue adds 1: 1 methanol aqueous solution that 200ml contains 1% acetic acid, stirring at room hydrolysis in 4 hours absorption, filter, filtrate evaporated under reduced pressure to do secoisolariciresinol diglycoside 3.5g.
Claims (10)
1, a kind ofly produce the method for secoisolariciresinol diglycoside, it is characterized in that it may further comprise the steps by linseed meal:
A, prepare pure water extract,
The linseed meal pulverizing is added in the resin acid alcohol solution, and stirring at room is extracted, and filters, and with filtrate steaming removal solvent, gets extract,
B, the preparation hydrolyzate aqueous solution,
Extract is added in the alkaline aqueous solution, and the stirring at room hydrolysis gets hydrolyzate solution,
The separation of C, secoisolariciresinol diglycoside,
With the hydrolyzed solution organic solvent extraction, separate, get the hurds lignan aqueous solution,
The purifying of D, secoisolariciresinol diglycoside,
The isolating hurds lignan aqueous solution is added the silica gel adsorption of alcohol back,, make secoisolariciresinol diglycoside with acidiferous pure hydrolysis absorption.
2, according to claim 1ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: the stirring at room extraction time described in the steps A is 22-26 hour, and the stirring at room hydrolysis time described in the step B is 5-7 hour.
3, according to claim 1ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: the resin acid alcohol that is used to extract secoisolariciresinol diglycoside in the steps A is methyl alcohol or ethanol, and pure water ratio is 0.5～1.5: 1.
4, according to claim 3ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: described pure water ratio is 1: 1.
5, according to claim 1ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: among the step B, the alkali that is used for hydrolysis extract is sodium hydroxide or potassium hydroxide; The concentration of alkali is 1～12%.
6, according to claim 5ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: the described alkali that is used for hydrolysis extract is sodium hydroxide; The concentration of alkali is 5%.
7, according to claim 1ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: among the step C, the organic solvent that is used for the extracting and separating secoisolariciresinol diglycoside is methylene dichloride, trichloromethane or ethyl acetate.
8, according to claim 7ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: described organic solvent is a methylene dichloride.
9, according to claim 1ly produce the method for secoisolariciresinol diglycoside by linseed meal, it is characterized in that: among the step D, the alcohol that uses when being used for purification of flax lignan absorption is methyl alcohol or ethanol, and the ratio of pure water is 0.25～0.75: 1; The alcohol that uses during hydrolysis absorption is methyl alcohol or ethanol, and the acid of using is acetic acid, hydrochloric acid or sulfuric acid, and using the ratio of acid is 0.5～1.5%.
10, according to claim 9ly produce the method for secoisolariciresinol diglycoside, it is characterized in that: describedly be used for the alcohol that purification of flax lignan absorption uses and be methyl alcohol by linseed meal; The ratio of alcohol water is 0.5: 1; The alcohol that uses during hydrolysis absorption is methyl alcohol; The acid of using is acetic acid, and using the ratio of acid is 1%.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011201991A CN1162438C (en) | 2001-07-11 | 2001-07-11 | Method for extracting, separating and purifying linolenic lignan by using linseed cake |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB011201991A CN1162438C (en) | 2001-07-11 | 2001-07-11 | Method for extracting, separating and purifying linolenic lignan by using linseed cake |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1394865A true CN1394865A (en) | 2003-02-05 |
| CN1162438C CN1162438C (en) | 2004-08-18 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011201991A Expired - Lifetime CN1162438C (en) | 2001-07-11 | 2001-07-11 | Method for extracting, separating and purifying linolenic lignan by using linseed cake |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1162438C (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1471070A1 (en) * | 2003-04-22 | 2004-10-27 | Royal Schouten Group N.V. | Method for recovering a secondary plant metabolite |
| CN1329406C (en) * | 2005-05-08 | 2007-08-01 | 龙井民康生物制品厂 | Method of preparing cerebroside compound from flax root |
| CN100344642C (en) * | 2005-04-20 | 2007-10-24 | 中国药科大学 | Process for preparing flaxseed lignan total glycoside extract and use thereof |
| CN100365005C (en) * | 2006-03-02 | 2008-01-30 | 江南大学 | Method for extracting and purifying secoisolariciresinol diglucoside from flax seed |
| CN100395222C (en) * | 2006-05-12 | 2008-06-18 | 中国科学院山西煤炭化学研究所 | Method for preparing dehydrated open loop secoisolariciresinol from flax seed |
| CN101139373B (en) * | 2007-07-31 | 2010-12-29 | 中国科学院过程工程研究所 | Method for rapid scale extraction and purification of flax lignan |
| CN101921298B (en) * | 2009-06-11 | 2013-02-13 | 丰宁京北第一草原原生态食品科技开发有限公司 | Method for extracting, separating and purifying seco-isolariciresinol diglucoside from linseed cake |
-
2001
- 2001-07-11 CN CNB011201991A patent/CN1162438C/en not_active Expired - Lifetime
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1471070A1 (en) * | 2003-04-22 | 2004-10-27 | Royal Schouten Group N.V. | Method for recovering a secondary plant metabolite |
| WO2004094443A1 (en) * | 2003-04-22 | 2004-11-04 | Acatris Specialities Holding B.V. | Method for recovering a secondary plant metabolite |
| CN100344642C (en) * | 2005-04-20 | 2007-10-24 | 中国药科大学 | Process for preparing flaxseed lignan total glycoside extract and use thereof |
| CN1329406C (en) * | 2005-05-08 | 2007-08-01 | 龙井民康生物制品厂 | Method of preparing cerebroside compound from flax root |
| CN100365005C (en) * | 2006-03-02 | 2008-01-30 | 江南大学 | Method for extracting and purifying secoisolariciresinol diglucoside from flax seed |
| CN100395222C (en) * | 2006-05-12 | 2008-06-18 | 中国科学院山西煤炭化学研究所 | Method for preparing dehydrated open loop secoisolariciresinol from flax seed |
| CN101139373B (en) * | 2007-07-31 | 2010-12-29 | 中国科学院过程工程研究所 | Method for rapid scale extraction and purification of flax lignan |
| CN101921298B (en) * | 2009-06-11 | 2013-02-13 | 丰宁京北第一草原原生态食品科技开发有限公司 | Method for extracting, separating and purifying seco-isolariciresinol diglucoside from linseed cake |
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| Publication number | Publication date |
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| CN1162438C (en) | 2004-08-18 |
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