CN101759731A - Extraction method of linseed gum and secoisolariciresin-ol diglucoside - Google Patents
Extraction method of linseed gum and secoisolariciresin-ol diglucoside Download PDFInfo
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- CN101759731A CN101759731A CN200810184476A CN200810184476A CN101759731A CN 101759731 A CN101759731 A CN 101759731A CN 200810184476 A CN200810184476 A CN 200810184476A CN 200810184476 A CN200810184476 A CN 200810184476A CN 101759731 A CN101759731 A CN 101759731A
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Abstract
The invention discloses a method for extracting linseed gum and secoisolariciresin-ol diglucoside from linseed or linseed mdal. The method simultaneously extracts the flaxseed gum and the secoisolariciresin-ol diglucoside with an extraction method with aqueous alkaline solution under room temperature, completes the extraction and the basic hydrolysis of the SDG at one step, and can obtain the high-purity SDG and the linseed gum by means of ethanol precipiration, macroporous absorption resin separation and alcohol or carbinol resolution.
Description
Technical field
The present invention relates to a kind of method of from linseed oil or flaxseed meal, extracting flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside simultaneously.
Background technology
Flaxseed gum claims Frank glue again, is present in the flax seed husk, and its content differs greatly with the difference of linseed oil kind, and general content is 10～15%.Flaxseed gum is the green food specialist additive that national green foods development center is assert, have the nutritive ingredient height, stickiness is big, water-absorbent is strong, emulsify well, heavy metal had characteristics such as adsorpting detoxication effect, the effect that also has skin care, beauty treatment, health care is widely used in foodstuffs industry, daily chemical industry and pharmaceutical industry.
Lignan is the important phytoestrogen of a class.Be rich in lignan in the linseed oil, wherein, open loop secoisolariciresinoldiglucoside diglucoside (SDG) is most important component, generally accounts for 0.9%～1.5% of seed weight, and is higher 100～800 times than other known 66 kinds of food that contain lignan.
The extraction process of existing flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside all is that the two extracts respectively.The extracting method of relevant flaxseed gum the earliest be the patent of people such as Bolly in employing acidic aqueous solution lixiviate flax glue from linseed oil of nineteen fifty-two application.After this, many reports that extract about flax glue are arranged successively, its technology mainly is to adopt water, sour water or sodium sulfite solution room temperature or add heat soaking.The existing technology for preparing SDG from linseed oil mainly comprises employing ethanol or methyl alcohol or aqueous acetone solution heating and refluxing extraction, carries out basic hydrolysis then, adopts organic solvent extraction again, silica gel, gel, C
18, column chromatography such as macroporous adsorbent resin carries out purifying, but all has the loaded down with trivial details shortcoming of leaching process.Patent 101139373A provides and has adopted the mixing solutions of fatty alcohol solution and alkali lye through supersound extraction, to extract with one step of basic hydrolysis and finish simultaneously, directly obtain the secoisolariciresinol diglycoside crude extract, again through organic solvent extraction, the macroporous adsorbent resin separation obtains the high purity secoisolariciresinol diglycoside, though simplified preparation process, need ultrasonic this specific installation, limited its production application.
Summary of the invention
The object of the present invention is to provide a kind of method of from linseed oil or flaxseed meal, extracting flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside simultaneously.
The present invention with linseed oil or the oil expression after flaxseed meal be raw material, adopt the method for alkali aqueous solution room temperature lixiviate, extract flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside simultaneously, and the extraction of SDG and one step of basic hydrolysis are finished, redissolve through ethanol sedimentation, macroporous adsorbent resin separation, ethanol or methyl alcohol, can obtain highly purified SDG and flaxseed gum.
The extracting method of a kind of flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside is characterized in that this method may further comprise the steps:
A. the flaxseed meal after linseed oil or the oil expression is pulverized, with normal hexane or No. 6 solvent oil degreasings;
B. the stirring and leaching under the alkali aqueous solution room temperature of the raw material after the degreasing is centrifugal, isolates glue and material slag;
C. expect stirring and leaching under the slag water room temperature, centrifugal, isolate glue;
D. the glue that obtains uses acid to transfer pH to 6～7, merges, and concentrates, and concentrated solution adds ethanol and precipitates, and gets supernatant liquor and precipitation;
E. precipitate desalination, drying gets flaxseed gum;
F. after supernatant liquor reclaims solvent, use water dissolution, last macroporous adsorbent resin carries out column chromatography, gets the open loop secoisolariciresinoldiglucoside diglucoside crude product;
G. the open loop secoisolariciresinoldiglucoside diglucoside crude product is redissolved with alcoholic solution, filter, filtrate is concentrated into dried, gets open loop secoisolariciresinoldiglucoside diglucoside.
The described alkali aqueous solution of B step of the present invention is selected from sodium hydroxide solution or potassium hydroxide solution.
The described acid of D step of the present invention is selected from sulfuric acid or hydrochloric acid.
The described alcoholic solution of G step of the present invention is selected from ethanolic soln or methanol solution.
Use method of the present invention, polysaccharide content is (a phenolsulfuric acid colorimetric method for determining) more than 95% in the flaxseed gum of preparation, SDG purity is (high effective liquid chromatography for measuring) more than 80%, and the extraction yield of the two is all higher, the extraction yield of flaxseed gum can reach 90～95%, and the extraction yield of SDG can reach 80～90%.The method technology that the present invention proposes is simple, and stablizes feasiblely, is suitable for that industry is big produces.
Characteristics of the present invention are: be to extract solvent with the alkaline aqueous solution, adopt the method for room temperature lixiviate, extract flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside simultaneously, and the extraction of SDG and one step of basic hydrolysis are finished, extract the Technology of alkaline hydrolysis compares with the elder generation of existing the two Technology extracted respectively and SDG again, simplified operation steps, raw materials for production have been saved, played the effect of comprehensive utilization, and leaching process need not heating, need not to use alcoholic solution or specific installation such as ultrasonic, greatly reduce production cost; Add ethanol in the employing extracting solution and carry out sedimentary method, flaxseed gum is separated with SDG, and solid glue post precipitation, through suction filtration, drying can be produced dried glue rubber powder, has avoided glue to be difficult to the shortcoming of concentrate drying, has improved the glue rate of putting forward; In the separation and purification process of SDG, save this step of organic solvent extraction; Utilize macroporous adsorbent resin separation and purification SDG, compare with other purification process such as silica gel, gel, C18 column chromatographies, simple to operate, the time is short, and cost is low, is convenient to large-scale production; Adopt the method for ethanol redissolution, further improve the purity of SDG, can obtain purity up to the SDG more than 80%, this method is simple.
Embodiment
Embodiment 1
Get the flaxseed meal after the oil expression, pulverize, with normal hexane heating and refluxing extraction 2 times, the consumption of each normal hexane is 3 times of raw material, return time 1.5 hours, each time extracting liquid filtering, filtrate recovery solvent.The cryodrying of material slag adds 10 times of amount 0.5mol/L sodium hydroxide solutions to solvent-free flavor, soaking at room temperature 1.0 hours, and mixture is centrifugal, isolates glue.The material slag adds flooding 2 times again, and each amount of water is 10 times, and soak time 2 hours is centrifugal, isolates glue.Each time glue is transferred pH to 6.0 with the 2mol/L sulphuric acid soln, merges, and concentrating under reduced pressure, concentrated solution add 3 times of amount ethanol and precipitate.Behind the throw out suction filtration, dialysis, drying is pulverized, and promptly gets flaxseed gum.The supernatant liquor decompression recycling ethanol is concentrated into driedly, adds suitable quantity of water dissolving, filters.D101 macroporous adsorbent resin on the filtrate, water successively, 15% ethanol, 35% ethanol elution is collected 35% ethanol eluate, decompression and solvent recovery, vacuum-drying, solid substance (purity is 50～60% open loop secoisolariciresinoldiglucoside diglucoside).Above-mentioned solid substance filters with 2 times of amount 95% dissolve with ethanol, and filtrate is concentrated into dried, gets solid substance (purity is the open loop secoisolariciresinoldiglucoside diglucoside more than 80%).
Embodiment 2
Get linseed oil, pulverize, with No. 6 solvent oil heating and refluxing extraction 2 times, the consumption of each normal hexane is 3 times of raw material, return time 1.5 hours, each time extracting liquid filtering, filtrate recovery solvent.The cryodrying of material slag adds 14 times of amount 1.0mol/L potassium hydroxide solutions to solvent-free flavor, soaking at room temperature 1.5 hours, and mixture is centrifugal, isolates glue.The material slag adds flooding 3 times again, and each amount of water is 14 times, and soak time 4 hours is centrifugal, isolates glue.Each time glue is transferred pH to 7.0 with the 4mol/L hydrochloric acid soln, merges, and concentrating under reduced pressure, concentrated solution add 3 times of amount ethanol and precipitate.Behind the throw out suction filtration, dialysis, drying is pulverized, and promptly gets flaxseed gum.The supernatant liquor decompression recycling ethanol is concentrated into driedly, adds suitable quantity of water dissolving, filters.D101 macroporous adsorbent resin on the filtrate, water successively, 15% ethanol, 35% ethanol elution is collected 35% ethanol eluate, decompression and solvent recovery, vacuum-drying, solid substance (purity is 50～60% open loop secoisolariciresinoldiglucoside diglucoside).Above-mentioned solid substance filters with 2 times of amount dissolve with methanol, and filtrate is concentrated into dried, gets solid substance (purity is the open loop secoisolariciresinoldiglucoside diglucoside more than 80%).
Embodiment 3
Get the flaxseed meal after the oil expression, pulverize, with normal hexane heating and refluxing extraction 2 times, the consumption of each normal hexane is 2 times of raw material, return time 1.5 hours, each time extracting liquid filtering, filtrate recovery solvent.The cryodrying of material slag adds 12 times of amount 0.5mol/L sodium hydroxide solutions to solvent-free flavor, soaking at room temperature 1.0 hours, and mixture is centrifugal, isolates glue.The material slag adds flooding 2 times again, and each amount of water is 12 times, and soak time 2 hours is centrifugal, isolates glue.Each time glue is transferred pH to 6.0 with the 2mol/L sulphuric acid soln, merges, and concentrating under reduced pressure, concentrated solution add 2 times of amount ethanol and precipitate.Behind the throw out suction filtration, carry out desalination with 50% ethanol, drying is pulverized, and promptly gets flaxseed gum.The supernatant liquor decompression recycling ethanol is concentrated into driedly, adds suitable quantity of water dissolving, filters.LSA30 macroporous adsorbent resin on the filtrate, water successively, 20% ethanol, 40% ethanol elution is collected 40% ethanol eluate, decompression and solvent recovery, vacuum-drying, solid substance (purity is 50～60% open loop secoisolariciresinoldiglucoside diglucoside).Above-mentioned solid substance filters with 4 times of amount 85% dissolve with ethanol, and filtrate is concentrated into dried, gets solid substance (purity is the open loop secoisolariciresinoldiglucoside diglucoside more than 80%).
Claims (4)
1. the extracting method of flaxseed gum and open loop secoisolariciresinoldiglucoside diglucoside is characterized in that this method may further comprise the steps:
A. the flaxseed meal after linseed oil or the oil expression is pulverized, with normal hexane or No. 6 solvent oil degreasings;
B. the stirring and leaching under the alkali aqueous solution room temperature of the raw material after the degreasing is centrifugal, isolates glue and material slag;
C. expect stirring and leaching under the slag water room temperature, centrifugal, isolate glue;
D. the glue that obtains uses acid to transfer pH to 6～7, merges, and concentrates, and concentrated solution adds ethanol and precipitates, and gets supernatant liquor and precipitation;
E. precipitate desalination, drying gets flaxseed gum;
F. after supernatant liquor reclaims solvent, use water dissolution, last macroporous adsorbent resin carries out column chromatography, gets the open loop secoisolariciresinoldiglucoside diglucoside crude product;
G. the open loop secoisolariciresinoldiglucoside diglucoside crude product is redissolved with alcoholic solution, filter, filtrate is concentrated into dried, gets open loop secoisolariciresinoldiglucoside diglucoside.
2. the method for claim 1, it is characterized in that: alkali aqueous solution is selected from sodium hydroxide solution or potassium hydroxide solution.
3. the method for claim 1, it is characterized in that: acid is selected from sulfuric acid or hydrochloric acid.
4. the method for claim 1, it is characterized in that: alcoholic solution is selected from ethanolic soln or methanol solution.
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| CN200810184476XA CN101759731B (en) | 2008-12-25 | 2008-12-25 | Extraction method of linseed gum and secoisolariciresin-ol diglucoside |
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| CN200810184476XA CN101759731B (en) | 2008-12-25 | 2008-12-25 | Extraction method of linseed gum and secoisolariciresin-ol diglucoside |
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| CN101759731B CN101759731B (en) | 2011-10-19 |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558252A (en) * | 2010-12-31 | 2012-07-11 | 西安天一生物技术有限公司 | Production process of secoisolariciresinol diglucoside |
| CN106977616A (en) * | 2017-03-28 | 2017-07-25 | 暨南大学 | A kind of method that utilization hydrogen peroxide oxidation edman degradation Edman prepares flaxseed gum oligosaccharide |
| CN109077319A (en) * | 2018-08-30 | 2018-12-25 | 祁景泉 | The method that lipid containing plant extract prepares ice cream, milk tea and pulvis |
| CN112336736A (en) * | 2014-05-30 | 2021-02-09 | 宾夕法尼亚大学董事会 | Use of Secoisolariciresinol Diglucoside (SDG) and related compounds for protecting against radiation and chemical damage |
| WO2023011102A1 (en) * | 2021-08-04 | 2023-02-09 | 暨南大学 | Subcritical composite solvent extraction and separation method for multiple components in flaxseed meal |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI110868B (en) * | 2001-01-22 | 2003-04-15 | Maa Ja Elintarviketalouden Tut | Procedure for the separation and purification of secoisolarisiresinol diglycoside (SDG) from flax seeds |
| ATE555673T1 (en) * | 2002-03-11 | 2012-05-15 | Suntory Holdings Ltd | METHOD FOR PRODUCING SDG |
| CN100344719C (en) * | 2006-01-19 | 2007-10-24 | 中国科学院山西煤炭化学研究所 | Method for producing linen glue |
| 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 |
-
2008
- 2008-12-25 CN CN200810184476XA patent/CN101759731B/en active Active
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558252A (en) * | 2010-12-31 | 2012-07-11 | 西安天一生物技术有限公司 | Production process of secoisolariciresinol diglucoside |
| CN112336736A (en) * | 2014-05-30 | 2021-02-09 | 宾夕法尼亚大学董事会 | Use of Secoisolariciresinol Diglucoside (SDG) and related compounds for protecting against radiation and chemical damage |
| CN106977616A (en) * | 2017-03-28 | 2017-07-25 | 暨南大学 | A kind of method that utilization hydrogen peroxide oxidation edman degradation Edman prepares flaxseed gum oligosaccharide |
| CN109077319A (en) * | 2018-08-30 | 2018-12-25 | 祁景泉 | The method that lipid containing plant extract prepares ice cream, milk tea and pulvis |
| WO2023011102A1 (en) * | 2021-08-04 | 2023-02-09 | 暨南大学 | Subcritical composite solvent extraction and separation method for multiple components in flaxseed meal |
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| CN101759731B (en) | 2011-10-19 |
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