CN1814608A - Method for extracting and purifying secoisolariciresinol diglucoside from flax seed - Google Patents
Method for extracting and purifying secoisolariciresinol diglucoside from flax seed Download PDFInfo
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Abstract
The invention relates to the method used to extract purification secoisolarciresinol di-glycoside from flax seed. It belongs to farm produce resource development and functionality health foods technique field. It includes the following steps: using flax seed as raw material; low temperature leaching degreasing by organic solvent; extracting by alcohol solution; adding alkali to hydrolyze; neutralizing and adjusting pH value; reducing pressure and condensing; micro-straining; and purifying. It has superiority in security, economical efficiency, preparation scale, and product purity. Its use is functionality food mixture or health foods.
Description
Technical field
A kind of method of extracting purifying secoisolariciresinoldiglucoside diglucoside from linseed oil the present invention relates to the extracting and purifying method of secoisolariciresinol diglycoside, belongs to agricultural resource exploitation and functional health-care food technical field.
Background technology
Lignan is a kind of material with estrogen activity that is present in the plant.Be rich in secoisolariciresinol diglycoside in the linseed oil, its main ingredient is an open loop secoisolariciresinoldiglucoside diglucoside, English name secoisolariciresinol diglucoside, abbreviate SDG as, it is a kind of diaryl butanes lignan that is polymerized by the plain bimolecular of phenylpropyl alcohol, has a kind of function that exactly likes human body female hormone of gentleness.It has the human breast cancer cell of inhibition growth, reduces breast tumor, reduces incidence of breast cancer, alleviates the menopausal women symptom, prevents colorectal carcinoma, suppresses the prostate cancer isoreactivity, also systemic lupus erythematosus, I-type diabetes and II-type diabetes is played the effect of assisting therapy.
Linseed oil is the most important source of SDG, and SDG content reaches 11.7~24.1g/ kilogram degreasing flaxseed meal in the linseed oil, is 75~800 times of SDG content in other crops.Simultaneously, the distribution of SDG in linseed oil mainly concentrates on the flax seed husk part, thereby selects the extraction raw material of flax seed husk as SDG for use.
The research of extracting or reclaiming SDG from linseed oil starts from the nineties in last century.At patent US6, in 806,356, aqueous acetone solution is used to extract secoisolariciresinol diglycoside, in patent US 6,767,565, aqueous ethanolic solution then is used to extract, and adopts ultrafiltration (MWCO 1000~5000) or resin absorption to carry out purifying then, and the purity of product can reach between 10%~40%.US 6,264, and 853 adopt aqueous ethanolic solution to extract the mixture of SDG and styracin glucosides and Hydroxymethylglutaryl, adopt separating ranges 30,000~100 then, and the column chromatography of 000Da is carried out separation and purification, and SDG content can reach 50% in the product.These methods are not carried out further chromatogram purification, and the purity of gained secoisolariciresinol diglycoside product is lower.
Aspect the preparation of high purity secoisolariciresinol diglycoside, patent US 5,705, adopt ethanol or methanol aqueous solution to extract in 618, adopt liquid/liquid distribution or anionite-exchange resin to carry out enrichment, carry out purifying then on the C18 reverse-phase chromatographic column, product purity reaches more than 90%.Patent CN01120199.1 and CN02803980.7 also adopt the method for silica gel adsorption and C18 reversed phase chromatography separation to prepare the secoisolariciresinol diglycoside product of purity more than 90% respectively.
Owing to be subjected to the restriction in separation and purification stage, this method cost for preparing SDG is higher, and scale is subjected to bigger restriction.When adopting silica gel adsorption, solvent for use comprises noxious solvents such as methyl alcohol, chloroform and methylene dichloride, so the application space is subjected to bigger restriction simultaneously.
Summary of the invention
The purpose of this invention is to provide a kind of method of from linseed oil, extracting purifying secoisolariciresinoldiglucoside diglucoside,, also provide a kind of functional food ingredient and protective foods simultaneously for the comprehensive utilization of linseed oil provides a kind of new method.
Technical scheme of the present invention: flax seed husk and/or flaxseed meal with pulverizing are raw material, adopt low polar organic solvent leach at low temperature degreasing, adopt ethanolic soln to extract then, adding alkali in the extracting solution is hydrolyzed, neutralization is also transferred pH, suction filtration, concentrating under reduced pressure, obtain clear liquid with dehydrated alcohol redissolution and micro-filtration, gel column carries out separation and purification on the filtrate.
(1) pulverize: it is 30~100 orders that flax seed husk and/or flaxseed meal are crushed to granularity.
(2) degreasing: add low polar organic solvent by 10~20mL/g linseed meal, at room temperature stir 1~2h, centrifugal then, supernatant liquor reclaims solvent and linseed oil, and residue adds low polar organic solvent degreasing under the same conditions by 5~10mL/g linseed meal once more.The used low polar organic solvent of degreasing is normal hexane or No. 6 solvent oils.This degreasing method has no adverse effects to secoisolariciresinol diglycoside, has also removed a large amount of impurity when ethanolic soln extracts simultaneously.
(3) extract: the ethanolic soln that adds volumetric concentration 40%~70% by 5~30mL/g degreasing linseed meal, stir extraction 2~4h at 25~65 ℃, centrifugal, the ethanolic soln that residue is pressed 5mL/g degreasing linseed meal adding volumetric concentration 40%~70% stirs extraction 1h once more at 25~65 ℃, and is centrifugal then.The ethanol consumption of the best is 15~20mL/g degreasing linseed meal during extraction, and the ethanol volumetric concentration is 50%~60%, and temperature is 50~60 ℃.Select 50~60 ℃ temperature, on the one hand SDG is not had obvious detrimentally affect, shortened extraction time greatly on the other hand, extraction time and temperature negative correlation.
(4) hydrolysis: merge the clear liquid that extracted twice obtains, add alkaline solution and make final concentration of lye at 0.25~0.5M, concussion or stirring 2h are hydrolyzed under 30 ℃.The used alkaline solution of hydrolysis is a sodium hydroxide solution.
(5) regulate pH: after hydrolysis finished, hydrolyzed solution was with sour neutralization bases and regulate pH 4~6, and used acid solution is a hydrochloric acid.
(6) suction filtration, concentrating under reduced pressure, redissolution and micro-filtration: adopt in the 30 μ m middling speed filter paper suction filtrations of aperture and after suspension liquid, ethanolic soln with an amount of volumetric concentration 40%~70% washs residue and merging filtrate then, filtrate is concentrated into dense thick pulp-like under reduced pressure, during concentrating under reduced pressure, temperature is controlled at below 70 ℃.Add an amount of dehydrated alcohol and redissolve, carry out micro-filtration with microfiltration membrane then, the used filter membrane of micro-filtration is the microfiltration membrane of aperture 0.45 μ m.
(7) gel column separation and purification: the direct upper prop of micro-filtrate, gel media is Sephadex LH-20, the post length-to-diameter ratio is controlled to be 70: 1, behind the last sample with the deionized water wash-out, linear rate of flow is at 0.5~0.7cm/min, adopt Ultraviolet Detector to detect under 280nm, elutriant finishes as wash-out during no absorption peak under 280nm; Gel column medium behind the sample wash-out cleans with ethanolic soln, uses for gel column separation and purification next time.
(8) lyophilize and product checking: gel column separates the open loop secoisolariciresinoldiglucoside diglucoside component that obtains, obtain lyophilized powder through lyophilize behind the concentrating under reduced pressure, this lyophilized powder is through HPLC-MS, UV and NMR checking, determine that open loop secoisolariciresinoldiglucoside diglucoside is the main component of product, content is more than 90%.
The cleaning of gel column medium: the gel column medium behind the target compound open loop secoisolariciresinoldiglucoside diglucoside wash-out, with the ethanolic soln of volumetric concentration 50%~95% cleaning medium progressively, adopt and progressively reduce alcohol concn again behind 2 column volumes of 95% washing with alcohol and clean until deionized water, the medium after the cleaning uses for gel column separation and purification next time; The used ethanol of cleaning medium is recycled.
Beneficial effect of the present invention: the present invention adopts the method for organic solvent extraction, Sephadex LH-20 gel column separation and purification SDG to have following characteristics: (1) has overcome the deficiency that batch is little, cost is high that exists in the prior art for preparing chromatogram, replaces the Sephadex LH-20 gel column chromatography of being convenient to amplify and comes separation and purification; (2) technical process is simple, and the product purity height is easy to utilize; (3) adopt ethanol for extracting and eluting solvent, improved production process and security of products, reclaim easily simultaneously, use the problem of the bigger organic solvent of toxicity when having overcome the silica gel adsorption desorb.
Utilize the method for extraction purifying SDG provided by the invention, can on security, economy, preparative-scale and product purity, embody its advantage.The purposes of SDG is functional food ingredient or protective foods.
Description of drawings
The technical process of Fig. 1 extraction and purifying SDG.
The HPLC collection of illustrative plates and the ultraviolet absorpting spectrum thereof of Fig. 2 purifying gained SDG product.
Fig. 3 SDG's
1The H-NMR spectrogram.
Fig. 4 SDG's
13The C-NMR spectrogram.
Embodiment
Method of the present invention is not to be defined in this embodiment.
Embodiment 1
Take by weighing flax seed husk 50g, be crushed to 30 orders, add volume 500mL normal hexane, at room temperature stir 1h, centrifugal then (3000rpm, 20min).Residue adopts the degreasing of 500mL normal hexane once more.The ethanolic soln that adds 1000mL 50% in the degreasing flax seed husk stirs extraction 4h down at 25 ℃.It is centrifugal then that (3000rpm, 20min), the ethanolic soln that adds 250mL 50% in the residue stirs and extracts 1h, and is centrifugal then.United extraction liquid adds 60mL 6M NaOH solution, stirs 2h down at 30 ℃, adds 6M hydrochloric acid then, regulates pH to 4.Suction filtration and with an amount of washing with alcohol residue, merging filtrate then.Filtrate is concentrated into dense thick pulp-like under reduced pressure, adds an amount of dehydrated alcohol and redissolve, then micro-filtration (0.45 μ m).Sample wash-out on the Sephadex LH-20 post then, column length 100cm, column diameter 1.60cm.With the deionized water wash-out, linear rate of flow is at 0.5cm/min behind the last sample, ultraviolet detection wavelength 280nm.Gel column separates the SDG component that obtains, and adopts HPLC-MS, UV and NMR checking, determines that SDG is a main component, and content is 94%.The HPLC collection of illustrative plates of SDG product and ultraviolet absorpting spectrum thereof,
1The H-NMR spectrogram and
13The C-NMR spectrogram is shown in accompanying drawing 2,3,4.
Gel column medium behind the target compound open loop secoisolariciresinoldiglucoside diglucoside wash-out, ethanolic soln with volumetric concentration 50%~95% progressively cleans, adopt and progressively reduce alcohol concn again behind 2 column volumes of 95% washing with alcohol and clean until deionized water, the medium after the cleaning uses for gel column separation and purification next time.The used ethanol of cleaning medium is recycled.
Embodiment 2
Take by weighing linseed oil 50g, be crushed to 100 orders, add No. 6 solvent oils of volume 1000mL, at room temperature stir 2h, centrifugal then (3000rpm, 20min).Residue adopts No. 6 solvent oil degreasings of 250mL once more.The ethanolic soln that adds 500mL 60% in the degreasing flax seed husk stirs extraction 2h down at 60 ℃.It is centrifugal then that (3000rpm, 20min), the ethanolic soln that adds 250mL 60% in the residue stirs and extracts 1h, and is centrifugal then.United extraction liquid adds 75mL 6M NaOH solution, stirs 2h down at 30 ℃, adds 6M hydrochloric acid then, regulates pH to 6.Suction filtration and with an amount of washing with alcohol residue, merging filtrate then.Filtrate is concentrated into dense thick pulp-like under reduced pressure, adds an amount of dehydrated alcohol and redissolve, then micro-filtration (0.45 μ m).Sample wash-out on the Sephadex LH-20 post then, column length 100cm, column diameter 1.60cm.With the deionized water wash-out, linear rate of flow is at 0.7cm/min behind the last sample, ultraviolet detection wavelength 280nm.Gel column separates the SDG component that obtains, and adopts HPLC-MS, UV and NMR checking, determines that SDG is a main component, and content is 96%.
Gel column medium behind the target compound open loop secoisolariciresinoldiglucoside diglucoside wash-out, ethanolic soln with volumetric concentration 50%~95% progressively cleans, adopt and progressively reduce alcohol concn again behind 2 column volumes of 95% washing with alcohol and clean until deionized water, the medium after the cleaning uses for gel column separation and purification next time.The used ethanol of cleaning medium is recycled.
Claims (8)
1, a kind of method of from linseed oil, extracting purifying secoisolariciresinoldiglucoside diglucoside, it is characterized in that: flax seed husk and/or flaxseed meal with pulverizing are raw material, adopt low polar organic solvent leach at low temperature degreasing, adopt ethanolic soln to extract then, add alkali in the extracting solution and be hydrolyzed, neutralization is also transferred pH, suction filtration, concentrating under reduced pressure obtains clear liquid with dehydrated alcohol redissolution and micro-filtration, and gel column carries out separation and purification on the filtrate;
(1) pulverize: it is 30~100 orders that flax seed husk and/or flaxseed meal are crushed to granularity;
(2) degreasing: add low polar organic solvent by 10~20mL/g linseed meal, at room temperature stir 1~2h, centrifugal then, supernatant liquor reclaims solvent and linseed oil, and residue adds low polar organic solvent degreasing under the same conditions by 5~10mL/g linseed meal once more;
(3) extract: the ethanolic soln that adds volumetric concentration 40%~70% by 5~30mL/g degreasing linseed meal, stir extraction 2~4h at 25~65 ℃, centrifugal, the ethanolic soln that residue is pressed 5mL/g degreasing linseed meal adding volumetric concentration 40%~70% stirs extraction 1h once more at 25~65 ℃, and is centrifugal then;
(4) hydrolysis: merge the clear liquid that extracted twice obtains, add alkaline solution and make final concentration of lye at 0.25~0.5M, concussion or stirring 2h are hydrolyzed under 30 ℃;
(5) regulate pH: after hydrolysis finished, hydrolyzed solution was with sour neutralization bases and regulate pH4~6;
(6) suction filtration, concentrating under reduced pressure, redissolution and micro-filtration: adopt in the 30 μ m middling speed filter paper suction filtrations of aperture and after suspension liquid, ethanolic soln with an amount of volumetric concentration 40%~70% washs residue and merging filtrate then, filtrate is concentrated into dense thick pulp-like under reduced pressure, add an amount of dehydrated alcohol and redissolve, carry out micro-filtration with microfiltration membrane then;
(7) gel column separation and purification: the direct upper prop of micro-filtrate, gel media is Sephadex LH-20, the post length-to-diameter ratio is controlled to be 70: 1, behind the last sample with the deionized water wash-out, linear rate of flow is at 0.5~0.7cm/min, adopt Ultraviolet Detector to detect under 280nm, elutriant finishes as wash-out during no absorption peak under 280nm; Gel column medium behind the sample wash-out cleans with ethanolic soln, uses for gel column separation and purification next time;
(8) lyophilize and product checking: gel column separates the open loop secoisolariciresinoldiglucoside diglucoside component that obtains, obtain lyophilized powder through lyophilize behind the concentrating under reduced pressure, this lyophilized powder is through HPLC-MS, UV and NMR checking, determine that open loop secoisolariciresinoldiglucoside diglucoside is the main component of product, content is more than 90%.
2, in accordance with the method for claim 1, it is characterized in that the used low polar organic solvent of degreasing is normal hexane or No. 6 solvent oils.
3, in accordance with the method for claim 1, the ethanol consumption of the best is 15~20mL/g degreasing linseed meal when it is characterized in that extracting, and the ethanol volumetric concentration is 50%~60%, and temperature is 50~60 ℃.
4, in accordance with the method for claim 1, it is characterized in that the used alkaline solution of hydrolysis is a sodium hydroxide solution.
5, in accordance with the method for claim 1, it is characterized in that regulating the used acid solution of pH is hydrochloric acid.
6, in accordance with the method for claim 1, it is characterized in that the used filter membrane of micro-filtration is the microfiltration membrane of aperture 0.45 μ m.
7, in accordance with the method for claim 1, when it is characterized in that concentrating under reduced pressure, temperature is controlled at below 70 ℃.
8, in accordance with the method for claim 1, it is characterized in that the cleaning of gel column medium: the gel column medium behind the target compound open loop secoisolariciresinoldiglucoside diglucoside wash-out, ethanolic soln with volumetric concentration 50%~95% progressively cleans, adopt and progressively reduce alcohol concn again behind 2 column volumes of 95% washing with alcohol and clean until deionized water, the medium after the cleaning uses for gel column separation and purification next time; The used ethanol of cleaning medium is recycled.
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Cited By (7)
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CN101117641B (en) * | 2007-07-27 | 2011-05-11 | 大连医诺生物有限公司 | Method for preparing secoisolariciresinol diglucoside |
CN102766174A (en) * | 2012-06-26 | 2012-11-07 | 中山市庄臣化工有限公司 | Method for extracting lignan from linseed oil residue |
CN103042023A (en) * | 2012-12-20 | 2013-04-17 | 菏泽瑞璞牡丹产业科技发展有限公司 | Comprehensive utilization method of peony shells |
CN101538294B (en) * | 2009-04-28 | 2013-04-17 | 中国科学院山西煤炭化学研究所 | Method for preparing SDG and ferulic acid glucoside or ester thereof |
CN104004034A (en) * | 2014-05-14 | 2014-08-27 | 中国科学院华南植物园 | Method for preparing secoisolariciresinol 9'-O-beta-xyloside |
CN106635389A (en) * | 2016-12-07 | 2017-05-10 | 中国农业科学院麻类研究所 | Extraction method of flaxseed oil |
CN107155304A (en) * | 2014-05-30 | 2017-09-12 | 宾夕法尼亚大学董事会 | Secoisolariciresinol diglucoside(SDG)It is used to protect radiation and the purposes of chemical damage with related compound |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
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US5705618A (en) * | 1995-03-31 | 1998-01-06 | Agriculture And Agri-Food Canada | Process for extracting lignans from flaxseed |
US6264853B1 (en) * | 1999-06-21 | 2001-07-24 | Agriculture And Agri-Food Canada | Complex containing lignan, phenolic and aliphatic substances from flax and process for preparing |
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 |
US6767565B2 (en) * | 2001-03-22 | 2004-07-27 | Archer Daniels Midland Company | Process for obtaining lignan |
CN1162438C (en) * | 2001-07-11 | 2004-08-18 | 北京万博力科技发展有限公司 | Method for extracting, separating and purifying linolenic lignan by using linseed cake |
US20030131737A1 (en) * | 2001-12-13 | 2003-07-17 | Wuwei Cui | Process and apparatus for flaxseed component separation |
WO2003084974A1 (en) * | 2002-04-02 | 2003-10-16 | Wiley Organics, Inc. | A process for recovering secoisolariciresinol diglycoside from de-fatted flaxseed |
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2006
- 2006-03-02 CN CNB2006100386341A patent/CN100365005C/en not_active Expired - Fee Related
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CN101117641B (en) * | 2007-07-27 | 2011-05-11 | 大连医诺生物有限公司 | Method for preparing secoisolariciresinol diglucoside |
CN101538294B (en) * | 2009-04-28 | 2013-04-17 | 中国科学院山西煤炭化学研究所 | Method for preparing SDG and ferulic acid glucoside or ester thereof |
CN102766174A (en) * | 2012-06-26 | 2012-11-07 | 中山市庄臣化工有限公司 | Method for extracting lignan from linseed oil residue |
CN102766174B (en) * | 2012-06-26 | 2015-05-20 | 中山市庄臣化工有限公司 | Method for extracting lignan from linseed oil residue |
CN103042023A (en) * | 2012-12-20 | 2013-04-17 | 菏泽瑞璞牡丹产业科技发展有限公司 | Comprehensive utilization method of peony shells |
CN104004034A (en) * | 2014-05-14 | 2014-08-27 | 中国科学院华南植物园 | Method for preparing secoisolariciresinol 9'-O-beta-xyloside |
CN104004034B (en) * | 2014-05-14 | 2016-02-03 | 中国科学院华南植物园 | One prepares the method for Secoisolariciresinol 9 '-O-β-xyloside |
CN107155304A (en) * | 2014-05-30 | 2017-09-12 | 宾夕法尼亚大学董事会 | Secoisolariciresinol diglucoside(SDG)It is used to protect radiation and the purposes of chemical damage with related compound |
CN106635389A (en) * | 2016-12-07 | 2017-05-10 | 中国农业科学院麻类研究所 | Extraction method of flaxseed oil |
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