CN101538293A - Method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester - Google Patents
Method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester Download PDFInfo
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Abstract
The invention relates to a method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester. The method comprises the following steps: after the impurity removal and the degumming are performed to the flax seeds, the flax seeds are mixed with alcoholic-alkaline solution, extracted for 2-5 h at the temperature of 40-60 DEG C and filtered, then the filter residue is extracted until the alcoholic-alkaline solution is achromatous, and then the merging is performed; the filtrate is added with acid to be adjusted to be neutral and concentrated until the weight is one sixth-one second of that of the original filtrate, then the water with volume 2-5 times of that of the concentrated solution is added in, the extraction is carried out through the organic solvent until the organic phase is achromatous and then the aqueous phase is collected; the secoisolariciresinol diglucoside and the ferulic acid glucoside ethyl ester in the aqueous phase are fully absorbed through macroporous resin, then the water and the alcohol solution are respectively taken as the mobile phases for elution, then the 20v percent, the 30v percent and the 40v percent of alcohol eluent are collected, merged and distilled to dryness to obtain secoisolariciresinol diglucoside; and the 70v percent, the 80v percent and the 90v percent of alcohol eluent are collected, merged and distilled to dryness to obtain ferulic acid glucoside ethyl ester. The invention has the advantages of entire simple and feasible process, stable process and low cost; and the secoisolariciresinol diglucoside and the ferulic acid glucoside ethyl ester or the ferulic acid glucoside can be obtained at the same time and the product reaches the higher purity.
Description
Technical field
The present invention relates to a kind of is the method that raw material prepares secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester simultaneously with the linseed oil.
Technical background
Linseed oil (Flaxseed) is a kind of important economic oil crops, is rich in lignan class material, and wherein the content of open loop secoisolariciresinoldiglucoside diglucoside (SDG) is the highest.In addition, also contain other phenols glucosides materials in the linseed oil, as coumaric acid glucoside, ferulic acid glucoside (seeing WO9630468A2).
Open loop secoisolariciresinoldiglucoside diglucoside (SDG) is polymerized by the plain bimolecular of phenylpropyl alcohol, it is a kind of anti-oxidant and active compound of phytoestrogen of having, be mainly derived from the product of cereal and other fiber-enriched, especially in linseed oil content up to 1-3%.That SDG has is antitumor, reduce serum cholesterol, immunomodulatory, delay senility, protect effects such as cardiovascular; especially suppress the growth of human body breast cancer cell, alleviate the menopausal women symptom, there is good effect aspects such as prevention colorectal carcinoma, prevention prostate cancer, on the treatment diabetes, also can play a significant role simultaneously.
Forulic acid (ferulic acid), chemistry 4-hydroxy 3-methoxybenzene vinylformic acid by name, be the ubiquitous a kind of phenolic acid of vegitabilia, be present in wheat bran, rice bran, linseed oil etc., the part of main and cell wall polysaccharides and the crosslinked formation cell walls of xylogen in plant.Multiple biological activitys such as that forulic acid has is anti-oxidant, antithrombotic, reducing blood-fat, antisepsis and anti-inflammation, removing free radical can be widely used in fields such as medicine, food, makeup.But because alkane is short and contain two keys in the forulic acid molecule, wetting ability is strong, is difficult to go deep into bring into play antioxygenation in the microbial film lipid bilayer structure, and this has also limited it in fat-soluble Application in Food Processing simultaneously.Studies show that ferulic acid glucoside and ferulic acid glucoside ethyl ester have good physiologically active and lower toxicity (seeing EP 0801945 A2) as ferulic acid derivative, and might improve the shortcoming of forulic acid lipophilicity difference.
Report seldom about the method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside and ethyl ester thereof simultaneously at present, research work mainly concentrates on the Analysis and Identification, used technique means is confined to chromatography, for example Pernilla Johnsson etc. separates with high performance liquid chromatography through column chromatography, utilize nuclear-magnetism to prove (Polymericfractions containing phenol glucosides in flaxseed.FoodChemistry.2002, (76): 207-212) of existing of ferulic acid glucoside in the linseed oil; People such as Eliasson C by efficient liquid phase chromatographic analysis the content of SDG and ferulic acid glucoside in the linseed oil after the basic hydrolysis (Highperformance liquid chromatographic analysis ofsecoisolariciresinol diglucoside and hydroxycinnamic acidglucosides in flaxseed by alkaline extraction.Journal ofChromatography A.2003, (1012): 151-159); People such as Vickram Bee jmohun utilize microwave to extract SDG and ferulic acid glucoside from linseed oil, examined or check the influence of power, time and the alkali concn of microwave to extraction yield, but do not make its both obtain separation and purification (Microwave-assisted Extraction of the Main Phenolic Compoundsin Flaxseed.Phytochemical Analysis.2007,18:275-282).People such as Xin Li have studied basic hydrolysis of lignan polymkeric substance and acid-hydrolyzed product, and with efficient liquid phase chromatographic analysis with separate these materials, comprising secoisolariciresinol diglycoside and ferulic acid glucoside and ethyl ester (Separation and determination of secoisolariciresinoldiglucoside oligomers and their hydrolysates in the flaxseedextract by high-performance liquid chromatography.Journal ofChromatography A thereof, 2008, (1185): 223-232).Comprehensive above document; mostly present research work is that SDG and ferulic acid derivative are used as a kind of product slightly to be carried and obtaining; effectively do not separate, or carry out Analysis and Identification by high performance liquid chromatography, also be far from reaching can large-scale production degree.
Summary of the invention
The purpose of this invention is to provide a kind of is the method for feedstock production high purity secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester with the linseed oil.
The present invention is to be raw material with the linseed oil, extracts with pure alkaline solution, through overregulating the pH value, concentrate, post separates, technologies such as drying, obtain highly purified secoisolariciresinol diglycoside and ferulic acid glucoside ethyl ester, ferulic acid glucoside ethyl ester can obtain ferulic acid glucoside through hydrolysis again.
Concrete operations step of the present invention is as follows:
(1) with after the linseed oil removal of impurities, coming unstuck, be that 10～13 pure alkaline solution mixes with 1: 2～8 weight ratio with pH, 40～60 ℃ were extracted 2～5 hours down, filtered, and it is colourless that filter residue is extracted into pure alkaline solution repeatedly, merging filtrate;
(2) add acid for adjusting pH to neutral in filtrate, be concentrated into the water that adds 2～5 times of concentrated solution volumes behind the 1/6-1/2 that weight is former filtrate, it is colourless to be extracted to organic phase repeatedly with organic solvent, collects water;
(3) water collected is adsorbed wherein secoisolariciresinol diglycoside and ferulic acid glucoside ethyl ester fully with macroporous resin, the ethanolic soln that adopts water, concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
Ferulic acid glucoside ethyl ester can as a kind of product, can also obtain ferulic acid glucoside with ferulic acid glucoside ethyl ester saponification in basic solution without saponification.
As described in step (1), pure alkaline solution is the solution that sodium hydroxide, potassium hydroxide, yellow soda ash or sodium bicarbonate and ethanol form.
As described in step (2), regulating the used acid of pH can be stronger organic acid of any acidity or mineral acid, preferred hydrochloric acid, phosphoric acid, acetic acid, acetic anhydride and sulfuric acid.
As described in step (2), organic solvent is halohydrocarbon, alcohol, ester, aromatic compounds, ether etc.Ethyl acetate, toluene, benzene, methyl acetate, chloroform, methylene dichloride, monochloro methane, 1,2-ethylene dichloride, propyl carbinol, amylalcohol, isopropylcarbinol, methyl ethyl ether or ether.
As described in step (3), macroporous resin is nonpolar or the low-pole resin, is the macroporous resin of D3250, D4020, X-5, AB-8, S-8 etc. as the resin model, preferred X-5, AB-8 macroporous resin.
As described in step (3), basic solution is sodium hydroxide, potassium hydroxide solution.The present invention has following advantage:
1, whole process is simple, process stabilizing, and cost is low, is fit to suitability for industrialized production.
2, obtain lignan and ferulic acid glucoside ethyl ester simultaneously, ferulic acid glucoside ethyl ester can obtain ferulic acid glucoside through hydrolysis, and product reaches higher purity.
3, take all factors into consideration other Products Development of linseed oil, the linseed oil behind the extraction separation also can continue on for the exploitation of other products.
Embodiment
Embodiment 1
Take by weighing the dry linseed oil after 200g comes unstuck, the 60 ℃ of water-baths of ethanol alkaline solution that add 400g pH value and be 10 sodium hydroxide are stirred down and were extracted 3 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with hydrochloric acid, it is 50g that extracting solution is concentrated into weight, add 250ml water, it is mutually colourless to be extracted to ethyl acetate repeatedly with ethyl acetate, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the X-5 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 2
Take by weighing the dry linseed oil after 400g comes unstuck, the 40 ℃ of water-baths of ethanol alkaline solution that add 1000g pH value and be 11 potassium hydroxide are stirred down and were extracted 2.5 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with sulfuric acid, it is 60g that extracting solution is concentrated into weight, add 120ml water, it is mutually colourless to be extracted to methyl acetate repeatedly with methyl acetate, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the AB-8 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
Embodiment 3
Take by weighing the dry linseed oil after 200g comes unstuck, the 50 ℃ of water-baths of ethanolic soln that add 1600g pH value and be 12 sodium hydroxide are stirred down and were extracted 2 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with acetic acid, it is 70g that extracting solution is concentrated into weight, add 300ml water, it is mutually colourless to be extracted to toluene repeatedly with toluene, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the AB-8 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 4
Take by weighing the dry linseed oil after 300g comes unstuck, the 50 ℃ of water-baths of ethanolic soln that add 1200g pH value and be 13 potassium hydroxide are stirred down and were extracted 5 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with phosphoric acid, it is 50g that extracting solution is concentrated into weight, add 150ml water, it is mutually colourless to be extracted to benzene repeatedly with benzene, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the S-8 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
Embodiment 5
Take by weighing the dry linseed oil after 400g comes unstuck, the 60 ℃ of water-baths of ethanolic soln that add 2400g pH value and be 12 yellow soda ash alcohol are stirred down and were extracted 4 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with acetic acid, it is 80g that extracting solution is concentrated into weight, add 300ml water, it is mutually colourless to be extracted to chloroform repeatedly with chloroform, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the D3250 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 6
Take by weighing the dry linseed oil after 350g comes unstuck, the 40 ℃ of water-baths of ethanolic soln that add 1750g pH value and be 13 sodium hydroxide alcohol are stirred down and were extracted 2 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with acetic anhydride, it is 80g that extracting solution is concentrated into weight, add 260ml water, it is mutually colourless to be extracted to ether repeatedly with ether, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the D4020 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 7
Take by weighing the dry linseed oil after 260g comes unstuck, the 60 ℃ of water-baths of ethanolic soln that add 780g pH value and be 10 sodium bicarbonate alcohol are stirred down and were extracted 3 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with hydrochloric acid, it is 50g that extracting solution is concentrated into weight, add 150ml water, it is mutually colourless to be extracted to monochloro methane repeatedly with monochloro methane, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the X-5 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
Embodiment 8
Take by weighing the dry linseed oil after 300g comes unstuck, the 50 ℃ of water-baths of ethanolic soln that add 2100g pH value and be 11 sodium bicarbonate alcohol are stirred down and were extracted 2.5 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with sulfuric acid, it is 100g that extracting solution is concentrated into weight, add 400ml water, it is mutually colourless to be extracted to methylene dichloride repeatedly with methylene dichloride, separatory, collect water, the water AB-8 that collects is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in potassium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 9
Take by weighing the dry linseed oil after 200g comes unstuck, the 50 ℃ of water-baths of ethanolic soln that add 1600g pH value and be 12 sodium hydroxide are stirred down and were extracted 2 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with sulfuric acid, it is 70g that extracting solution is concentrated into weight, add 300ml water, with 1, the 2-ethylene dichloride is extracted to 1 repeatedly, the 2-ethylene dichloride is mutually colourless, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the AB-8 macroporous resin, adopt water and concentration to be followed successively by 10v% then respectively, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, the ethanolic soln of 90v% is made the moving phase wash-out, collects 20v%, 30v% and 40v% ethanol eluate merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 10
Take by weighing the dry linseed oil after 300g comes unstuck, the 50 ℃ of water-baths of ethanolic soln that add 1200g pH value and be 13 potassium hydroxide are stirred down and were extracted 5 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with phosphoric acid, it is 50g that extracting solution is concentrated into weight, add 150ml water, it is mutually colourless to be extracted to propyl carbinol repeatedly with propyl carbinol, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the S-8 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
Embodiment 11
Take by weighing the dry linseed oil after 400g comes unstuck, the 60 ℃ of water-baths of ethanolic soln that add 2400g pH value and be 12 yellow soda ash alcohol are stirred down and were extracted 4 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with acetic acid, it is 80g that extracting solution is concentrated into weight, add 300ml water, it is mutually colourless to be extracted to isopropylcarbinol repeatedly with isopropylcarbinol, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the D3250 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 12
Take by weighing the dry linseed oil after 350g comes unstuck, the 40 ℃ of water-baths of ethanolic soln that add 1750g pH value and be 13 sodium hydroxide alcohol are stirred down and were extracted 2 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with acetic anhydride, it is 80g that extracting solution is concentrated into weight, add 260ml water, it is mutually colourless to be extracted to amylalcohol repeatedly with amylalcohol, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the D4020 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in sodium hydroxide solution, promptly gets ferulic acid glucoside.
Embodiment 13
Take by weighing the dry linseed oil after 260g comes unstuck, the 60 ℃ of water-baths of ethanolic soln that add 780g pH value and be 10 sodium bicarbonate alcohol are stirred down and were extracted 3 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with hydrochloric acid, it is 50g that extracting solution is concentrated into weight, add 150ml water, it is mutually colourless to be extracted to methyl ethyl ether repeatedly with methyl ethyl ether, separatory, collect water, the water collected is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with the X-5 macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
Embodiment 14
Take by weighing the dry linseed oil after 300g comes unstuck, the 50 ℃ of water-baths of ethanolic soln that add 2100g pH value and be 11 sodium bicarbonate alcohol are stirred down and were extracted 2.5 hours, filtration, and filter residue is extracted into extracting liquid colourless repeatedly with above-mentioned extracting solution, merging filtrate.Regulate filtrate to neutral with hydrochloric acid, it is 100g that extracting solution is concentrated into weight, add 400ml water, it is mutually colourless to be extracted to methyl acetate repeatedly with methyl acetate, separatory, collect water, the water AB-8 that collects is adsorbed wherein SDG and ferulic acid glucoside ethyl ester fully with macroporous resin, the ethanolic soln that adopts water and concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester; Ferulic acid glucoside ethyl ester is saponification in potassium hydroxide solution, promptly gets ferulic acid glucoside.
Claims (9)
1, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester is characterized in that comprising the steps:
Concrete operations step of the present invention is as follows:
(1) with after the linseed oil removal of impurities, coming unstuck, be that 10～13 pure alkaline solution mixes with 1: 2～8 weight ratio with pH, 40～60 ℃ were extracted 2～5 hours down, filtered, and it is colourless that filter residue is extracted into pure alkaline solution repeatedly, merging filtrate;
(2) add acid for adjusting pH to neutral in filtrate, be concentrated into the water that adds 2～5 times of concentrated solution volumes behind the 1/6-1/2 that weight is former filtrate, it is colourless to be extracted to organic phase repeatedly with organic solvent, collects water;
(3) water collected is adsorbed wherein secoisolariciresinol diglycoside and ferulic acid glucoside ethyl ester fully with macroporous resin, the ethanolic soln that adopts water, concentration to be followed successively by 10v%, 20v%, 30v%, 40v%, 50v%, 60v%, 70v%, 80v%, 90v% is respectively made the moving phase wash-out then, collect 20v%, 30v% and 40v% ethanol eluate, merge evaporate to dryness and promptly get secoisolariciresinol diglycoside; Collect 70v%, 80v%, 90v% ethanol eluate, merge evaporate to dryness and promptly get ferulic acid glucoside ethyl ester.
2, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 1 is characterized in that described ferulic acid glucoside ethyl ester can also saponification obtain ferulic acid glucoside in basic solution.
3, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 1 or 2 is characterized in that the described pure alkaline solution of step (1) is the solution that sodium hydroxide, potassium hydroxide, yellow soda ash or sodium bicarbonate and ethanol form.
4, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 1 or 2 is characterized in that the used acid of step (2) described adjusting pH is organic acid or mineral acid.
5, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 4 is characterized in that organic acid is acetic acid or acetic anhydride, and mineral acid is hydrochloric acid, phosphoric acid or sulfuric acid.
6, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 1 or 2, its feature is halohydrocarbon, alcohol, ester, aromatic compounds or ether at the described organic solvent of step (2).
7, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 6, its feature is chloroform, methylene dichloride, monochloro methane or 1 at halohydrocarbon, the 2-ethylene dichloride, alcohol is propyl carbinol, amylalcohol or isopropylcarbinol, ester is ethyl acetate or methyl acetate, aromatic compounds is toluene or benzene, and ether is methyl ethyl ether or ether.
8, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 1 or 2 is characterized in that the described macroporous resin of step (3) is that the resin model is the macroporous resin of D3250, D4020, X-5, AB-8 or S-8.
9, a kind of method for preparing secoisolariciresinol diglycoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester as claimed in claim 8 is characterized in that macroporous resin is that the resin model is X-5 or AB-8 macroporous resin.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2009100742640A CN101538293B (en) | 2009-04-28 | 2009-04-28 | Method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester |
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| CN2009100742640A CN101538293B (en) | 2009-04-28 | 2009-04-28 | Method for preparing secoisolariciresinol diglucoside and ferulic acid glucoside or ferulic acid glucoside ethyl ester |
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| CN101538293A true CN101538293A (en) | 2009-09-23 |
| CN101538293B CN101538293B (en) | 2011-06-22 |
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| CN106674305A (en) * | 2016-12-27 | 2017-05-17 | 中国人民解放军第四军医大学 | Method for extracting monomer medicine for promoting cold acclimatization ability of organism, and application thereof |
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| 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 |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106674305A (en) * | 2016-12-27 | 2017-05-17 | 中国人民解放军第四军医大学 | Method for extracting monomer medicine for promoting cold acclimatization ability of organism, and application thereof |
| CN106674305B (en) * | 2016-12-27 | 2019-11-12 | 中国人民解放军第四军医大学 | A kind of extracting method and application of the monomer medicine promoting body cold acclimatization ability |
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