CN104163754A - Method for extraction and separating of high purity resveratrol from peanut root - Google Patents
Method for extraction and separating of high purity resveratrol from peanut root Download PDFInfo
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- CN104163754A CN104163754A CN201410343453.4A CN201410343453A CN104163754A CN 104163754 A CN104163754 A CN 104163754A CN 201410343453 A CN201410343453 A CN 201410343453A CN 104163754 A CN104163754 A CN 104163754A
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- C07—ORGANIC CHEMISTRY
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- C07C37/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring
- C07C37/004—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom of a six-membered aromatic ring by obtaining phenols from plant material or from animal material
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Abstract
The invention relates to a method for extraction and separating of high purity resveratrol from peanut root, and the method comprises the following steps: (1) using ethanol for low temperature ultrasonic vibration extraction of the peanut root; (2) reducing pressure for recovering ethanol from the extracting solution at 60 DEG C below until the ethanol is not smelt; (3) first using a macroporous adsorption resin column for adsorption and elution of the alcohol extract for removing impurities, and then using a polyamide resin adsorption column for adsorption separation; (4) tracing and checking by thin layer chromatography, collecting a resveratrol flow component, decolorizing with activated carbon, performing vacuum concentration at low temperature, freezing, and drying; and (5) recrystallizing with the ethanol to obtain the high purity resveratrol. The process steps of the method is simple and practical, by use of polyamide resin, adsorption, separation and purification can be completed in one step, a used solvent is non-toxic, safe and reliable, product purity is high, cost is low, and the method is suitable for industrialized mass production.
Description
Technical field
The present invention relates to a kind of from Roots of Peanut the method for rapid extraction separating high-purity trans-resveratrol.
Background technology
Trans-resveratrol, is the non-flavones polyphenolic compound that contains stilbene class formation, be plant be subject to stress time self synthetic a kind of toxinicide.That trans-resveratrol mainly contains is antitumor, anti-inflammatory, antibacterial, anti-oxidant, Green Tea Extract, protection liver, protect the cardiovascular and function such as resist myocardial ischemia, wherein, attract people's attention most and the most promising be antitumor action, be called another green cancer therapy drug newly continue taxol after; Simultaneously the anti-ageing canon > of Ye Bei U.S. monograph < < > mono-book is classified one of " 100 kinds the most popular effective anti-ageing material " as, therefore the application of trans-resveratrol in medicine, foodstuffs industry is more and more wider, and marketable value is high.
Trans-resveratrol (Resveratrol), has another name called resvertrol, chemistry (E)-5-(4-hydroxystyryl)benzene-1,3-diol (3,5,4 ' one trihydrolystilbene) by name, and molecular formula is C
14h
120
3molecular weight is 228.2, white needle-like crystals, is insoluble in water, and the solvability in organic solvent is sequentially roughly: acetone > ethanol > methyl alcohol > ethyl acetate > ether > chloroform; Under the UV-irradiation of 366nm, produce purple fluorescence, comparatively stable under low temperature, lucifuge condition, unstable in alkaline environment.Suitable, trans two kinds of structures that trans-resveratrol has are mainly to exist with transconfiguration at occurring in nature.Trans-resveratrol extensively distributes at nature, within 1940, from the root of hair leaf black false hellebore, obtain first, at least in 72 kind of plant of 21Ge section, 31 genus, find at present: as the Vitis of Vitaceae, Ampelopsis, the Arachis of pulse family, Cassia, Sophora, liliaceous Veratrum, the Polygonum of polygonaceae etc.
Trans-resveratrol is a kind of important phytoalexin, in the plants such as grape, giant knotweed, peanut, content is relatively high, at each positions such as the root of peanut, stem, flower, fruits, found at present the existence of this material, absolutely prove that peanut is a kind of valuable source of exploitation trans-resveratrol, it is tens times of Testa arachidis hypogaeaes and Semen Vitis viniferae hundred times that Chinese scholar determines resveratrol from peanut root content, but take the rare report of research that Roots of Peanut carries out trans-resveratrol exploitation as raw material.In China, Roots of Peanut is waste and aboundresources originally, and the Resveratrol content in peanut rhizome is also considerable, with it, extracting trans-resveratrol can turn waste into wealth, to have more the market competitiveness, and can increase farmers' income, will be more meaningful for the utility value that improves peanut.
The extractive technique of trans-resveratrol comprises organic solvent extraction, ultrasonic wave or microwave-assisted extraction method, enzymolysis process, supercritical extraction etc.; Purification technique has column chromatography, thin-layer chromatography, high performance countercurrent chromatography etc.At present, the process patent that extracts separated trans-resveratrol from Roots of Peanut is few, mainly contains:
CN101074188A utilizes the method for enriching and purifying macroporous resin resveratrol from peanut root
The method of CN1903815A supersound extraction resveratrol from peanut root
The production method of CN1709846A resveratrol extracted from peanut root
CN101353675A utilizes the method for fermentation of Aspergillus niger resveratrol extracted from peanut root
CN101597214A method that extracts resveratrol from peanut root
Five above-mentioned patents, sample is all to adopt conventional method to extract, comprise organic solvent extraction, ultrasonic extraction, biological mould fermented extracted etc., in to the purge process of extract, be mostly first to adopt macroporous adsorption resin technology to carry out removal of impurities, and then carry out silica gel column chromatography, use mixed organic solvents gradient elution, collect flow point, also have the high performance liquid preparative chromatography of employing or adopt Co 2 supercritical fluid chromatogram to carry out purifying.
The weak point of several above-mentioned patents is operating process more complicated, and silica gel column chromatography operates length consuming time, uses a large amount of organic solvents, and toxicity is larger, and environmental pollution is serious, and product Determination of Residual Organic Solvents is high.High performance liquid preparative chromatography is harsh to requirement for experiment condition, must adopt the laboratory apparatus of high-end precision and expensive chromatographically pure reagent, and product yield is few, makes preparation cost very high and operate wayward.Although Co 2 supercritical fluid chromatogram has solved yield problem, the purity of product is not high, does not reach food grade or pharmaceutical grade requirement, and has introduced during the course a large amount of carbonic acid gas, and operation steps only limits to laboratory, and product can not be realized industrialization.
Summary of the invention
The technical problem that the present invention mainly solves is to provide a kind of Roots of Peanut that can solve in purified resveratrol process, step is complicated, length consuming time, and solvent for use toxicity is large, product yield is low, can not realize the method for rapid extraction separating high-purity trans-resveratrol from Roots of Peanut of industrialization.
Technical solution of the present invention is achieved in that a kind of method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises the steps:
(1) Roots of Peanut is ground into fine powder, with the ultrasonic concussion of ethanol, extracts, and extracting temperature is 20 ℃-60 ℃, and extraction time is 30-60 minute, extracts twice, united extraction liquid;
(2) extracting solution reclaims ethanol, is concentrated into relative density and is the clear cream of 1.18-1.22, cooling;
(3) macroporous adsorptive resins absorption on the clear cream of above-mentioned (2), colourless to elutriant with water, 70% ethanol elution respectively, then use 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use polyamide resin column fractionation by adsorption, the mixed solution of alcohol-acid of take carries out chromatographic separation as elutriant again;
(4) thin-layer chromatography is followed the tracks of and is detected, and collects trans-resveratrol flow point, with after activated carbon decolorizing, filters, and filtrate is in 50 ℃-70 ℃ under logical nitrogen protection, and concentrate under reduced pressure at low temperature to relative density is 1.15-1.18, lyophilize;
(5) with ethyl alcohol recrystallization, obtain more than 95% high-purity resveratrol.
Preferably, in described step (1), the ratio of Roots of Peanut fine powder and ethanol is 1:10-1:20(g/ml).
Preferably, in described step (1), alcohol concn is 40%-95%.
Preferably, in described step (1), alcohol concn is 60%.
Preferably, in described step (2), extracting solution reclaims ethanol, refers to 60 ℃ of following reclaim under reduced pressure.
Preferably, described step (3) macroporous adsorbent resin is D101 or AB-8 or DM130 or HPD600 or HPD400, and the granularity of macroporous adsorbent resin is 30-50 order, and consumption is: resin: clear cream=10-20:1(g/g), the blade diameter length ratio of resin column is 1:20.
Preferably, in described step (3), the granularity of polyamide resin is 60-100 order, and consumption is: resin: clear cream=10-20:1(g/g), the blade diameter length ratio of resin column is 1:20.
Preferably, the mixed solution of alcohol-acid of take in described step (3) is elutriant, alcohol comprises 10%-95%(V/V) ethanol or dehydrated alcohol, acid comprises 10%-30%(V/V) formic acid or 10%-100%(V/V) and acetic acid, alcohol in elutriant: the ratio of acid is 2:1-1:2(V/V).
Preferably, the 2%-3% (g/100ml) that the consumption of described step (4) gac is liquor capacity.
Due to the utilization of technique scheme, the present invention compared with prior art has following advantages:
The present invention adopts macroporous resin to carry out after preliminary purification sample, by controlling chromatographic separation condition, adopt a kind of separation system, can directly carry out polymeric amide chromatography separated, by thin-layer chromatography, follow the tracks of detection again, directly can obtain trans-resveratrol sterling, separation, purifying one step are completed, make easy to operation.The solvent of only having used two kinds of food grade in whole process, has guaranteed product safety, nontoxic; Technological process of the present invention is simple, makes Roots of Peanut obtain recycling as waste, has also solved Roots of Peanut in purified resveratrol process simultaneously, and step is complicated, length consuming time, and solvent for use toxicity is large, and product yield is low, can not realize the problems such as industrialization.
Accompanying drawing explanation
Accompanying drawing 1 is the high-efficient liquid phase chromatogram of trans-resveratrol reference substance;
Accompanying drawing 2 is high-efficient liquid phase chromatograms not purified after 60% ethanol ultrasonic extraction for Roots of Peanut sample;
Accompanying drawing 3 is sample high-efficient liquid phase chromatograms that the method for rapid extraction separating high-purity trans-resveratrol obtains from Roots of Peanut of the present invention.
Embodiment
embodiment 1
A method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises following steps:
(1) Roots of Peanut is ground into fine powder, crosses 60 mesh sieves, takes 1 kg, adds the ultrasonic concussion of 10L40% ethanol and extracts, and extracting temperature is 40 ℃, extracts twice, each 30min at every turn, united extraction liquid; (2) the following decompression recycling ethanols of 60 ℃ of extracting solutions are to without alcohol taste, are concentrated into relative density and are 1.20 clear cream, cooling; (3) AB-8 macroporous adsorptive resins absorption on the clear cream of above-mentioned (2), colourless to elutriant with water, 70% ethanol elution respectively, use again 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use again polyamide resin column (resin demand is heavy 10 times of cream, and the blade diameter length ratio of post is 1:20) fractionation by adsorption, with 95% ethanol: 36% acetic acid (2:1) is wash-out (V/V); (4) thin-layer chromatography is followed the tracks of and is detected, collect trans-resveratrol flow point, with (the 2%-3% that the consumption of gac is liquor capacity (g/100ml) after charcoal absorption, be that the amount of adding gac in every 100ml solution is 2g-3g), filter, it is 1.15-1.18 that filtrate is concentrated into relative density in 60 ℃ of low-temperature reduced-pressures (logical nitrogen protection), lyophilize; (5) with ethyl alcohol recrystallization, obtain purity and be 95.3% trans-resveratrol, yield is 0.1%.
embodiment 2
A method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises following steps:
(1) Roots of Peanut is ground into fine powder, crosses 60 mesh sieves, takes 1 kg, adds the ultrasonic concussion of 10L60% ethanol and extracts, and extracting temperature is 40 ℃, extracts twice, each 30min at every turn, united extraction liquid; (2) the following decompression recycling ethanols of 60 ℃ of extracting solutions are to without alcohol taste, are concentrated into relative density and are 1.20 clear cream, cooling; (3) upper D101 macroporous adsorptive resins absorption, colourless to elutriant with water, 70% ethanol elution respectively, use again 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use again polyamide resin column (resin demand is heavy 20 times of cream, and the blade diameter length ratio of post is 1:20) fractionation by adsorption, with ethanol: 36% acetic acid (2:1) wash-out; (4) thin-layer chromatography is followed the tracks of and is detected, collect trans-resveratrol flow point, with (the 2%-3% that the consumption of gac is liquor capacity (g/100ml) after charcoal absorption, be that the amount of adding gac in every 100ml solution is 2g-3g), filter, it is 1.15-1.18 that filtrate is concentrated into relative density in 60 ℃ of low-temperature reduced-pressures (logical nitrogen protection), lyophilize; (5) with ethyl alcohol recrystallization, obtain purity and be 97.5% trans-resveratrol, yield is 0.09%.
embodiment 3
A method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises following steps:
(1) Roots of Peanut is ground into fine powder, crosses 60 mesh sieves, takes 1 kg, adds the ultrasonic concussion of 20L40% ethanol and extracts, and extracting temperature is 50 ℃, extracts twice, each 30min at every turn, united extraction liquid; (2) the following decompression recycling ethanols of 60 ℃ of extracting solutions are to without alcohol taste, are concentrated into relative density and are 1.20 clear cream, cooling; (3) upper HPD-600 macroporous adsorptive resins absorption, colourless to elutriant with water, 70% ethanol elution respectively, use again 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use again polyamide resin column (resin demand is heavy 15 times of cream, and the blade diameter length ratio of post is 1:20) fractionation by adsorption, with 95% ethanol: 10% formic acid (2:1) wash-out; (4) thin-layer chromatography is followed the tracks of and is detected, collect trans-resveratrol flow point, with (the 2%-3% that the consumption of gac is liquor capacity (g/100ml) after charcoal absorption, be that the amount of adding gac in every 100ml solution is 2g-3g), filter, it is 1.15-1.18 that filtrate is concentrated into relative density in 60 ℃ of low-temperature reduced-pressures (logical nitrogen protection), lyophilize; (5) with ethyl alcohol recrystallization, obtain purity and be 95.8% trans-resveratrol, yield is 0.09%.
embodiment 4
A method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises following steps:
(1) Roots of Peanut is ground into fine powder, crosses 60 mesh sieves, takes 1 kg, adds the ultrasonic concussion of 20L60% ethanol and extracts, and extracting temperature is 40 ℃, extracts twice, each 30min at every turn, united extraction liquid; (2) the following decompression recycling ethanols of 60 ℃ of extracting solutions are to without alcohol taste, are concentrated into relative density and are 1.22 clear cream, cooling; (3) upper DM130 macroporous adsorptive resins absorption, colourless to elutriant with water, 70% ethanol elution respectively, use again 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use again polyamide resin column (resin demand is heavy 10 times of cream, and the blade diameter length ratio of post is 1:20) fractionation by adsorption, with 95% ethanol: 20% acetic acid (2:1) wash-out; (4) thin-layer chromatography is followed the tracks of and is detected, collect trans-resveratrol flow point, with (the 2%-3% that the consumption of gac is liquor capacity (g/100ml) after charcoal absorption, be that the amount of adding gac in every 100ml solution is 2g-3g), filter, it is 1.15-1.18 that filtrate is concentrated into relative density in 60 ℃ of low-temperature reduced-pressures (logical nitrogen protection), lyophilize; (5) with ethyl alcohol recrystallization, obtain purity and be 96.1% trans-resveratrol, yield is 0.12%.
embodiment 5
A method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises following steps:
(1) Roots of Peanut is ground into fine powder, crosses 60 mesh sieves, takes 1 kg, adds the ultrasonic concussion of 10L40% ethanol and extracts, and extracting temperature is 40 ℃, extracts twice, each 30min at every turn, united extraction liquid; (2) the following decompression recycling ethanols of 60 ℃ of extracting solutions are to without alcohol taste, are concentrated into relative density and are 1.22 clear cream, cooling; (3) upper HPD600 macroporous adsorptive resins absorption, colourless to elutriant with water, 70% ethanol elution respectively, use again 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use again polyamide resin column (resin demand is heavy 20 times of cream, and the blade diameter length ratio of post is 1:20) fractionation by adsorption, with 95% ethanol: 36% acetic acid (1:1) wash-out; (4) thin-layer chromatography is followed the tracks of and is detected, collect trans-resveratrol flow point, with (the 2%-3% that the consumption of gac is liquor capacity (g/100ml) after charcoal absorption, be that the amount of adding gac in every 100ml solution is 2g-3g), filter, it is 1.15-1.18 that filtrate is concentrated into relative density in 60 ℃ of low-temperature reduced-pressures (logical nitrogen protection), lyophilize; (5) with ethyl alcohol recrystallization, obtain purity and be 96.3% trans-resveratrol, yield is 0.1%.
embodiment 6
A method of extracting separating high-purity trans-resveratrol from Roots of Peanut, comprises following steps:
(1) Roots of Peanut is ground into fine powder, crosses 60 mesh sieves, takes 1 kg, adds the ultrasonic concussion of 10L40% ethanol and extracts, and extracting temperature is 40 ℃, extracts twice, each 30min at every turn, united extraction liquid; (2) the following decompression recycling ethanols of 60 ℃ of extracting solutions are to without alcohol taste, are concentrated into relative density and are 1.20 clear cream, cooling; (3) upper AB-8 macroporous adsorptive resins absorption, colourless to elutriant with water, 70% ethanol elution respectively, use again 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use again polyamide resin column (resin demand is heavy 10 times of cream, and the blade diameter length ratio of post is 1:20) fractionation by adsorption, with 95% ethanol: 36% acetic acid (1:2) wash-out; (4) thin-layer chromatography is followed the tracks of and is detected, collect trans-resveratrol flow point, with (the 2%-3% that the consumption of gac is liquor capacity (g/100ml) after charcoal absorption, be that the amount of adding gac in every 100ml solution is 2g-3g), filter, it is 1.15-1.18 that filtrate is concentrated into relative density in 60 ℃ of low-temperature reduced-pressures (logical nitrogen protection), lyophilize; (5) with ethyl alcohol recrystallization, obtain purity and be 98.8% trans-resveratrol, yield is 0.08%.
The beneficial effect of above-described embodiment is: the present invention is by controlling thin-layer chromatography separation condition, directly carry out polymeric amide chromatography separated, by thin-layer chromatography, follow the tracks of detection, can directly obtain EGCG sterling, see accompanying drawing 1,2,3, rather than mixture, make like this separation, purifying one step complete, make easy to operation; And in whole process, only used etoh solvent, acetic acid (or formic acid) and the gac of food grade, guaranteed product safety, nontoxic.
Above-described embodiment is only explanation technical conceive of the present invention and feature; its object is to allow person skilled in the art can understand content of the present invention and be implemented; can not limit the scope of the invention with this; all equivalences that spirit is done according to the present invention change or modify, and all should be encompassed in protection scope of the present invention.
Claims (9)
1. from Roots of Peanut, extract a method for separating high-purity trans-resveratrol, it is characterized in that, comprise the steps:
(1) Roots of Peanut is ground into fine powder, with the ultrasonic concussion of ethanol, extracts, and extracting temperature is 20 ℃-60 ℃, and extraction time is 30-60 minute, extracts twice, united extraction liquid;
(2) extracting solution reclaims ethanol, is concentrated into relative density and is the clear cream of 1.18-1.22, cooling;
(3) macroporous adsorptive resins absorption on the clear cream of above-mentioned (2), colourless to elutriant with water, 70% ethanol elution respectively, then use 95% ethanol elution, collect the flow point of 95% wash-out, reclaim ethanol extremely without alcohol taste, use polyamide resin column fractionation by adsorption, the mixed solution of alcohol-acid of take carries out chromatographic separation as elutriant again;
(4) thin-layer chromatography is followed the tracks of and is detected, and collects trans-resveratrol flow point, with after activated carbon decolorizing, filters, and filtrate is in 50 ℃-70 ℃ under logical nitrogen protection, and concentrate under reduced pressure at low temperature to relative density is 1.15-1.18, lyophilize;
(5) with ethyl alcohol recrystallization, obtain more than 95% high-purity resveratrol.
2. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, is characterized in that: in described step (1), the ratio of Roots of Peanut fine powder and ethanol is 1:10-1:20(g/ml).
3. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, is characterized in that: in described step (1), alcohol concn is 40%-95%.
4. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 3, is characterized in that: in described step (1), alcohol concn is 60%.
5. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, is characterized in that: in described step (2), extracting solution reclaims ethanol, refers to 60 ℃ of following reclaim under reduced pressure.
6. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, it is characterized in that: described step (3) macroporous adsorbent resin is D101 or AB-8 or DM130 or HPD600 or HPD400, the granularity of macroporous adsorbent resin is 30-50 order, consumption is: resin: clear cream=10-20:1(g/g), the blade diameter length ratio of resin column is 1:20.
7. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, it is characterized in that: in described step (3), the granularity of polyamide resin is 60-100 order, consumption is: resin: clear cream=10-20:1(g/g), the blade diameter length ratio of resin column is 1:20.
8. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, it is characterized in that: the mixed solution of alcohol-acid of take in described step (3) is elutriant, alcohol comprises 10%-95%(V/V) ethanol or dehydrated alcohol, acid comprises 10%-30%(V/V) formic acid or 10%-100%(V/V) acetic acid, alcohol in elutriant: the ratio of acid is 2:1-1:2(V/V).
9. the method for extracting separating high-purity trans-resveratrol from Roots of Peanut according to claim 1, is characterized in that: the 2%-3% (g/100ml) that the consumption of described step (4) gac is liquor capacity.
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| CN105418385A (en) * | 2015-12-16 | 2016-03-23 | 刘静 | Device and method for extracting and separating resveratrol by using composite raw materials |
| CN106008173A (en) * | 2016-05-22 | 2016-10-12 | 深圳市先康达生物科技有限公司 | Method for extracting anticancer resveratrol from peanut roots |
| WO2021004000A1 (en) * | 2019-07-10 | 2021-01-14 | 中国农业科学院农产品加工研究所 | Method for producing peanut oil rich in resveratrol |
| CN114276218A (en) * | 2021-12-06 | 2022-04-05 | 武汉轻工大学 | Method for improving extraction rate of resveratrol in peanut roots |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105418385A (en) * | 2015-12-16 | 2016-03-23 | 刘静 | Device and method for extracting and separating resveratrol by using composite raw materials |
| CN106008173A (en) * | 2016-05-22 | 2016-10-12 | 深圳市先康达生物科技有限公司 | Method for extracting anticancer resveratrol from peanut roots |
| WO2021004000A1 (en) * | 2019-07-10 | 2021-01-14 | 中国农业科学院农产品加工研究所 | Method for producing peanut oil rich in resveratrol |
| CN114276218A (en) * | 2021-12-06 | 2022-04-05 | 武汉轻工大学 | Method for improving extraction rate of resveratrol in peanut roots |
| CN114276218B (en) * | 2021-12-06 | 2024-01-26 | 武汉轻工大学 | Method for improving extraction rate of resveratrol in peanut root |
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Application publication date: 20141126 |