CN101817816A - Method for preparing silybin - Google Patents
Method for preparing silybin Download PDFInfo
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- CN101817816A CN101817816A CN200910264449A CN200910264449A CN101817816A CN 101817816 A CN101817816 A CN 101817816A CN 200910264449 A CN200910264449 A CN 200910264449A CN 200910264449 A CN200910264449 A CN 200910264449A CN 101817816 A CN101817816 A CN 101817816A
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- silibinin
- ethyl acetate
- benzene
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- silybin
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Abstract
The invention relates to a method for preparing silybin. The method comprises the following process steps: crushing silybin seeds into 20 to 40 meshes, and degreasing the crushed silybin seeds thrice by using n-hexane; refluxing and extracting degreased coarse materials by using dilute ethanol; concentrating the extract under reduced pressure till the extract has no ethanol smell, extracting the concentrate by using ethyl acetate, stirring and drying ester phase and silica gel, then injecting a dried product to a column, eluting the dried product by using benzene or benzene-ethyl acetate, collecting the elute by sections, combining the elute to obtain main elute component of the silybin, concentrating the elute under reduced pressure, dissolving the elute in ethanol solution, adding active carbon into the solution, stirring the solution, decolorizing the solution for 0.5 to 1 hour, filtering the active carbon from the decolorized solution, concentrating the decolorized solution under reduced pressure to 40 to 60 percent of the primary volume, cooling the concentrate to separate out crystals, crystallizing the crystals by using hot ethanol, and repeating the crystallization step for 2 to 4 times to obtain the silybin. The method for producing the silybin has the advantages of simple process, low solvent toxicity, low production cost, and easy realization of industrialization.
Description
Technical field:
The present invention relates to the extraction and purification process of silibinin, particularly a kind of method of using silica gel column chromatography and crystallization extraction purifying silibinin.
Background technology:
Silibinin
Another name: silybin, Silibinin, legalon
Chemical name: 2,3-Dihydro-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-6-(3,5,7-trihydroxy-4-oxobenzopyran-2-yl) benzodioxin
Molecular formula and molecular weight: C
25H
22O
10, 482.44
Character: off-white color crystalline powder.Odorless, mildly bitter flavor are puckery, have draw moist.Be soluble in acetone, ethyl acetate, methyl alcohol, ethanol, slightly be dissolved in chloroform, water-soluble hardly.Monohydrate (methanol-water), mp.180 ℃; Anhydride, mp.158 ℃ (180 ℃ of decomposition).
Pharmacological action: silibinin has significant protection and stablizes hepatocellular effect, is used for the treatment of diseases such as acute, chronic hepatitis, liver cirrhosis, liver poisoning.Hepatitis symptom, liver function are all improved significantly.Has biomembranous effect in stabilized cell and the cell.Has radiation-resistant effect.Can suppress formaldehyde-caused peritonitis.
Silymarin (Silmyarin, Herba Silybi mariani total flavones) is meant a kind of flavanolignan compounds that extracts gained from the kind skin of composite family medicinal plant Silymarin seed, is yellow powder, bitter.Main activeconstituents has silibinin (Silybin), Isosilybin (Isosilybin), Silychristin (Silychristin) and Silydianin four kinds of isomerss such as (Silydianin), sometimes also refer in particular to silibinin, wherein silibinin content is 50～70%.
China silymarin manufacturer is numerous, but technical matters is comparatively backward.The preparation of silibinin is normally extracted with the ethyl acetate method, and this method silibinin content is few, yield low [history sturdy pines, Sun Dafeng turn round and look at Gong's equality. the improvement of silymarin extraction process and discussion [J], Chinese wild plant resource .2006,12 (25): 52-54].Zhang Shouqin etc. " normal-temperature superhigh pressure extracts the research of silymarin " have reported a kind of method of utilizing superhighpressure technology to extract silymarin, and this method pressure condition is very high to the requirement of extractor, makes cost of investment raise greatly; Chinese patent CN1317486 " process for preparing sematron by aceton method " has reported a kind of acetone extraction of using, the method for preparing silibinin of petroleum ether degreasing, degreasing is after extracting in this method, lipid becomes branch to influence extraction effect, extraction time is increased, and sherwood oil toxicity is bigger, is unfavorable for enlarging producing; And for example Chinese patent CN101260105 " a kind of extracting method of silibinin " has reported and has a kind ofly been begun by silymarin, the method for alcohol reflux system silibinin, and this method ethanol consumption is many, and energy consumption is big, the production cost height; The gorgeous grade of Wang Cui " research of silibinin extracting method " has been narrated refluxing extraction and two kinds of methods that prepare silibinin of supersound extraction for another example, and degreasing all uses sherwood oil and consumption big, and being used for producing has very big harm to human body.
Summary of the invention:
The objective of the invention is in order to provide a kind of technology simple, solvent toxicity is little, and production cost is low, is easy to realize industrialized silibinin extracting method.
The object of the present invention is achieved like this:
1. degreasing: it is 20～40 orders that the Silymarin seed is pulverized, and adds normal hexane degreasing 3 times, gets the degreasing coarse fodder;
2. extract: the degreasing coarse fodder adds the Diluted Alcohol refluxing extraction 2～3 times, merge extracting solution;
3. extraction: extracting solution is evaporated to does not have the alcohol flavor, and the concentrated solution ethyl acetate extraction is got acetic acid ethyl fluid;
4. silica gel column chromatography:,, merge and obtain Silymarin main component elutriant with benzene, benzene-eluent ethyl acetate with acetic acid ethyl fluid and silica gel mixed sample oven dry back upper prop;
5. decolouring: silibinin elutriant concentrating under reduced pressure is a medicinal extract, until whole dissolvings, adds gac with the ethanolic soln stirring heating, decolours 0.5～1 hour, filters, and gets destainer;
6. condensing crystal: destainer is evaporated to 40～60% of original volume, puts cold analysis and go out crystal, crystal is with the saturated dissolving of hot ethanol, puts coldly, separates out silibinin, leaches silibinin, repeats 2～4 times, promptly gets the white crystals product.
The preparation method of above-mentioned silibinin is characterized in that the each consumption of described normal hexane is 8～10 times of amounts of raw materials quality, and each degreasing time is 1.5～2 hours.
The preparation method of above-mentioned silibinin is characterized in that described Diluted Alcohol concentration is 40～50%, and each consumption is 4～6 times of amounts of raw materials quality.
The preparation method of above-mentioned silibinin is characterized in that described ethyl acetate consumption is 3～4 times of amounts of raw materials quality.
The preparation method of above-mentioned silibinin is characterized in that described silicagel column volume is 5L, and silica gel is 200～300 orders.
The preparation method of above-mentioned silibinin, it is characterized in that described stepwise elution process is: flow velocity all keeps 5L/h, colourless with the benzene eluting silica gel earlier until effluent liquid, benzene-eluent ethyl acetate of using 6～4: 1 (v/v) again is to colourless, benzene-eluent ethyl acetate of using 2～1: 1 (v/v) at last is to colourless, benzene-the eluent ethyl acetate of 2～1: 1 (v/v) is with every part of 200ml Fractional Collections, and wash-out finishes the back and detects with UV-light, and the Silymarin main component elutriant that colour developing is identical merges.
The preparation method of above-mentioned silibinin is characterized in that described decolouring step ethanolic soln concentration is 50～60%, and consumption is 6～8 times of amounts of elutriant concentrated extract quality.
The preparation method of above-mentioned silibinin is characterized in that described decolouring step activated carbon dosage is 0.5～1% of a solution amount.
The preparation method of above-mentioned silibinin is characterized in that described crystallisation step hot ethanol concentration is 70～80%, and temperature is 60～70 ℃.
There is following advantage in the present invention:
1) selects for use normal hexane to replace the relatively poor degreasing solvents of security such as sherwood oil, non-leaded gasoline, chloroform, make production safer.
2) can finish the elementary purifying of silibinin with less energy consumption with the method for silica gel column chromatography and stepwise elution;
3) ethanol repetition crystallization can improve product purity, and the toxicity than methyl alcohol is lower simultaneously.
Further specify the present invention below in conjunction with embodiment, but the scope of protection of present invention is not limited to following embodiment.
Embodiment:
Embodiment 1:
It is 20 orders that the Silymarin seed is pulverized, get 10kg (silibinin content 0.96%) and add the 80L normal hexane, and degreasing 3 times, each 1.5 hours, leaching the dregs of a decoction was the degreasing coarse fodder.Add 40L40% Diluted Alcohol refluxing extraction 3 times in the degreasing coarse fodder, being evaporated to behind the united extraction liquid does not have the alcohol flavor, adds the 30L ethyl acetate extraction, gets extraction liquid.The 5L silicagel column will be gone up behind extraction liquid and 200～300 order silica gel mixed samples, successively use benzene-ethyl acetate stepwise elution of benzene, 4: 1 and 2: 1 (v/v) with the flow velocity of 5L/h, colourless with effluent liquid separately is terminal point, benzene-eluent ethyl acetate liquid with every part of 200ml Fractional Collections 2: 1 (v/v), wash-out finishes the back and detects with UV-light, 13～21 sections elutriants that colour developing is identical merge, and decompression and solvent recovery gets medicinal extract 113g.Medicinal extract adds 800ml 50% ethanolic soln heated and stirred to all dissolvings, add the 8g gac again, reflux and stir, decoloured 0.5 hour, leach gac, destainer is evaporated to about 480ml, with 60 ℃ the saturated dissolving of 70% hot ethanol, leave standstill put cold, separate out the silibinin crystal, leach crystal, repeat crystallization 2 times with the equal state hot ethanol again, dry in the shade needle finished product 67g (silibinin content 98.2%).
Embodiment 2:
It is 40 orders that the Silymarin seed is pulverized, get 10kg (silibinin content 0.99%) and add the 90L normal hexane, and degreasing 3 times, each 1.5 hours, leaching the dregs of a decoction was the degreasing coarse fodder.Add 50L45% Diluted Alcohol refluxing extraction 3 times in the degreasing coarse fodder, being evaporated to behind the united extraction liquid does not have the alcohol flavor, adds the 35L ethyl acetate extraction, gets extraction liquid.The 5L silicagel column will be gone up behind extraction liquid and 200～300 order silica gel mixed samples, successively use benzene-ethyl acetate stepwise elution of benzene, 5: 1 and 1: 1 (v/v) with the flow velocity of 5L/h, colourless with effluent liquid separately is terminal point, benzene-eluent ethyl acetate liquid with every part of 200ml Fractional Collections 1: 1 (v/v), wash-out finishes the back and detects with UV-light, 13～21 sections elutriants that colour developing is identical merge, and decompression and solvent recovery gets medicinal extract 119g.Medicinal extract adds 900ml 55% ethanolic soln heated and stirred to all dissolvings, add the 6g gac again, reflux and stir, decoloured 0.6 hour, leach gac, destainer is evaporated to about 450ml, with 65 ℃ the saturated dissolving of 75% hot ethanol, leave standstill put cold, separate out the silibinin crystal, leach crystal, repeat crystallization 3 times with the equal state hot ethanol again, dry in the shade needle finished product 69g (silibinin content 98.5%).
Embodiment 3:
It is 40 orders that the Silymarin seed is pulverized, get 10kg (silibinin content 0.98%) and add the 100L normal hexane, and degreasing 3 times, each 2 hours, leaching the dregs of a decoction was the degreasing coarse fodder.Add 55L50% Diluted Alcohol refluxing extraction 2 times in the degreasing coarse fodder, being evaporated to behind the united extraction liquid does not have the alcohol flavor, adds the 35L ethyl acetate extraction, gets extraction liquid.The 5L silicagel column will be gone up behind extraction liquid and 200～300 order silica gel mixed samples, successively use benzene-ethyl acetate stepwise elution of benzene, 6: 1 and 2: 1 (v/v) with the flow velocity of 5L/h, colourless with effluent liquid separately is terminal point, benzene-eluent ethyl acetate liquid with every part of 200ml Fractional Collections 2: 1 (v/v), wash-out finishes the back and detects with UV-light, 13～21 sections elutriants that colour developing is identical merge, and decompression and solvent recovery gets medicinal extract 124g.Medicinal extract adds 1000ml 60% ethanolic soln heated and stirred to all dissolvings, add the 5g gac again, reflux and stir, decoloured 1 hour, leach gac, destainer is evaporated to about 400ml, with 70 ℃ the saturated dissolving of 80% hot ethanol, leave standstill put cold, separate out the silibinin crystal, leach crystal, repeat crystallization 4 times with the equal state hot ethanol again, dry in the shade needle finished product 68g (silibinin content 98.7%).
Embodiment 4:
It is 40 orders that the Silymarin seed is pulverized, get 10kg (silibinin content 0.98%) and add the 100L normal hexane, and degreasing 3 times, each 2 hours, leaching the dregs of a decoction was the degreasing coarse fodder.Add 60L50% Diluted Alcohol refluxing extraction 2 times in the degreasing coarse fodder, being evaporated to behind the united extraction liquid does not have the alcohol flavor, adds the 40L ethyl acetate extraction, gets extraction liquid.With 5L silicagel column on extraction liquid and 200～300 order silica gel mixed samples, successively use benzene-ethyl acetate stepwise elution of benzene, 4: 1 and 1: 1 (v/v) with the flow velocity of 5L/h, colourless with effluent liquid separately is terminal point, benzene-eluent ethyl acetate liquid with every part of 200ml Fractional Collections 1: 1 (v/v), wash-out finishes the back and detects with UV-light, 13～21 sections elutriants that colour developing is identical merge, and decompression and solvent recovery gets medicinal extract 126g.Medicinal extract adds 1000ml 60% ethanolic soln heated and stirred to all dissolvings, add the 10g gac again, reflux and stir, decoloured 1 hour, leach gac, destainer is evaporated to about 400ml, with 60 ℃ the saturated dissolving of 70% hot ethanol, leave standstill put cold, separate out the silibinin crystal, leach crystal, repeat crystallization 3 times with the equal state hot ethanol again, dry in the shade needle finished product 71g (silibinin content 99.2%).
Claims (9)
1. the preparation method of a silibinin is characterized in that comprising following step:
1. degreasing: it is 20～40 orders that the Silymarin seed is pulverized, and adds normal hexane degreasing 3 times, gets the degreasing coarse fodder;
2. extract: the degreasing coarse fodder adds the Diluted Alcohol refluxing extraction 2～3 times, merge extracting solution;
3. extraction: extracting solution is evaporated to does not have the alcohol flavor, and the concentrated solution ethyl acetate extraction is got acetic acid ethyl fluid;
4. silica gel column chromatography:,, merge and obtain Silymarin main component elutriant with benzene, benzene-eluent ethyl acetate with acetic acid ethyl fluid and silica gel mixed sample oven dry back upper prop;
5. decolouring: silibinin elutriant concentrating under reduced pressure is a medicinal extract, until whole dissolvings, adds gac with the ethanolic soln stirring heating, decolours 0.5～1 hour, filters, and gets destainer;
6. condensing crystal: destainer is evaporated to 40～60% of original volume, puts cold analysis and go out crystal, crystal is with the saturated dissolving of hot ethanol, puts coldly, separates out silibinin, leaches silibinin, repeats 2～4 times, promptly gets the white crystals product.
2. according to the preparation method of the described silibinin of claim 1, it is characterized in that the each consumption of described normal hexane is 8～10 times of amounts of raw materials quality, each degreasing time is 1.5～2 hours.
3. according to the preparation method of the described silibinin of claim 1, it is characterized in that described Diluted Alcohol concentration is 40～50%, each consumption is 4～6 times of amounts of raw materials quality.
4. according to the preparation method of the described silibinin of claim 1, it is characterized in that described ethyl acetate consumption is 3～4 times of amounts of raw materials quality.
5. according to the preparation method of the described silibinin of claim 1, it is characterized in that described silicagel column volume is 5L, silica gel is 200～300 orders.
6. according to the preparation method of the described silibinin of claim 1, it is characterized in that described stepwise elution process is: flow velocity all keeps 5L/h, colourless with the benzene eluting silica gel earlier until effluent liquid, benzene-eluent ethyl acetate of using 6～4: 1 (v/v) again is to colourless, benzene-eluent ethyl acetate of using 2～1: 1 (v/v) at last is to colourless, benzene-the eluent ethyl acetate of 2～1: 1 (v/v) is with every part of 200ml Fractional Collections, wash-out finishes the back and detects with UV-light, and the Silymarin main component elutriant that colour developing is identical merges.
7. according to the preparation method of the described silibinin of claim 1, it is characterized in that described decolouring step ethanolic soln concentration is 50～60%, consumption is 6～8 times of amounts of elutriant concentrated extract quality.
8. according to the preparation method of the described silibinin of claim 1, it is characterized in that described decolouring step activated carbon dosage is 0.5～1% of a solution amount.
9. according to the preparation method of the described silibinin of claim 1, it is characterized in that described crystallisation step hot ethanol concentration is 70～80%, temperature is 60～70 ℃.
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| CN200910264449A CN101817816A (en) | 2009-12-23 | 2009-12-23 | Method for preparing silybin |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102225085A (en) * | 2011-06-20 | 2011-10-26 | 黑龙江大学 | Method for extracting holy thistle total flavonoids from holy thistle stalks |
| CN102731486A (en) * | 2011-12-25 | 2012-10-17 | 大兴安岭林格贝有机食品有限责任公司 | New method for purifying silymarin |
| CN103012384A (en) * | 2012-12-13 | 2013-04-03 | 三原润禾植化有限公司 | Method for extracting silymarin from silybum marianum |
| CN103408538A (en) * | 2013-08-27 | 2013-11-27 | 白心亮 | Method for extracting silymarin |
| CN105693708A (en) * | 2014-11-25 | 2016-06-22 | 河南智晶生物科技股份有限公司 | Silymarin extraction method |
| CN106083834A (en) * | 2016-06-21 | 2016-11-09 | 江苏中兴药业有限公司 | A kind of high-purity silymarin isolation and purification method |
| CN107805245A (en) * | 2017-12-14 | 2018-03-16 | 湖南千金协力药业有限公司 | A kind of purification process of legalon |
| CN108285443A (en) * | 2017-01-09 | 2018-07-17 | 天津天士力圣特制药有限公司 | A kind of process for purification of silibinin |
| CN108578263A (en) * | 2018-06-20 | 2018-09-28 | 吉林农业科技学院 | Silymarin Skin whitening care cosmetics |
| CN108658955A (en) * | 2017-04-01 | 2018-10-16 | 南京泽朗生物科技有限公司 | A kind of preparation method of silibinin |
| CN103641821B (en) * | 2013-11-25 | 2019-03-22 | 宁波绿之健药业有限公司 | A kind of preparation method of the low molten residual milk thistle extract of high-content |
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2009
- 2009-12-23 CN CN200910264449A patent/CN101817816A/en active Pending
Cited By (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102225085B (en) * | 2011-06-20 | 2012-09-05 | 黑龙江大学 | Method for extracting holy thistle total flavonoids from holy thistle stalks |
| CN102225085A (en) * | 2011-06-20 | 2011-10-26 | 黑龙江大学 | Method for extracting holy thistle total flavonoids from holy thistle stalks |
| CN102731486A (en) * | 2011-12-25 | 2012-10-17 | 大兴安岭林格贝有机食品有限责任公司 | New method for purifying silymarin |
| CN102731486B (en) * | 2011-12-25 | 2015-03-11 | 大兴安岭林格贝有机食品有限责任公司 | New method for purifying silymarin |
| CN103012384A (en) * | 2012-12-13 | 2013-04-03 | 三原润禾植化有限公司 | Method for extracting silymarin from silybum marianum |
| CN103012384B (en) * | 2012-12-13 | 2015-06-17 | 三原润禾植化有限公司 | Method for extracting silymarin from silybum marianum |
| CN103408538A (en) * | 2013-08-27 | 2013-11-27 | 白心亮 | Method for extracting silymarin |
| CN103408538B (en) * | 2013-08-27 | 2015-06-24 | 白心亮 | Method for extracting silymarin |
| CN103641821B (en) * | 2013-11-25 | 2019-03-22 | 宁波绿之健药业有限公司 | A kind of preparation method of the low molten residual milk thistle extract of high-content |
| CN105693708A (en) * | 2014-11-25 | 2016-06-22 | 河南智晶生物科技股份有限公司 | Silymarin extraction method |
| CN106083834B (en) * | 2016-06-21 | 2018-07-17 | 江苏中兴药业有限公司 | A kind of silibinin isolation and purification method |
| CN106083834A (en) * | 2016-06-21 | 2016-11-09 | 江苏中兴药业有限公司 | A kind of high-purity silymarin isolation and purification method |
| CN108285443A (en) * | 2017-01-09 | 2018-07-17 | 天津天士力圣特制药有限公司 | A kind of process for purification of silibinin |
| CN108285443B (en) * | 2017-01-09 | 2023-05-23 | 江苏天士力帝益药业有限公司 | Refining method of silybin |
| CN108658955A (en) * | 2017-04-01 | 2018-10-16 | 南京泽朗生物科技有限公司 | A kind of preparation method of silibinin |
| CN107805245A (en) * | 2017-12-14 | 2018-03-16 | 湖南千金协力药业有限公司 | A kind of purification process of legalon |
| CN107805245B (en) * | 2017-12-14 | 2020-11-03 | 湖南千金协力药业有限公司 | Method for purifying silybin |
| CN108578263A (en) * | 2018-06-20 | 2018-09-28 | 吉林农业科技学院 | Silymarin Skin whitening care cosmetics |
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Application publication date: 20100901 |