CN101973864A - Method for extracting shikonin from lithospermum - Google Patents
Method for extracting shikonin from lithospermum Download PDFInfo
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- CN101973864A CN101973864A CN2010102357621A CN201010235762A CN101973864A CN 101973864 A CN101973864 A CN 101973864A CN 2010102357621 A CN2010102357621 A CN 2010102357621A CN 201010235762 A CN201010235762 A CN 201010235762A CN 101973864 A CN101973864 A CN 101973864A
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- shikonin
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- asian puccoon
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Abstract
The invention relates to a method for extracting shikonin from lithospermum, which comprises the following steps of: crushing lithospermum raw materials and adding alkaline aqueous solution with the pH value being 9 to 10 for percolating and extracting; regulating the pH of the extracting solution to 7, 5 and 3, adding a macroporous resin column to adsorb for three times, eluting by using 70 to 80-percent ethanol, concentrating the eluent and crystallizing in ethanol; dissolving in sodium bicarbonate solution with the pH value being 10 to 11, regulating the pH value to 1 to 3 and precipitating, and refluxing and dissolving the precipitates in acetone and ethyl acetate in turn and recrystallizing. The method for producing the shikonin can reduce the use amount of toxic reagent and reduce production cost. The process is simple in operation and easy in industrialization.
Description
Technical field:
The present invention relates to a kind of method of from Asian puccoon, extracting Shikonin, particularly relate to a kind of method with the macroporous resin purification Shikonin.
Background technology:
The Shikonin naphthoquinone compound is Tokyo Violet, shikonin, d-alkanin again.
Molecular formula: C
16H
16O
5
Molecular weight: 288.31
Molecular structural formula:
Physico-chemical property: purple plate crystal or crystalline powder.147～149 ℃ of fusing points.Specific rotation+138 ° (benzene).Water insoluble, be dissolved in ethanol, organic solvent and vegetables oil.Be soluble in buck, chance acid precipitates again separates out.
That Asian puccoon have is anticancer, anti-inflammatory, effect such as antibiotic.Clinical acute and chronic hepatitis, the liver cirrhosis (ascites) of being used for the treatment of.Skin liver section is used for the treatment of verruca plana, psoriatic, topical application treatment burn and promotion wound healing.Eye drops is used for the treatment of herpes simplex keratitis, and epitheliated type dendroid and shallow essential layer dendritic keratitis are had certain curative effect.Finish is used for the treatment of baby's dermatitis, eczema, vaginitis, trachelitis etc.Also can add in the toothpaste and can prevent and treat tooth dental caries and gingivitis.
At present, Shikonin mainly extracts from Radix Arnebiae (Radix Lithospermi).Extracting method mostly is ether defatting, regulates the ph extraction, and benzene is dissolving crystallized.Or silicagel column is handled or supercritical extraction.
As Chinese patent (application number CN200310124125.7) " preparation method of Shikonin or iso-alkannin "; the method of this patent disclosure is that Shikonin ester derivative or iso-alkannin ester derivative and the normal lithium hydroxide of 2-200 are mixed in the solvent; under protection of inert gas; control reaction temperature is at 0～60 ℃; stirred 24～240 hours; the dripping hydrochloric acid aqueous solution in reaction system; promptly obtain the solution of Shikonin or iso-alkannin; after the dripping hydrochloric acid aqueous solution to system becomes redness fully; it is an amount of to add water again; with ethyl acetate extraction three times, combining extraction liquid is successively with sodium bicarbonate aqueous solution; water; saturated sodium-chloride water solution washing extraction liquid; use anhydrous sodium sulfate drying; silica gel column chromatography with the petrol ether/ethyl acetate wash-out, promptly obtains pure Shikonin or iso-alkannin solid again.This method treatment capacity is little, is fit to prepared in laboratory.
As Chinese patent (application number CN00122127.2) " process for extracting arnebia root's extract ", this patent disclosure method is to use CO
2As a kind of special solvent, work as CO
2Be under liquid state and the supercritical state, just in temperature was 10 ℃～50 ℃ scopes, pressure was 6.0 * 10
6Pa-6.5 * 10
6Under the Pa condition, CO
2All can from Radix Arnebiae (Radix Lithospermi), extract Shikonin, be dissolved with the CO of Shikonin
2The condition of therefrom isolating Shikonin is that above-mentioned fluid must be through reducing pressure 3 * 10
6Pa-7.0 * 10
6The Pa simultaneous temperature is controlled at 40 ℃～60 ℃, at CO
2In the process of extraction Shikonin, CO
2Can add a certain proportion of agent of carrying in advance under above-mentioned extraction conditions, as adding a kind of in ethanol, methyl alcohol, propyl alcohol, Virahol, the butanols, the process of Shikonin is extracted in favourable acceleration.This method equipment used costs an arm and a leg.
Hu Kun etc. " the method for separating and preparing research of Shikonin " delivered for another example, the document also is to adopt supercritical extraction.
As mentioned above, existing method exists the toxicity organic reagent big or treatment capacity is little.
Summary of the invention:
The present invention wants the technical solution problem to provide a kind of method of extracting Shikonin from Asian puccoon, and this method uses the consumption of toxicity organic reagent little, and treatment capacity is big in the cycle.
Technical solution of the present invention is:
A kind of method of extracting Shikonin from Asian puccoon is characterized in that comprising following steps:
1) diacolation extracts: Radix Arnebiae (Radix Lithospermi) raw material pulverizing usefulness, add 15-30 and doubly measure the extraction of alkaline aqueous solution diacolation, get extracting solution;
2) resin absorption: with said extracted liquid, gradient is regulated ph, adds macroporous resin adsorption, and after absorption finished, washing was neutral, uses 6-8BV ethanolic soln wash-out again, and the reclaim under reduced pressure elutriant is placed crystallization, leach coarse crystallization;
3) alkali extraction and acid precipitation: use the sodium hydrogen carbonate solution of ph10-11 to dissolve above-mentioned coarse crystallization, filter, regulate the ph1-3 precipitation,, get crude product with 3-10 times of calorimetric water washing precipitate;
4) recrystallization: above-mentioned crude product is used acetone, ethyl acetate backflow dissolving-recrystallization successively, and cryodrying promptly gets product.
The alkaline aqueous solution of described step 1) is: alkali is a kind of of sodium bicarbonate, yellow soda ash or sodium hydroxide, ph9-11.
Described step 2) the resin absorption condition is: it is ph7, ph5 and ph3 that gradient is regulated ph, a kind of among the optional XDA-1 of macroporous resin model, XDA-8 or the LSA-7, and the eluting solvent alcohol concn is 70-80%.
The acid that is described adjusting ph is the 5-10% hydrochloric acid soln.
The present invention adopts the alkaline water diacolation to extract resin absorption, and energy consumption is low, and turnout is big, has solved extraction cost height, an inefficient difficult problem, reduces follow-up crystallization purifying step, and whole technological operation is easy, and cost is lower.
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:
Getting the impurity elimination of Radix Arnebiae (Radix Lithospermi) raw material pulverizes, weighing 1kg drops into percolator, sodium bicarbonate aqueous solution diacolation with 20kgph9 got percolate in 48 hours, 5% hydrochloric acid is regulated ph to 7 and is added 1LXDA-1 macroporous resin adsorption, following fluid injection re-adjustment ph5, ph3 absorption twice, washing is neutral, use 8L70% ethanolic soln wash-out again, decompression recycling ethanol is placed crystallization, leach coarse crystallization, with the sodium hydrogen carbonate solution dissolving of ph11, filter, regulate the ph3 precipitation, leach throw out and get 65g, use the 400ml hot wash, get crude product, use acetone more successively, ethyl acetate backflow dissolving-recrystallization, cryodrying get product Shikonin 15g, content 95%.
Embodiment 2:
Getting the impurity elimination of Radix Arnebiae (Radix Lithospermi) raw material pulverizes, weighing 1kg drops into percolator, aqueous sodium carbonate diacolation with 15kgph11 got percolate in 38 hours, 10% hydrochloric acid is regulated ph to 7 and is added 1L XDA-8 macroporous resin adsorption, following fluid injection re-adjustment ph5, ph3 absorption twice, washing is neutral, use 6L80% ethanolic soln wash-out again, decompression recycling ethanol is placed crystallization, leach coarse crystallization, with the sodium hydrogen carbonate solution dissolving of ph10, filter, regulate the ph1 precipitation, leach throw out and get 78g, use the 700ml hot wash, get crude product, use acetone more successively, ethyl acetate backflow dissolving-recrystallization, cryodrying get product Shikonin 19g, content 98%.
Embodiment 3:
Getting the impurity elimination of Radix Arnebiae (Radix Lithospermi) raw material pulverizes, weighing 1kg drops into percolator, sodium hydroxide sodium water solution diacolation with 18kgph10 got percolate in 48 hours, 5% hydrochloric acid is regulated ph to 7 and is added 1L LSA-7 macroporous resin adsorption, following fluid injection re-adjustment ph5, ph3 absorption twice, washing is neutral, use 7L75% ethanolic soln wash-out again, decompression recycling ethanol is placed crystallization, leach coarse crystallization, with the sodium hydrogen carbonate solution dissolving of ph11, filter, regulate the ph1 precipitation, leach throw out and get 59g, use the 500ml hot wash, get crude product, use acetone more successively, ethyl acetate backflow dissolving-recrystallization, cryodrying get product Shikonin 13g, content 94%.
Embodiment 4:
Getting the impurity elimination of Radix Arnebiae (Radix Lithospermi) raw material pulverizes, weighing 10kg drops into percolator, sodium bicarbonate aqueous solution diacolation with 150kgph9 got percolate in 48 hours, 5% hydrochloric acid is regulated ph to 7 and is added 10LXDA-1 macroporous resin adsorption, following fluid injection re-adjustment ph5, ph3 absorption twice, washing is neutral, use 8L70% ethanolic soln wash-out again, decompression recycling ethanol is placed crystallization, leach coarse crystallization, with the sodium hydrogen carbonate solution dissolving of ph11, filter, regulate the ph3 precipitation, leach throw out and get 700g, use the 4L hot wash, get crude product, use acetone more successively, ethyl acetate backflow dissolving-recrystallization, cryodrying get product Shikonin 162g, content 96%.
Claims (4)
1. method of extracting Shikonin from Asian puccoon is characterized in that comprising following steps:
1) diacolation extracts: Radix Arnebiae (Radix Lithospermi) raw material pulverizing usefulness, add 15-30 and doubly measure the extraction of alkaline aqueous solution diacolation, get extracting solution;
2) resin absorption: with said extracted liquid, gradient is regulated ph, adds macroporous resin adsorption, and after absorption finished, washing was neutral, uses 6-8BV ethanolic soln wash-out again, and the reclaim under reduced pressure elutriant is placed crystallization, leach coarse crystallization;
3) alkali extraction and acid precipitation: use the sodium hydrogen carbonate solution of ph10-11 to dissolve above-mentioned coarse crystallization, filter, regulate the ph1-3 precipitation,, get crude product with 3-10 times of calorimetric water washing precipitate;
4) recrystallization: above-mentioned crude product is used acetone, ethyl acetate backflow dissolving-recrystallization successively, and cryodrying promptly gets product.
2. extract the method for Shikonin according to claim 1 from Asian puccoon, it is characterized in that the alkaline aqueous solution of described step 1) is: alkali is a kind of of sodium bicarbonate, yellow soda ash or sodium hydroxide, ph9-11.
3. from Asian puccoon, extract the method for Shikonin according to claim 1, it is characterized in that described step 2) the resin absorption condition is: it is ph7, ph5 and ph3 that gradient is regulated ph, a kind of among the optional XDA-1 of macroporous resin model, XDA-8 or the LSA-7, the eluting solvent alcohol concn is 70-80%.
4. from Asian puccoon, extract the method for Shikonin according to claim 1, it is characterized in that the acid of described adjusting ph is the 5-10% hydrochloric acid soln.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2010102357621A CN101973864A (en) | 2010-07-26 | 2010-07-26 | Method for extracting shikonin from lithospermum |
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|---|---|---|---|
| CN2010102357621A CN101973864A (en) | 2010-07-26 | 2010-07-26 | Method for extracting shikonin from lithospermum |
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329209A (en) * | 2011-07-26 | 2012-01-25 | 苏州宝泽堂医药科技有限公司 | Method for extracting emodin from giant knotweed rhizome |
| CN103054925A (en) * | 2012-12-20 | 2013-04-24 | 蚌埠丰原涂山制药有限公司 | Extraction method and obtained extractive and application of alkanet |
| CN105949043A (en) * | 2016-05-11 | 2016-09-21 | 江苏耐雀生物工程技术有限公司 | Preparation method of antisepsis and anti-inflammation compound |
| CN107929344A (en) * | 2017-12-29 | 2018-04-20 | 吉林省肿瘤医院 | A kind of Asian puccoon compound for being used to preventing and treating laryngocarcinoma |
| CN108918739A (en) * | 2018-08-28 | 2018-11-30 | 华南协同创新研究院 | A kind of pre-treating method and efficient liquid-phase chromatography method measuring alkannin in O/W type Asian puccoon skin care milk |
| CN112028759A (en) * | 2020-08-20 | 2020-12-04 | 华中农业大学 | Preparation method for obtaining high-content and high-purity alkannin |
| CN115015402A (en) * | 2022-03-21 | 2022-09-06 | 宁波海关技术中心 | Method for measuring content of 3 alkannin natural pigments in food |
-
2010
- 2010-07-26 CN CN2010102357621A patent/CN101973864A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102329209A (en) * | 2011-07-26 | 2012-01-25 | 苏州宝泽堂医药科技有限公司 | Method for extracting emodin from giant knotweed rhizome |
| CN103054925A (en) * | 2012-12-20 | 2013-04-24 | 蚌埠丰原涂山制药有限公司 | Extraction method and obtained extractive and application of alkanet |
| CN103054925B (en) * | 2012-12-20 | 2014-07-30 | 安徽丰原药业股份有限公司 | Extraction method and obtained extractive and application of alkanet |
| CN105949043A (en) * | 2016-05-11 | 2016-09-21 | 江苏耐雀生物工程技术有限公司 | Preparation method of antisepsis and anti-inflammation compound |
| CN107929344A (en) * | 2017-12-29 | 2018-04-20 | 吉林省肿瘤医院 | A kind of Asian puccoon compound for being used to preventing and treating laryngocarcinoma |
| CN107929344B (en) * | 2017-12-29 | 2020-07-28 | 吉林省肿瘤医院 | Lithospermum compound composition for preventing and treating laryngeal cancer |
| CN108918739A (en) * | 2018-08-28 | 2018-11-30 | 华南协同创新研究院 | A kind of pre-treating method and efficient liquid-phase chromatography method measuring alkannin in O/W type Asian puccoon skin care milk |
| CN112028759A (en) * | 2020-08-20 | 2020-12-04 | 华中农业大学 | Preparation method for obtaining high-content and high-purity alkannin |
| CN115015402A (en) * | 2022-03-21 | 2022-09-06 | 宁波海关技术中心 | Method for measuring content of 3 alkannin natural pigments in food |
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Application publication date: 20110216 |
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