CN102477053A - Method for extracting morroniside and loganin from Macrocarpium officinalis - Google Patents
Method for extracting morroniside and loganin from Macrocarpium officinalis Download PDFInfo
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- CN102477053A CN102477053A CN201010557777XA CN201010557777A CN102477053A CN 102477053 A CN102477053 A CN 102477053A CN 201010557777X A CN201010557777X A CN 201010557777XA CN 201010557777 A CN201010557777 A CN 201010557777A CN 102477053 A CN102477053 A CN 102477053A
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Abstract
The present invention relates to a method for extracting morroniside and loganin from Macrocarpium officinalis. The method comprises ultrasonically extracting with 70% ethanol, extracting with n-butanol, concentrating an extractive solution and recovering n-butanol to near dryness to obtain crude morroniside and loganin, adopting an n-butanol-ethanol-water system as a two-phase solvent system, dissolving the crude morroniside and loganin in a bottom phase, separating by high-speed countercurrent chromatography, concentrating eluates under a reduced pressure to near dryness, respectively, crystallizing with n-butanol and ethyl acetate for 2-3 times, respectively, filtering out crystal, and drying to obtain the final products. The method has a simple process and low cost. The products have high purity.
Description
Technical field:
The present invention relates to a kind of technology of from skunk bush, extracting morroniside and loganin, particularly a kind of high speed adverse current chromatogram separates the technology of morroniside and loganin.
Background technology:
Skunk bush (Fructus Corni) is the dry pulp of Cornaceae plant skunk bush Cornus Officinalis Sieb.et Zucc., has another name called Fructus Corni, medicine jujube, meat jujube etc.Be a kind of nourishing type rare medicinal herbs, have tonify the liver and kidney, effect that puckery essence is taken off admittedly.Recent study shows, skunk bush has anti-hemorrhagic shock, anticoagulant, immunomodulatory, anti-inflammatory, effect such as hypoglycemic, anti-oxidant, anticancer, antibiotic.Skunk bush mainly contains compositions such as iridoid glycoside, polysaccharide, organic acid, tannin, and is the highest with morroniside and loganin content.
China just has skunk bush to be applied to the record of mellitus (traditional Chinese medical science is claimed " diabetes ") treatment from ancient times; The present pharmaceutical research of lot of domestic and foreign shows; Skunk bush iridoid glycosides material is the main reactive site of hypoglycemic, and Xu Huiqin etc. have studied the provide protection that the skunk bush iridoid glycoside becomes experiment type dn-; Pi Wenxia etc. " extraction process of the anti-ageing efficient part of the preferred skunk bush of Orthogonal Method " show the skunk bush iridoid glycosides except have hypoglycemic and the anti-diabetic complication, also have anti-aging effects.
Iridoids in the skunk bush, water-soluble, low-carbon alcohol is insoluble to sherwood oil, is slightly soluble in chloroform, ETHYLE ACETATE.
Existing morroniside separation method mostly adopts water extract-alcohol precipitation and macroporous resin column absorption.Like patent " preparation method of Fructus Corni extract morroniside and purposes " (application number is 200410014771.2), this patent disclosed method is that the skunk bush medicinal material is used extraction using alcohol, concentrating under reduced pressure; The liquid concentrator aqueous precipitation, supernatant carries out column chromatography with macroporous adsorbent resin or gac, water and rare pure flush away impurity; Use ethanol elution again, collect elutriant, after concentrating under reduced pressure and the drying; Obtain Powdered Fructus Corni extract morroniside through the reverse phase silica gel separation, this method water and rare pure wash-out impurity are used ethanol elution effective constituent again; Products obtained therefrom purity is high, but loss of effective components is more, thereby has reduced extraction yield.Patent " preparation method of morroniside and new purposes thereof " (application number is 200710113824.X), the disclosed preparation method of this patent is with skunk bush medicinal material water extract-alcohol precipitation, precipitation solution is transferred pH to 1-3; Macroporous resin on twice, water and low-concentration ethanol wash-out, the elutriant low-temperature reduced-pressure is dry; Crystallization promptly gets product, though this method is simple to operate, precipitation solution need add acid and transfer pH; And morroniside belongs to iridoid glycosides, and responsive to acid, structure is prone to change.The extraction and separation method of loganin then seldom.
Summary of the invention:
The objective of the invention is for a kind of technology of from skunk bush, extracting morroniside and loganin is provided.
The objective of the invention is to realize like this:
A kind of method of from skunk bush, extracting morroniside and loganin is characterized in that comprising following step:
1) extracts: dry skunk bush is pulverized, doubly measure with 6-8 70% ethanol ultrasonic extraction 2-3 hour, extracted united extraction liquid 2-3 time;
2) extraction: said extracted liquid is concentrated into nothing alcohol, adds water-dispersion, add isopyknic n-butanol extraction 2-4 time, butanol extraction liquid concentrates and reclaims propyl carbinol, to dried, obtains thick glycosides;
3) high speed adverse current chromatogram separates: with propyl carbinol-alcohol-water is the two-phase solvent system, will above-mentioned thick glycosides with phased soln down, more than be stationary phase mutually, under be moving phase mutually, elute difference evaporated under reduced pressure;
4) crystallization: with above-mentioned dry thing propyl carbinol heating for dissolving, add 5-8 again and doubly measure ETHYLE ACETATE crystallization 2-3 time, be drying to obtain product.
(4～5: 1～3: 5～7), the chromatographic instrument rotating speed is 800～1000r/min to the two-phase solvent that uses in the step 3), and the flow velocity of moving phase is 1～2.5ml/min as propyl carbinol-alcohol-water.
In sum, there is following advantage in the present invention:
1) alcoholic solution extract at room temperature, energy consumption is low.
2) adopt HSCCC, good separating effect, solvent load is little, need not to use carrier, has reduced the loss in the process.
To combine embodiment to further specify the present invention below, but the scope that the present invention requires to protect is not limited to following embodiment.
Embodiment:
Embodiment 1:
Get the dry skunk bush of 1kg and pulverize,, extract united extraction liquid 3 times with 6L70% ethanol ultrasonic extraction 3 hours; Concentrating does not have alcohol, adds the 1L water-dispersion, adds isopyknic n-butanol extraction 4 times, and n-butanol layer concentrates and reclaims propyl carbinol to doing; Obtain thick glycosides, get 800ml propyl carbinol, 200ml ethanol and 1000ml water, ultra-sonic oscillation are mixed, and are transferred to separating funnel; Standing demix is told phase up and down, more than be stationary phase mutually, is moving phase mutually down.Above-mentioned thick glycosides is filled chromatographic column with pump with the flow of 10ml/min with phased soln under the 350ml with last mutually, and the head end and the sampling valve of post joined the opening speed unit; Making the rotation of spiral tube CW, when the chromatographic instrument rotating speed is 950r/min, is that 2.5ml/min pumps into moving phase with the flow velocity, and through the sampling valve sample introduction; Each sample size is 150mg, collects morroniside composition and loganin composition respectively, respectively evaporated under reduced pressure; Dry thing is used 200ml propyl carbinol heating for dissolving respectively, adds 1L ETHYLE ACETATE crystallization 3 times again, leaches the dry morroniside 7.3g that promptly gets of dry and hard crystalline substance; Content 95.1%, loganin 6.1g, content 95.3%.
Embodiment 2:
Get the dry skunk bush of 1kg and pulverize,, extract united extraction liquid 2 times with 8L 70% ethanol ultrasonic extraction 3 hours; Concentrating does not have alcohol, adds the 800ml water-dispersion, adds isopyknic n-butanol extraction 3 times, and n-butanol layer concentrates and reclaims propyl carbinol to doing; Obtain thick glycosides, get 700ml propyl carbinol, 400ml ethanol and 1000ml water, ultra-sonic oscillation are mixed, and are transferred to separating funnel; Standing demix is told phase up and down, more than be stationary phase mutually, is moving phase mutually down.Above-mentioned thick glycosides is filled chromatographic column with pump with the flow of 10ml/min with phased soln under the 300ml with last mutually, and the head end and the sampling valve of post joined the opening speed unit; Making the rotation of spiral tube CW, when the chromatographic instrument rotating speed is 900r/min, is that 2ml/min pumps into moving phase with the flow velocity, and through the sampling valve sample introduction; Each sample size is 250mg, collects morroniside composition and loganin composition respectively, respectively evaporated under reduced pressure; Dry thing is used 300ml propyl carbinol heating for dissolving respectively, adds 2.4L ETHYLE ACETATE crystallization 2 times again, leaches and is drying to obtain morroniside 7.8g; Content 92%, loganin 7.0g, content 93.6%.
Embodiment 3:
Get the dry skunk bush of 2kg and pulverize,, extract united extraction liquid 3 times with 15L 70% ethanol ultrasonic extraction 2 hours; Concentrating does not have alcohol, adds the 1.5L water-dispersion, adds isopyknic n-butanol extraction 2 times, and n-butanol layer concentrates and reclaims propyl carbinol to doing; Obtain thick glycosides, get 1600ml propyl carbinol, 500ml ethanol and 1800ml water, ultra-sonic oscillation are mixed, and are transferred to separating funnel; Standing demix is told phase up and down, more than be stationary phase mutually, is moving phase mutually down.Above-mentioned thick glycosides is filled chromatographic column with pump with the flow of 12ml/min with phased soln under the 700ml with last mutually, and the head end and the sampling valve of post joined the opening speed unit; Making the rotation of spiral tube CW, when the chromatographic instrument rotating speed is 950r/min, is that 1ml/min pumps into moving phase with the flow velocity; And through the sampling valve sample introduction, each sample size is 150mg, collects morroniside composition and loganin composition respectively; The difference evaporated under reduced pressure, dry thing is used 250ml propyl carbinol heating for dissolving respectively, adds 1.5L ETHYLE ACETATE crystallization 2 times again; Leach and be drying to obtain morroniside 18.5g content 95.5%, loganin 18.4g, content 93.8%.
Embodiment 4:
Get the dry skunk bush of 2kg and pulverize,, extract united extraction liquid 3 times with 14L 70% ethanol ultrasonic extraction 3 hours; Concentrating does not have alcohol, adds the 1.8L water-dispersion, adds isopyknic n-butanol extraction 3 times, and n-butanol layer concentrates and reclaims propyl carbinol to doing; Obtain thick glycosides, get 1600ml propyl carbinol, 800ml ethanol and 2400ml water, ultra-sonic oscillation are mixed, and are transferred to separating funnel; Standing demix is told phase up and down, more than be stationary phase mutually, is moving phase mutually down.Above-mentioned thick glycosides is filled chromatographic column with pump with the flow of 12ml/min with phased soln under the 600ml with last mutually, and the head end and the sampling valve of post joined the opening speed unit; Making the rotation of spiral tube CW, when the chromatographic instrument rotating speed is 1000r/min, is that 2.5ml/min pumps into moving phase with the flow velocity, and through the sampling valve sample introduction; Each sample size is 150mg, collects morroniside composition and loganin composition respectively, respectively evaporated under reduced pressure; Dry thing is used 500ml propyl carbinol heating for dissolving respectively, adds 3 ETHYLE ACETATE crystallizations 2 times again, leaches and is drying to obtain morroniside 17.5g; Content 96%, loganin 15.7g, content 96.2%.
Embodiment 5:
Get the dry skunk bush of 5kg and pulverize,, extract united extraction liquid 3 times with 40L70% ethanol ultrasonic extraction 3 hours; Concentrating does not have alcohol, adds the 3L water-dispersion, adds isopyknic n-butanol extraction 3 times, and n-butanol layer concentrates and reclaims propyl carbinol to doing; Obtain thick glycosides, get 3.2L propyl carbinol, 1.6L ethanol and 5.6L water, ultra-sonic oscillation are mixed, and are transferred to separating funnel; Standing demix is told phase up and down, more than be stationary phase mutually, is moving phase mutually down.Above-mentioned thick glycosides is filled chromatographic column with pump with the flow of 20ml/min with phased soln under the 1.5L with last mutually, and the head end and the sampling valve of post joined the opening speed unit; Making the rotation of spiral tube CW, when the chromatographic instrument rotating speed is 800r/min, is that 1.5ml/min pumps into moving phase with the flow velocity; And through the sampling valve sample introduction, each sample size is 200mg, collects morroniside composition and loganin composition respectively; The difference evaporated under reduced pressure, dry thing is used 1.5L propyl carbinol heating for dissolving respectively, adds 10L ETHYLE ACETATE crystallization 3 times again; Leach and be drying to obtain morroniside 39.1g, content 95.2%, loganin 36.7g content is 94.1%.
Claims (2)
1. method of from skunk bush, extracting morroniside and loganin is characterized in that comprising following step:
1) extracts: dry skunk bush is pulverized, doubly measure with 6-8 70% ethanol ultrasonic extraction 2-3 hour, extracted united extraction liquid 2-3 time;
2) extraction: said extracted liquid is concentrated into nothing alcohol, adds water-dispersion, add isopyknic n-butanol extraction 2-4 time, butanol extraction liquid concentrates and reclaims propyl carbinol, to dried, obtains thick glycosides;
3) high speed adverse current chromatogram separates: with propyl carbinol-alcohol-water is the two-phase solvent system, will above-mentioned thick glycosides with phased soln down, more than be stationary phase mutually, under be moving phase mutually, elute difference evaporated under reduced pressure;
4) crystallization: with above-mentioned dry thing propyl carbinol heating for dissolving, add 5-8 again and doubly measure ETHYLE ACETATE crystallization 2-3 time, be drying to obtain product.
2. the method for from skunk bush, extracting morroniside as claimed in claim 1; It is characterized in that the two-phase solvent that uses in the step 3) is propyl carbinol-alcohol-water (4～5: 1～3: 5～7); The chromatographic instrument rotating speed is 800～1000r/min, and the flow velocity of moving phase is 1～2.5ml/min.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201010557777XA CN102477053A (en) | 2010-11-25 | 2010-11-25 | Method for extracting morroniside and loganin from Macrocarpium officinalis |
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| CN201010557777XA CN102477053A (en) | 2010-11-25 | 2010-11-25 | Method for extracting morroniside and loganin from Macrocarpium officinalis |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360443A (en) * | 2013-07-30 | 2013-10-23 | 天津科丝美特生物科技有限公司 | Method for extraction and purification of four iridoid glycosides in cornus officinalis |
| CN106632521A (en) * | 2017-01-22 | 2017-05-10 | 鲁南制药集团股份有限公司 | Method for extracting high-purity loganin from cornus officinalis fruits |
| CN107231945A (en) * | 2017-06-26 | 2017-10-10 | 松桃苗族自治县继梅养殖专业合作社 | A kind of cultural method of agaric |
| CN108467416A (en) * | 2018-06-21 | 2018-08-31 | 长沙爱扬医药科技有限公司 | The method that Fructus Corni extracts morroniside, loganin and ursolic acid |
| CN108558970A (en) * | 2018-01-26 | 2018-09-21 | 北京联合大学 | The method that cornel extractive prepares high-purity morroniside and loganin simultaneously |
| CN111066824A (en) * | 2019-12-31 | 2020-04-28 | 菏泽学院 | Method for effectively controlling pine wilt disease by biologically controlling monochamus alternatus |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1424319A (en) * | 2002-12-30 | 2003-06-18 | 首都医科大学宣武医院 | Extracts of cornus officinalis and its preparation and use |
| CN101385735A (en) * | 2007-09-13 | 2009-03-18 | 山东绿叶天然药物研究开发有限公司 | Preparation method of morroniside and new use thereof |
-
2010
- 2010-11-25 CN CN201010557777XA patent/CN102477053A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1424319A (en) * | 2002-12-30 | 2003-06-18 | 首都医科大学宣武医院 | Extracts of cornus officinalis and its preparation and use |
| CN101385735A (en) * | 2007-09-13 | 2009-03-18 | 山东绿叶天然药物研究开发有限公司 | Preparation method of morroniside and new use thereof |
Non-Patent Citations (1)
| Title |
|---|
| LIANGPO LIU: "Preparative Purification of Morroniside and Loganin from Fructus corni by Combination of Macroporous Absorption Resin and HSCCC", 《JOURNAL OF CHROMATOGRAPHIC SCIENCE》 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103360443A (en) * | 2013-07-30 | 2013-10-23 | 天津科丝美特生物科技有限公司 | Method for extraction and purification of four iridoid glycosides in cornus officinalis |
| CN106632521A (en) * | 2017-01-22 | 2017-05-10 | 鲁南制药集团股份有限公司 | Method for extracting high-purity loganin from cornus officinalis fruits |
| CN106632521B (en) * | 2017-01-22 | 2019-09-27 | 鲁南制药集团股份有限公司 | A method of purifying loganin from cornus fruit |
| CN107231945A (en) * | 2017-06-26 | 2017-10-10 | 松桃苗族自治县继梅养殖专业合作社 | A kind of cultural method of agaric |
| CN108558970A (en) * | 2018-01-26 | 2018-09-21 | 北京联合大学 | The method that cornel extractive prepares high-purity morroniside and loganin simultaneously |
| CN108467416A (en) * | 2018-06-21 | 2018-08-31 | 长沙爱扬医药科技有限公司 | The method that Fructus Corni extracts morroniside, loganin and ursolic acid |
| CN111066824A (en) * | 2019-12-31 | 2020-04-28 | 菏泽学院 | Method for effectively controlling pine wilt disease by biologically controlling monochamus alternatus |
| CN111066824B (en) * | 2019-12-31 | 2021-08-27 | 菏泽学院 | Method for effectively controlling pine wilt disease by biologically controlling monochamus alternatus |
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Application publication date: 20120530 |