CN101862385A - Sanguisorba saponins and preparation method of sanguisorbin I - Google Patents
Sanguisorba saponins and preparation method of sanguisorbin I Download PDFInfo
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Abstract
The invention relates to a method for separating and purifying sanguisorba saponins and sanguisorbin I by using alkaline liquid medicine through macroporous resin, comprising the following steps of: carrying out hot reflux extraction or percolation on cut-off sanguisorba, which is a traditional Chinese medicine and used as a raw material, more than one time with water or alcohol/water, and processing extracts by using alkali to regulate pH value to 10-15; adsorbing and separating the filtered extracts by using the macroporous resins, eluting the extracts by using alkaline water or water and about 30% of alcohol to remove impurities, and then desorbing and eluting by using organic solvents; carrying out decompression concentration, concentration, standing and filtration on eluent, and then collecting sediments to obtain the sanguisorba saponins; or directly sedimentating by using the alkali, regulating the pH of the filtered liquid medicine to 4-6 after filtration, concentrating to recover alcohol; standing to separate out and obtain a sanguisorba saponins mixture, and washing the eluted resins by using the organic solvents for repeated use; and recrystallizing the sanguisorba saponins mixture by using alcohol water to obtain the sanguisorbin I with the content more than 98%. Saponins and other impurities are separated and extracted in the method, and the method has the advantages of low cost, high efficiency, simplicity, convenience and suitability for industrial production and can be used for obtaining high-purity sanguisorba saponins and sanguisorbin I.
Description
Technical field
The present invention relates to the method for a kind of separation and purification radix sanguisorbae total saponin and Ziyuglycoside I, belong to medical technical field.
Background technology
Radix Sanguisorbae is a rosaceous plant, contains tannin, triterpene, sanguisorbin isoreactivity composition, has multiple efficacies such as heat-clearing and toxic substances removing, antibiotic, antioxidation, is the raw material of medicine and cosmetics.At present the extracting method of sanguisorbin is more, as: with the Radix Sanguisorbae powder with defat with petroleum ether after, use dehydrated alcohol extraction; Collect extracting solution, reclaim under reduced pressure; The extract water dissolution, the water layer n-butanol extraction is collected the n-butanol layer reclaim under reduced pressure and is got the sanguisorbin crude product; The crude product water dissolution, it is saturated to add sodium chloride, the reuse n-butanol extraction is washed to water layer then and is faint yellow, collects the n-butanol layer reclaim under reduced pressure, dry, the dark yellow powder be the refining reference substance of saponin [former Herba Cymbidii Goeringii, Li Zongxiao, Yang Peiyun. the extraction of ursolic acid [J] in the Radix Sanguisorbae. Chinese Journal of Pharmaceuticals, 2002,33 (10): 478].This method adopts solvent extraction, relates to multiple organic solvent, complicated operation, the cost height, dangerous high in the production process, and still contain a large amount of tannins, require from medicine, used organic solvent all needs to do limit handling in product, and difficulty strengthens in the production.Wang Manli etc. have reported that elder generation is with dry Radix Sanguisorbae root piece 70 grams, pulverize and be coarse powder, added water-ethanol (3: 1) mixed liquid dipping 1-2 hour, repeat 9 times, merge leachate, liquid reduced pressure, again by column chromatography for separation tannin and Saponin [Wang Manli etc., extract tannin and Saponin, Guizhou Polytechnical College journal, in June, 1993 from Radix Sanguisorbae, the 22nd the 2nd phase of volume], what this method adopted is alumina column, uses pump as power, and operation easier is big, and yield is 0.86%, the macroporous resin that the column packing price is used far above the present invention, less economical, the big difficulty of producing.Application number discloses new purposes of Radix Sanguisorbae total glycosides extractive and preparation method thereof for the CN200310119248.1 patent application, a kind of chemical compound and total glycosides mixture thereof of leukocyte increasing are provided, it is to adopt Radix Sanguisorbae, pulverize back water, methanol or ethanol, or aqueous alcohols, room temperature or heating extraction 1-3 hour, can repeat to extract 1-3 time, elimination medicinal residues then, filtrate is concentrated into finite concentration, stand for standby use under normal pressure or decompression; To extract concentrated solution again and adsorb with polyamide column, be the ethanol elution pillar of 30-90% with concentration, after the eluent reclaim under reduced pressure then, can repeat with polyamide column absorption 1-3 time, get extractum, become dry powder through vacuum or lyophilization, the radix sanguisorbae total saponin content of this method preparation is 55% of gross weight.In addition, the alkalescence alcohol deposition method also is to remove tannin method commonly used, " being the decocting liquid of Chinese medicine to be concentrated add ethanol; make it contain the alcohol amount and reach 80% or higher, place at cold place, filtering post precipitation; transferring to pH with 40% sodium hydroxide is 8; tannin generated sodium salt and was insoluble to ethanol and separates out this moment, through placement, can filter and remove ".The pH value of alcohol extract should not surpass 8 in this method, otherwise active component is damaged easily.
At present, the method that on producing, does not have a kind of radix sanguisorbae total saponin of separation and purification high level preferably.
Summary of the invention
Technical scheme of the present invention has provided a kind of method that obtains high-purity radix sanguisorbae total saponin and Ziyuglycoside I.
The invention provides a kind of method of separation and purification radix sanguisorbae total saponin, it is to carry out according to the following steps:
A, extraction: Radix Sanguisorbae medical material water or alcohol/water extraction are more than 1 time;
B, merge extractive liquid, are regulated pH value with alkali and be 10～15, and be centrifugal, gets filtrate;
C, with filtrate cross macroporous adsorbent resin, earlier with aqueous alkali or water or ethanol liquid eluting, reuse organic solvent eluting is collected the organic solvent eluent, is concentrated, leaves standstill, and filters, collecting precipitation promptly gets radix sanguisorbae total saponin;
Or filtrate is added sour adjust pH is 4～6, is concentrated into the generation precipitate, leaves standstill, centrifugal, collecting precipitation, drying, radix sanguisorbae total saponin.
Wherein, the described extraction of a step is with the cut-out of Radix Sanguisorbae medical material or water or alcohol/water reflux or percolation extraction after beating powder, and the concentration of alcohol/water is 10%v/V～90%v/v.
Wherein, the alkali described in b step and the c step comprises sodium hydroxide, calcium hydroxide, magnesium hydroxide, potassium hydroxide or ammonia, and transferring the temperature of alkali is 0-90 ℃.Further preferably, the described alkali of b step is calcium hydroxide.
Wherein, the described filtrate flow of c step is 0.5V through the speed of macroporous adsorptive resins bed
Post～5V
Post/ hour; The volume of aqueous alkali or water is 2～15 times of column volume; Alcoholic acid volumetric concentration is 10-30%.
Wherein, described alcoholic acid volumetric concentration is 30%.
Wherein, the macroporous adsorptive resins described in the c step is nonpolar and/or the low pole macroporous adsorbent resin, comprises one or more mixing among resin HPD100, HPD300 that the styrene skeleton forms, D101, HPD100A, HPD700, the LD140.
Wherein, the organic solvent described in the step c comprise in ethanol, methanol, ethyl acetate, acetone, dichloromethane, chloroform, the n-butyl alcohol one or more mixture or with the mixture of water.
The present invention also provides a kind of method for preparing Ziyuglycoside I, and it is that above-mentioned radix sanguisorbae total saponin is obtained through recrystallization, and wherein, the used solvent of recrystallization comprises one or more the mixture in methanol, ethanol, ethyl acetate, the water.
Wherein, the structural formula of Ziyuglycoside I is:
Sanguisorbin-I:3-O-α-L-arabinose base-19 Alpha-hydroxy ursol-12 alkene-28-carboxylic
Acid-28-O-β-D-glucosyl group ester (ziyu-glycoside I).
Compared with prior art, the present invention has the following advantages:
1, tannin is removed comparatively clean: this method utilization adds the way of alkali, the impurity tannin main in the Radix Sanguisorbae and the differentiation of polyphenols and saponin have been improved, tannin and polyphenols be the energy salify under alkali condition, it is big that polarity becomes, not adsorbed by macroporous adsorbent resin, and saponin polarity is constant, still can be adsorbed, therefore regulate pH value, more effective tannin and the polyphenols removed by alkali liquor;
2, adopt alkaline alcohol deposition method to remove tannin, pH is 8 o'clock, and tannin can not be removed fully in the radix sanguisorbae total saponin extract with this understanding, and the content of saponin is extremely low, about 10%; After the Radix Sanguisorbae that the present invention uses is extracted, regulating pH value with alkali is 10～15 alkaline alcohol deposition method, the prejudice that pH value should not too high (being no more than 8) when having broken through prior art neutral and alkali alcohol deposition method and removing tannin, under the situation of not destroying radix sanguisorbae total saponin constituents structure successful separation and Extraction high-load radix sanguisorbae total saponin;
3, total saponins enrichment height: after this transferred alkali treatment, the saponin content in the enriched substance improved greatly, improves 20 times approximately, and the eluting lower prop obtains the content of Ziyuglycoside I greater than 98% through recrystallization again after concentrate, leave standstill and separate out radix sanguisorbae total saponin;
4, technological operation of the present invention is easy, the efficient height, and the radix sanguisorbae total saponin yield is more than 3.0%.
5, cost is low: can only utilize the silica gel detached dowel to prepare the defective of radix sanguisorbae total saponin in a small amount at laboratory before the inventive method has overcome, and greatly reduce cost than the alumina column partition method, and post bed low price own, and iterative regenerable uses.
6, the suitability for industrialized production for radix sanguisorbae total saponin provides a kind of new isolation and purification method.
Obviously, according to foregoing of the present invention,,, can also make modification, replacement and the change of other various ways not breaking away under the above-mentioned basic fundamental thought prerequisite of the present invention according to the ordinary skill knowledge and the customary means of this area.
The specific embodiment of form is described in further detail foregoing of the present invention again by the following examples.But this should be interpreted as that the scope of the above-mentioned theme of the present invention only limits to following example.All technology that realizes based on foregoing of the present invention all belong to scope of the present invention.
The specific embodiment
Embodiment 1: the preparation of radix sanguisorbae total saponin
Radix Sanguisorbae decoction pieces 30kg adds 30% ethanol 240L heating and refluxing extraction 1h, and filtering residue reuse 180L30% alcohol heating reflux extracts 1h, merging filtrate adds the dilution of 600L water, stirs to add sodium hydroxide solution (the 3.5kg sodium hydroxide is dissolved in the 24L water) down, adjust pH is 14.2, leave standstill, centrifugal filtrate is by D101 type macroporous adsorbent resin, flow velocity is 1.5 column volumes/h, gone up 4 column volume 30% ethanol elutions of reuse behind the medicinal liquid, and then water to be eluted to effluent colourless, use 70% ethanol elution of 3 times of bed volumes at last, collect 70% ethanol stream fluid, vacuum concentration stops to concentrate after have measured quantity of material to separate out, and leaves standstill more than 2 hours, decompress filter, use 40% washing with alcohol, drain, take out filter cake, vacuum drying, pulverize, get Radix Sanguisorbae total glycosides powder 1.05kg, yield is 3.50%.Detect through colorimetry, radix sanguisorbae total saponin content is 87%, and the content that detects Ziyuglycoside I through high performance liquid chromatography is 70%, has improved 20 times than the content in the extracting solution solid content.
Embodiment 2: the preparation of radix sanguisorbae total saponin
Radix Sanguisorbae decoction pieces 30kg, add 60% ethanol 300L heating and refluxing extraction 1h, filter filtrate, add the dilution of 450L water, stir that to add potassium hydroxide solution (the 2.5kg sodium hydroxide is dissolved in the 25L water) adjust pH down be 10.5, leave standstill, centrifugal filtrate, by macroporous adsorbent resin HPD100, flow velocity is 1.2 column volumes/h, and the reuse water elution is colourless to effluent behind the upward intact medicinal liquid, uses the acetone eluting of 4 times of bed volumes then, collect the acetone eluent, vacuum concentration, the vacuum drying oven drying is pulverized, get Radix Sanguisorbae total glycosides powder 1.09kg, yield is 3.63%, detects through colorimetry, and radix sanguisorbae total saponin content is 71%, the content that detects Ziyuglycoside I through high performance liquid chromatography is 43%, significantly improves than the content in the extracting solution solid content.
Embodiment 3: the preparation of radix sanguisorbae total saponin
Radix Sanguisorbae decoction pieces 30kg, add 45% ethanol 240L heating and refluxing extraction 1h, filtering residue reuse 180L30% alcohol heating reflux extracts 1h, merging filtrate, add the dilution of 600L water, stir adding calcium hydroxide suspension (the 3kg calcium hydroxide is suspended from the 30L water) adjust pH 14 down, leave standstill, filter filtrate, by macroporous adsorbent resin D101, flow velocity is 1.8 column volumes/h, 4 column volumes of intact back reuse, 1.0% sodium hydroxide solution eluting on the medicinal liquid, then the reuse water elution is colourless to effluent, use 30% ethanol elution of 3 times of bed volumes then, use 75% ethanol elution of 3 times of bed volumes at last, collect 75% ethanol elution, vacuum concentration, to there not being the alcohol flavor, residue concentrate vacuum drying oven drying is pulverized, get Radix Sanguisorbae total glycosides powder 1.01kg, yield is 3.37%.Detect through colorimetry, radix sanguisorbae total saponin content is 79%, and the content that detects Ziyuglycoside I through high performance liquid chromatography is 58%, has improved more than 10 times than the content in the extracting solution solid content.
Embodiment 4: the preparation of radix sanguisorbae total saponin
Radix Sanguisorbae decoction pieces 30kg, add 450L water heating and refluxing extraction 1h, filtering residue reuse 300L water heating and refluxing extraction 1h, filtering residue reuse 300L water heating and refluxing extraction 1h, merging filtrate stirs adding calcium hydroxide suspension (the 2kg calcium hydroxide is suspended from the 20L water) adjust pH 13 down, leaves standstill, centrifugal filtrate, hydrochloric acid with an amount of 2M is transferred pH to 4～6, and vacuum concentration is emitted to producing precipitate (about 50～60L volume), leave standstill more than the 2h, centrifugal, collecting precipitation, vacuum drying oven drying, pulverize, get Radix Sanguisorbae total glycosides powder, detect through colorimetry, radix sanguisorbae total saponin content is 53%, the content that detects Ziyuglycoside I through high performance liquid chromatography is 39%, significantly improves than the content in the extracting solution solid content.
Embodiment 5: the preparation of Ziyuglycoside I
With the foregoing description 1 gained Radix Sanguisorbae total glycosides powder with dehydrated alcohol (1g: 5ml) reflux 10min, filtered while hot treats that filtrate is chilled to room temperature, stir and drip water down, muddy to occurring, and do not disappear, stop, leave standstill 12h, sucking filtration precipitates with 30% washing with alcohol, collect, vacuum drying is pulverized, time recrystallized product of winning.Recrystallization one to twice repeatedly again, Ziyuglycoside I, the purity that detects Ziyuglycoside I through high performance liquid chromatography is 99.2%.
Embodiment 6: the preparation of Ziyuglycoside I
With the foregoing description 2 routine gained Radix Sanguisorbae total glycosides powder, with methanol (1g: 5ml) reflux 10min, filtered while hot, treat that filtrate is chilled to room temperature, stir and drip water down, muddy to occurring, and do not disappear, stop, leaving standstill 12h, sucking filtration, with 30% washing with alcohol precipitation, collect vacuum drying, pulverize time recrystallized product of winning.Recrystallization one to twice repeatedly again, Ziyuglycoside I, the purity that detects Ziyuglycoside I through high performance liquid chromatography is 99.4%.
The contrast experiment of the preparation method of embodiment 7 radix sanguisorbae total saponins of the present invention and the method for patent disclosure
The content that relates to radix sanguisorbae total saponin in the number of patent application 200310119248.1 is lower than the total saponins for preparing among the present invention, and key is the utilization of the preceding alkali of post, has improved the differentiation of tannin and saponin.
The contrast test data are as follows:
This test proves that fully the inventive method obviously is better than contrasting the method for patent disclosure, and coupling by alkali and macroporous adsorbent resin has improved the content of total saponins and saponin I in the Radix Sanguisorbae greatly, has reduced the content of main impurity tannin significantly.
Claims (9)
1. the method for a separation and purification radix sanguisorbae total saponin is characterized in that carrying out according to the following steps:
A, extraction: Radix Sanguisorbae medical material water or alcohol/water extraction are more than 1 time;
B, merge extractive liquid, are regulated pH value with alkali and be 10～15, and be centrifugal, gets filtrate;
C, filtrate is crossed macroporous adsorbent resin, earlier with aqueous alkali or water or ethanol liquid eluting, reuse organic solvent eluting is collected the organic solvent eluent, is concentrated, leaves standstill, and filters, and collecting precipitation promptly gets radix sanguisorbae total saponin;
Or filtrate is added sour adjust pH is 4～6, is concentrated into the generation precipitate, leaves standstill, centrifugal, collecting precipitation, drying, radix sanguisorbae total saponin.
2. the preparation method of radix sanguisorbae total saponin according to claim 1 is characterized in that: the described extraction of a step is the Radix Sanguisorbae medical material to be cut off or beats water or alcohol/water reflux or percolation extraction behind the powder, and the concentration of alcohol/water is 10%v/v～90%v/v.
3. the preparation method of radix sanguisorbae total saponin according to claim 1, it is characterized in that: the alkali described in b step and the c step comprises sodium hydroxide, calcium hydroxide, magnesium hydroxide, potassium hydroxide or ammonia, transferring the temperature of alkali is 0-90 ℃.
4. the preparation method of radix sanguisorbae total saponin according to claim 3, it is characterized in that: the described alkali of b step is calcium hydroxide.
5. the preparation method of radix sanguisorbae total saponin according to claim 1, it is characterized in that: the described filtrate flow of c step is 0.5V through the speed of macroporous adsorptive resins bed
Post～5V
Post/ hour; The volume of aqueous alkali or water is 2～15 times of column volume; Alcoholic acid volumetric concentration is 10-30%.
6. the preparation method of radix sanguisorbae total saponin according to claim 5, it is characterized in that: described alcoholic acid volumetric concentration is 30%.
7. the preparation method of radix sanguisorbae total saponin according to claim 1, it is characterized in that: the macroporous adsorptive resins described in the c step is nonpolar and/or the low pole macroporous adsorbent resin, comprises one or more mixing among resin HPD100, HPD300 that the styrene skeleton forms, D101, HPD100A, HPD700, the LD140.
8. the preparation method of radix sanguisorbae total saponin according to claim 1 is characterized in that: the organic solvent described in the step c comprise in ethanol, methanol, ethyl acetate, acetone, dichloromethane, chloroform, the n-butyl alcohol one or more mixture or with the mixture of water.
9. method for preparing Ziyuglycoside I, it is that radix sanguisorbae total saponin with claim 1 preparation obtains through recrystallization, wherein, the used solvent of recrystallization comprises one or more the mixture in methanol, ethanol, ethyl acetate, the water.
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102631441A (en) * | 2011-04-29 | 2012-08-15 | 成都科尔医药技术有限公司 | Separation and purification method of total saponins of sanguisorba officinalis |
| CN103223036A (en) * | 2013-04-16 | 2013-07-31 | 阚兆云 | Traditional Chinese medicinal composition |
| CN105147804A (en) * | 2015-08-28 | 2015-12-16 | 四川英路维特医药科技有限公司 | Total ziyuglycoside extract and preparation method and application thereof |
| CN105920137A (en) * | 2016-06-02 | 2016-09-07 | 中国药科大学 | Application of sanguisorba total saponin to treatment of inflammatory bowel diseases |
| CN107496547A (en) * | 2017-09-15 | 2017-12-22 | 中山大学 | One kind suppresses the garden burnet crude extract and preparation method of classical Wnt/β catenin paths |
| CN108478492A (en) * | 2018-05-23 | 2018-09-04 | 布伟年 | A kind of Radix Sangusorbae extract and the preparation method and application thereof |
| CN108503680A (en) * | 2018-03-29 | 2018-09-07 | 佛山科学技术学院 | A kind of preparation method of sanguisorbin II |
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| CN1935147B (en) * | 2002-12-02 | 2010-05-19 | 成都地奥制药集团有限公司 | New use of radix sanguisorbae total saponin extract |
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Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102631441A (en) * | 2011-04-29 | 2012-08-15 | 成都科尔医药技术有限公司 | Separation and purification method of total saponins of sanguisorba officinalis |
| CN103223036A (en) * | 2013-04-16 | 2013-07-31 | 阚兆云 | Traditional Chinese medicinal composition |
| CN105147804A (en) * | 2015-08-28 | 2015-12-16 | 四川英路维特医药科技有限公司 | Total ziyuglycoside extract and preparation method and application thereof |
| CN105147804B (en) * | 2015-08-28 | 2019-04-09 | 四川英路维特医药科技有限公司 | A kind of radix sanguisorbae total saponin extract and its preparation method and application |
| CN105920137A (en) * | 2016-06-02 | 2016-09-07 | 中国药科大学 | Application of sanguisorba total saponin to treatment of inflammatory bowel diseases |
| CN107496547A (en) * | 2017-09-15 | 2017-12-22 | 中山大学 | One kind suppresses the garden burnet crude extract and preparation method of classical Wnt/β catenin paths |
| CN108503680A (en) * | 2018-03-29 | 2018-09-07 | 佛山科学技术学院 | A kind of preparation method of sanguisorbin II |
| CN108478492A (en) * | 2018-05-23 | 2018-09-04 | 布伟年 | A kind of Radix Sangusorbae extract and the preparation method and application thereof |
| CN112274522A (en) * | 2020-11-12 | 2021-01-29 | 成都中医药大学 | New anti-inflammatory application of phenol glycoside compounds in garden burnet and extraction and separation method thereof |
| CN112274522B (en) * | 2020-11-12 | 2022-10-28 | 成都中医药大学 | New anti-inflammatory application of phenolic glycoside compounds in garden burnet root and extraction and separation method thereof |
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