CN104592322A - Method for extracting and separating curculigoside from curculigo gaertn plants - Google Patents
Method for extracting and separating curculigoside from curculigo gaertn plants Download PDFInfo
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- CN104592322A CN104592322A CN201410780382.4A CN201410780382A CN104592322A CN 104592322 A CN104592322 A CN 104592322A CN 201410780382 A CN201410780382 A CN 201410780382A CN 104592322 A CN104592322 A CN 104592322A
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- curculigoside
- ethyl acetate
- extraction
- curculigo
- isolation
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/06—Separation; Purification
- C07H1/08—Separation; Purification from natural products
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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Abstract
The invention discloses a production method for extracting and separating curculigoside from curculigo gaertn plants. The method comprises main steps of extracting with ethyl acetate, recovering a solvent to obtain crude paste, dissolving crude paste in water, extracting ethyl acetate by means of countercurrent, performing chromatography and recrystallization, drying, and packaging. In the method, by making use of the characteristics of each chemical constituent in rhizoma curculiginis, firstly, the curculigoside is extracted and separated out by means of ethyl acetate extraction, wherein the residue formed after ethyl acetate extraction can be used for producing polysaccharide, starch, drinkable liquor, and on the like, so that the use ratio of rhizoma curculiginis resources is improved. The production method provided by the invention is reasonable in process, low in energy consumption and low in cost, and is safe and environment-friendly.
Description
Technical field
The present invention is a kind of method of extracting effective components from herbal medicine, specifically a kind of method of extraction and isolation curculigoside from Curculigo.
Background technology
Thizoma curculiginis is the widely used Chinese medicine of a class, has multiple biological activity, and the research of the aspects such as the chemical composition of thizoma curculiginis and bio-pharmacology activity makes some progress.At present can hyoscine have thizoma curculiginis, great Ye thizoma curculiginis and Shortscape Curculigo.
Thizoma curculiginis is as a kind of traditional Chinese medicine material, complicated ingredient contained by it has multiple biological activity, mostly application forms clinically, be the decoction with prescription compatibility of medicines, and its different prescriptions being monarch drug in a prescription by thizoma curculiginis can treat the various diseases such as such as impotence, involution syndrome, cyclomastopathy.Market also having other formulations such as such as tablet, granule etc., is main disease in order to treat osteoporosis.Containing cycloartane type compound in thizoma curculiginis, similar to main component in rattletop, therefore it is also carrying out the research of anti-tumor activity.At present, the activity research of people to thizoma curculiginis focuses mostly on alcohol extract and aqueous extract, is also the traditional role of some thizoma curculiginises.For concrete monomeric compound pharmacological research not deeply, pharmacology aspect is not deep in the dose-effect of compound and animal, structure activity relationship yet.These aspects are all worth research further.
The method of curculigoside is extracted from thizoma curculiginis Botanical gardens, just like " a kind of extracting method of curculigoside " CN10234471A and " a kind of method extracting curculigo rhizome total glycoside material from thizoma curculiginis " CN103417762A in patent application, known from document: the method leached from the mono-Walk of thizoma curculiginis plant extract curculigoside is mainly with water, methyl alcohol or ethanol, but there is not yet directly with ethyl acetate lixiviate, water, methyl alcohol, ethanol person be all polarity stronger solvent, the impurity extracted is more, cause separating-purifying difficulty below, employing ethyl acetate is extracted, the impurity not only extracted is few, be convenient to be separated, productive rate is high, and the starch that can not destroy in leaching process in thizoma curculiginis, protein, the compositions such as polysaccharide, residue after extraction can be used for producing thizoma curculiginis polysaccharide, starch, beverage wine or make feed, improve the utilization ratio of Curculigo resource.
Summary of the invention
The present invention's one is separated curculigoside and production method side from Curculigo, follows these steps to extraction and isolation curculigoside.(1) pulverize: thizoma curculiginis medicinal material is dried or after drying, is crushed to 100 ~ 120 orders, obtains thizoma curculiginis pulverizing medicinal materials material; (2) extract: thizoma curculiginis pulverizing medicinal materials material ethyl acetate backflow extracts to obtain ethyl acetate extract; (3) underpressure distillation is reclaimed ethyl acetate and is obtained the thick cream of curculigoside; (4) dissolve: with the thick cream of water heating for dissolving curculigoside, filter to obtain the thick cream aqueous solution of curculigoside; (5) extract: be extracted with ethyl acetate, retain ethyl acetate phase, obtain ethyl acetate curculigoside extract; (6) underpressure distillation is reclaimed ethyl acetate and is obtained curculigoside medicinal extract; (7) dissolve: obtain curculigoside ethyl acetate solution with acetic acid ethyl dissolution curculigoside medicinal extract; (8) upper silicagel column: the upper silicagel column of curculigoside ethyl acetate solution transfer; (9) add methanol elution gradient by ethyl acetate and obtain elutriant; (10) underpressure distillation is reclaimed elutriant and is obtained curculigoside crude product; (11) ethyl alcohol recrystallization obtains thizoma curculiginis finished product; (12) at 70 DEG C, vacuum-drying curculigoside obtains product.
Step (2) adds the ethyl acetate of 15-20L by per kilogram thizoma curculiginis pulverizing medicinal materials material, and point three refluxing extraction, each reflux extracting time is 50 minutes to 60 minutes.
The thick cream of step (4) curculigoside must be measured than being 1:2.2 ~ 2.5 with water.
Step (5), the method be extracted with ethyl acetate is counter-current extraction; The consumption of ethyl acetate is 4.5 ~ 5.5 times of the aqueous solution.
Step (9), what collect during gradient elution be the volume ratio of ethyl acetate and methyl alcohol is the wash-out of 10:1 ~ 9:1.
Be from pure ethyl acetate during gradient elution in step (9), progressively increase the ratio of methyl alcohol, till without curculigoside.
The solvent that in step (11), recrystallization is used is that concentration is greater than 95% ethanol, adds activated carbon decolorizing in recrystallization process.
The present invention utilizes the feature of each chemical composition in thizoma curculiginis, isolates curculigoside separately, and the residue wherein in step (1) after ethyl acetate extraction can be used for producing starch, beverage wine or making feed, improves the utilization ratio of thizoma curculiginis resource.
Innovative point of the present invention is: (1) is without water extraction, employing ethyl acetate is extracted, the composition such as starch, protein, polysaccharide in thizoma curculiginis can not be destroyed in leaching process, after extracting the many glycosides of thizoma curculiginis, residue can be used for producing thizoma curculiginis polysaccharide, starch, beverage wine or making feed, improves the utilization ratio of thizoma curculiginis resource; (2) a kind of production method being separated curculigoside from Curculigo is provided; (3) the present invention is fewer than the step of traditional technology in conjunction with counter-current extraction, chromatography, and traditional technology at least wants twice chromatographic, and the present invention only needs a chromatography.(4) the present invention is in conjunction with counter-current extraction, chromatography, and rational technology, yield are high, energy consumption is low, cost is lower, constant product quality.(5) raw material availability of the present invention is high; (6) safety of the present invention, environmental protection, slag and effluent is few.
Accompanying drawing explanation
Fig. 1 is present invention process schematic flow sheet.
Embodiment
example 1: thizoma curculiginis medicinal material 10kg, is ground into meal, drops into extractor, adds 60L ethyl acetate backflow and extract three times, each 1 hour, obtain thick cream 130g after acetic acid ethyl acetate extract recycling design; Thick cream water 300ml heated and stirred is dissolved, aqueous solution 1500ml ethyl acetate counter-current extraction, ethyl acetate phase recycling design; Obtain medicinal extract 100g; Medicinal extract adds ethyl acetate 150ml, fully dissolves, and filters, and filtrate loads in silica gel column chromatography (wet method dress post), with ethyl acetate and methanol solution gradient elution, with the triangle bottle graft elutriant of 50ml, approximately meets 20ml and changes a triangular flask; Collect the elutriant of 10:1 to 9:1, recycling design obtains thizoma curculiginis many glycosides crude product 15g; Crude product 95% ethanol 50ml heated and stirred is dissolved, and add 3g activity backflow carbon and decolour 30 minutes, filter, filtrate recrystallization, suction filtration, obtains crystallization 14g; Crystallization vacuum-drying below 70 DEG C, pulverizes to obtain the curculigoside of product 12g.
example 2: thizoma curculiginis medicinal material 50kg, is ground into meal, drops into extractor, adds 300L ethyl acetate backflow and extract three times, each 2 hours, obtain thick cream 650g after acetic acid ethyl acetate extract recycling design; Thick cream water 1300ml heated and stirred is dissolved, aqueous solution 7500ml ethyl acetate counter-current extraction, ethyl acetate phase recycling design; Obtain medicinal extract 505g; Medicinal extract adds ethyl acetate 1000ml, fully dissolves, and filters, and filtrate loads in silica gel column chromatography (wet method dress post), with ethyl acetate and methanol solution gradient elution, with the triangle bottle graft elutriant of 250ml, approximately meets 100ml and changes a triangular flask; Collect the elutriant of 10:1 to 9:1, recycling design obtains thizoma curculiginis many glycosides crude product 76g; Crude product 95% ethanol 250ml heated and stirred is dissolved, and add 15g activity backflow carbon and decolour 30 minutes, filter, filtrate recrystallization, suction filtration, obtains crystallization 70.5g; Crystallization vacuum-drying below 70 DEG C, pulverizes to obtain product 60.2g.
example 3:thizoma curculiginis medicinal material 100kg, is ground into meal, drops into extractor, adds 600L ethyl acetate backflow and extract three times, each 1.5 hours, obtain thick cream 1350g after acetic acid ethyl acetate extract recycling design; Thick cream water 3000ml heated and stirred is dissolved, aqueous solution 15000ml ethyl acetate counter-current extraction, ethyl acetate phase recycling design; Obtain medicinal extract 1050g; Medicinal extract adds ethyl acetate 1500ml, fully dissolves, and filters, and filtrate loads in silica gel column chromatography (wet method dress post), with ethyl acetate and methanol solution gradient elution, with the triangle bottle graft elutriant of 500ml, approximately meets 200ml and changes a triangular flask; Collect the elutriant of 10:1 to 9:1, recycling design obtains thizoma curculiginis many glycosides crude product 160g; Crude product 95% ethanol 500ml heated and stirred is dissolved, and add 30g activity backflow carbon and decolour 30 minutes, filter, filtrate recrystallization, suction filtration, obtains crystallization 148g; Crystallization vacuum-drying below 70 DEG C, pulverizes to obtain product 125g.
Claims (7)
1. from a method for Curculigo extraction and isolation curculigoside, it is characterized in that following these steps to extraction and isolation curculigoside: (1) pulverizes: thizoma curculiginis medicinal material is dried or after drying, is crushed to 100 ~ 120 orders, obtains thizoma curculiginis pulverizing medicinal materials material; (2) extract: thizoma curculiginis pulverizing medicinal materials material ethyl acetate backflow extracts to obtain ethyl acetate extract; (3) underpressure distillation is reclaimed ethyl acetate and is obtained the thick cream of curculigoside; (4) dissolve: with the thick cream of water heating for dissolving curculigoside, filter to obtain the thick cream aqueous solution of curculigoside; (5) extract: be extracted with ethyl acetate, retain ethyl acetate phase, obtain ethyl acetate curculigoside extract; (6) underpressure distillation is reclaimed ethyl acetate and is obtained curculigoside medicinal extract; (7) dissolve: obtain curculigoside ethyl acetate solution with acetic acid ethyl dissolution curculigoside medicinal extract; (8) upper silicagel column: the upper silicagel column of curculigoside ethyl acetate solution transfer; (9) add methanol elution gradient by ethyl acetate and obtain elutriant; (10) underpressure distillation is reclaimed elutriant and is obtained curculigoside crude product; (11) ethyl alcohol recrystallization obtains thizoma curculiginis finished product; (12) at 70 DEG C, vacuum-drying curculigoside obtains product.
2. by the method for a kind of Curculigo extraction and isolation curculigoside according to claim 1, it is characterized in that step (2) adds the ethyl acetate of 15-20L by per kilogram thizoma curculiginis pulverizing medicinal materials material, divide three refluxing extraction, each reflux extracting time is 50 minutes to 60 minutes.
3., by the method for a kind of Curculigo extraction and isolation curculigoside according to claim 1, it is characterized in that must measuring than being 1:2.2 ~ 2.5 of the thick cream of step (4) curculigoside and water.
4., by the method for a kind of Curculigo extraction and isolation curculigoside according to claim 1, it is characterized in that step (5), the method be extracted with ethyl acetate is counter-current extraction; The consumption of ethyl acetate is 4.5 ~ 5.5 times of the aqueous solution.
5. by the method for a kind of Curculigo extraction and isolation curculigoside according to claim 1, it is characterized in that step (9), what collect during gradient elution be the volume ratio of ethyl acetate and methyl alcohol is the wash-out of 10:1 ~ 9:1.
6., by the method for a kind of Curculigo extraction and isolation curculigoside according to claim 1, be from pure ethyl acetate when it is characterized in that gradient elution in step (9), progressively increase the ratio of methyl alcohol, till without curculigoside.
7., by the method for a kind of Curculigo extraction and isolation curculigoside according to claim 1, it is characterized in that the solvent that in step (11), recrystallization is used is that concentration is greater than 95% ethanol, in recrystallization process, add activated carbon decolorizing.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410780382.4A CN104592322A (en) | 2014-12-17 | 2014-12-17 | Method for extracting and separating curculigoside from curculigo gaertn plants |
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| CN201410780382.4A CN104592322A (en) | 2014-12-17 | 2014-12-17 | Method for extracting and separating curculigoside from curculigo gaertn plants |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105638662A (en) * | 2016-01-21 | 2016-06-08 | 苏州派腾生物医药科技有限公司 | Application of curculigoside in preparing insecticide |
| CN106353446A (en) * | 2016-08-12 | 2017-01-25 | 上海黄海制药有限责任公司 | Identification and content measuring method of climacteric-syndrome-soothing granules |
| CN113189256A (en) * | 2021-05-12 | 2021-07-30 | 劲牌有限公司 | Method for extracting curculigoside from curculigo orchioides |
-
2014
- 2014-12-17 CN CN201410780382.4A patent/CN104592322A/en active Pending
Non-Patent Citations (3)
| Title |
|---|
| JINYONG PENG，等: "Optimization suitable conditions for preparative isolation and separation of curculigoside and curculigoside B from Curculigo orchioides by high-speed counter-current chromatography", 《SEPARATION AND PURIFICATION TECHNOLOGY》 * |
| 曹大鹏，等: "仙茅的酚苷和木脂素类成分的分离和鉴定", 《第二军医大学学报》 * |
| 陈昌祥，等: "仙茅根茎中的配糖体", 《化学研究与应用》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105638662A (en) * | 2016-01-21 | 2016-06-08 | 苏州派腾生物医药科技有限公司 | Application of curculigoside in preparing insecticide |
| CN106353446A (en) * | 2016-08-12 | 2017-01-25 | 上海黄海制药有限责任公司 | Identification and content measuring method of climacteric-syndrome-soothing granules |
| CN113189256A (en) * | 2021-05-12 | 2021-07-30 | 劲牌有限公司 | Method for extracting curculigoside from curculigo orchioides |
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Application publication date: 20150506 |