CN105968159B - The preparation method of mogrosides V - Google Patents
The preparation method of mogrosides V Download PDFInfo
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- CN105968159B CN105968159B CN201610018650.8A CN201610018650A CN105968159B CN 105968159 B CN105968159 B CN 105968159B CN 201610018650 A CN201610018650 A CN 201610018650A CN 105968159 B CN105968159 B CN 105968159B
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Abstract
Disclosed herein is a kind of preparation method of mogrosides V：1) Momordica grosvenori crushes, and with flooding, filters, concentrates, centrifugation, obtains Aqueous extracts；2) Aqueous extracts are subjected to macroporous adsorbent resin column chromatography, eluted with ethanol solution, crossed decolorizing resin after eluent concentration, be eluted with water, eluent concentration, obtain saponin crude extract；3) saponin crude extract is subjected to high speed adverse current chromatogram separation, dicyandiamide solution uses ethyl acetate, n-butanol and water, the upper phase of standing separation is stationary phase after being mixed using ethyl acetate, n-butanol and water, and lower floor's liquid phase of standing separation is mobile phase after being mixed using ethyl acetate, n-butanol and water；Then efflux is collected according to the ultraviolet detection collection of illustrative plates of effluent in detector, concentrated, vacuum drying, obtain saponin powder；4) saponin powder is subjected to silica gel post separation, eluted with chloroform, methanol and water mixed solution, collect efflux, concentrated, vacuum drying, obtain mogrosides V.
Description
【Technical field】
The present invention relates to a kind of preparation method of mogrosides V, especially a kind of high speed adverse current chromatogram separation preparation side
Method.
【Background technology】
Momordica grosvenori is the fruit of Curcurbitaceae Genus Siraitia Merr, and it is the distinctive economy in China, integration of drinking and medicinal herbs crop, its medicine
Existing more than 300 years with history, have moisten the lung and relieve the cough, laxation defaecation, clearing heat and cooling blood and other effects, health ministry, traditional Chinese medicine management
Office is included in first " be both food and the kind list of medicine ".The medical value of Momordica grosvenori is very high, and its pharmacology is lived
Property mainly have cough-relieving apophlegmatic, promoting blood circulation and removing blood stasis, liver protection, antibacterial, anticancer, anti-oxidant, enhancing immunity of organisms, reducing blood lipid, hypoglycemic
Deng.In recent years research shows that the nonsugar triterpenes components mogrosides of strong sweet taste are its main active ingredient, are had
Sugariness is high, and heat is low, lighter color, and water-soluble and stability is good, the characteristics of edible safety.Wherein mogrosides V are Momordica grosvenori
Middle content (account for total sweet tea salidroside content 30%~40%) and the sugariness composition higher (for 256~344 times of sweetness of cane sugar),
It is one of most important active component for playing its medical value, therefore, usually using the content of saponin V as evaluation Momordica grosvenori
One of quality of soaping agents product.In recent years, many scholars in China and foreign countries to mogrosides class compound medical mechanism and activity into
The mechanism of action divided is studied, and establishes some research methods, but these research mechanism of action are still not clear.To be further
The mechanism of action of mogrosides is inquired into, preparing for high-purity saponin V is significant.Isolate and purify Momordica grosvenori soap at present
The method of glucoside mainly has UF membrane, pillar layer separation, preparative high performance liquid chromatography separation etc., but UF membrane and pillar layer separation
Separation cycle length, operating process is complicated, and is difficult the monomer for obtaining high-purity, though preparative high performance liquid chromatography can separate
To the monomer of mogrosides V, but quantity of sample handling is small, and cost is higher.Therefore, a kind of fast and effectively separation system is established
The method of standby high-purity Momordica grosvenori saponin V is significant.
【The content of the invention】
For above mentioned problem of the prior art, the present invention provides a kind of preparation method of mogrosides V, separation week
Phase is short, separating rate is fast, and the purity height of product, yield are high, and cost is also greatly reduced.
The technical scheme is that：
A kind of preparation method of mogrosides V, comprises the following steps：
1) Momordica grosvenori crushes, and with flooding, filters, concentrates, centrifugation, and centrifugation gained supernatant liquor is Momordica grosvenori Aqueous extracts；
2) the Momordica grosvenori Aqueous extracts obtained by step 1) are subjected to macroporous adsorbent resin column chromatography, are eluted, washed with ethanol solution
Decolorizing resin is crossed after de- liquid concentration, is eluted with water, eluent concentration, obtains mogrosides crude extract；
3) the mogrosides crude extract obtained by step 2) is subjected to high speed adverse current chromatogram separation, dicyandiamide solution uses acetic acid
Ethyl ester, n-butanol and water, the upper phase of standing separation is stationary phase after being mixed using ethyl acetate, n-butanol and water, with acetic acid
Lower floor's liquid phase of standing separation is mobile phase after ethyl ester, n-butanol and water mixing；Then according in detector effluent it is ultraviolet
Detect collection of illustrative plates and collect efflux, concentrate, vacuum drying, obtain mogrosides powder；
4) the mogrosides powder obtained by step 3) is subjected to silica gel post separation, with chloroform, methanol and water mixed solution
Elution, efflux is collected, concentrated, vacuum drying, obtain mogrosides V.
Preferably, step 1) with flooding specifically refer to mangosteen powder mince volume 3~5 times of water in 70~
80 DEG C are extracted 1~3 time, extract 1~3h every time.
Preferably, the centrifugation of step 1), which specifically refers to 5000~8000r/min, centrifuges 10~30min.
Preferably, the ethanol water that it is 60-80% that the ethanol solution of step 2), which is volume fraction, the ethanol solution
Flow velocity is 2-3mL/min.
Preferably, the high speed adverse current chromatogram separation of step 3) controls separation temperature stable 20 by constant temperature circulating tank
~30 DEG C.
Preferably, the volume ratio of the ethyl acetate of step 3), n-butanol, water is (1~4):(1~5):(5~6).
Preferably, step 3) is specifically referred to according to wavelength according to the ultraviolet detection collection of illustrative plates of effluent collection efflux
210nm ultraviolet chromatogram, collect efflux corresponding with first peak retention time.
Preferably, step 1)~4) concentration specifically refer to be concentrated into the 1/4 of original volume on the rotary evaporator, step
3), vacuum drying 4) specifically refers to be freeze-dried under -60~-40 DEG C, relative degree of vacuum -0.1~-0.08MPa.
The present invention can produce following beneficial technique effect：
1) purity of mogrosides V prepared height is separated by the inventive method, by step 1)~3 of the present invention) obtain
Mogrosides powder in the content of saponin V be higher than 55%, then through silicagel column after purification the purity of saponin V be higher than 95%, and
Recovery rate can meet to enter the mechanism of action of mogrosides class compound medical mechanism and active component more than 90%
The purity requirement of row research, and recovery rate is significantly lifted, and can further reduce cost, improves utilization ratio.
2) preparation method of the invention makes macroporous absorbent resin, high speed adverse current chromatogram and silica gel column chromatography technical tie-up
With.Macroporous absorbent resin technology carries out simple process to Momordica grosvenori Aqueous extracts, eliminates the impurity such as polysaccharide, protein, crude extract
High speed adverse current chromatogram separation can be directly carried out, the efficiency of processing can be effectively improved；Using high speed adverse current chromatogram to crude extract
Further separated, eliminate the impurity such as the Polyphenols such as flavones, the active ingredients such as mogrosides are collected, can be with
The purity of mogrosides V is promoted to more than 55%, and preparation amount is big, and separating rate is fast；Continue to use silica gel column chromatography
High speed adverse current chromatogram prepared product is further separated, eliminates other saponin materials of non-mogrosides V, significantly
Disengaging time is shortened, and final product purity is higher than 95%, can generally reach more than 98%.Macroporous absorbent resin, high speed
Adverse current chromatogram uses with silica gel column chromatography technical tie-up, is fitted to each other, the saponin V in Momordica grosvenori Aqueous extracts is divided successively
From reducing interfering between component, separating rate can reach 5-10 milli Grams Per Hours.Therefore, preparation method of the invention
Compared with the preparation method of mogrosides V in the prior art, have the characteristics that easy, quick, saving solvent, yield are high,
With good actual application value.
3) high speed adverse current chromatogram is a kind of liquid liquid partition chromatography technology without using solid-phase support or liquid, is in recent years
A kind of new isolation technics to grow up, not only disengaging time is short, and expense is low, it is thus also avoided that the sample that solid phase carrier is brought
The problems such as high sample loss brought with Irreversible Adsorption of pre-processing requirements, inactivation denaturation, while also big with preparation amount, separation
Effect is good, the advantages such as speed is fast.But at present high speed adverse current chromatogram be widely used in being used for flavones, Tea Polyphenols etc. it is fat-soluble
Prepared by the separation of good material, and prepared by the separation of the less material for good water solubility.The present invention is suitable molten by selecting
Agent and the suitable preparation condition of regulation, high speed adverse current chromatogram are applied to the preparation of the mogrosides V of good water solubility, and take
Good effect was obtained, and maintains the advantages that preparation amount is big, processing speed is fast, there is provided a kind of high-purity mogrosides V
High efficiency preparation method, have also been enlarged the application of high speed adverse current chromatogram.
【Brief description of the drawings】
Fig. 1 is the flow chart of preparation method of the present invention；
Fig. 2 is the high speed adverse current chromatogram figure of mogrosides crude extract in the present invention；
Fig. 3 is the standard items (a) of saponin V, mogrosides high speed adverse current chromatogram peak 1 (b), mogrosides in the present invention
The high-efficient liquid phase chromatogram spectrum at high speed adverse current chromatogram peak 2 (c), the product (d) of mogrosides V；
Fig. 4 is the product HPLC-MS first mass spectrometric figure (a) of mogrosides V and second order mses figure
(b)。
Description of symbols：Peak 1, first peak of wavelength 210nm ultraviolet chromatogram；Peak 2, wavelength 210nm ultraviolet chromatogram
First peak of figure；AU, response, represent the height of concentration.
【Embodiment】
Below in conjunction with specific embodiment, the present invention is described further.
Embodiment provided below and being not used to limits the scope that the utility model is covered, and described step is not yet
It is to limit its execution sequence.Those skilled in the art the present invention is done with reference to existing common knowledge it is conspicuously improved,
Also fall within the protection domain of application claims.
The of embodiment one
The preparation method of mogrosides V comprises the following steps in the present embodiment：
1) after Momordica grosvenori is crushed, with volume equivalent to mangosteen powder mince volume 3.5 times of water in 75 DEG C extract 2
It is secondary, extract 2h every time, merge Aqueous extracts, with the filtered through gauze of 200 mesh, the concentration of filtrate rotary evaporation, concentrate 6000r/min from
Heart 20min, obtain Momordica grosvenori Aqueous extracts.
2) Aqueous extracts carry out ADS-8 macroporous adsorbent resin column chromatographies, are eluted with 65% ethanol water, flow velocity 2.5mL/
Min, collect eluent, rotary evaporation concentration.Concentrate crosses 700B decolorizing resins, is eluted with pure water, after eluent concentration, vacuum
Dry, it is mogrosides crude extract to obtain pale yellow powder.
3) high speed adverse current chromatogram combinesPrime plus high-pressure pumps and a constant temperature circulating tank are used for Momordica grosvenori
The separation of saponin V.With ethyl acetate：N-butanol：Water=1:5:6(V:V:V it is) dicyandiamide solution of high speed adverse current chromatogram, configuration
2000mL mixed liquor, after magnetic agitation 30min, stand overnight, separation phase up and down, the above mutually be used as stationary phase, and lower phase is flows
Dynamic phase.The water bath with thermostatic control circulatory system is opened, temperature stabilization is at 25 DEG C or so.Start to be pumped into stationary phase with 10mL/min speed, treat
Stationary phase is full of whole stream, opens high-speed counter-current chromatograph main frame, the rotating speed of regulation borded pile coil is 900r/min, then
Mobile phase, while open detection device are pumped into 2.5mL/min speed.Treat that mobile phase flows out two phase solvent system in chromatography column
In when reaching balance, mogrosides crude extract is dissolved in the mobile phase of 20~30 times of volumes, injects high speed adverse current chromatogram
Separated, Detection wavelength 210nm, efflux corresponding to first peak (peak 1) of collection, Momordica grosvenori soap is dried in vacuo to obtain after concentration
Glucoside powder.
4) mogrosides powder presses 1 with silica gel:1(M:M ratio) mixes, dry method loading, is first rushed with chloroform full whole
Pillar, then change chloroform：Methanol：Water=90:10:0.5、70:30:0.5、80:36:0.2(V:V:V eluent) is washed successively
It is de-.Efflux 100mL concentrations are collected every time to be evaporated, and with thin-layer chromatography qualitative analysis is carried out after a small amount of methanol dissolving, work as outflow
When liquid is equal with the Rf value Rf of the standard items of saponin V, now the chloroform of ratio used, methanol and water mixed liquid continue to elute use,
Until this collection part flows completely out.Corresponding efflux is collected, is concentrated, is the prepared product of mogrosides V after vacuum drying.
As shown in figure 1, being separated through high speed adverse current chromatogram for mogrosides crude extract can obtain 2 in the embodiment of the present invention one
Chromatographic peak.Through efficient liquid phase chromatographic analysis and area normalization standard measure, the content of first peak (peak 1) mogrosides V is
57.8%, yield 94.22%；The content of second peak (peak 2) mogrosides V is 17.5%, yield 5.39%.Receive
Efflux corresponding to collecting first peak (peak 1), is dried in vacuo to obtain mogrosides powder after concentration.The prepared product is again through silicagel column
Chromatography, the mogrosides V of preparation of the embodiment of the present invention are produced, its purity is 98.32%, extraction rate reached to 92.36%.
As shown in figure 3, the quasi-molecular ion peak [M-H] of the prepared product of mogrosides V prepared by the embodiment of the present invention one-
For 1285 m/z, show the relative molecular mass 1286 of its molecule, molecular formula C60H102O29, second order mses provide mass-to-charge ratio m/
Z be 1123.5,961.5,799.4,637.4 characteristic fragment ion peak, the mass spectral characteristic and mogrosides of the prepared product
V mass spectral characteristic matches, and it is mogrosides V to illustrate the prepared product.
The of embodiment two
The preparation method of mogrosides V comprises the following steps in the present embodiment：
1) after Momordica grosvenori is crushed, with volume equivalent to mangosteen powder mince volume 5 times of water in 80 DEG C extract 2 times,
Extraction 1h every time, merge Aqueous extracts, with the filtered through gauze of 200 mesh, the concentration of filtrate rotary evaporation, concentrate 8000r/min centrifugations
10min, obtain Momordica grosvenori Aqueous extracts.
2) Aqueous extracts carry out ADS-8 macroporous adsorbent resin column chromatographies, are eluted with 80% ethanol solution, flow velocity 3mL/min,
Collect eluent, rotary evaporation concentration.Concentrate crosses 700B decolorizing resins, is eluted with pure water, and after eluent concentration, vacuum is done
Dry, it is mogrosides crude extract to obtain pale yellow powder.
3) high speed adverse current chromatogram combinesPrime plus high-pressure pumps and a constant temperature circulating tank are used for Momordica grosvenori
The separation of saponin V.With ethyl acetate：N-butanol：Water=2:3:5(V:V:V it is) dicyandiamide solution of high speed adverse current chromatogram, configuration
2000mL mixed liquor, after magnetic agitation 30min, stand overnight, separation phase up and down, the above mutually be used as stationary phase, and lower phase is flows
Dynamic phase.The water bath with thermostatic control circulatory system is opened, temperature stabilization is at 20 DEG C or so.Start to be pumped into stationary phase with 10mL/min speed, treat
Stationary phase is full of whole stream, opens high-speed counter-current chromatograph main frame, the rotating speed of regulation borded pile coil is 1000r/min, so
Mobile phase, while open detection device are pumped into 3mL/min speed afterwards.Treat that mobile phase flows out two phase solvent system in chromatography column
In when reaching balance, mogrosides crude extract is dissolved in the mobile phase of 20~30 times of volumes, injects high speed adverse current chromatogram
Separated, Detection wavelength 210nm, efflux corresponding to first peak (peak 1) of collection, Momordica grosvenori soap is dried in vacuo to obtain after concentration
Glucoside powder.
4) mogrosides powder presses 1 with silica gel:2(M:M ratio) mixes, dry method loading, is first rushed with chloroform full whole
Pillar, then change chloroform：Methanol：Water=90:10:0.5、70:30:0.5、80:36:0.2(V:V:V eluent) is washed successively
It is de-.Efflux 100mL concentrations are collected every time to be evaporated, and with thin-layer chromatography qualitative analysis is carried out after a small amount of methanol dissolving, work as outflow
When liquid is equal with the Rf value Rf of the standard items of saponin V, now the chloroform of ratio used, methanol and water mixed liquid continue to elute use,
Until this collection part flows completely out.Corresponding efflux is collected, is concentrated, is the prepared product of mogrosides V after vacuum drying.
By being with the detection of the identical of embodiment one, the mogrosides V of the preparation of the embodiment of the present invention two, its purity
95%, extraction rate reached to 90%.
The of embodiment three
The preparation method of mogrosides V comprises the following steps in the present embodiment：
1) after Momordica grosvenori is crushed, extracted 3 times in 70 DEG C with water of the volume equivalent to 3 times, extract 1h every time, merge water extraction
Liquid, with the filtered through gauze of 200 mesh, the concentration of filtrate rotary evaporation, concentrate 5000r/min centrifugation 30min, obtain Momordica grosvenori water extraction
Liquid.
2) Aqueous extracts carry out ADS-8 macroporous adsorbent resin column chromatographies, are eluted with 60% ethanol solution, flow velocity 2mL/min,
Collect eluent, rotary evaporation concentration.Concentrate crosses 700B decolorizing resins, is eluted with pure water, and after eluent concentration, vacuum is done
Dry, it is mogrosides crude extract to obtain pale yellow powder.
3) high speed adverse current chromatogram combinesPrime plus high-pressure pumps and a constant temperature circulating tank are used for Momordica grosvenori
The separation of saponin V.With ethyl acetate：N-butanol：Water=4:1:5(V:V:V it is) dicyandiamide solution of high speed adverse current chromatogram, configuration
2000mL mixed liquor, after magnetic agitation 30min, stand overnight, separation phase up and down, the above mutually be used as stationary phase, and lower phase is flows
Dynamic phase.The water bath with thermostatic control circulatory system is opened, temperature stabilization is at 30 DEG C or so.Start to be pumped into stationary phase with 10mL/min speed, treat
Stationary phase is full of whole stream, opens high-speed counter-current chromatograph main frame, the rotating speed of regulation borded pile coil is 800r/min, then
Mobile phase, while open detection device are pumped into 2mL/min speed.Treat that mobile phase flows out two phase solvent system in chromatography column
When reaching balance, mogrosides crude extract is dissolved in the mobile phase of 20~30 times of volumes, injection high speed adverse current chromatogram enters
Row separation, Detection wavelength 210nm, efflux corresponding to first peak (peak 1) of collection, mogrosides are dried in vacuo to obtain after concentration
Powder.
4) mogrosides powder presses 1 with silica gel:1(M:M ratio) mixes, dry method loading, is first rushed with chloroform full whole
Pillar, then change chloroform：Methanol：Water=90:10:0.5、70:30:0.5、80:36:0.2(V:V:V eluent) is washed successively
It is de-.Efflux 100mL concentrations are collected every time to be evaporated, and with thin-layer chromatography qualitative analysis is carried out after a small amount of methanol dissolving, work as outflow
When liquid is equal with the Rf value Rf of the standard items of saponin V, now the chloroform of ratio used, methanol and water mixed liquid continue to elute use,
Until this collection part flows completely out.Corresponding efflux is collected, is concentrated, is the prepared product of mogrosides V after vacuum drying.
By being with the detection of the identical of embodiment one, the mogrosides V of the preparation of the embodiment of the present invention three, its purity
99.2%, extraction rate reached to 95.8%.
Above-mentioned steps 1) -4) in concentration refer both to be concentrated into the 1/4 of original volume on the rotary evaporator, step 3), 4) in
Vacuum drying refer both to be freeze-dried under -60~-40 DEG C, relative degree of vacuum -0.1~-0.08MPa.
The model HSCCC-TBE300A (Shanghai Tongtian Biotechnology Co., Ltd.) of above-mentioned high speed adverse current chromatogram.
Claims (7)
1. a kind of preparation method of mogrosides V, it is characterised in that comprise the following steps：
1) Momordica grosvenori crushes, and with flooding, filters, concentrates, centrifugation, and centrifugation gained supernatant liquor is Momordica grosvenori Aqueous extracts；
2) the Momordica grosvenori Aqueous extracts obtained by step 1) are subjected to macroporous adsorbent resin column chromatography, eluted with ethanol solution, eluent
Decolorizing resin is crossed after concentration, is eluted with water, eluent concentration, obtains mogrosides crude extract；
3) by obtained by step 2) mogrosides crude extract carry out high speed adverse current chromatogram separation, dicyandiamide solution use volume ratio for
(1~4):(1~5):Ethyl acetate, n-butanol and the water of (5~6), standing separation after being mixed with ethyl acetate, n-butanol and water
Upper phase be stationary phase, using ethyl acetate, n-butanol and water mix after standing separation lower floor's liquid phase as mobile phase；Then
Efflux is collected according to the ultraviolet detection collection of illustrative plates of effluent in detector, concentrated, vacuum drying, obtains mogrosides powder；
4) the mogrosides powder obtained by step 3) is subjected to silica gel post separation, eluted with chloroform, methanol and water mixed solution,
Efflux is collected, is concentrated, vacuum drying, obtains mogrosides V.
2. the preparation method of mogrosides V according to claim 1, it is characterised in that the step 1) uses water logging
Carry specifically refer to mangosteen powder mince volume 3~5 times of water in 70~80 DEG C extract 1~3 time, every time extract 1~3h.
3. the preparation method of mogrosides V according to claim 1, it is characterised in that the centrifugation tool of the step 1)
Body refers to that 5000~8000r/min centrifuges 10~30min.
4. the preparation method of mogrosides V according to claim 1, it is characterised in that the ethanol of the step 2) is molten
Liquid is the ethanol water that volume fraction is 60-80%, and the ethanol solution flow velocity is 2-3mL/min.
5. the preparation method of mogrosides V according to claim 1, it is characterised in that the high speed of the step 3) is inverse
Flow chromatography separation controls separation temperature stable at 20~30 DEG C by constant temperature circulating tank.
6. the preparation method of mogrosides V according to claim 1, it is characterised in that the step 3) according to stream
The ultraviolet detection collection of illustrative plates collection efflux for going out thing specifically refers to the ultraviolet chromatogram according to wavelength 210nm, collected and first peak
Efflux corresponding to retention time.
7. the preparation method of mogrosides V according to claim 1, it is characterised in that the step 1) -4) it is dense
Contracting specifically refers to be concentrated into the 1/4 of original volume on the rotary evaporator, the step 3), vacuum drying 4) specifically refer to-
60~-40 DEG C, be freeze-dried under relative degree of vacuum -0.1~-0.08MPa.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102180930A (en) * | 2011-01-24 | 2011-09-14 | 南京泽朗医药科技有限公司 | Method for purifying siamenoside I |
| CN104059122A (en) * | 2014-05-06 | 2014-09-24 | 义乌章舸生物工程有限公司 | Method for preparing high-purity triterpene glucoside V |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102942611A (en) * | 2012-12-07 | 2013-02-27 | 上海交通大学 | Method for preparing high-purity siamenoside I |
| CN103993064B (en) * | 2014-05-16 | 2016-01-20 | 广西壮族自治区中国科学院广西植物研究所 | The preparation method of a kind of sweeting agent Simon glycosides I |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102180930A (en) * | 2011-01-24 | 2011-09-14 | 南京泽朗医药科技有限公司 | Method for purifying siamenoside I |
| CN104059122A (en) * | 2014-05-06 | 2014-09-24 | 义乌章舸生物工程有限公司 | Method for preparing high-purity triterpene glucoside V |
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