CN106967142A - It is a kind of at the same extract momordica glycoside V, VI and 11 O base glycosides V method - Google Patents
It is a kind of at the same extract momordica glycoside V, VI and 11 O base glycosides V method Download PDFInfo
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- 229930182470 glycoside Natural products 0.000 title claims abstract description 123
- 150000002338 glycosides Chemical class 0.000 title claims abstract description 123
- 235000009815 Momordica Nutrition 0.000 title claims abstract description 57
- 241000218984 Momordica Species 0.000 title claims abstract description 57
- 238000000034 method Methods 0.000 title claims abstract description 34
- 239000000284 extract Substances 0.000 title claims abstract description 19
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims abstract description 82
- 239000004952 Polyamide Substances 0.000 claims abstract description 37
- 229920002647 polyamide Polymers 0.000 claims abstract description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 36
- 241001409321 Siraitia grosvenorii Species 0.000 claims abstract description 29
- 238000002425 crystallisation Methods 0.000 claims abstract description 29
- 230000008025 crystallization Effects 0.000 claims abstract description 29
- 235000011171 Thladiantha grosvenorii Nutrition 0.000 claims abstract description 28
- 239000012452 mother liquor Substances 0.000 claims abstract description 28
- 239000012141 concentrate Substances 0.000 claims abstract description 25
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 21
- LTDANPHZAHSOBN-IPIJHGFVSA-N (2R,3R,4S,5S,6R)-2-[[(2R,3S,4S,5R,6R)-6-[[(3S,8R,9R,10S,11R,13R,14S,17R)-17-[(2R,5R)-5-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-6-hydroxy-6-methylheptan-2-yl]-11-hydroxy-4,4,9,13,14-pentamethyl-2,3,7,8,10,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C([C@H]1O[C@H]([C@@H]([C@@H](O)[C@@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O[C@H](CC[C@@H](C)[C@@H]1[C@]2(C[C@@H](O)[C@@]3(C)[C@@H]4C(C([C@@H](O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO[C@H]6[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O6)O)O5)O[C@H]5[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O5)O)CC4)(C)C)=CC[C@@H]3[C@]2(C)CC1)C)C(C)(C)O)O[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O LTDANPHZAHSOBN-IPIJHGFVSA-N 0.000 claims abstract description 16
- 239000013078 crystal Substances 0.000 claims abstract description 13
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 238000001914 filtration Methods 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 21
- 230000001476 alcoholic effect Effects 0.000 claims description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 238000010828 elution Methods 0.000 claims description 15
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 7
- KTUQUZJOVNIKNZ-UHFFFAOYSA-N butan-1-ol;hydrate Chemical compound O.CCCCO KTUQUZJOVNIKNZ-UHFFFAOYSA-N 0.000 claims description 2
- 239000004760 aramid Substances 0.000 claims 1
- 229920003235 aromatic polyamide Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 230000007613 environmental effect Effects 0.000 abstract description 3
- 239000000243 solution Substances 0.000 description 16
- 229930189775 mogroside Natural products 0.000 description 13
- 241001122767 Theaceae Species 0.000 description 11
- 235000009508 confectionery Nutrition 0.000 description 11
- 239000000203 mixture Substances 0.000 description 10
- 239000012535 impurity Substances 0.000 description 7
- 238000000926 separation method Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 5
- 150000008442 polyphenolic compounds Chemical class 0.000 description 5
- 235000013824 polyphenols Nutrition 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 4
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 4
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000010812 external standard method Methods 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 229930003944 flavone Natural products 0.000 description 2
- 150000002213 flavones Chemical class 0.000 description 2
- 235000011949 flavones Nutrition 0.000 description 2
- 150000004676 glycans Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229920001282 polysaccharide Polymers 0.000 description 2
- 239000005017 polysaccharide Substances 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 235000021022 fresh fruits Nutrition 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 229930182478 glucoside Natural products 0.000 description 1
- 150000008131 glucosides Chemical group 0.000 description 1
- 125000002791 glucosyl group Chemical group C1([C@H](O)[C@@H](O)[C@H](O)[C@H](O1)CO)* 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 235000021096 natural sweeteners Nutrition 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- DKVBOUDTNWVDEP-NJCHZNEYSA-N teicoplanin aglycone Chemical compound N([C@H](C(N[C@@H](C1=CC(O)=CC(O)=C1C=1C(O)=CC=C2C=1)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)OC=1C=C3C=C(C=1O)OC1=CC=C(C=C1Cl)C[C@H](C(=O)N1)NC([C@H](N)C=4C=C(O5)C(O)=CC=4)=O)C(=O)[C@@H]2NC(=O)[C@@H]3NC(=O)[C@@H]1C1=CC5=CC(O)=C1 DKVBOUDTNWVDEP-NJCHZNEYSA-N 0.000 description 1
- -1 triterpene glucoside Chemical class 0.000 description 1
- 150000003648 triterpenes Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J17/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, having an oxygen-containing hetero ring not condensed with the cyclopenta(a)hydrophenanthrene skeleton
- C07J17/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cosmetics (AREA)
Abstract
It is a kind of at the same extract momordica glycoside V, VI and 11 O base glycosides V method, comprise the following steps：（1）Momordica glycoside V refinement mother liquor is dissolved, extracting n-butyl alcohol obtains n-butanol layer；（2）Concentration, cooling, crystallization, filtering obtains crystal and crystallization mother liquor, and crystal is dried, and obtains mogroside VI；（3）By crystallization mother liquor concentrations to without alcohol, dissolving crosses polyamide chromatography post, collects efflux, concentrate, dries, obtain momordica glycoside V；（4）Successively chromatographic column is eluted with low alcohol and height alcohol, height alcohol eluen is collected, concentrated, cooling, crystallization is filtered, and is dried, is obtained the O base glycosides V of Momordica grosvenori 11.Purity >=97% of mogroside VI, yield >=83%, purity >=89% of momordica glycoside V, yield >=89%, 11 O base glycosides V purity >=96%, yield >=85% obtained by the inventive method；The inventive method mild condition, safety and environmental protection, suitable for industrialized production.
Description
Technical field
The present invention relates to a kind of method for extracting mogroside, and in particular to a kind of to extract momordica glycoside V, VI simultaneously
With 11-O base glycosides V method.
Background technology
Momordica grosvenori is the traditional medicinal and edible plant of China, and mogroside is its main functional component, is that a class is high
The preferable natural sweetener of sugariness, low-calorie, the concern of people is enjoyed because it has multiple biological activities.Mogroside
Be divided into it is a variety of, research show that mogroside is a kind of triterpene glucoside, its with Aglycone be triterpene alcohol, have two by
The glucoside side chain of less than four glucose unit compositions, is connected with β-glycosidic bond with aglycon, the company between side chain glucose sugar
Key is connect for β -1,6 and β -1,2 glycosidic bonds.Wherein, the content highest of momordica glycoside V, next to that 11-O base glycosides V and glycosides VI, three
The molecular formula for planting sweet tea glycosides is as follows：
Momordica glycoside V
Momordica grosvenori 11-O base glycosides V mogrosides VI
The extraction of mogroside has industrialization experience for many years at home, the separation and purification for momordica glycoside V
Research is than wide.
CN101029071A discloses a kind of method that high-purity Momordia grosvenori aglycone V is prepared from Momordica grosvenori, is with Momordica grosvenori
Fresh fruit is raw material, is extracted by alcohol reflux, ethyl acetate and extracting n-butyl alcohol, polyamide and silica gel column chromatography, obtains Momordica grosvenori
Glycosides V.But, this method is excessively complicated, and production cost is high, and can only obtain a kind of composition of momordica grosvenori glycoside V.
CN106074669A discloses a kind of extracting method of Momordica grosvenori polyphenol, is, using Momordica grosvenori pericarp as raw material, to pass through
It dry, pulverize, EtOH Sonicate is extracted, polycaprolactam, elution, the step such as concentration obtains Momordica grosvenori polyphenol extract.But, should
Method is not directed to the separation method of mogroside.
CN1375499A discloses a kind of method that separation multiple components are extracted from Momordica grosvenori, is using Momordica grosvenori as original
Material, is extracted by buck, fatty alcohol precipitation, the processing such as ion exchange resin, macroreticular resin, polyamide, obtains Momordica grosvenori
Sweet tea glycosides, momordica grosvenori polysaccharide and grosvenor momordica flavonoid.But, the mogroside that this method is obtained is the mixture of a variety of sweet tea glycosides, and
The high purity product of each sweet tea glycosides is not obtained.
CN101851265A discloses a kind of method that various active composition is extracted from dried fructus momordicae, is first by dry arhat
Fruit is enucleated, then is carried by the sudden strain of a muscle that adds water, and is centrifuged, multiple polyamide chromatography, and D213 decolourizes, alcohol precipitation, the step such as enzymolysis, respectively obtains sweet tea
The compositions such as glycosides, polyphenol, polysaccharide, oligosaccharide and amino acid.But, the mogroside that this method is obtained equally is a variety of sweet tea glycosides
Mixture, does not obtain the high purity product of each sweet tea glycosides.
From the foregoing, it will be observed that the existing report for separating and purifying on Momordica grosvenori 11-O base glycosides V and glycosides VI is seldom.In actual production
Obtained Fructus Monordicae extract is typically the mixture of the total glycosides of Momordica grosvenori, therefore, in the urgent need to finding a kind of method, is realized single
The separation of composition, and realize industrialization.
The content of the invention
The technical problems to be solved by the invention are that the drawbacks described above for overcoming prior art to exist is produced there is provided one kind gained
Product purity, high income, cost are low, and process conditions are gentle, and safety and environmental protection extracts mogroside while suitable for industrialized production
V, VI and 11-O base glycosides V method.
The technical solution adopted for the present invention to solve the technical problems is as follows：It is a kind of to extract momordica glycoside V, VI and simultaneously
11-O base glycosides V method, comprises the following steps：
（1）Extracting n-butyl alcohol：Momordica glycoside V refinement mother liquor water is dissolved, n-butanol is added and is extracted, separate aqueous layer,
Obtain n-butanol layer；
（2）Concentrate crystallization：By step（1）Gained n-butanol layer is concentrated under reduced pressure, cooling, stirring and crystallizing, and filtering obtains crystal and positive fourth
Alcohol crystallization mother liquor, crystal is dried, and obtains mogroside VI；
（3）Polyamide chromatography：By step（2）Gained n-butanol crystallization mother liquor is concentrated under reduced pressure into no alcohol, by gained concentrate water
Dissolving, by polyamide chromatography post, collects upper prop efflux, is concentrated under reduced pressure, dry, obtain momordica glycoside V；
（4）Gradient elution：Successively with low alcoholic solution and height alcoholic solution to step（3）Cross the progress of the polyamide chromatography post after post
Elution, collects height alcohol eluen, concentrates, cooling, and crystallization is filtered, and is dried, is obtained Momordica grosvenori 11-O base glycosides V.
Preferably, step（1）In, in the momordica glycoside V refinement mother liquor, the mass content of mogroside VI is 10
~30%, the mass content that the mass content of momordica glycoside V is 10~15%, 11-O base glycosides V is 5~20%.Sieve of the present invention
Chinese fruit sweet tea glycosides V refinement mother liquors are derived from using Fructus Monordicae extract as raw material, and high-purity momordica is prepared with organic solvent crystallization
Produced mother liquor during glycosides V.
Preferably, step（1）In, the mass ratio of the momordica glycoside V refinement mother liquor, water and n-butanol is 1:5~10:
4~30（More preferably 1:5~10:5~15）.The present inventor's research finds, the water miscible impurity of water dissolvable of addition, pigment with
And inorganic salts etc., by being retained in remove in water layer, and the n-butanol added is moderate to the solubility of total glycosides, and can be with moisture
Layer, realizes the separation of impurity and total glycosides, this is that other solvents are irreplaceable.If the consumption of n-butanol is very few, the extraction of total glycosides
Take not thorough；If the consumption of n-butanol is excessive, the task amount of concentration will be increased, and increase material loss.
Preferably, step（2）、（3）In, the temperature being concentrated under reduced pressure be 70~90 DEG C, the vacuum being concentrated under reduced pressure for-
0.06~-0.09MPa, the mass concentration for being concentrated into concentrate is 20~35%（More preferably 25~30%）.If the concentration after concentration
Liquid concentration is too low, then does not reach the concentration of the crystallization of Momordia grosvenori aglycone VI, and Momordia grosvenori aglycone VI can not be separated out fully；If the concentration after concentration
Liquid excessive concentration, then impurity also will precipitation, the purity of reduction product.
Preferably, step（2）In, the temperature of the stirring and crystallizing is 15~30 DEG C, and rotating speed is 60~120r/min, time
For 12~36h.Under the conditions of the crystallization so that the crystal of precipitation is high-purity mogroside VI, other without separating out
Sweet tea glycosides or impurity.
Preferably, step（3）In, the consumption of the water is 18~50 times of concentrate quality（More preferably 20~30 times）.
The purpose dissolved with water is to make concentrate with the state of the aqueous solution by polyamide chromatography column chromatography, is more beneficial for absorption.Polyamides
The absorption of amine is " hydrogen bond principle ", and only the material ability with polyamide formation hydrogen bond is adsorbable thereon, and resin adsorption
There is an optimal concentration, will all cause adsorption rate to decline higher or lower than this concentration, so, it is water-soluble if the consumption of water is very few
The excessive concentration of total material in liquid, then polyamide can not adsorb the impurity such as 11-O base glycosides V and flavones, polyphenol, cause Momordica grosvenori
Sweet tea glycosides V can not be separated with 11-O base glycosides V and impurity；If the consumption of water is excessive, the time of upper prop will be extended, cause manpower, thing
The waste of power.
Preferably, step（3）In, the mesh number of the polyamide is 50~200 mesh, and consumption is the 4~20 of concentrate quality
Times（More preferably 5~10 times）, the ratio of height to diameter of polyamide chromatography post is 1~20:1（More preferably 5~15:1）.Use the mesh of polyamide
Be absorption 11-O base glycosides V so that 11-O base glycosides V and momordica glycoside V separation.If the consumption of polyamide is very few, or chromatography
The ratio of height to diameter of post is too small, will all cause 11-O base glycosides V not to be adsorbed sufficiently；If the consumption of polyamide is excessive, or chromatographic column
Ratio of height to diameter it is excessive, all will increase elution difficulty and the time.
Preferably, step（3）In, the flow velocity of upper prop is 0.5~2.0BV/h.Post bed body in 1BV=1 described in the inventive method
Product.
Preferably, step（4）In, the alcohol in the low alcoholic solution and height alcoholic solution is methanol, ethanol, isopropanol
Or the one or more in n-butanol etc.；The volumetric concentration of the low alcoholic solution is 10~40%（More preferably 15~30%）, institute
The volumetric concentration for stating height alcoholic solution is 50~85%（More preferably 70~80%）.It is different with the polarity of height alcohol using low alcohol,
Carry out gradient elution, gradient elution first removes the impurity such as flavones, polyphenol with low alcohol elution, then with height alcohol by target product
11-O base glycosides V is eluted and collected.
Preferably, step（4）In, the consumption of the low alcoholic solution is 2~5BV, the consumption of height alcoholic solution for 2~
5BV；The flow velocity of the elution is 0.5~2.0BV/h.
Preferably, step（4）In, the temperature of the concentration is 60~80 DEG C, and the mass concentration for being concentrated into concentrate is 25
~45%.
Preferably, step（4）In, the temperature of the crystallization is 15~30 DEG C, and the time is 12~36 h.
The principle of the inventive method is：The composition of momordica glycoside V refinement mother liquor except containing a small amount of momordica glycoside V it
Outside, main composition is 11-O base glycosides V and mogroside VI.Mogroside VI, momordica grosvenori glycoside V and 11-O are extracted at the same time
During base glycosides V, due to mogroside VI, proportion is high in mother liquor, and its polarity is all smaller than other two kinds of sweet tea glycosides, can be just
Crystallize and separate out in butanol, so extracting mogroside VI first；11-O base glycosides V can be with polyamide shape because of its distinctive structure
Into hydrogen bond, therefore polyamide chromatography post can be adsorbed in, and momordica glycoside V can not form hydrogen bond with polyamide, so polyamides
Amine is not adsorbed to momordica glycoside V, thus is separated.
The inventive method has the beneficial effect that：
（1）Momordica glycoside V, VI and 11-O base glycosides V are white powder obtained by the inventive method, are examined through high performance liquid chromatography
Survey, purity >=97% of mogroside VI, yield >=83%, purity >=89% of momordica glycoside V, yield >=89%, 11-O base
Glycosides V purity >=96%, yield >=85%；Realize and extract momordica glycoside V, VI from momordica glycoside V refinement mother liquor simultaneously
With 11-O base glycosides V, the utilization rate of Momordica grosvenori resource is improved, value-added content of product is added；
（2）Separation and purification mode mild condition that the inventive method is used, safety and environmental protection, to equipment without particular/special requirement, suitably
Industrialization production.
Embodiment
With reference to embodiment, the invention will be further described.
Momordica glycoside V refinement mother liquor used in the embodiment of the present invention is limited from Hunan China really living resources share
Company prepares mother liquor produced during high-purity momordica glycoside V with organic solvent crystallization using Fructus Monordicae extract as raw material, warp
High-performance liquid chromatography detection, wherein, the mass content of mogroside VI is 20.1%, and the quality of momordica glycoside V contains
Measure as 10.9%, Momordica grosvenori 11-O base glycosides V mass content is 15.5%；Polyamide used in the embodiment of the present invention（Mesh
Number is 50~100 mesh）It is purchased from Solution on Chemical Reagents in Shanghai company of Chinese Medicine group；Raw material used in the embodiment of the present invention and chemistry
Reagent, unless otherwise specified, is obtained by routine business approach.
Embodiment 1
（1）Extracting n-butyl alcohol：100g momordica glycoside Vs refinement mother liquor 500g water is dissolved, 500g n-butanols is added and is extracted
Take, separate aqueous layer obtains n-butanol layer；
（2）Concentrate crystallization：By step（1）Gained n-butanol layer is concentrated under reduced pressure into concentration in the case where 80 DEG C, vacuum are -0.07MPa
The mass concentration of liquid is 25%, cooling, under 15 DEG C, rotating speed 120r/min, stirring and crystallizing 12h, and filtering obtains crystal and n-butanol
Crystallization mother liquor, crystal is dried, and obtains 18.2g mogrosides VI；
（3）Polyamide chromatography：By step（2）Gained n-butanol crystallization mother liquor is depressurized dense in the case where 80 DEG C, vacuum are -0.07MPa
No alcohol is reduced to, gained 70g concentrates 1750g water is dissolved, polyamide chromatography post is passed through with 1BV/h flow velocity（Wherein, polyamides
The consumption of amine is 420g, and the ratio of height to diameter of chromatographic column is 10:1）, upper prop efflux is collected, is -0.07MPa in 80 DEG C, vacuum
Under, it is concentrated under reduced pressure, dries, obtain 10.8g momordica glycoside Vs；
（4）Gradient elution：First with the ethanol solution that 2BV volumetric concentrations are 20%, with 0.5BV/h flow velocity to step（3）Cross after post
Polyamide chromatography post eluted, then with 4BV volumetric concentrations be 80% ethanol solution, washed with 0.5BV/h flow velocity
De-, collected volume concentration is the eluent of 80% ethanol solution, and at 65 DEG C, the mass concentration for being concentrated into concentrate is 30%,
Cooling, at 25 DEG C, the h of crystallization 24 is filtered, and is dried, is obtained 13.8g Momordica grosvenori 11-O base glycosides V.
Momordica glycoside V, VI and 11-O base glycosides V are white powder obtained by the present embodiment, through high performance liquid chromatography external standard
Method detects that the purity of gained mogroside VI is 97.5%, and yield is 88.28%；The purity of momordica glycoside V is 91.9%, is received
Rate is 91.06%；Momordica grosvenori 11-O base glycosides V purity is 98.2%, and yield is 87.43%.
Embodiment 2
（1）Extracting n-butyl alcohol：200g momordica glycoside Vs refinement mother liquor 1600g water is dissolved, 2400g n-butanols is added and carries out
Extraction, separate aqueous layer obtains n-butanol layer；
（2）Concentrate crystallization：By step（1）Gained n-butanol layer is concentrated under reduced pressure into concentration in the case where 85 DEG C, vacuum are -0.08MPa
The mass concentration of liquid is 30%, cooling, under 30 DEG C, rotating speed 80r/min, stirring and crystallizing 36h, filtering, obtains crystal and n-butanol analysis
Brilliant mother liquor, crystal is dried, and obtains 34.3g mogrosides VI；
（3）Polyamide chromatography：By step（2）Gained n-butanol crystallization mother liquor is depressurized dense in the case where 85 DEG C, vacuum are -0.08MPa
No alcohol is reduced to, gained 135g concentrates 2700g water is dissolved, polyamide chromatography post is passed through with 0.5BV/h flow velocity（Wherein,
The consumption of polyamide is 1350g, and the ratio of height to diameter of chromatographic column is 8:1）, collect upper prop efflux, 85 DEG C, vacuum for-
Under 0.08MPa, it is concentrated under reduced pressure, dries, obtain 20.8g momordica glycoside Vs；
（4）Gradient elution：First with the methanol solution that 3BV volumetric concentrations are 15%, with 1BV/h flow velocity to step（3）Cross after post
Polyamide chromatography post is eluted, then with the methanol solution that 5BV volumetric concentrations are 75%, is eluted with 1BV/h flow velocity, is received
Collect eluent of the volumetric concentration for 75% methanol solution, at 60 DEG C, the mass concentration for being concentrated into concentrate is 35%, cooling,
At 15 DEG C, the h of crystallization 18 is filtered, and is dried, is obtained 27.3g Momordica grosvenori 11-O base glycosides V.
Momordica glycoside V, VI and 11-O base glycosides V are white powder obtained by the present embodiment, through high performance liquid chromatography external standard
Method detects that the purity of gained mogroside VI is 98%, and yield is 83.62%；The purity of momordica glycoside V is 93.5%, yield
For 89.21%；Momordica grosvenori 11-O base glycosides V purity is 96.9%, and yield is 85.33%.
Embodiment 3
（1）Extracting n-butyl alcohol：150g momordica glycoside Vs refinement mother liquor 900g water is dissolved, 900g n-butanols is added and is extracted
Take, separate aqueous layer obtains n-butanol layer；
（2）Concentrate crystallization：By step（1）Gained n-butanol layer is concentrated under reduced pressure into concentration in the case where 75 DEG C, vacuum are -0.06MPa
The mass concentration of liquid is 30%, cooling, under 25 DEG C, rotating speed 60r/min, the h of stirring and crystallizing 24, and filtering obtains crystal and n-butanol
Crystallization mother liquor, crystal is dried, and obtains 25.8g mogrosides VI；
（3）Polyamide chromatography：By step（2）Gained n-butanol crystallization mother liquor is depressurized dense in the case where 75 DEG C, vacuum are -0.06MPa
No alcohol is reduced to, gained 100g concentrates 2000g water is dissolved, polyamide chromatography post is passed through with 1.5BV/h flow velocity（Wherein,
The consumption of polyamide is 500g, and the ratio of height to diameter of chromatographic column is 15:1）, collect upper prop efflux, 75 DEG C, vacuum for-
Under 0.06MPa, it is concentrated under reduced pressure, dries, obtain 16.9g momordica glycoside Vs；
（4）Gradient elution：First with the aqueous isopropanol that 3BV volumetric concentrations are 30%, with 1.5BV/h flow velocity to step（3）Cross post
Polyamide chromatography post afterwards is eluted；The aqueous isopropanol that 5BV volumetric concentrations are 70% is added, is entered with 1.5BV/h flow velocity
Row elution, collected volume concentration is the eluent of 70% aqueous isopropanol, at 75 DEG C, is concentrated into the mass concentration of concentrate
For 40%, cooling, at 30 DEG C, the h of crystallization 36 is filtered, and is dried, is obtained 20.2g Momordica grosvenori 11-O base glycosides V.
Momordica glycoside V, VI and 11-O base glycosides V are white powder obtained by the present embodiment, through high performance liquid chromatography external standard
Method detects that the purity of gained mogroside VI is 97.1wt%, and yield is 83.09%；The purity of momordica glycoside V is 89.6%,
Yield is 92.61%；Momordica grosvenori 11-O base glycosides V purity is 97.9wt%, and yield is 85.06%.
Claims (10)
1. it is a kind of at the same extract momordica glycoside V, VI and 11-O base glycosides V method, it is characterised in that comprise the following steps：
（1）Extracting n-butyl alcohol：Momordica glycoside V refinement mother liquor water is dissolved, n-butanol is added and is extracted, separate aqueous layer,
Obtain n-butanol layer；
（2）Concentrate crystallization：By step（1）Gained n-butanol layer is concentrated under reduced pressure, cooling, stirring and crystallizing, and filtering obtains crystal and positive fourth
Alcohol crystallization mother liquor, crystal is dried, and obtains mogroside VI；
（3）Polyamide chromatography：By step（2）Gained n-butanol crystallization mother liquor is concentrated under reduced pressure into no alcohol, by gained concentrate water
Dissolving, by polyamide chromatography post, collects upper prop efflux, is concentrated under reduced pressure, dry, obtain momordica glycoside V；
（4）Gradient elution：Successively with low alcoholic solution and height alcoholic solution to step（3）Cross the progress of the polyamide chromatography post after post
Elution, collects height alcohol eluen, concentrates, cooling, and crystallization is filtered, and is dried, is obtained Momordica grosvenori 11-O base glycosides V.
2. according to claim 1 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, it is characterised in that：Step
Suddenly（1）In, in the momordica glycoside V refinement mother liquor, the mass content of mogroside VI is 10~30%, momordica glycoside V
Mass content be 10~15%, 11-O base glycosides V mass content be 5~20%.
3. it is according to claim 1 or claim 2 at the same extract momordica glycoside V, VI and 11-O base glycosides V method, it is characterised in that：
Step（1）In, the mass ratio of the momordica glycoside V refinement mother liquor, water and n-butanol is 1:5~10:4~30.
4. according to one of claims 1 to 3 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（2）、（3）In, the temperature being concentrated under reduced pressure be 70~90 DEG C, the vacuum being concentrated under reduced pressure be -0.06~-
0.09MPa, the mass concentration for being concentrated into concentrate is 20~35%.
5. according to one of Claims 1 to 4 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（2）In, the temperature of the stirring and crystallizing is 15~30 DEG C, and rotating speed is 60~120r/min, and the time is 12~36h.
6. according to one of Claims 1 to 5 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（3）In, the consumption of the water is 18~50 times of concentrate quality.
7. according to one of claim 1~6 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（3）In, the mesh number of the polyamide is 50~200 mesh, and consumption is 4~20 times of concentrate quality, aramid layer
The ratio of height to diameter for analysing post is 1~20:1；The flow velocity of upper prop is 0.5~2.0BV/h.
8. according to one of claim 1~7 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（4）In, during the alcohol in the low alcoholic solution and height alcoholic solution is methanol, ethanol, isopropanol or n-butanol
One or more；The volumetric concentration of the low alcoholic solution is 10~40%, the volumetric concentration of the height alcoholic solution for 50~
85%。
9. according to one of claim 1~8 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（4）In, the consumption of the low alcoholic solution is 2~5BV, and the consumption of height alcoholic solution is 2~5BV；The elution
Flow velocity be 0.5~2.0BV/h.
10. according to one of claim 1~9 simultaneously extract momordica glycoside V, VI and 11-O base glycosides V method, its feature
It is：Step（4）In, the temperature of the concentration is 60~80 DEG C, and the mass concentration for being concentrated into concentrate is 25~45%；It is described
The temperature of crystallization is 15~30 DEG C, and the time is 12~36 h.
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| CN110343141A (en) * | 2019-07-22 | 2019-10-18 | 湖南艾达伦科技有限公司 | A kind of preparation method and applications of high-content triterpene glucoside monomer product |
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| CN111333691A (en) * | 2020-04-24 | 2020-06-26 | 永州华茂生物科技有限责任公司 | Preparation method of mogroside V |
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| CN113461765A (en) * | 2021-08-06 | 2021-10-01 | 湖南华诚生物资源股份有限公司 | Separation method of mogroside V and rare mogroside substances |
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| CN113773360A (en) * | 2021-09-13 | 2021-12-10 | 湖南华诚生物资源股份有限公司 | Method for separating mogrol from momordica grosvenori |
| CN113773360B (en) * | 2021-09-13 | 2022-05-31 | 湖南华诚生物资源股份有限公司 | Method for separating mogrol from fructus momordicae |
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Denomination of invention: A method for simultaneous extraction of Mogroside V, VI and 11-o-glycoside V from Siraitia grosvenorii Effective date of registration: 20210422 Granted publication date: 20190702 Pledgee: CITIC Bank Changsha branch Pledgor: HUNAN HUACHENG BIOTECH, Inc. Registration number: Y2021980002898 |
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