CN108484711A - A method of preparing gypenoside LI - Google Patents
A method of preparing gypenoside LI Download PDFInfo
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- CN108484711A CN108484711A CN201810243192.7A CN201810243192A CN108484711A CN 108484711 A CN108484711 A CN 108484711A CN 201810243192 A CN201810243192 A CN 201810243192A CN 108484711 A CN108484711 A CN 108484711A
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- damulin
- gynostemma
- gypenoside
- gynostemma pentaphylla
- silica gel
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- 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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/02—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material
- B01J20/10—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising inorganic material comprising silica or silicate
- B01J20/12—Naturally occurring clays or bleaching earth
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/22—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof comprising organic material
- B01J20/24—Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
Abstract
The invention discloses a kind of methods preparing gypenoside LI,This method is to belong to but the heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv of different subgenus substitute gynostemma pentaphylla Gynostemma pentaphyllum (Thunb.) Makino as raw material,A large amount of gypenoside LVI can be prepared with extraction separation and purification,XLVI,L,LI,Damulin A and damulin B,Gypenoside LVI,XLVI,L,LI,The content of damulin A and damulin B in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv leaves is 10 50 times of the content in gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino leaves respectively；And heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv are not commercialized, unrestrained field be nobody shows any interest in all over the fields, and cost can be ignored.
Description
Technical field
The invention belongs to biomedicine fields, and in particular to a method of preparing gypenoside LI.
Background technology
Gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino also known as Herb Gynostemmae Pentaphylli, Radix Rhodiolae, Herba Gynostemmatis
Deng being the herbaceous perennial vine plant of Curcurbitaceae gynostemma pentaphyllum genus, the area on the south the Qinling Mountains and the Changjiang river be mainly grown in China.
It is first recorded in the Ming Dynasty《Herbal for Relief of Famines》, make edible wild herbs use,《Compendium of Materia Medica》In start its with the name of " Japanese Cayratia Herb " being used as medicine.
《The strong pharmacy of China》：" tri- two-way of Tong Tiao, clearing heat and detoxicating, cough-relieving apophlegmatic.For chronic bronchitis, virus hepatitis, renal plevis kidney
Inflammation, gastroenteritis, diarrhea, hypertension, arteriosclerosis, hyperlipidemia, ulcerative carbuncle pyogenic infections, snake bite ".Main chemical compositions in gynostemma pentaphylla
For saponin(e and polysaccharide, in addition also contain a small amount of flavone compound, terpene, organic acid, protein, vitamin, fat, fiber
Equal ingredients and zinc, copper, magnesium, iron, manganese, selenium and other trace elements.Gynostemma pentaphylla has antitumor, hypoglycemic, anti-aging, anti-liver fiber
The pharmacological actions such as change, principle active component gypenoside excessive use is also without side-effects, thus in health food and novel
There is huge application prospect on drug research and development, is a kind of new medical and edible dual purpose plant resource.
The saponin constituent contained in gynostemma pentaphylla is numerous, study it is more, active it is preferable have gypenoside LVI, XLVI, L,
LI, damulin A (DamulinA) and damulin B (Damulin B).Wherein, gypenoside LVI, XLVI contents are higher, other
Four kinds are the extremely low rare saponin(e of content (for the converted product of gypenoside LVI, XLVI).
Currently, gypenoside LVI, XLVI are obtained by raw material extraction separation and purification of gynostemma pentaphylla, gypenoside L, LI,
Damulin A and damulin B obtain (document using the gynostemma pentaphylla processed by heating as raw material extraction separation and purification：
Determination by UPLC-MS of four dammaranetype saponins from heat-processed
Gynostemma pentaphyllum；Bioscience,Biotechnology,andBiochemistry,2014；Vol.78,
No.2,311-316).Gypenoside LVI, XLVI, L, LI, damulin A and damulin B are prepared using gynostemma pentaphylla as raw material to exist
2 points insufficient：
First, gynostemma pentaphylla price is relatively high, of high cost.Since State Scientific and Technological Commission in 1986 in Spark Program strand
Indigo plant is classified as the first place of " rare traditional Chinese medicine " leaved for development, and the market price of gynostemma pentaphylla is just apparent to go up.
Second, it is very low not heat gypenoside L, LI, damulin A and damulin B in the gynostemma pentaphylla of processing, and separation is pure
It is big to change difficulty；Heating processing is bothersome, and gypenoside L, LI, the content of damulin A and damulin B and asynchronous increasing after heating
Add, acid extraction is difficult to control (above-mentioned citation can also embody this phenomenon).
Gynostemma pentaphyllum genus shares 2 subgenus, 13 kind of 2 mutation, and 2 subgenus are gynostemma pentaphylla subgenus, beak fruit rattan subgenus, above-mentioned gynostemma pentaphylla
Gynostemmapentaphyllum (Thunb.) Makino is one kind (document in gynostemma pentaphylla subgenus：Gynostemma plant
Categorizing system and distribution, Acta Phytotaxonomica Sinica, 1995).Research invention, gynostemma plant all contain gynostemma pentaphylla soap substantially
Glycosides, and type is essentially identical, but the content difference of specific gypenoside is larger in the different plants of the category.Originate from Hu Beixi
The heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv in portion, Southern Shaanxi and Sichuan belong to beak fruit rattan
Subgenus, it is capsule to be mainly characterized by fruit, and top is cracked along ventral suture when ripe, has the 3 pieces of beak styles harbored, other features
It is then almost the same with gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino.Open strand is not yet had been reported that at present
Blue saponin(e LVI, XLVI, L, LI, damulin A, B are in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex
Content in Oliv is significantly higher than gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino.
Invention content
Present invention aims at provide a kind of method preparing gypenoside LI.
Above-mentioned purpose is achieved through the following technical solutions：
Gypenoside LVI, XLVI, L, LI, damulin A and damulin B preparation method include the following steps：
Step S1 collects the leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv, dries in the shade,
With ethanol water heating and refluxing extraction, filtered through gauze, merging filtrate is concentrated into no alcohol taste；
The extracting solution for being concentrated into no alcohol taste is splined on D101 large pore resin absorption columns by step S2, and resin blade diameter length ratio is 1:
10, sample resin accounts for resin total amount 1/10 is mixed, wet method dress post mixes resin loading；First use 30% ethyl alcohol of 10BV with 10BV/h's
Flow velocity elution removal of impurities, then eluted with the flow velocity of 10BV/h with 85% ethyl alcohol of 10BV, 3-10BV eluents are collected, no alcohol is concentrated into
Taste obtains total saposins aqueous solution；
Total saposins aqueous solution is adjusted pH value to 6.0, chitosan/attapulgite clay compound, room temperature is added by step S3
Stirring is stood, filtering, collects filtrate, adjusts pH value to neutrality, freeze-drying obtains refined total saposins powder；
Refined total saposins powder is splined on normal phase silicagel column by step S4, and silica gel blade diameter length ratio is 1:10, it mixes sample silica gel and accounts for silicon
The 1/10 of glue total amount, dry column-packing mix silica gel loading；It is 20 to use volume ratio successively:1:2、10:1:2、5:1:2、2:1:The two of 2
Chloromethanes/methanol/acetone mixed solvent elutes 10BV, 6BV, 5BV, 3BV respectively with the flow-rate gradient elution of 12BV/h；
Step S5, collects 20 respectively:1:The eluent concentration of 2 methylene chloride/methanols/acetone elution 7-8BV, 9-10BV is dry
It is dry to obtain damulin B, damulin A；10 are collected respectively:1:The eluent of 2 methylene chloride/methanols/acetone elution 3-4BV, 5-6BV
Concentrate drying obtains gypenoside L, gypenoside LI；Collect 5:1:2 methylene chloride/methanols/acetone elution 4-5BV's washes
De- liquid is concentrated and dried to obtain gypenoside XLVI；Collect 2:1:The eluent of 2 methylene chloride/methanols/acetone elution 2-3BV is dense
Contracting is dried to obtain gypenoside LVI.
Preferably, chitosan/attapulgite clay compound preparation method is：1g chitosans are dissolved in 100mL mass fractions
To obtain chitosan colloidal sol in 1% aqueous acetic acid, 8g attapulgite clay is added into the colloidal sol, stirring at normal temperature 48h is quiet
Upper solution is poured out after setting 2h, 50 DEG C of drying of residue, grinding, drying.
Preferably, step S1 ethanol waters concentration expressed in percentage by volume is 75%.
Preferably, the solid-to-liquid ratio of step S1 extractions is 1:20.
Preferably, 50g chitosans/attapulgite clay compound is added in 1L total saposins aqueous solutions in step S3.
Preferably, step S3 is stirred for 24 hours after chitosan/attapulgite clay compound is added, and is filtered after standing 2h.
Preferably, step S3 hydrochloric acid and ammonium hydroxide adjust pH.
The technology of the present invention advantage：
1, the present invention is to belong to but the heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex of different subgenus
Gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino are as raw material for Oliv replacements, can be with extraction separation and purification system
It is standby to obtain a large amount of gypenoside LVI, XLVI, L, LI, damulin A and damulin B, gypenoside LVI, XLVI, L, LI, reach
The content difference of the wooden woods A and damulin B in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv leaves
It is 10-50 times of the content in gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino leaves；And heart seed strand
Blue Gynostemma cardiospermum Cogn.ex Oliv are not commercialized, and unrestrained field be nobody shows any interest in all over the fields, and cost can neglect
Slightly.
2, step S3 of the present invention refines total saposins aqueous solution with chitosan/attapulgite clay compound, effectively
The impurity in total saposins is reduced, follow-up normal phase silica gel column chromatography technique is greatlied simplify, product purity is high.
Description of the drawings
Fig. 1 is the efficient liquid phase chromatographic analysis spectrogram of step S2 total saposins aqueous solutions；
Fig. 2 is the efficient liquid phase chromatographic analysis spectrogram that step S3 refines total saposins powder；
Fig. 3 is the efficient liquid phase chromatographic analysis spectrogram for the damulin B that silica gel chromatography obtains；
Fig. 4 is the efficient liquid phase chromatographic analysis spectrogram for the damulin A that silica gel chromatography obtains；
Fig. 5 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside L that silica gel chromatography obtains；
Fig. 6 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside LI that silica gel chromatography obtains；
Fig. 7 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside XLVI that silica gel chromatography obtains；
Fig. 8 is the efficient liquid phase chromatographic analysis spectrogram for the gypenoside LVI that silica gel chromatography obtains.
Specific implementation mode
The essentiality content of the present invention is specifically introduced with reference to embodiment, but it will be appreciated by those skilled in the art that not
Protection scope of the present invention should be confined to these specific embodiments.
One, experiment material
The leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv is collected from Hubei Shiyan City room
The leaf in county, gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino makes collected from Hunan Shaoyang Suining after drying in the shade
With.
Chitosan/attapulgite clay compound preparation method is：It is 1% that 1g chitosans, which are dissolved in 100mL mass fractions,
Chitosan colloidal sol is obtained in aqueous acetic acid, and 8g attapulgite clay, stirring at normal temperature 48h, after standing 2h are added into the colloidal sol
Upper solution is poured out, 50 DEG C of drying of residue, grinding, drying.
Different concentration ethanol refers both to the ethanol water of different volumes percentage concentration.
Two, experimental method
1, the preparation of gypenoside LVI, XLVI, L, LI, damulin A and damulin B
Include the following steps：
Step S1 collects the leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv, dries in the shade,
The ethanol water heating and refluxing extraction for being 75% with concentration expressed in percentage by volume, solid-to-liquid ratio 1:20, it extracts 3 times, each 2h, gauze
Filtering, merging filtrate are concentrated into no alcohol taste；
The extracting solution for being concentrated into no alcohol taste is splined on D101 large pore resin absorption columns by step S2, and resin blade diameter length ratio is 1:
10, sample resin accounts for resin total amount 1/10 is mixed, wet method dress post mixes resin loading；First use 30% ethyl alcohol of 10BV with 10BV/h's
Flow velocity elution removal of impurities, then eluted with the flow velocity of 10BV/h with 85% ethyl alcohol of 10BV, 3-10BV eluents are collected, no alcohol is concentrated into
Taste obtains total saposins aqueous solution；
It is compound that chitosan/attapulgite clay is added in total saposins aqueous solution salt acid for adjusting pH value to 6.0 by step S3
50g chitosans/attapulgite clay compound is added in object, 1L total saposins aqueous solutions, and stirring for 24 hours, is filtered after standing 2h, collects filter
Liquid, ammonium hydroxide adjust pH value to neutrality, and freeze-drying obtains refined total saposins powder；
Refined total saposins powder is splined on normal phase silicagel column by step S4, and silica gel blade diameter length ratio is 1:10, it mixes sample silica gel and accounts for silicon
The 1/10 of glue total amount, dry column-packing, mix silica gel loading (refined total saposins powder dissolved with methanol after with mix sample silica gel and mix
It is even, dry, refined total saposins powder and the mass ratio 1 for mixing sample silica gel:1)；It is 20 to use volume ratio successively:1:2、10:1:2、5:1:
2、2:1:2 methylene chloride/methanol/acetone mixed solvent with the flow-rate gradient elution of 12BV/h, elute respectively 10BV, 6BV,
5BV、3BV；
Step S5, collects 20 respectively:1:The eluent concentration of 2 methylene chloride/methanols/acetone elution 7-8BV, 9-10BV is dry
It is dry to obtain damulin B, damulin A；10 are collected respectively:1:The eluent of 2 methylene chloride/methanols/acetone elution 3-4BV, 5-6BV
Concentrate drying obtains gypenoside L, gypenoside LI；Collect 5:1:2 methylene chloride/methanols/acetone elution 4-5BV's washes
De- liquid is concentrated and dried to obtain gypenoside XLVI；Collect 2:1:The eluent of 2 methylene chloride/methanols/acetone elution 2-3BV is dense
Contracting is dried to obtain gypenoside LVI.
2, efficient liquid phase chromatographic analysis condition
Chromatograph：LC-20ADXR high-pressure pumps；SPD-M20A diode array ultraviolet-visible detectors；CTO-20AC columns
Incubator；CBM-20A system controllers；SIL-20ACXR autosamplers；
Chromatographic column：Agilent ZORBAX Extend-C18 (250mm × 4.6mm, 5 μm)；
Mobile phase A phase：Water (contains 5/10000ths tetrahydrofurans)；
Mobile phase B phase：Acetonitrile (contains 5/10000ths tetrahydrofurans)；
Elution program：0-3min, 20%B phase；3-15min, 20% → 40%B phase；15-30min, 40% → 80%B phase；
Flow velocity：1.0mL/min；
Column temperature：30℃；
Detection wavelength：203nm；
Sample size：10μL.
Three, experimental result
It takes step S2 total saposins aqueous solutions to dilute 5 times and is used as high performance liquid chromatography sample introduction solution, step S3 is taken to refine total soap
Glycosides powder uses the mobile phase of initial proportion to be dissolved into the solution of 0.5mg/mL as high performance liquid chromatography sample introduction solution.Fig. 1 is step
The efficient liquid phase chromatographic analysis spectrogram of rapid S2 total saposins aqueous solutions, Fig. 2 are the high-efficient liquid phase color that step S3 refines total saposins powder
Spectrum analysis spectrogram.From Fig. 1,2 as it can be seen that total saposins aqueous solution complicated component obtained by step S2, step S3 refine impurity in total saposins
Ingredient greatly reduces, and illustrates that chitosan/attapulgite clay compound can the total soap of effective Adsorption under the conditions of 6.0 pH
Impurity component in glycosides aqueous solution.By removal of impurities, contribute to the technology difficulty for reducing follow-up silica gel column chromatography.
Refined total saposins obtained after step S4, S5 silica gel column chromatography separating purification gypenoside LVI, XLVI, L,
LI, damulin A and damulin B monomer.Fig. 3 is the efficient liquid phase chromatographic analysis spectrum for the damulin B that silica gel chromatography obtains
Figure, Fig. 4 are the efficient liquid phase chromatographic analysis spectrogram for the damulin A that silica gel chromatography obtains, and Fig. 5 is silica gel chromatography
The efficient liquid phase chromatographic analysis spectrogram of obtained gypenoside L, Fig. 6 are the gypenoside LI that silica gel chromatography obtains
Efficient liquid phase chromatographic analysis spectrogram, Fig. 7 is the high performance liquid chromatography of gypenoside XLVI that silica gel chromatography obtains
Analysis of spectra, Fig. 8 are the efficient liquid phase chromatographic analysis spectrogram for the gypenoside LVI that silica gel chromatography obtains.From Fig. 3-8
As it can be seen that gypenoside LVI, XLVI, L, LI, damulin A and damulin B purity are very high, 95% or more.By a silicon
Gypenoside LVI, XLVI, L, LI, damulin A and the damulin B of such high-purity can be prepared in plastic column chromatography, mainly
Have benefited from the refining and edulcoration of step S3 chitosans/attapulgite clay compound.
The invention has the advantages that：
The present invention is to belong to but the heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex of different subgenus
Gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino are as raw material for Oliv replacements, can be with extraction separation and purification system
It is standby to obtain a large amount of gypenoside LVI, XLVI, L, LI, damulin A and damulin B, gypenoside LVI, XLVI, L, LI, reach
The content difference of the wooden woods A and damulin B in heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv leaves
It is 12,11,45,37,42,55 times of the content in gynostemma pentaphylla Gynostemmapentaphyllum (Thunb.) Makino leaves
(operating method：The dried leaf of two kinds of gynostemma pentaphylla, solid ratio 1 are directly extracted with methanol:Then height is used in 40, ultrasonic 40min, filtering
Effect liquid phase chromatogram method analyzes filtrate, according to the peak face of gypenoside LVI, XLVI, L, LI, damulin A and damulin B
Its content ratio in two kinds of filtrate is roughly calculated in product ratio)；And heart seed gynostemma pentaphylla Gynostemma cardiospermum
Cogn.ex Oliv are not commercialized, and unrestrained field be nobody shows any interest in all over the fields, and cost of material can be ignored.
Step S3 of the present invention refines total saposins aqueous solution with chitosan/attapulgite clay compound, effectively drops
Impurity in low total saposins, greatlies simplify follow-up normal phase silica gel column chromatography technique, and product purity is high.
Claims (7)
1. a kind of method preparing gypenoside LI, which is characterized in that including as follows：
Step S1 collects the leaf of heart seed gynostemma pentaphylla Gynostemma cardiospermum Cogn.ex Oliv, dries in the shade, use second
Alcohol solution heating and refluxing extraction, filtered through gauze, merging filtrate are concentrated into no alcohol taste；
The extracting solution for being concentrated into no alcohol taste is splined on D101 large pore resin absorption columns by step S2, and resin blade diameter length ratio is 1:10, it mixes
Sample resin accounts for the 1/10 of resin total amount, and wet method dress post mixes resin loading；First washed with the flow velocity of 10BV/h with 30% ethyl alcohol of 10BV
It removes miscellaneous, then is eluted with the flow velocity of 10BV/h with 85% ethyl alcohol of 10BV, collect 3-10BV eluents, be concentrated into no alcohol taste and obtain
Total saposins aqueous solution；
Total saposins aqueous solution is adjusted pH value to 6.0, chitosan/attapulgite clay compound is added, room temperature stirs by step S3
It mixes, stand, filter, collect filtrate, adjust pH value to neutrality, freeze-drying obtains refined total saposins powder；
Refined total saposins powder is splined on normal phase silicagel column by step S4, and silica gel blade diameter length ratio is 1:10, mixing sample silica gel, to account for silica gel total
The 1/10 of amount, dry column-packing mixes silica gel loading；It is 20 to use volume ratio successively:1:2、10:1:2 methylene chloride/methanol/acetone
Mixed solvent elutes 10BV, 6BV respectively with the flow-rate gradient elution of 12BV/h；
Step S5 collects 10:1:The eluent of 2 methylene chloride/methanols/acetone elution 5-6BV is concentrated and dried to obtain gynostemma pentaphylla soap
Glycosides LI.
2. according to the method described in claim 1, it is characterized in that, chitosan/attapulgite clay compound preparation method is：
1g chitosans, which are dissolved in the aqueous acetic acid that 100mL mass fractions are 1%, obtains chitosan colloidal sol, and it is recessed that 8g is added into the colloidal sol
Upper solution is poured out after standing 2h by convex stick stone clay, stirring at normal temperature 48h, 50 DEG C of drying of residue, grinding, drying.
3. according to the method described in claim 1, it is characterized in that：Step S1 ethanol water concentration expressed in percentage by volumes are 75%.
4. according to the method described in claim 3, it is characterized in that：The solid-to-liquid ratio of step S1 extractions is 1:20.
5. according to the method described in claim 1, it is characterized in that：In step S3 1L total saposins aqueous solution be added 50g chitosans/
Attapulgite clay compound.
6. according to the method described in claim 5, it is characterized in that：Chitosan/attapulgite clay compound is added in step S3
After stir for 24 hours, stand 2h after filter.
7. according to the method described in claim 1, it is characterized in that：Step S3 hydrochloric acid and ammonium hydroxide adjust pH.
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| CN201810243192.7A CN108484711B (en) | 2018-03-23 | 2018-03-23 | A method of preparing gypenoside LI |
| PCT/CN2018/093947 WO2019178980A1 (en) | 2018-03-23 | 2018-07-01 | Method for preparing gynostemma pentaphylla makino saponin lvi, xlvi, l, li, damulin a or damulin b |
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| CN110522756A (en) * | 2019-09-06 | 2019-12-03 | 华侨大学 | Gypenoside LVI is preparing the application in antidepressants |
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