CN108440617A - A method of extracting glucoside compound from the coptis - Google Patents
A method of extracting glucoside compound from the coptis Download PDFInfo
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- CN108440617A CN108440617A CN201810652319.0A CN201810652319A CN108440617A CN 108440617 A CN108440617 A CN 108440617A CN 201810652319 A CN201810652319 A CN 201810652319A CN 108440617 A CN108440617 A CN 108440617A
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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
Abstract
The method that the invention discloses a kind of to extract glucoside compound from the coptis, the extracting method include the following steps：Step A takes coptis root, adds flooding, obtains rhizoma extracting liquid；Step B takes rhizoma extracting liquid, adjusts pH value and carries out the biological alkali process of acidification precipitation, filtrate is adjusted back pH value after filtering, it is spare to collect liquid；Step C, the liquid that the step B is collected carry out separating-purifying and obtain compound shown in formula (I).Highly safe a small amount of ethyl alcohol and completely harmless water are used only in overall process of the present invention as solvent, the higher purity of hypoglycemic medical value can be extracted and be up to glucoside compound shown in 95% or more formula (I), berbine alkaloid can be obtained again as byproduct, this method is environmentally protective, it will not result in waste of resources, be conducive to realize the comprehensive utilization to active ingredient in the coptis.
Description
Technical field
The present invention relates to medicinal chemistry arts, and in particular to a method of extracting glucoside compound from the coptis.
Background technology
The coptis (Coptis chinensis Franch.) belongs to Ranunculaceae, Coptis herbaceos perennial.Most early in
《Sheng Nong's herbal classic》In it is just on the books, color is yellow due to its rhizome is in beaded, is China tradition medium-height grass so being referred to as " coptis "
Medicine.Coptis bitter taste cold in nature, the thoughts of returning home, liver, large intestine channel.Energy heat-clearing and damp-drying drug, purging intense heat and detonicating are suitable for pyreticosis high fever, chase after the absurd row of blood, the heart
The illnesss such as fiery dysphoria, gastropyretic vomiting, damp-heat dysentery, sore swell and ache curative.Wild or cultivation is in the mountain valley of height above sea level 1000-1900m
In cool wet concealment thick forest, it is distributed mainly on the provinces such as Sichuan, Chongqing, Hubei, Hunan, Shaanxi and Gansu.Its chemical composition mainly has
2 class of alkaloid and lignanoid, includes additionally phenolic acid, volatile oil, flavonoids, cumarin, terpene, steroidal, polysaccharide etc..It is modern
Pharmaceutical research confirms that coptis extract has antibacterial anti-inflammatory, anti diar rhea, tranquilizing soporific, antiulcer, blood pressure lowering, blood fat and blood
Sugar, anti-arrhythmia, it is antitumor the effects that.
Existing literature《The separation and identification of coptis Aqueous extracts chemical composition》(Li Xuegai etc., Shenyang Pharmaceutical University's journal,
The 3rd phase of volume 29 in March, 2012, the 193-198 pages) in the compound 15 reported detach obtain from coptis plant for the first time, but
It is there are extraction step complexity, cost is higher, and yield and the relatively low problem of purity.
Invention content
The technical problem to be solved by the present invention is to：For glucoside compound shown in extraction formula (1) in the prior art
Method is complex, and yield and purity are relatively low, and the present invention provides the one kind to solve the above problems, and glucosides is extracted from the coptis
The method of class compound.
The present invention is achieved through the following technical solutions：
A method of extracting glucoside compound from the coptis, shown in the structural formula such as formula (I) of the compound,
The extracting method includes the following steps：
Step A takes coptis root, adds water or alcohol steep or refluxing extraction, obtains rhizoma extracting liquid；
Step B takes rhizoma extracting liquid, control ph to carry out that biological alkali process is precipitated, and it is spare that liquid is collected after filtering；
Step C, the liquid that the step B is collected carry out separating-purifying and obtain compound shown in formula (I).
Preferably, in the step A, coptis root powder is first taken to impregnate 20~30min, wherein coptis root and water or 0-
The quality proportioning of 100% ethanol water is 1:2~1:20.
Preferably, in the step A, after dipping, then through soak at room temperature 8-30h；Or heat water to 30~100 DEG C
Extraction takes 0.5~4h；Or 0.5~4h of refluxing extraction.
Preferably, in the step B, control ph is between 3~7,0.5~30h of stewing process；Filtrate pH value after filtering
Control is in 3~7 ranges.
Preferably, in the step B, first the rhizoma extracting liquid is carried out to be concentrated into the 1/20~1/ of former extracting liquid volume
After 2, then carry out that biological alkali process is precipitated.
Preferably, in the step C, the liquid of collection is subjected to separating-purifying through macroporous resin column, reversed-phase column successively.
Preferably, before using macroporous resin column separating-purifying, will first prepare the sample pH control of upper post separation 6~
10。
Preferably, during using macroporous resin column separating-purifying, pure water, 5%v/v ethyl alcohol, 15%v/v second are used successively
Alcohol is eluted；Or eluted successively using pure water, the buck that pH is 8~13, finally merge and collects containing formula (I) compound
Eluent.
Preferably, during using reversed-phase column separating-purifying, 0 → 50% 0.5~3h of gradient elution of ethanol water is used；
Or 0 → 50% 0.5~3h of gradient elution of methanol aqueous solution is used, finally merge and collects the eluent containing formula (I) compound.
Preferably, it after using macroporous resin column and reversed-phase column separating-purifying, is detected by thin-layer chromatography tracking and HPLC
It determines target fraction, finally remerges and collect the eluent containing formula (I) compound.
Preferably, the macroporous resin column or use 4 × 40cm glass chromatography columns, or 5 × 30cm glass chromatography columns are used,
Or 10 × 150cm glass chromatography columns are used, or 3 × 30cm glass chromatography columns are used, with D101 macroreticular resins or AB-8 macropore trees
Fat or D3520 macroreticular resins or X-5 macroreticular resins are that filler loads pillar, and column temperature is room temperature, and pressure is atmospheric pressure；It is described anti-
To column or the glass column for the ODS-SM-50C for using 37 × 300mm, filler is Cosmosil 75C18-PREP, or is used
Flash prepacked columns, filler AQ-C18, specification 120g or 300g.
The present invention has the advantage that and advantageous effect：
1, the present invention provides this method for extracting compound from coptis root, and coptis root is first passed through flooding, acid
Change is handled, and is contained the extracting solution of (I) glucoside compound to greatest extent, and eliminates most of biological alkaloid substance, finally
It is corresponding improve, optimization isolates and purifies operation, can obtain that yield is higher and purity be up to 95% or more formula (I) glycoside
Compound, integrated operation step simply, conveniently, take shorter；
2, compound shown in the formula (I) that preparation method of the present invention obtains has good blood sugar decreasing effect, in treatment glycosuria
There is higher application value in terms of disease and diabetic complication；
3, the extract of berbine alkaloid component can be obtained in preparation method of the present invention simultaneously, specifically, in step B
In, after acidification, the filter residue obtained through filtering can get berbine alkaloid after the processing of prior art means, therefore
Method provided by the invention is environmentally protective, will not result in waste of resources, and is conducive to realize and be extracted to the comprehensive of active ingredient in the coptis
It utilizes.
Specific implementation mode
To make the objectives, technical solutions, and advantages of the present invention clearer, with reference to embodiment, the present invention is made
Further to be described in detail, exemplary embodiment of the invention and its explanation are only used for explaining the present invention, are not intended as to this
The restriction of invention.
Embodiment 1
The method that the present embodiment provides a kind of to extract compound shown in formula I from the coptis, concrete operation step are as follows：
1) impurity elimination is cleaned into coptis root, crushed after being dried obtains coptis powder, weighs 100g coptis powders, and the water of 8 times of amounts is added
20min is impregnated, 30 DEG C of water-bath temperature extractions take 4h；Filtering extracts the filter residue repetition above method once again, and merging is filtered twice
Liquid obtains Rhizoma Coptidis extracting solution；
2) Rhizoma Coptidis extracting solution is concentrated under reduced pressure into the 1/6 of former extracting solution, uses a concentration of 35~37% concentrated hydrochloric acid
The pH value for adjusting concentrate is 4, stands acidification 1h so that alkaloid is fully at salting out, filtering is water-soluble with 10% sodium hydroxide
The pH value of filtrate is pulled back to 6 by liquid；
3) filtrate is concentrated, upper macroporous resin column is detached, and is first eluted using the pure water of 2 times of column volumes, then
5% ethyl alcohol of 1 times of column volume, 15% ethanol elution of 2 times of column volumes are used successively, by eluent fraction and are detected, are closed
And it collects and contains formula (I) combinations of materials solution concentrate.Wherein, macroporous resin column uses 4 × 40cm glass chromatography columns, with D101
Macroreticular resin is that filler loads pillar, and column temperature is room temperature, and pressure is atmospheric pressure；Fraction detection method tracks for thin-layer chromatography, makes
It is detected with sugared chromogenic reagent.
The concentrate loading of substance solution containing glycoside after macroreticular resin is isolated and purified is water-soluble using ethyl alcohol to reversed-phase column
0 → 25% automatic gradient elution 2h of liquid, automatic gradient table is as shown in table 1, detects fraction, merges, collects elution fraction, i.e.,
Formula (I) combinations of materials ingredient must be contained.Wherein, reversed column uses the glass column of the ODS-SM-50C of 37 × 300mm, filler
For Cosmosil 75C18-PREP.Preparative chromatograph is pressed in the MP200 that instrument is Agela Technologies；Its fraction is examined
Survey method is identical as macroreticular resin fraction detection, is tracked using thin layer, after primarily determining the fraction containing target product, selectivity
Carry out HPLC detections after to determine final goal fraction.
The yield of final obtained product is that detect its purity be 95.67% to 66%, HPLC.
1 reverse phase gradient table of table
Product purity detection method is as follows：
Product obtained is detected using LC-16 Shimadzus high performance liquid chromatograph, precision weighs 5mg final products and sets
After dissolving constant volume in 5mL volumetric flasks, purity detecting is carried out to it under following chromatographic condition.
Chromatographic column：Diamosil C18(2)(250×4.6mm,5μm)
Detection wavelength：220nm
Flow velocity：1.0mL/min
Column temperature：30℃
Sample size：20μL
Mobile phase：- 0.1% trifluoroacetic acid aqueous solution of acetonitrile (gradient is shown in Table 2)
2 HPLC gradients of table
Embodiment 2
The method that the present embodiment provides a kind of to extract compound shown in formula I from the coptis, concrete operation step are as follows：
1) impurity elimination is cleaned into coptis root, crushed after being dried obtains coptis powder, weighs 300g coptis powders, and the water of 10 times of amounts is added
25min is impregnated, 100 DEG C of water-bath temperature extractions take 0.5h；The filter residue repetition above method is extracted once, merges two by filtering again
Secondary filtrate obtains Rhizoma Coptidis extracting solution；
2) Rhizoma Coptidis extracting solution is concentrated under reduced pressure into the 1/8 of former extracting solution, uses a concentration of 35~37% concentrated hydrochloric acid
The pH value for adjusting concentrate is 3.5, stands acidification 1.2h so that alkaloid filters, fully at salting out with 10% sodium hydroxide
The pH value of filtrate is pulled back to 6.5 by aqueous solution；
3) filtrate is concentrated, upper macroporous resin column is detached, and is first eluted using the pure water of 2 times of column volumes, then
5% ethyl alcohol of 1 times of column volume, 15% ethanol elution of 2 times of column volumes are used successively, by eluent fraction and are detected, are closed
And it collects and contains formula (I) combinations of materials solution concentrate.Wherein, macroporous resin column uses 4 × 40cm glass chromatography columns, with AB-8
Macroreticular resin is that filler loads pillar, and column temperature is room temperature, and pressure is atmospheric pressure；Fraction detection method tracks for thin-layer chromatography, makes
It is detected with sugared chromogenic reagent.
The concentrate loading of substance solution containing glycoside after macroreticular resin is isolated and purified is water-soluble using ethyl alcohol to reversed-phase column
0 → 30% gradient elution 2h of liquid, automatic gradient table is as shown in table 3, detect fraction, merge, collect elution fraction to get containing
Formula (I) combinations of materials ingredient.Wherein, reversed column uses the glass column of the ODS-SM-50C of 37 × 300mm, filler to be
Cosmosil 75C18-PREP.Preparative chromatograph is pressed in the MP200 that instrument is Agela Technologies；Its fraction detects
Method is identical as macroreticular resin fraction detection, is tracked using thin layer, selective after primarily determining the fraction containing target product
Final goal fraction is had determined that after carrying out HPLC detections.
The yield of final obtained product is that 65%, HPLC detection purity is 97.03%.Method for detecting purity is the same as " embodiment
Detection in 1 ".
3 reverse phase gradient table of table
Embodiment 3
The method that the present embodiment provides a kind of to extract compound shown in formula I from the coptis, concrete operation step are as follows：
1) impurity elimination is cleaned into coptis root, crushed after being dried obtains coptis powder, weighs 220g coptis powders, and the water of 6 times of amounts is added
30min is impregnated, 80 DEG C of water-bath temperature extractions take 1.5h；The filter residue repetition above method is extracted once, is merged twice by filtering again
Filtrate obtains Rhizoma Coptidis extracting solution；
2) Rhizoma Coptidis extracting solution is concentrated under reduced pressure into the 1/10 of former extracting solution, uses a concentration of 35~37% concentrated hydrochloric acid
The pH value for adjusting concentrate is 4.5, stands acidification 1.5h so that alkaloid filters, fully at salting out with 10% sodium hydroxide
The pH value of filtrate is pulled back to 5.6 by aqueous solution；
3) filtrate is concentrated, upper macroporous resin column is detached, and is first eluted using the pure water of 2 times of column volumes, then
5% ethyl alcohol of 1 times of column volume, 15% ethanol elution of 2 times of column volumes are used successively, by eluent fraction and are detected, are closed
And it collects and contains formula (I) combinations of materials solution concentrate.Wherein, macroporous resin column uses 4 × 40cm glass chromatography columns, with D101
Macroreticular resin is that filler loads pillar, and column temperature is room temperature, and pressure is atmospheric pressure；Fraction detection method tracks for thin-layer chromatography, makes
It is detected with sugared chromogenic reagent.
The concentrate loading of substance solution containing glycoside after macroreticular resin is isolated and purified is water-soluble using ethyl alcohol to reversed-phase column
0 → 25% automatic gradient elution 2h of liquid, automatic gradient table is as shown in table 1, detects fraction, merges, collects elution fraction, i.e.,
Formula (I) combinations of materials ingredient must be contained.Wherein, reversed column uses the glass column of the ODS-SM-50C of 37 × 300mm, filler
For Cosmosil 75C18-PREP.Preparative chromatograph is pressed in the MP200 that instrument is Agela Technologies；Its fraction is examined
Survey method is identical as macroreticular resin fraction detection, is tracked using thin layer, after primarily determining the fraction containing target product, selectivity
Carry out HPLC detections after have determined that final goal fraction.
The yield of final obtained product is that 63%, HPLC detection purity is 95%, and method for detecting purity is the same as in " embodiment 1 "
Detection.
Embodiment 4
The method that the present embodiment provides a kind of to extract compound shown in formula I from the coptis, concrete operation step are as follows：
1) impurity elimination is cleaned into coptis root, crushed after being dried obtains coptis powder, weighs 400g coptis powders, 2 times of amounts of addition
15% ethanol water impregnates 30min, refluxing extraction 2h；The filter residue repetition above method is extracted once, is merged by filtering again
Filtrate obtains Rhizoma Coptidis extracting solution twice；
2) Rhizoma Coptidis extracting solution is concentrated under reduced pressure into the 1/4 of former extracting solution, the pH value for measuring concentrate is 5.67, is stood
Overnight, so that alkaloid is fully precipitated, filtering；
3) filtrate is concentrated, after concentrate pH is adjusted to 8.96 using 10% sodium hydrate aqueous solution, upper macroporous resin column
Detached, first eluted using the pure water of 2 times of column volumes, then use 4 times of column volumes buck (pH=10~12) into
Row elution, by eluent fraction and is detected, and merges and collects containing formula (I) combinations of materials solution concentrate.Wherein, macropore tree
Fat column uses 5 × 30cm glass chromatography columns, loads pillar by filler of D101 macroreticular resins, column temperature is room temperature, and pressure is air
Pressure；Fraction detection method tracks for thin-layer chromatography, is detected using sugared chromogenic reagent.
The concentrate loading of substance solution containing glycoside after macroreticular resin is isolated and purified is water-soluble using ethyl alcohol to reversed-phase column
Liquid gradient elution 1.5h, gradient table is as shown in table 4, detects fraction, merges, collects elution fraction to get containing formula (I) chemical combination
Object material composition.Wherein, reversed column uses the Flash prepacked columns of 120g, filler AQ-C18.Instrument is Agela
Preparative chromatograph is pressed in the MP200 of Technologies；Its fraction detection method is identical as macroreticular resin fraction detection, and use is thin
Layer tracking, after primarily determining the fraction containing target product, final goal fraction is had determined that after selective carry out HPLC detections.
The yield of final obtained product is that 63%, HPLC detection purity is 95.97%, and method for detecting purity is the same as " embodiment
Detection in 1 ".
4 reverse phase gradient table of table
Embodiment 5
The method that the present embodiment provides a kind of to extract compound shown in formula I from the coptis, concrete operation step are as follows：
1) impurity elimination is cleaned into coptis root, crushed after being dried obtains coptis powder, weighs 500g coptis powders, and the water of 20 times of amounts is added
It impregnates for 24 hours；Filtering extracts the filter residue repetition above method once again, merges filtrate twice and obtains Rhizoma Coptidis extracting solution；
2) Rhizoma Coptidis extracting solution is concentrated under reduced pressure into the 1/20 of former extracting solution, uses a concentration of 35~37% concentrated hydrochloric acid
The pH value for adjusting concentrate is 4.9, stands acidification 4h so that alkaloid filters fully at salting out；
3) filtrate is concentrated, after concentrate pH is adjusted to 9.31 using 10% sodium hydrate aqueous solution, upper macroporous resin column
It is detached, is first eluted using the pure water of 2 times of column volumes, then the buck (pH=12-13) of 5 times of column volumes is used to wash
It is de-, it by eluent fraction and is detected, merges and collect containing formula (I) combinations of materials solution concentrate.Wherein, macroporous resin column
Using 10 × 150cm glass chromatography columns, pillar is loaded by filler of D101 macroreticular resins, column temperature is room temperature, and pressure is atmospheric pressure；
Fraction detection method tracks for thin-layer chromatography, is detected using sugared chromogenic reagent.
The concentrate loading of substance solution containing glycoside after macroreticular resin is isolated and purified is water-soluble using methanol to reversed-phase column
Liquid gradient elution 1.5h, automatic gradient table is as shown in table 5, detects fraction, merges, collects elution fraction to get containing formula (I)
Combinations of materials ingredient.Wherein, reversed column uses the Flash prepacked columns of 300g, filler AQ-C18.Instrument is Agela
Preparative chromatograph is pressed in the MP200 of Technologies；Its fraction detection method is identical as macroreticular resin fraction detection, and use is thin
Layer tracking, after primarily determining the fraction containing target product, final goal fraction is had determined that after selective carry out HPLC detections.
The yield of final obtained product is that 72%, HPLC detection purity is 95.98%, and method for detecting purity is the same as " embodiment
Detection in 1 ".
5 reverse phase gradient table of table
Above-described specific implementation mode has carried out further the purpose of the present invention, technical solution and advantageous effect
It is described in detail, it should be understood that the foregoing is merely the specific implementation mode of the present invention, is not intended to limit the present invention
Protection domain, all within the spirits and principles of the present invention, any modification, equivalent substitution, improvement and etc. done should all include
Within protection scope of the present invention.
Claims (10)
1. a kind of method for extracting glucoside compound from the coptis, which is characterized in that the structural formula of the compound such as formula (I)
It is shown,
The extracting method includes the following steps：
Step A takes coptis root, adds water or alcohol steep or refluxing extraction, obtains rhizoma extracting liquid；
Step B takes rhizoma extracting liquid, control ph to carry out that biological alkali process is precipitated, and it is spare that liquid is collected after filtering；
Step C, the liquid that the step B is collected carry out separating-purifying and obtain compound shown in formula (I).
2. a kind of method for extracting glucoside compound from the coptis according to claim 1, which is characterized in that the step
In rapid A, coptis root powder is first taken to impregnate, wherein coptis root and the quality proportioning of water or 0~100% ethanol water are 1:
2~1:20.
3. a kind of method for extracting glucoside compound from the coptis according to claim 2, which is characterized in that the step
In rapid A, after dipping, then through soak at room temperature 8-30h；Or it heats water to 30~100 DEG C of extractions and takes 0.5~4h；Or reflux
Extract 0.5~4h.
4. a kind of method for extracting glucoside compound from the coptis according to claim 1, which is characterized in that the step
In rapid B, control ph is between 3~7,0.5~30h of stewing process；The control of filtrate pH value is in 3~7 ranges after filtering.
5. a kind of method for extracting glucoside compound from the coptis according to claim 1, which is characterized in that the step
In rapid B, first the rhizoma extracting liquid is carried out after being concentrated into the 1/20~1/2 of former extracting liquid volume, then carry out precipitation alkaloid
Processing.
6. a kind of method for extracting glucoside compound from the coptis according to claim 1, which is characterized in that the step
In rapid C, the liquid of collection is subjected to separating-purifying through macroporous resin column, reversed-phase column successively.
7. a kind of method for extracting glucoside compound from the coptis according to claim 6, which is characterized in that using big
Before the resin column separating-purifying of hole, first the sample pH for preparing upper post separation is controlled 6~10.
8. a kind of method for extracting glucoside compound from the coptis according to claim 6, which is characterized in that using big
During the resin column separating-purifying of hole, eluted successively using pure water, ethyl alcohol；Or pure water is used successively, the alkali that pH is 8~13
Water is eluted, and is finally merged and is collected the eluent containing formula (I) compound.
9. a kind of method for extracting glucoside compound from the coptis according to claim 6, which is characterized in that using anti-
In phase post separation purification process, ethanol water gradient elution is used；Or the water-soluble gradient elution of methanol is used, finally merge and collects
Eluent containing formula (I) compound.
10. a kind of method for extracting glucoside compound from the coptis according to claim 6, which is characterized in that use
After macroporous resin column and reversed-phase column separating-purifying, target fraction is determined by thin-layer chromatography tracking and HPLC detections, finally again
Merge and collects the eluent containing formula (I) compound.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112442099A (en) * | 2019-09-03 | 2021-03-05 | 四川大学 | Process for extracting glucopyranoside derivative from crassula argentea |
| CN112442097A (en) * | 2019-08-28 | 2021-03-05 | 四川大学 | Process for extracting glucopyranoside derivative from coptis chinensis |
| CN115677795A (en) * | 2021-07-23 | 2023-02-03 | 四川大学 | Extraction method of glucopyranoside derivative |
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| CN1386527A (en) * | 2001-05-23 | 2002-12-25 | 周亚伟 | Chinese medicine composition for treating diabetes and its preparing process |
| CN107519191A (en) * | 2016-06-22 | 2017-12-29 | 成都中创蜀洋生物科技有限公司 | Glucoside compound is preparing the purposes in treating diabetes medicament |
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| CN1386527A (en) * | 2001-05-23 | 2002-12-25 | 周亚伟 | Chinese medicine composition for treating diabetes and its preparing process |
| CN107519191A (en) * | 2016-06-22 | 2017-12-29 | 成都中创蜀洋生物科技有限公司 | Glucoside compound is preparing the purposes in treating diabetes medicament |
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| SHOJI YAHARA, 等: "Isolation and characterization of phenolic compounds from coptidis rhizome", 《CHEMICAL & PHARMACEUTICAL BULLETIN》 * |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112442097A (en) * | 2019-08-28 | 2021-03-05 | 四川大学 | Process for extracting glucopyranoside derivative from coptis chinensis |
| CN112442099A (en) * | 2019-09-03 | 2021-03-05 | 四川大学 | Process for extracting glucopyranoside derivative from crassula argentea |
| CN115677795A (en) * | 2021-07-23 | 2023-02-03 | 四川大学 | Extraction method of glucopyranoside derivative |
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| CN108440617B (en) | 2020-08-11 |
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