CN106632542A - Preparation method of cimicifugoside and 5-O-methylvisammioside reference substances - Google Patents
Preparation method of cimicifugoside and 5-O-methylvisammioside reference substances Download PDFInfo
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
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Abstract
The invention discloses a preparation method of cimicifugoside and 5-O-methylvisammioside reference substances. Particularly, the method comprises the following steps: (i) supplying an alcohol extraction mixture of cimicifugoside and 5-O-methylvisammioside; (ii) mixing the alcohol extraction mixture with a solvent to obtain a first mixture, and separating the first mixture by using a medium-pressure preparation column to obtain a cimicifugoside coarse product and a 5-O-methylvisammioside coarse product; and (iii) recrystallizing the cimicifugoside coarse product and the 5-O-methylvisammioside coarse product by using the solvent to obtain a cimicifugoside reference substance and/or a 5-O-methylvisammioside reference substance. The preparation method can realize synchronous separation of the cimicifugoside and the 5-O-methylvisammioside; with large preparation volume, high yield and high product purity, the preparation method is suitable for industrial production.
Description
Technical field
The invention belongs to modernization of Chinese medicine technical field, is related to a kind of preparation method of traditional Chinese chemical contrast, it is concrete next
Say, the invention provides one kind is from separating high-purity cimicifugoside in Radix Saposhnikoviae medical material and 5-O-methyl-visamminol reference substance
Method.
Background technology
Radix Saposhnikoviae does not take out scape for umbelliferae Saposhnikovia divaricata Saposhnikovia divaricata (Turcz.) Schischk.
Dry root.The ground such as Heilungkiang, the Inner Mongol, Liaoning, Jilin, Hebei and Shandong, adaptability distributed more widely are distributed mainly on now
By force, it is one of the most frequently used Chinese medicine of China, acrid in the mouth glycosides is warm in nature, returns bladder, liver, spleen channel, with inducing diaphoresis to dispel wind, wins wet, only
Effect of convulsion.Cure mainly affection of exogenous wind-cold, headache and dizziness, use up the diseases such as pain, wind and cold paralysis, arthralgia, extremity contraction urgency all over the body.
Cimicifugoside and 5-O-methyl-visamminol are the index components recorded in version in 2010, cimifugin
Glycosides (Prim-O-glucosylcimifugin), molecular formula is C22H28O11, 5-O-methyl-visamminol (5-O-
Methylvisamminol β-D-glucopyranoside), molecular formula is C22H28O10, their structural formula is as follows：
Cimicifugoside and 5-O in Chinese medicine preparation (such as magnolia flower rhinitis-treating pill, YUPINGFENG SAN, virgin Kangping etc.) for Radix Saposhnikoviae composition
The patent of the detection method of methyl visamminol glycosides is more, and the patent application publication of such as application number 201310504883.5 is " pungent
The assay method of smooth ' Biyanwan ' for treating rhinitis content ".And it is at present domestic with regard to cimicifugoside and 5-O-methyl-visamminol reference substance
Isolate and purify document report seldom, in addition, cimicifugoside and 5-O-methyl-visamminol are arranged in 2010 editions pharmacopeia
For standard, the demand of both reference substances is increasing, and especially 5-O-methyl-visamminol content in medical material is very low,
Monomer is isolated from medical material extremely difficult, therefore cimicifugoside and 5-O-methyl-visamminol are isolated and purified from Radix Saposhnikoviae
Reference substance seems very necessary, is with a wide range of applications.
The content of the invention
It is an object of the invention to provide the separation of a kind of cimicifugoside and 5-O-methyl-visamminol reference substance is pure
Change method.The method is not only capable of achieving the separated in synchronization of cimicifugoside and 5-O-methyl-visamminol reference substance, and separates
Efficiency high, process stabilizing are with low cost, can prepare cimicifugoside of the purity more than 99% and 5-O- methyl Wei Sia in a large number
Rice alcohol glycosides reference substance.
A first aspect of the present invention provides the preparation of a kind of cimicifugoside and 5-O-methyl-visamminol reference substance
Method, described method are comprised the following steps：
I () provides the alcohol extraction mixture of cimicifugoside and 5-O-methyl-visamminol；
(ii) the alcohol extraction mixture described in is mixed with solvent, obtains the first mixture, and the standby post separation institute of compacting in utilizing
The first mixture stated, so as to obtain cimicifugoside crude product and 5-O-methyl-visamminol crude product；With
(iii) recrystallization is carried out to cimicifugoside crude product and/or 5-O-methyl-visamminol crude product using solvent, from
And obtain cimicifugoside reference substance and/or 5-O-methyl-visamminol reference substance.
In another preference, the step (ii) also includes step：
(ii-1) using 30-35% (v/v) methanol solutions as the first eluant of the standby post of middle compacting, carrying out the first stage washes
De-, concentrate eluant is obtaining cimicifugoside crude product；With
(ii-2) using 45-50% (v/v) methanol solutions as the second eluant of the standby post of middle compacting, carry out second stage and wash
De-, concentrate eluant is obtaining 5-O-methyl-visamminol crude product.
In another preference, the middle compacting in the step (ii) is provided with post pressure 0-2MPa, preferably 0.5- for post
2MPa。
In another preference, the middle compacting in the step (ii) is selected from the group for the post pressure limit of post：0MPa、
0.1MPa, 0.2MPa, 0.3MPa, 0.4MPa or 0.5MPa.
In another preference, the middle compacting in the step (ii) is selected from the group for the post pressure upper limit of post：2MPa、
2.1MPa, 2.2MPa, 2.3MPa, 2.4MPa or 2.5MPa.
Herein, when the post pressure of the standby post of central compacting is 0MPa, refer to that the standby post of middle compacting is depressed in standard atmosphere.
In another preference, the middle compacting in the step (ii) is octadecylsilane bonded silica for the filler of post
Glue.
In another preference, the middle compacting in the step (ii) is 40-60 μm for the packing material size of post.
In another preference, described cimicifugoside crude product purity >=93.0%.
In another preference, described 5-O-methyl-visamminol crude product purity >=98.0%.
In another preference, the step (iii) also includes step：
(iii-1) the cimicifugoside crude product described in is mixed with pure water and acetone, makes described cimicifugoside crude product mixed
Recrystallization is carried out in bonding solvent；Gained crystal is separated and be dried, that is, obtains cimicifugoside reference substance；And/or
(iii-2) the 5-O-methyl-visamminol crude product described in is mixed with methanol and acetone, makes described 5-O-
Methyl visamminol glycosides crude product carries out recrystallization in mixed solvent；Gained crystal is separated and be dried, that is, obtains 5-O- first
Base visamminol glycosides reference substance.
In another preference, the step (iii-2) is before the step (iii-1), or synchronously carries out.
In another preference, 45-55% (v/v) methanol solutions and described cimicifugoside used in the step (ii)
Mixed with the alcohol extraction mixture of 5-O-methyl-visamminol.
In another preference, pure electrical conductivity of water≤18.2 μ s/cm in the step (iii-1).
In another preference, in the step (iii-2), the purity of methanol is >=99.5%.
In another preference, purity >=99.5% of the acetone of the step (iii-1) and (iii-2).
In another preference, in the step (iii-1), the acetone of addition measures (v/v) for 5-10 times of pure water；With/
Or
In described step (iii-2), the acetone of addition measures (v/v) for 5-10 times of methanol.
In another preference, in the step (iii-1), recrystallization operation number of repetition is more than or equal to 2 times.
In another preference, in the step (iii-2), recrystallization operation number of repetition is more than or equal to 2 times.
In another preference, described cimicifugoside reference substance purity >=99.0%, it is preferred that purity >=99.3%,
More preferably, purity >=99.5%.
In another preference, described 5-O-methyl-visamminol reference substance purity purity >=99.0%, preferably
Ground, purity >=99.5, more preferably, purity >=99.6%.
In another preference, the alcohol extraction mixture of described cimicifugoside and 5-O-methyl-visamminol is by including
The method of following steps is prepared：
(i-1) Radix Saposhnikoviae medical material and ethanol solution, merceration alcohol extraction, concentrated liquid part after solid-liquid separation, so as to obtain are mixed
First concentrated solution；
(i-2) using the first concentrated solution described in macroporous resin adsorption, then respectively with the washing removing impurities of 4-5 times of column volume
Matter, then with the 55-65% ethanol solution eluting objects of 1-2 times of column volume, eluent is collected, concentrate to obtain the second concentration
Liquid；With
(i-3) the second described concentrated solution is separated using silica gel column chromatography, using dichloromethane:Methanol-eluted fractions agent is washed
It is de-, eluent is collected, is concentrated and is mixed with the alcohol extraction for obtaining cimicifugoside and 5-O-methyl-visamminol described in step (i)
Compound.
In another preference, described ethanol solution is measured with 5-8 (L/kg) times with Radix Saposhnikoviae medical material and is mixed.
In another preference, the concentration of volume percent of described ethanol solution is 70-90% (v/v), it is preferred that being
80% (v/v).
In another preference, described macroporous resin is polystyrene type nonpolar adsorption resin.
In another preference, the porosity of described macroporous resin is 42-46%.
In another preference, described dichloromethane:In methanol-eluted fractions agent, the volume ratio of each component is 10:1-5:1.
A second aspect of the present invention provides a kind of cimicifugoside reference substance and/or 5-O-methyl-visamminol is compareed
Product, described cimicifugoside reference substance and/or 5-O-methyl-visamminol reference substance are by as described in the first aspect of the invention
Method prepare.
It should be understood that within the scope of the present invention, above-mentioned each technical characteristic of the present invention and have in below (eg embodiment)
Can be combined with each other between each technical characteristic of body description, so as to constitute new or preferred technical scheme.As space is limited, exist
This no longer tires out one by one states.
Description of the drawings
HPLC detection collection of illustrative plates of the Fig. 1 for 1 gained cimicifugoside reference substance of embodiment.
HPLC detection collection of illustrative plates of the Fig. 2 for 1 gained 5-O-methyl-visamminol reference substance of embodiment.
Specific embodiment
The present inventor develops a kind of high-purity cimicifugoside and 5-O- methyl dimension first through extensively and in depth studying
The preparation method of this ammiol glycosides reference substance.The standby column separating purification cimicifugoside of this preparation method compacting using in and 5-O- methyl
Visamminol glycosides ethanol extract, under certain pressure, separation efficiency is greatly improved, and by recrystallization further improving
The purity of target substance.On this basis, complete the present invention.
For achieving the above object, the technical solution used in the present invention is as follows：
A kind of preferred technical scheme of the present invention is as follows：
A. raw material is extracted：The ethanol solution of 5～8 times of amounts, merceration is added to carry according to volume mass than L/Kg Radix Saposhnikoviae medical material
Extraction 72h is taken, sucking filtration, merging filtrate are concentrated into without alcohol taste；
The concentration of volume percent of described ethanol solution is 80%；
B. macroporous resin enrichment：By the concentrated solution of step A with macroporous resin static adsorption overnight, then respectively with 4-5 times
The water elution impurity of column volume, then with 65% ethanol solution eluting object of 1-2 times of column volume, collect eluent, be concentrated into
The 1/10 of original volume；
C. silica gel column chromatography：By the concentrated solution of the step B silica gel mixed sample of 100-200 mesh, pulverize after drying, take 200-
300 mesh silica gel, dichloromethane wet method dress post.After loading, using dichloromethane：Methanol-eluted fractions agent, and press 10:1-5:1 volume
Than gradient elution from high to low, TLC tracing detections, eluent is collected, cimicifugoside semi-finished product is concentrated to give and 5-O- methyl is tieed up this
The semi-finished product of ammiol glycosides；
D. middle compacting is standby:By 50% methanol of semi-finished product of the cimicifugoside and 5-O-methyl-visamminol of step C
In on water dissolution, the standby post of compacting, uses 33% methanol-eluted fractions, is concentrated to give purity for 93% or so and obtains cimicifugoside crude product；With 48%
Methanol solution eluting, is concentrated to give the 5-O-methyl-visamminol crude product that purity is 98% or so；
E. Product recycling：By step D obtain 93% or so cimicifugoside crude product with after a small amount of pure water heating for dissolving
The acetone dilution of 5 times of amounts is added, cold preservation crystallization in 4 DEG C of refrigerators is transferred to, after waiting crystal to separate out, sucking filtration solid, then again with pure
Recrystallization is diluted with the acetone of 5 times of amounts after water heating for dissolving, obtain purity for more than 99% after 2-3 lyophilization of repetitive operation
Cimicifugoside reference substance；98% or so the 5-O-methyl-visamminol crude product that step D is obtained is added with a small amount of methanol
The acetone dilution of 5 times of amounts is added after heat of solution, cold preservation crystallization in 4 DEG C of refrigerators is transferred to, after waiting crystal to separate out, sucking filtration solid, then
Again with the acetone dilution recrystallization after methanol heating for dissolving with 5 times of amounts, obtaining purity after 2-3 lyophilization of repetitive operation is
More than 99% 5-O-methyl-visamminol reference substance.
Main advantages of the present invention
1st, Product recycling is carried out using recrystallization method, product yield is high, and purity is high；
2nd, solvent consumption is few, all recyclable recycling of the solvent in technical process；
3rd, solvent toxicity is little, and solvent used is ethanol, methanol, pure water, and environmental pollution is little；
4th, easy to operate, with short production cycle, separation efficiency is high, and process stabilizing reliability, favorable reproducibility are with low cost, is adapted to
Industrialized production；
With reference to specific embodiment, the present invention is expanded on further.It should be understood that these embodiments are merely to illustrate the present invention
Rather than limit the scope of the present invention.The experimental technique of unreceipted actual conditions in the following example, generally according to conventional strip
Part, or according to the condition proposed by manufacturer.Unless otherwise indicated, otherwise percentage ratio and number are calculated by weight.
Embodiment 1
The preparation method of cimicifugoside and 5-O-methyl-visamminol reference substance, is carried out by following processing step：
A. raw material is extracted；By Radix Saposhnikoviae medical material 10Kg, the ethanol solution merceration that 50L volume fractions are 80% is added to extract 72h,
Filter, merging filtrate is concentrated into without alcohol taste, common 5L；
B. macroporous resin enrichment：4KgAB-8 macroporous adsorbent resins are weighed, the concentrated solution of step A is static with macroporous resin
12 hours of absorption, then with the water elution impurity of 40L, then with the 65% ethanol solution eluting object of 6L, collect eluent,
It is concentrated into 100ml；
C. silica gel column chromatography：The 100ml concentrated solutions of step B are mixed into sample with 100-200 mesh silica gel 100g, are pulverized after drying,
200-300 mesh silica gel 500g are taken, dichloromethane wet method dress post is used.After loading, using dichloromethane：Methanol-eluted fractions agent, and press 10:
1-5:1 volume ratio gradient elution from high to low, TLC tracing detections are collected eluent, are concentrated to give cimicifugoside semi-finished product respectively
8.7g and 5-O-methyl-visamminol semi-finished product 6.5g；
D. middle compacting is standby：The cimicifugoside semi-finished product 8.7g of step C is used for post with upper middle compacting after 30ml water dissolutioies
33% methanol-eluted fractions, are concentrated to give the cimicifugoside crude product 5.2g that purity is 93%；By the 5-O- methyl visamminols of step C
The glycosides semi-finished product 6.5g upper middle compactings of methanol dissolving of 20ml are concentrated to give 98% 5-O- for post with 48% methanol-eluted fractions
Methyl visamminol glycosides crude product 4.2g；
E. Product recycling：By step D obtain 93% or so cimicifugoside crude product 5.2g it is molten with the heating of the pure water of 10ml
The acetone dilution of 50ml is added after solution, cold preservation 12 hours in 4 DEG C of refrigerators are transferred to, after waiting crystal to separate out, sucking filtration solid, then again
With the acetone dilution recrystallization after pure water heating for dissolving with 5 times of amounts, purity is obtained after 2-3 lyophilization of repetitive operation for 99%
Above cimicifugoside reference substance 4.1g；The 5-O-methyl-visamminol crude product 4.2g use of 98% or so that step D is obtained
The acetone dilution of 5 times of amounts is added after the methanol heating for dissolving of 10ml, cold preservation 12 hours in 4 DEG C of refrigerators is transferred to, is waited crystal to separate out
Afterwards, sucking filtration solid, then recrystallization is diluted with the acetone of 5 times of amounts with after methanol heating for dissolving again, 2-3 freezing of repetitive operation is dry
Purity is obtained after dry for more than 99% 5-O-methyl-visamminol reference substance 3.6g.
HPLC detection collection of illustrative plates of the Fig. 1 for 1 gained cimicifugoside reference substance of embodiment, Fig. 2 is 1 gained 5-O- methyl of embodiment
The HPLC detection collection of illustrative plates of visamminol glycosides reference substance.Gained cimicifugoside reference substance Jing HPLC purity assays are 99.3%, 5-
O- methyl visamminol glycosides reference substance Jing HPLC purity assays are 99.6%.
Embodiment 2
The preparation method of cimicifugoside and 5-O-methyl-visamminol reference substance, is carried out by following processing step：
A. raw material is extracted；By Radix Saposhnikoviae medical material 5Kg, the ethanol solution merceration that 35L volume fractions are 80% is added to extract 72h,
Filter, merging filtrate is concentrated into without alcohol taste, common 3L；
B. macroporous resin enrichment：2KgAB-8 macroporous adsorbent resins are weighed, the concentrated solution of step A is static with macroporous resin
12 hours of absorption, then with the water elution impurity of 20L, then with the 65% ethanol solution eluting object of 3L, collect eluent,
It is concentrated into 50ml；
C. silica gel column chromatography：The 50ml concentrated solutions of step B are mixed into sample with 100-200 mesh silica gel 50g, is pulverized after drying, is taken
200-300 mesh silica gel 300g, use dichloromethane wet method dress post.After loading, using dichloromethane：Methanol-eluted fractions agent, and press 10:1-
5:1 volume ratio gradient elution from high to low, TLC tracing detections are collected eluent, are concentrated to give cimicifugoside semi-finished product respectively
4.8g and 5-O-methyl-visamminol semi-finished product 4.3g；
D. middle compacting is standby：The cimicifugoside semi-finished product 4.8g of step C is used for post with upper middle compacting after 20ml water dissolutioies
33% methanol-eluted fractions, are concentrated to give the cimicifugoside crude product 3.7g that purity is 95%；By the 5-O- methyl visamminols of step C
The glycosides semi-finished product 4.2g upper middle compactings of methanol dissolving of 10ml are concentrated to give 97% 5-O- for post with 48% methanol-eluted fractions
Methyl visamminol glycosides crude product 3.2g；
E. Product recycling：The cimicifugoside crude product 3.7g pure water heating for dissolving of 6ml of 95% or so that step D is obtained
The acetone dilution of 30ml is added afterwards, is transferred to cold preservation 12 hours in 4 DEG C of refrigerators, after waiting crystal to separate out, sucking filtration solid, then use again
After pure water heating for dissolving with 5 times amount acetone dilution recrystallization, obtain after 2-3 lyophilization of repetitive operation purity be 99% with
Upper cimicifugoside reference substance 3.2g；The 5-O-methyl-visamminol crude product 3.2g use of 98% or so that step D is obtained
The acetone dilution of 5 times of amounts is added after the methanol heating for dissolving of 100ml, cold preservation 12 hours in 4 DEG C of refrigerators is transferred to, is waited crystal to separate out
Afterwards, sucking filtration solid, then recrystallization is diluted with the acetone of 5 times of amounts with after methanol heating for dissolving again, 2-3 freezing of repetitive operation is dry
Purity is obtained after dry for more than 99% 5-O-methyl-visamminol reference substance 2.5g.
Gained cimicifugoside reference substance Jing HPLC purity assays are 99.5%, 5-O-methyl-visamminol reference substance Jing
HPLC purity assays are 99.5%.
The all documents referred in the present invention are all incorporated as reference in this application, independent just as each document
It is incorporated as with reference to such.In addition, it is to be understood that after the above-mentioned teachings for having read the present invention, those skilled in the art can
To make various changes or modifications to the present invention, these equivalent form of values equally fall within the model limited by the application appended claims
Enclose.
Claims (10)
1. a kind of preparation method of cimicifugoside and 5-O-methyl-visamminol reference substance, it is characterised in that described side
Method is comprised the following steps：
I () provides the alcohol extraction mixture of cimicifugoside and 5-O-methyl-visamminol；
(ii) the alcohol extraction mixture described in is mixed with solvent, obtains the first mixture, and in utilizing described in the standby post separation of compacting
First mixture, so as to obtain cimicifugoside crude product and 5-O-methyl-visamminol crude product；With
(iii) recrystallization is carried out to cimicifugoside crude product and/or 5-O-methyl-visamminol crude product using solvent, so as to obtain
Obtain cimicifugoside reference substance and/or 5-O-methyl-visamminol reference substance.
2. preparation method as described in claim 1, it is characterised in that the step (ii) also includes step：
(ii-1) using 30-35% (v/v) methanol solutions as the first eluant of the standby post of middle compacting, first stage eluting is carried out,
Concentrate eluant is obtaining cimicifugoside crude product；With
(ii-2) using 45-50% (v/v) methanol solutions as the second eluant of the standby post of middle compacting, second stage eluting is carried out,
Concentrate eluant is obtaining 5-O-methyl-visamminol crude product.
3. method as described in claim 1, it is characterised in that the middle compacting in the step (ii) is provided with post pressure 0- for post
2MPa, preferably 0.5-2MPa.
4. preparation method as described in claim 1, it is characterised in that the step (iii) also includes step：
(iii-1) the cimicifugoside crude product described in is mixed with pure water and acetone, makes described cimicifugoside crude product mix molten
Recrystallization is carried out in agent；
Gained crystal is separated and be dried, that is, obtains cimicifugoside reference substance；And/or
(iii-2) the 5-O-methyl-visamminol crude product described in is mixed with methanol and acetone, makes described 5-O- methyl
Visamminol glycosides crude product carries out recrystallization in mixed solvent；
Gained crystal is separated and be dried, that is, obtains 5-O-methyl-visamminol reference substance.
5. preparation method as described in claim 4, it is characterised in that the step (iii-2) is at the step (iii-1)
Before, or synchronously carry out.
6. preparation method as described in claim 4, it is characterised in that in the step (iii-1), the acetone of addition is pure
5-10 times of water measures (v/v)；And/or
In described step (iii-2), the acetone of addition measures (v/v) for 5-10 times of methanol.
7. preparation method as described in claim 1, it is characterised in that described cimicifugoside reference substance purity >=
99.0%, it is preferred that purity >=99.3%, more preferably, purity >=99.5%.
8. preparation method as described in claim 1, it is characterised in that described 5-O-methyl-visamminol reference substance
Purity purity >=99.0%, it is preferred that purity >=99.5, more preferably, purity >=99.6%.
9. method as described in claim 1, it is characterised in that described cimicifugoside and 5-O-methyl-visamminol
Alcohol extraction mixture prepared by the method for comprising the following steps：
(i-1) Radix Saposhnikoviae medical material and ethanol solution, merceration alcohol extraction, concentrated liquid part after solid-liquid separation, so as to obtain first are mixed
Concentrated solution；
(i-2) using the first concentrated solution described in macroporous resin adsorption, then respectively with the water elution impurity of 4-5 times of column volume,
Again with the 55-65% ethanol solution eluting objects of 1-2 times of column volume, eluent is collected, concentrate to obtain the second concentrated solution；With
(i-3) the second described concentrated solution is separated using silica gel column chromatography, using dichloromethane:Methanol-eluted fractions agent carries out eluting,
Eluent is collected, is concentrated and is mixed with the alcohol extraction for obtaining cimicifugoside and 5-O-methyl-visamminol described in step (i)
Thing.
10. a kind of cimicifugoside reference substance and/or 5-O-methyl-visamminol reference substance, it is characterised in that described liter
Numb element glycosides reference substance and/or 5-O-methyl-visamminol reference substance are prepared by the method for claim 1.
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| CN201611191636.4A CN106632542B (en) | 2016-12-21 | 2016-12-21 | Preparation method of cimicidin glycoside and 5-O-methylvisammioside reference substance |
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| CN112505232A (en) * | 2020-12-15 | 2021-03-16 | 北京中医药大学 | Ledebouriella chromone control extract and preparation method and application thereof |
| CN113219086A (en) * | 2021-04-01 | 2021-08-06 | 滨州医学院 | Method for preparing cimicifugan, cimicifugan and 5-O-methylvisammioside from radix Saposhnikoviae |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN110835362A (en) * | 2018-08-17 | 2020-02-25 | 上海诗丹德标准技术服务有限公司 | Preparation method of pectolinarin reference substance |
| CN110835362B (en) * | 2018-08-17 | 2023-04-07 | 上海诗丹德标准技术服务有限公司 | Preparation method of pectolinarin reference substance |
| CN112505232A (en) * | 2020-12-15 | 2021-03-16 | 北京中医药大学 | Ledebouriella chromone control extract and preparation method and application thereof |
| CN112505232B (en) * | 2020-12-15 | 2023-06-16 | 北京中医药大学 | Radix saposhnikoviae chromone control extract, and preparation method and application thereof |
| CN113219086A (en) * | 2021-04-01 | 2021-08-06 | 滨州医学院 | Method for preparing cimicifugan, cimicifugan and 5-O-methylvisammioside from radix Saposhnikoviae |
| CN115166079A (en) * | 2022-07-04 | 2022-10-11 | 广州白云山中一药业有限公司 | Multi-component content determination method of magnolia flower rhinitis preparation |
| CN115166079B (en) * | 2022-07-04 | 2024-05-03 | 广州白云山中一药业有限公司 | Multi-component content determination method for magnolia flower rhinitis preparation |
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