CN103845397A - Method for extracting phenylethanoid glycoside in lamiophlomis rotata - Google Patents
Method for extracting phenylethanoid glycoside in lamiophlomis rotata Download PDFInfo
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- CN103845397A CN103845397A CN201210498062.0A CN201210498062A CN103845397A CN 103845397 A CN103845397 A CN 103845397A CN 201210498062 A CN201210498062 A CN 201210498062A CN 103845397 A CN103845397 A CN 103845397A
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Abstract
The invention discloses a method for extracting phenylethanoid glycoside in lamiophlomis rotata. The invention adopts a plant lamiophlomis rotata whole herb of Labiatae as a raw material; a water extraction alcohol precipitation or ethanol percolation water precipitation or ethanol percoaltion method is used to obtain an extracting solution; copper sulfate or activated clay is employed to further improve the chlorophyll interference in the active ingredient extraction process of green plants to obtain a crude extract; and then the crude extract is subjected to chromatographic separation by macroporous resin adsorption columns with different polarity, so as to obtain a purified phenylethanoid glycoside extract with content of 50%.
Description
technical field
The invention belongs to field of medicaments, relate to take single plant Radix Lamiophlomidis Rotatae as raw material and to extract, to separate and obtain the phenethyl alcohol glycosides material that purity is higher.
Background technology
Phenethyl alcohol glycoside compounds (phenylethanoid glycosides) is that a class contains (hydroxyl, methoxyl group) substituted benzene ethyl and (hydroxyl, methoxyl group) replaces cinnamoyl; conventionally the natural glucosides that contains ester bond and oxygen glycosidic bond take β-glucose as parent nucleus, is extensively present in dicotyledon.Much research in recent years shows, that this compounds has is antibacterial, antiinflammatory, antiviral, antitumor, antioxidation, immunomodulating, hypermnesis, protect the liver, the effect such as heart tonifying, especially with significantly (Chinese Pharmaceutical Journal, 1995,30(5) of antibacterial activity: 269).Thereby, along with new structure is constantly found, the raising of pharmacologically active experimental technique, the completing of more activity index, phenethyl alcohol glycoside gets a good chance of becoming that new class is antibacterial, antitumor and improve human immunologic function's glycoside medicine.
Tibet medicine lamivphlomis root is labiate, after the inflammation of primary treatment spongy bone, fracture, contusion, bones and muscles pain, gunshot wound, traumatic injury, edema, flows yellow fluid, hydrarthrosis.Chinese Patent Application No. 200410022734.6 discloses from Radix Lamiophlomidis Rotatae plant water sources or ethanol extraction, separates a kind of extract obtaining through macroporous resin, and the main component of extract is total glycosides and total flavones.But in fact we study and find that in Radix Lamiophlomidis Rotatae, flavones content is lower, in fact take methods of glycosides as main.Chinese Patent Application No. 200510035064.6 discloses the extracting solution that application alcohol extracting-water precipitating or ethanol percolate extraction method obtain, after macroporous resin adsorption, through polyamide or silica gel column chromatography separating purification, obtain the phenethyl alcohol glycosides active substance take dry product content as 22-90% again.But this patent is not made concrete confirmation to extract active component, and complex process, use polyamide column cost higher.
Summary of the invention
The present invention seeks to set up phenethyl alcohol glycosides material extracting method in process route Radix Lamiophlomidis Rotatae simple, with low cost.
It is raw material that the present invention adopts labiate Radix Lamiophlomidis Rotatae herb, utilize water extract-alcohol precipitation or ethanol extraction water precipitation or alcohol percolation method to obtain extracting solution, further improve the interference of green plants extraction active component process Determination of Chlorophyll with copper sulfate or active hargil, the crude extract obtaining, again after opposed polarity macroporous resin adsorption column chromatography for separation, the phenethyl alcohol glycoside extract that the content that obtains purification is 50%.
The phenethyl alcohol glycoside that the present invention obtains is phenylethanoid glycosides, product after its hydrolysis is hydroxytyrosol, high cephrol, 3,4-dimethoxy phenethanol, caffeic acid, ferulic acid, 3,4-dimethoxy-cinnamic acid, thereby can be with these six kinds of materials product in contrast, carry out qualitative, quantitative and measure the content of corresponding composition in actual sample.
An extracting method for phenethyl alcohol glycoside in Radix Lamiophlomidis Rotatae, is characterized in that the method has the following step successively:
A extracts: adopting labiate Radix Lamiophlomidis Rotatae herb is raw material, sieves after remove impurity, obtains extracting solution through water extract-alcohol precipitation, ethanol extraction water precipitation method or ethanol percolate extraction method;
B purification: add copper sulfate or active hargil in extracting solution, the precipitation in extracting solution is effectively deposited;
C separates: above-mentioned B step gained extracting solution is separated by the macroporous resin of low pole, by concentrated extracting solution rear all loadings, first use distilled water drip washing, the continuous alcoholic solution with different content is eluting respectively, concentration and recovery ethanol elution;
D enrichment: after the eluent of above-mentioned C step gained ethanol is concentrated, be splined on another non-polar macroporous resin refining, adopt the eluent eluting of opposed polarity, first use distilled water drip washing, continuous with different content alcoholic solution eluting respectively, concentration and recovery ethanol elution, and by its vacuum drying, obtain the extract of phenethyl alcohol glycoside;
E measures: the desciccate that enrichment is obtained is hydrolyzed, and makes the phenethyl alcohol glycoside complete hydrolysis in the extract of phenethyl alcohol glycoside discharge phenethanol and cinnamic acid compound; The solution obtaining after hydrolysis supplies liquid chromatogram measuring with methanol dilution.
For method of the present invention, concrete preferred version is as follows:
Step 1) of the present invention is extracted:
A decoction and alcohol sedimentation technique: take medicinal material coarse powder, add decocting in water 1 ~ 5 time, merge water cooking liquid, when being concentrated into relative density and being 25 ℃ 1.02 ~ 1.12, add 50% ~ 90% ethanol, leave standstill, after precipitating completely, sucking filtration obtains supernatant, and concentrated medicament to density 1.02 ~ 1.12 is for subsequent use;
B ethanol extract from water precipitation: take medicinal material coarse powder, add 60% ~ 95% alcohol reflux 1 ~ 5 time, merge alcohol and boil liquid, reclaim ethanol, being concentrated into relative density is 1.02 ~ 1.12, adds 5 ~ 8 times of volume distilled water, leaves standstill, after precipitating completely, sucking filtration obtains supernatant, and concentrated medicament to density 1.02 ~ 1.12 is for subsequent use.
C alcohol percolation method: take medicinal material coarse powder, add the soak with ethanol of 30% ~ 85wt%, collect percolate, reclaim ethanol, when being concentrated into relative density and being 25 ℃ 1.02 ~ 1.12, add 5 ~ 8 times of volume distilled water, leave standstill, after precipitating completely, sucking filtration obtains supernatant, and concentrated medicament to density 1.02 ~ 1.12 is for subsequent use.
A the present invention is by 1) add the CuSO of medicinal material coarse powder quality 5% ~ 10% in a or b or c extracting solution
4, leave standstill, after precipitation is separated out completely, incline and supernatant, medicinal liquid is concentrated into relative density and surveys 1.02 ~ 1.14 in the time of 25 ℃, for subsequent use.
B the present invention is by 1) a, b, adds the active hargil of medicinal material coarse powder quality 5% ~ 10% in c extracting solution, leave standstill, and after precipitation is separated out completely, inclines and supernatant, and medicinal liquid is concentrated into relative density and surveys 1.02 ~ 1.14 in the time of 25 ℃, for subsequent use.
Step 3) of the present invention separates:
The present invention is by 2) extract the medicinal liquid obtaining by macroporous resin, the present invention's first low pole macroporous resin used is HPD-100, WLD, D-101, AB-8.
Carry out eluting with the distilled water eluant of 5 ~ 10 times of amounts of volume ratio.
Carry out eluting with the ethanol elution agent of 5 ~ 10 times of amounts of volume ratio.
The content of ethanol elution is 30% ~ 50%.
Step 4) enrichment of the present invention:
The present invention is by 3) after eluent is concentrated with Rotary Evaporators, be Diaion HP-10 ,-20 ,-30 ,-40 ,-50 by non-polar macroporous resin again.
Carry out eluting with the distilled water eluant of 5 ~ 10 times of amounts of volume ratio.
Carry out eluting with the ethanol elution agent of 5 ~ 10 times of amounts of volume ratio.
The content of ethanol elution is 50% ~ 70% to carry out eluting.
Step 5) of the present invention is measured:
Extract and preparation that assay method of the present invention is applicable to the former plant of Radix Lamiophlomidis Rotatae and is prepared by former plant.
In the chromatographic column (ODS) that liquid chromatogram measuring of the present invention is is filler at octadecyl silane, separate, chromatographic isolation mobile phase used is methanol/10 mmol/L potassium dihydrogen phosphate buffer solution (30/70, V/V), with phosphorus acid for adjusting pH be 3.0, add tetrabutyl ammonium bromide to Ion reagent, make the concentration of tetrabutyl ammonium bromide in mobile phase reach 5 ~ 100 mmol/L.The flow velocity of mobile phase is 1.0 ml/min.
Liquid chromatogram measuring of the present invention detects in UV-detector, and detecting the wavelength using is 290nm.
The present invention adopts opposed polarity macroporous resin to carry out separation and purification; obtain the phenethyl alcohol glycoside compounds of high-load; not only solve traditional processing technology and can not effectively extract the difficulty of phenethyl alcohol glycoside, and realize the technical guarantee that large-scale industrial is produced and further its biological activity of exploitation provides raw material to produce of phenethyl alcohol glycoside in Radix Lamiophlomidis Rotatae.The invention provides a kind of purer Radix Lamiophlomidis Rotatae effective ingredient, better control product quality, and the extraction and preparation technique of phenethyl alcohol glycoside is provided.
The extracting method of phenethyl alcohol glycosides material provided by the invention compared with the conventional method tool has the following advantages:
It is the phenethyl alcohol glycoside material that 50% purity is higher that method provided by the invention can obtain productive rate.Extract the macroporous resin adopting and can activate rear regeneration, production cost is low; In leaching process, use copper sulfate or active hargil to help heavy, can effectively improve deposition efficiency, save extraction time, the method is easy to realize industrial-scale production.
Accompanying drawing explanation
Fig. 1 is the high-efficient liquid phase chromatogram of six kinds of reference substances.Wherein: 1. hydroxytyrosol, 2. high cephrol, 3. 3,4-dimethoxy phenethanol, 4. caffeic acid, 5. ferulic acid, 6. 3,4-dimethoxy-cinnamic acid.
Fig. 2 is the high-efficient liquid phase chromatogram of the former plant of Radix Lamiophlomidis Rotatae.Wherein: 1. hydroxytyrosol, 2. high cephrol, 3. 3,4-dimethoxy phenethanol, 4. caffeic acid, 5. ferulic acid, 6. 3,4-dimethoxy-cinnamic acid.
Chromatographic condition: with Waters 2487 chromatographs detections, Diamonsil C18 chromatographic column (5 μ m, 416 mm × 250 mm), mobile phase is potassium dihydrogen phosphate aqueous solution-(30:70 of methanol-10 mM, V/V), with phosphorus acid for adjusting pH be 3.0, add 60 mM tetrabutyl ammonium bromide to Ion reagent, detecting wavelength is 290 nm, and flow velocity is 1.0 mL/min.
the specific embodiment
The present invention will be described in detail by specific embodiment.
The Radix Lamiophlomidis Rotatae herb that accurately takes 100.0 g pulverizing joins in 2000 mL flasks, with 1000 mL 60% alcohol heating reflux extractions, extracts altogether 3 times.The extracting solution of 3 gained is merged, after concentrated, add the distilled water of 800 mL, add the copper sulfate of 5 g, hold over night, after filtering with buchner funnel, Rotary Evaporators distillation and concentration to 100 mL, gained medicinal liquid is by AB-8 macroporous resin adsorption, after sample is all by resin column, with 1000 mL distilled water flushing resin columns, until eluent is colourless, continue and carry out eluting with the alcoholic solution of 1000 mL 30%, reclaim ethanol elution, eluent is concentrated into 100 mL, be splined on again Diaion HP-10 resin, with 1000 mL distilled water flushing resin columns, continue and carry out eluting with the alcoholic solution of 1000 mL 50%, reclaim ethanol elution, after eluent is concentrated, obtain desciccate, the content of chromatogram quantitative analysis of the liquid phase phenethyl alcohol glycoside is 50.2%.
The Radix Lamiophlomidis Rotatae herb that accurately takes 100.0 g pulverizing joins in 2000 mL flasks, by 1000 mL distilled water water heating and refluxing extraction, extracts altogether 3 times.The extracting solution of 3 gained is merged, after concentrated, add 80% ethanol of 800 mL, add the active hargil of 5 g, hold over night, after filtering with buchner funnel, Rotary Evaporators distillation and concentration to 100 mL, gained medicinal liquid is by DM130 macroporous resin adsorption, after sample is all by resin column, with 1000 mL distilled water flushing resin columns, until eluent is colourless, continue and carry out eluting with the alcoholic solution of 1000 mL 30%, reclaim ethanol elution, eluent is concentrated into 100 mL, be splined on again Diaion HP-30 resin, with 1000 mL distilled water flushing resin columns, continue and carry out eluting with the alcoholic solution of 1000 mL 60%, reclaim ethanol elution, after eluent is concentrated, obtain desciccate, the content of chromatogram quantitative analysis of the liquid phase phenethyl alcohol glycoside is 40.8%.
The Radix Lamiophlomidis Rotatae herb that accurately takes 100.0 g pulverizing joins in 2000 mL flasks, with 1000 mL 60% ethanol percolations, after extracting solution is concentrated, add the distilled water of 800 mL, add the copper sulfate of 5 g, hold over night, after filtering with buchner funnel, Rotary Evaporators distillation and concentration to 100 mL, gained medicinal liquid is by D101 macroporous resin adsorption, after sample is all by resin column, with 1000 mL distilled water flushing resin columns, until eluent is colourless, continue and carry out eluting with the alcoholic solution of 1000 mL 40%, reclaim ethanol elution, eluent is concentrated into 100 mL, be splined on again Diaion HP-10 resin, with 1000 mL distilled water flushing resin columns, continue and carry out eluting with the alcoholic solution of 1000 mL 60%, reclaim ethanol elution, after eluent is concentrated, obtain desciccate, the content of chromatogram quantitative analysis of the liquid phase phenethyl alcohol glycoside is 32.9%.
The Radix Lamiophlomidis Rotatae herb that accurately takes 100.0 g pulverizing joins in 2000 mL flasks, with 1000 mL 80% alcohol heating reflux extractions, extracts altogether 3 times.The extracting solution of 3 gained is merged, after concentrated, add the distilled water of 800 mL, add the active hargil of 10 g, hold over night, after filtering with buchner funnel, Rotary Evaporators distillation and concentration to 100 mL, gained medicinal liquid is by AB-8 macroporous resin adsorption, after sample is all by resin column, with 1000 mL distilled water flushing resin columns, until eluent is colourless, continue and carry out eluting with the alcoholic solution of 1000 mL 20%, reclaim ethanol elution, eluent is concentrated into 100 mL, be splined on again Diaion HP-10 resin, with 1000 mL distilled water flushing resin columns, continue and carry out eluting with the alcoholic solution of 1000 mL 50%, reclaim ethanol elution, after eluent is concentrated, obtain desciccate, the content of chromatogram quantitative analysis of the liquid phase phenethyl alcohol glycoside is 53.1%.
Claims (7)
1. an extracting method for phenethyl alcohol glycoside in Radix Lamiophlomidis Rotatae, is characterized in that the method has the following step successively:
A extracts: adopting labiate Radix Lamiophlomidis Rotatae herb is raw material, sieves after remove impurity, obtains extracting solution through water extract-alcohol precipitation, ethanol extraction water precipitation method or ethanol percolate extraction method;
B purification: add copper sulfate or active hargil in extracting solution, the precipitation in extracting solution is effectively deposited;
C separates: above-mentioned B step gained extracting solution is separated by the macroporous resin of low pole, by concentrated extracting solution rear all loadings, first use distilled water drip washing, the continuous alcoholic solution with different content is eluting respectively, concentration and recovery ethanol elution;
D enrichment: after the eluent of above-mentioned C step gained ethanol is concentrated, be splined on another non-polar macroporous resin refining, adopt the eluent eluting of opposed polarity, first use distilled water drip washing, continuous with different content alcoholic solution eluting respectively, concentration and recovery ethanol elution, and by its vacuum drying, obtain the extract of phenethyl alcohol glycoside;
E measures: the desciccate that enrichment is obtained is hydrolyzed, and makes the phenethyl alcohol glycoside complete hydrolysis in the extract of phenethyl alcohol glycoside discharge phenethanol and cinnamic acid compound; The solution obtaining after hydrolysis supplies liquid chromatogram measuring with methanol dilution.
2. the method for claim 1, it is characterized in that decoction and alcohol sedimentation technique: take medicinal material coarse powder, add decocting in water 1 ~ 5 time, merge water cooking liquid, when being concentrated into relative density and being 25 ℃ 1.02 ~ 1.12, add 50% ~ 90% ethanol, leave standstill, after precipitating completely, sucking filtration obtains supernatant, and concentrated medicament is to density 1.02 ~ 1.12.
3. the method for claim 1, it is characterized in that ethanol extract from water precipitation: take medicinal material coarse powder, add 60% ~ 95% alcohol reflux 1 ~ 5 time, merge alcohol and boil liquid, reclaim ethanol, being concentrated into relative density is 1.02 ~ 1.12, add 5 ~ 8 times of volume distilled water, leave standstill, after precipitating completely, sucking filtration obtains supernatant, and concentrated medicament is to density 1.02 ~ 1.12.
4. the method for claim 1, it is characterized in that alcohol percolation method: take medicinal material coarse powder, add the soak with ethanol of 30% ~ 85wt%, collect percolate, reclaim ethanol, when being concentrated into relative density and being 25 ℃ 1.02 ~ 1.12, add 5 ~ 8 times of volume distilled water, leave standstill, after precipitating completely, sucking filtration obtains supernatant, and concentrated medicament is to density 1.02 ~ 1.12.
5. the method as described in any one in claim 1-4, is characterized in that purification:
The CuSO of medicinal material coarse powder quality 5% ~ 10% will be added in extracting solution
4, leave standstill, after precipitation is separated out completely, incline and supernatant, medicinal liquid is concentrated into relative density and surveys 1.02 ~ 1.14 in the time of 25 ℃; Or
To in extracting solution, add the active hargil of medicinal material coarse powder quality 5% ~ 10%, leave standstill, after precipitation is separated out completely, incline and supernatant, medicinal liquid is concentrated into relative density and surveys 1.02 ~ 1.14 in the time of 25 ℃.
6. the method for claim 1, is characterized in that separating: extract the medicinal liquid obtaining by macroporous resin, first low pole macroporous resin used is HPD-100, WLD, D-101, AB-8; Carry out eluting with the distilled water eluant of 5 ~ 10 times of amounts of volume ratio; Carry out eluting with the ethanol elution agent of 5 ~ 10 times of amounts of volume ratio; The content of ethanol elution is 30% ~ 50%.
7. the method for claim 1, is characterized in that enrichment: after eluent is concentrated with Rotary Evaporators, be Diaion HP-10 ,-20 ,-30 ,-40 ,-50 again by non-polar macroporous resin; Carry out eluting with the distilled water eluant of 5 ~ 10 times of amounts of volume ratio; Carry out eluting with the ethanol elution agent of 5 ~ 10 times of amounts of volume ratio; The content of ethanol elution is 50% ~ 70% to carry out eluting.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753658A (en) * | 2014-12-16 | 2016-07-13 | 中国科学院兰州化学物理研究所 | Preparation method for hydroxytyrosol in Lamiophlomis rotata |
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| CN1260122A (en) * | 1999-01-08 | 2000-07-19 | 仲伟德 | Bactericide agricultural chemicals with plant as raw material |
| CN1876018A (en) * | 2005-06-10 | 2006-12-13 | 广州陈李济药厂 | A herbal extract, its preparation method and use |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1260122A (en) * | 1999-01-08 | 2000-07-19 | 仲伟德 | Bactericide agricultural chemicals with plant as raw material |
| CN1876018A (en) * | 2005-06-10 | 2006-12-13 | 广州陈李济药厂 | A herbal extract, its preparation method and use |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105753658A (en) * | 2014-12-16 | 2016-07-13 | 中国科学院兰州化学物理研究所 | Preparation method for hydroxytyrosol in Lamiophlomis rotata |
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Application publication date: 20140611 |