CN104961716A - Method for separating high-purity lactone type lovastatin from fermentum rubrum powder - Google Patents
Method for separating high-purity lactone type lovastatin from fermentum rubrum powder Download PDFInfo
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- CN104961716A CN104961716A CN201510285307.5A CN201510285307A CN104961716A CN 104961716 A CN104961716 A CN 104961716A CN 201510285307 A CN201510285307 A CN 201510285307A CN 104961716 A CN104961716 A CN 104961716A
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- lovastatin
- lactone type
- colouring agent
- red colouring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/30—Oxygen atoms, e.g. delta-lactones
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Abstract
The present invention discloses a new method for separating lactone type lovastatin from fermentum rubrum. According to the method, commercially available functional fermentum rubrum powder is adopted as a raw material, ethanol extraction and vacuum suction filtration are performed, silica gel column chromatography one-step separation is performed, and purity analysis and structure identification are performed respectively through a chromatography method and a spectroscopy method after concentration crystallization so as to obtain the lovastatin crystal having the purity of more than or equal to 98% and having the lactone type structure, wherein the extraction rate is more than or equal to 85%. According to the present invention, the method has characteristics of simple production equipment, simple and feasible process, simple operation, short time consuming, high bulk drug utilization rate and low production cost, and is the energy-saving and environmental protection method.
Description
Technical field
[the present invention relates in Hongqu powder (red colouring agent) the novel method being separated lactone type lovastatin, particularly relate to the method utilizing column chromatography silica gel to resolve separating high-purity lactone type lovastatin, belong to the extraction separation and purification field of active substance.
Background technology
Lovastatin is a kind of common treatment hyperlipidemia, within about 1976, is found and be separated first to obtain by Japanese biochemist rattan far away chapter (End ō Akira) from Chinese Hongqu powder (red colouring agent).It is hydroxymethyl glutaryl coenzyme A reductase (HMGR) inhibitor, can suppress the synthesis of cholesterol from root.Become novel lipid regulating agent in the eighties listing, be once called Ming Weixin, Luo Te, glad dew etc., its special effect with commodity, be described as the milestone for the treatment of cardiovascular system diseases, be used for the treatment of hypercholesterolemia and combined hyperlipidemia familial.At present, with lovastatin or with its for intermediate synthesis statins still for treatment hyperlipidaemia leading medicine.The effects such as modern study shows, lovastatin is except can treating many cardiovascular and cerebrovascular diseases, and it also has anti-inflammatory, and inhibition of cell proliferation breaks up, antitumor, treatment osteoporosis, have high practical value and economic worth.
It is with Merk company be representative one-step or two-step silica gel chromatography or resin adsorption method that the extraction and purification process of existing lovastatin mainly contains two kinds: one, although this method finished product quality is higher, but step is many, complicated operation, is unfavorable for large-scale industrial production.Another kind directly utilizes solvent phase inversion crystallization process, although this method is easy and simple to handle, disadvantage is that meal crystallization yield only has about 50%.Chinese patent CN102432573A discloses " a kind of method preparing lovastatin ", with commercially available red koji fermentation thing for raw material, reflux with at ethanolic soln 40 ~ 60 DEG C, use ultra-filtration membrane twice filtration again, finally use macroporous resin adsorption, distilled water recoils, ethanolic soln wash-out, collect wash-out effluent liquid, reduction vaporization is concentrated and obtain.This technique not only process is complicated, and ultra-filtration membrane price is more expensive, and cost is high; Have the full absorption of macroporous resin first time again, detect that effluent liquid stopped post when having lovastatin out, can lose some lovastatins, and can not ensure that lovastatin can adsorb completely, second time uses distilled water desorption of impurities, also can lose some lovastatins; Finally the lovastatin desorb be adsorbed on resin got off with 45% ethanolic soln, process complexity is very long, consuming time, is not easy to control wash-out degree, wastes water and alcohol, and lovastatin loss is comparatively large, and productive rate is low, and production cost is high, is unfavorable for industrial production.
Summary of the invention
The object of the invention is, for the deficiency of existing extraction lovastatin method, to provide a kind of production process simple and feasible, consuming time short, easy and simple to handle, controllability good, bulk drug utilization ratio is high, and production cost is low, the method preparing lactone type lovastatin of energy-conserving and environment-protective.
One, lactone type gets the extraction of lovastatin
The present invention extracts the method that lactone type gets lovastatin, comprises following processing step:
(1) preparation of lovastatin crude extract medicinal extract: with commercially available Hongqu powder (red colouring agent) for raw material, with ethanolic soln refluxing extraction 3 ~ 8h at 70 ~ 80 DEG C; Then under 0.05 ~ 0.09Mpa with Suction filtration device suction filtration while hot, obtain filtrate and filter residue; Lovastatin crude extract medicinal extract is obtained after concentrating filter liquor; Filter residue can be made animal feedstuff additive or extract raw material by imitating element after reclaiming.The volume fraction of ethanolic soln is 40% ~ 100%; The proportioning of Hongqu powder (red colouring agent) and ethanolic soln is 1:25 ~ 1:50 g/mL.
(2) separation of monomer ginkgolides type lovastatin in lovastatin crude extract medicinal extract: lovastatin crude extract medicinal extract and column chromatography silica gel are mixed sample post-drying with the mass ratio of 1:0.5 ~ 1:3, again with the column chromatography silica gel dress post mixing sample column chromatography silica gel 9 ~ 12 times of quality, then sherwood oil and ethyl acetate (volume ratio is 1:1 ~ 1:2) is used to be moving phase, at the flow velocity undershoot post wash-out of 0.5 ~ 5mL/min, every 1 ~ 3.5mL is a flow point, and number consecutively; When moving phase is eluted to Article 1 red zone or the outflow of Article 2 yellow band, stops rushing post, detect with thin-layer chromatography, merge identical component, obtain the pinniform white lactone type lovastatin crystallization that purity is higher.
Principle of the present invention is: the compound good solubility in ethanolic soln containing hydroxyl according to lovastatin extracts the lovastatin in red colouring agent for food, also used as a Chinese medicine.Acid type and the lactone type lovastatin of almost equivalent is contained in red colouring agent for food, also used as a Chinese medicine, when using alcohol reflux under the high temperature conditions, acid type lovastatin in red colouring agent for food, also used as a Chinese medicine almost can all be converted into stable lactone type, namely common lovastatin, and the lovastatin of lactone type is due to stable and polarity is little compared with acid type structure, so be easy to be separated on column chromatography silica gel post.Therefore, containing a large amount of lactone type lovastatins in the crude extract that ethanol high temperature reflux obtains after extracting, the recycling polar adsorption of column chromatography silica gel and the polarity desorb principle of moving phase, all separate disposable for the lactone type lovastatin in crude extract.
Two, lactone type gets the qualification of lovastatin product
(1) thin-layer chromatography qualification
With the kapillary of 0.3 × 100mm, by the lactone type lovastatin standard substance of the white crystals that is separated in red colouring agent for food, also used as a Chinese medicine and 2mg/mL (purchased from reference material center, Sichuan, lot number is 130320) contrast point sample on the self-control silica gel thin-layer plate of 25.4 × 76.2mm, developping agent is sherwood oil: ethyl acetate=1:4, ultraviolet lamp 254nm, recording Rf value is all 0.69; Be all sorrel after 5% sulfuric acid ethanol colour developing, as accompanying drawing 1.From accompanying drawing 1, it is identical with the thin-layer chromatography feature of lactone type lovastatin standard substance that red colouring agent for food, also used as a Chinese medicine prepared by the present invention is separated product.
(2)
1h NMR Structural Identification
By the lactone type lovastatin standard substance of 10mg and the white crystals be separated in the red colouring agent for food, also used as a Chinese medicine of 10mg, after dissolving with deuterated DMSO respectively, load nuclear magnetic tube, the hydrogen obtaining standard substance and white crystals under 300 MHz respectively composes the ownership at peak, as following table 1, its thaumatropy is as accompanying drawing 2.The data presentation of table 1, red colouring agent for food, also used as a Chinese medicine prepared by the present invention is separated product and lactone type lovastatin standard substance
1the ownership at H NMR peak is almost identical, is all accredited as the lactone type Lovastatin of accompanying drawing 2.
(3) efficient liquid phase chromatographic analysis
Chromatographic condition is: Lichrospher C
18post (7 μm, 4.6 × 250mm), column temperature room temperature 25 DEG C.Ultraviolet detection wavelength 237.8nm, moving phase is acetonitrile: 0.1g/dL phosphoric acid water=65:35(
v/v), sample size is 20 μ L.
The preparation of lactone type lovastatin standard solution: be 0.34mg/mL lactone type lovastatin standard solution with methyl alcohol compound concentration.
The preparation of acid type lovastatin reference substance solution and preparation: the NaOH solution (70% ethanol preparation) of the 0.2mol/L of the lactone type lovastatin standard substance 10mL of 3.4mg is reacted 1h under 50 DEG C of water-baths, is measured by high performance liquid chromatography areas of peak normalization method.
The lovastatin solution preparation that the present invention is separated: be mixed with the liquid to be measured that concentration is 1.53mg/mL with methyl alcohol.
The preparation of red colouring agent for food, also used as a Chinese medicine extracting solution: get the lovastatin crude extract medicinal extract 10mg extracted in red colouring agent for food, also used as a Chinese medicine, with dissolve with methanol, supersound extraction 1 hour at 50 DEG C, constant volume in 10mL volumetric flask.
Fig. 3 is the high-efficient liquid phase chromatogram of acid type lovastatin and lactone type lovastatin.Fig. 3 shows, and under above-mentioned chromatographic condition, the retention time of acid type lovastatin is 8.575 min, and the retention time of lactone type lovastatin is 14.004min.Analyze known lactone type lovastatin and be entirely converted into acid type structure, purity is greater than 98.8%, transformation efficiency is greater than 98.8%, and lactone type lovastatin standard substance are separated product high performance liquid chromatography peak retention time with red colouring agent for food, also used as a Chinese medicine is consistent, and areas of peak normalization method is analyzed purity is all greater than 98%.Figure is lactone type lovastatin and the lovastatin high performance liquid phase comparison diagram be separated in red colouring agent for food, also used as a Chinese medicine.As can be seen from Figure 4, being separated the monomer obtained is lactone type lovastatin, has no acid type structure.Analyzing reason may be that alcohol reflux temperature is high in leaching process, and acid type lovastatins a large amount of in red colouring agent for food, also used as a Chinese medicine at 75 DEG C is converted into lactone type structure, so what obtain is almost the lactone type lovastatin of pinniform crystallization entirely.
Precision Experiment: in one day, get 0.017,0.085, the lactone type lovastatin standardized solution of 0.17mg/mL respectively according to described chromatographic condition METHOD FOR CONTINUOUS DETERMINATION six times, calculating average RSD% is 1.39(withinday precision); Within continuous six days, get 0.017,0.085, the lactone type lovastatin standardized solution of 0.17mg/ml measures according to described chromatographic condition respectively, calculating average RSD% is 1.62(day to day precision), illustrate that precision is good.
The lovastatin of lactone type lovastatin standard substance, acid type lovastatin reference substance, separation is detected with HPLC respectively and analyzes, and to measure the content of lactone type lovastatin in Hongqu powder (red colouring agent) be 30.658mg/g.The amount of the lactone type lovastatin extracted from Hongqu powder (red colouring agent) by the inventive method, can calculate the extraction yield extracting lactone type lovastatin from Hongqu powder (red colouring agent).
In sum, the present invention receives relatively has technology to have following beneficial effect:
1, employing high temperature alcohol extracting method can remove the polysaccharide in Hongqu powder (red colouring agent) effectively, protein etc., and the lovastatin being extracted the rock steady structure in Hongqu powder (red colouring agent) efficiently, and raw material availability is high; Adopt column chromatography silica gel post to resolve to be separated, all separate disposable for the lactone type lovastatin in crude extract, extraction efficiency high (extraction yield is more than 85%), product purity high (more than 98%), can be applicable to the industries such as medicine, chemical industry, health, health care;
2, technological process is simple, and operation controllability is high, and adopt reflux, Suction filtration device, column chromatography silica gel post, the conventional equipments such as vacuum concentrating apparatus, production cost is low, is applicable to big-and-middle-sized industrial production.
3, involved raw material and solvent are all recycled, and achieve making full use of of resource: the organic solvent involved by each process is all recycle and reuse almost; The filter residue that vacuum filtration obtains is rich in polysaccharide, protein etc., can be used for the additive of animal-feed; Silicagel column after wash-out can further with the separation for monascorubin after methanol-eluted fractions.
Accompanying drawing explanation
The thin-layer chromatography of lactone type lovastatin (2) of Fig. 1 for being separated in lactone type lovastatin standard substance (1), red colouring agent for food, also used as a Chinese medicine; Wherein, the colour developing figure of A---ultraviolet lamp under 254nm wavelength, B---spray the colour developing figure after 5% sulfuric acid ethanol.
The conversion figure of Fig. 2 lovastatin two kinds of configurations.
The high-efficient liquid phase chromatogram of Fig. 3 acid type lovastatin and lactone type lovastatin.
Fig. 4 lactone type lovastatin standard substance and the lovastatin high-efficient liquid phase chromatogram be separated in red colouring agent for food, also used as a Chinese medicine.
Embodiment
Below by specific embodiment the method for lactone type lovastatin is separated from red colouring agent for food, also used as a Chinese medicine to the present invention and product is described further.
Embodiment 1
(1) preparation of lovastatin crude extract medicinal extract
By commercially available Hongqu powder (red colouring agent) (purchased from Zhejiang Sanhe Bioengineering Co., Ltd., lot number is 2014012301, the content of lovastatin is 30.658mg/g) successively to add the round-bottomed flask of 1000mL with the ratio of 10g/ 500mL with 100% straight alcohol, the temperature regulating heating unit is 75 DEG C, timing is started during backflow, refluxing extraction 5h, unload reflux, with Suction filtration device suction filtration while hot under vacuum pump pressure is 0.08Mpa, obtain filtrate and filter residue, filtrate pumps into vacuum concentrating apparatus, after concentrated, obtain lovastatin crude extract medicinal extract; Ethanol recycling in filtrate, filter residue is rich in polysaccharide, protein etc., the recyclable additive for animal-feed.
(2) separation of monomer ginkgolides type lovastatin
The lovastatin crude extract medicinal extract obtain step (1) and column chromatography silica gel (200 ~ 300 order) are that 2g:2g mixes sample post-drying with mass ratio, with 20g column chromatography silica gel dress post, moving phase is made by sherwood oil and ethyl acetate (volume ratio is 1:1), normal pressure or the wash-out that suitably pressurizes, ensure that flow velocity is 3mL/min, every 3mL is a flow point, and number consecutively; When moving phase is eluted to the outflow of Article 2 yellow band, stop wash-out, detect with thin-layer chromatography, merge identical component, obtain the pinniform white lactone type lovastatin crystallization that 300mg purity is 98%.Extraction yield is 97.9%.
Rush the sherwood oil in post flow point and ethyl acetate recovery, can reuse after fractionation; Silicagel column adsorptive also can further with the separation that can be used for monascorubin after methanol-eluted fractions; Methyl alcohol is also recyclable to be utilized again.
Embodiment 2
(1) preparation of lovastatin crude extract medicinal extract
Ethanolic soln adopts the ethanol of percent by volume 95%, and the ratio of Hongqu powder (red colouring agent) and ethanolic soln is 10g/250mL, and reflux temperature is 80 DEG C, and the time is 4 hours; During suction filtration, vacuum pump pressure is 0.07Mpa, and other and embodiment 1 are together.
(2) separation of monomer ginkgolides type lovastatin:
Column chromatography silica gel is 100 ~ 200 orders, lovastatin crude extract medicinal extract and column chromatography silica gel mass ratio 1g:2g mix sample, with 24g column chromatography silica gel dress post, moving phase sherwood oil and ethyl acetate volume ratio are 1:2, flow velocity is 4mL/min, every 2mL is a flow point, when moving phase is eluted to the outflow of Article 1 red zone, stops wash-out.The other the same as in Example 1.Obtain the pinniform white lactone type lovastatin crystallization that 290mg purity is higher, extraction yield is 94.6%.
Claims (7)
1. from red colouring agent for food, also used as a Chinese medicine, separating high-purity extracts a method for lovastatin, comprises following processing step:
(1) preparation of lovastatin crude extract medicinal extract: with commercially available Hongqu powder (red colouring agent) for raw material, with ethanolic soln refluxing extraction 3 ~ 8h at 70 ~ 80 DEG C; Then under 0.05 ~ 0.09Mpa with Suction filtration device suction filtration while hot, obtain filtrate and filter residue; Lovastatin crude extract medicinal extract is obtained after concentrating filter liquor;
(2) then the separation of monomer ginkgolides type lovastatin in lovastatin crude extract medicinal extract: lovastatin crude extract medicinal extract and column chromatography silica gel are mixed sample post-drying, fills post with column chromatography silica gel is that moving phase rushes post wash-out by sherwood oil and ethyl acetate; When flowing out to Article 1 red zone or Article 2 yellow band, stop rushing post, detect with thin-layer chromatography, merge identical component, obtain the pinniform white lactone type lovastatin crystallization that purity is higher.
2. the method for separating high-purity lactone type lovastatin from red colouring agent for food, also used as a Chinese medicine as claimed in claim 1, it is characterized in that: in step (1), the volume fraction of ethanolic soln is 40% ~ 100%; The proportioning of Hongqu powder (red colouring agent) and ethanolic soln is 1:25 ~ 1:50 g/mL.
3. the method for separating high-purity lactone type lovastatin from red colouring agent for food, also used as a Chinese medicine as claimed in claim 1, it is characterized in that: in step (2), lovastatin crude extract medicinal extract and column chromatography silica gel mix sample with the mass ratio of 1:0.5 ~ 1:3.
4. the method for separating high-purity lactone type lovastatin from red colouring agent for food, also used as a Chinese medicine as claimed in claim 1, it is characterized in that: in step (2), column chromatography silica gel dress post amount is 9 ~ 12 times that mix sample column chromatography silica gel quality.
5. the method for separating high-purity lactone type lovastatin from red colouring agent for food, also used as a Chinese medicine as claimed in claim 1, it is characterized in that: in step (2), the volume ratio of moving phase sherwood oil and ethyl acetate is 1:1 ~ 1:2.
6. the method for separating high-purity lactone type lovastatin from red colouring agent for food, also used as a Chinese medicine as claimed in claim 1, it is characterized in that: in step (2), moving phase rushes the flow velocity 0.5 ~ 5mL/min of post wash-out, and every 1 ~ 3.5mL is a flow point, and number consecutively.
7. the method for separating high-purity lactone type lovastatin from red colouring agent for food, also used as a Chinese medicine as claimed in claim 1, it is characterized in that: in step (2), the particle diameter of column chromatography silica gel is at 100 ~ 300 orders.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566268A (en) * | 2016-03-09 | 2016-05-11 | 福州大学 | Purification and preparation method of monascus-lovastatin |
| CN107510047A (en) * | 2017-09-14 | 2017-12-26 | 浙江天草生物科技股份有限公司 | Red yeast rice concentrate of high Lovastatin content and preparation method thereof and the Hongqu powder (red colouring agent) of high Lovastatin content and preparation method thereof |
| CN115947708A (en) * | 2022-12-20 | 2023-04-11 | 浙江天草生物科技股份有限公司 | Method for separating high-purity acid lovastatin from red yeast rice |
| CN115947708B (en) * | 2022-12-20 | 2024-07-12 | 浙江天草生物科技股份有限公司 | Method for separating high-purity acid lovastatin from monascus |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102432573A (en) * | 2011-12-26 | 2012-05-02 | 重庆大学 | Method for preparing lovastatin |
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2015
- 2015-05-29 CN CN201510285307.5A patent/CN104961716B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN102432573A (en) * | 2011-12-26 | 2012-05-02 | 重庆大学 | Method for preparing lovastatin |
Non-Patent Citations (1)
| Title |
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| 李明起等: "柱层析分离纯化功能性红曲米中的有效成分", 《中国酿造》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105566268A (en) * | 2016-03-09 | 2016-05-11 | 福州大学 | Purification and preparation method of monascus-lovastatin |
| CN107510047A (en) * | 2017-09-14 | 2017-12-26 | 浙江天草生物科技股份有限公司 | Red yeast rice concentrate of high Lovastatin content and preparation method thereof and the Hongqu powder (red colouring agent) of high Lovastatin content and preparation method thereof |
| CN115947708A (en) * | 2022-12-20 | 2023-04-11 | 浙江天草生物科技股份有限公司 | Method for separating high-purity acid lovastatin from red yeast rice |
| CN115947708B (en) * | 2022-12-20 | 2024-07-12 | 浙江天草生物科技股份有限公司 | Method for separating high-purity acid lovastatin from monascus |
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