CN102146109A - Method for preparing high-purity geniposide - Google Patents
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- CN102146109A CN102146109A CN2010101055408A CN201010105540A CN102146109A CN 102146109 A CN102146109 A CN 102146109A CN 2010101055408 A CN2010101055408 A CN 2010101055408A CN 201010105540 A CN201010105540 A CN 201010105540A CN 102146109 A CN102146109 A CN 102146109A
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Abstract
The invention discloses a method for preparing high-purity geniposide by extracting and purifying a cape jasmine fruit. The method comprises the following steps of: preparing a cape jasmine extract by adopting a water extraction and alcohol precipitation method; preparing a geniposide rough extract by purifying through adopting a macroporous resin adsorption eluting technology; and refining the geniposide by adopting an aluminum oxide column chromatography technology or n-butyl alcohol extraction technology to obtain the high-purity geniposide. The preparation method disclosed by the invention has the advantages of simplicity in operation, low cost, high product purity, high yield and no environmental pollution and is suitable for industrial production.
Description
Technical field
The present invention relates to medical technical field, be specifically related to a kind of method that purifying prepares high-purity gardenoside of from cape jasmine fruit, extracting.
Background technology
Cape jasmine is the dry mature fruit of madder wort cape jasmine Gardenia jasminoides Ellis..Gathered when the 9-11 month, fruit maturation was reddish yellow.Remove carpopodium and impurity, steam to Shanghai Automobile Factory or put the boiling water part omitted and scald, take out, dry [Chinese Pharmacopoeia Commission. Pharmacopoeia of People's Republic of China (version was an one in 2005) [S]. Beijing: Chemical Industry Press, 2005:173].The nature and flavor bitter cold is gone into the heart, liver, lung, stomach, three warmers, has the effect of purging intense heat relieving restlessness, clearing heat and promoting diuresis, removing pattogenic heat from the blood and toxic material from the body, swelling and pain relieving.
Contain a large amount of iridoid glycoside compounds [Wang Gangli in the cape jasmine, Chen Dechang, Zhao Shujie. Gardenia Ellis plant chemical ingredient progress [J]. CHINA JOURNAL OF CHINESE MATERIA MEDICA, 1996,21 (2): 67-72], comprise Geniposide, Gardenoside, genipin gentiobiose glycosides, shanzhiside, cape jasmine ketoside, Herba Paederiae time glycosides methyl esters, asperuloside, deacetylation woodruff thuja acid, deacetylation woodruff thuja acid methyl esters, Geniposidic acid (Geniposidic acid), coumaric acyl genipin gentiobiose glycosides; The organic acid composition comprises chlorogenic acid, ursolic acid, bitter Zang Honghua acid; Flavones ingredient: gardenin A, gardenin B, gardenin C, gardenin D, gardenin E, 3,4,5-trimethoxy wogonin, 3,4-dimethoxy wogonin, 4-dihydroxyl wogonin, 3,4-dihydroxyl wogonin, 3,4,5-trihydroxy-wogonin, 5,7,3,4-tetrahydroxy-6, flavonoid compounds such as 8-dimethoxy flavone.Jasminoidin (geniposide) is main iridoid glycoside compound; it is the main chemical compositions in the cape jasmine; pharmaceutical research shows that jasminoidin and metabolite thereof have: to the provide protection of liver, pancreatic cell; can promote choleresis, regulate the stomach function, increase SBF, and step-down, analgesic, antibiotic, anti-inflammatory, effect such as antitumor.Its structural formula is as follows:
At present, many when preparing jasminoidin with cape jasmine fruit both at home and abroad with traditional method separation and purification jasminoidin, as methods such as silica gel column chromatography, alumina column chromatography and recrystallizations.Traditional separation method needs to use a large amount of poisonous organic reagents in preparation process, causes environmental pollution easily.And Wang Lan adopts modern separation technology to prepare type RP-HPLC to extract, separate the monomeric complete method of jasminoidin from the cape jasmine medicinal material.The jasminoidin of preparation is through four spectrum (nucleus magnetic resonance, infrared spectra, UV spectrum, mass spectrums, figure is slightly) the common detection, and contrast with the document data, determine that purity can reach 99.9%, specification of quality [the Wang Lan of conformance with standard material, open mirror .RP-HPLC preparative chromatography and separate the jasminoidin monomer. Chinese patent medicine .2003,25 (9): 764-765].But during its pre-treatment, need remove other composition to greatest extent, improve the content of jasminoidin in the sample solution, thereby increase the preparation amount of unit preparation time.Make to prepare the sample method complexity, yield is low, is not suitable for scale operation.
Macroporous adsorbent resin is a class organic high molecular polymer sorbent material that grows up over past ten years, genus polyporus sexual intercourse linked polymer.It has good reticulated structure and higher specific surface area, by physical property adsorb organic compound matter selectively from the aqueous solution, separates the purpose of purifying thereby reach.Its influence, plurality of advantages such as regeneration is easy, desorption condition is gentle, life cycle is long, cost saving of having physical and chemical stability height, adsorption selectivity uniqueness, not existed by inorganics in addition are widely used in the separation and purification of compound in the Chinese medicine.Shen Rongguang [Shen Rongguang, Chen Zhenghang. the separation and purification of jasminoidin in the cape jasmine medicinal material. foodstuffs industry science and technology, 2006,4 (27): 123-127], obtain through lyophilize again that purity is 65.8%, the jasminoidin of yield 91% with the jasminoidin in the initial gross separation of macroporous adsorbent resin X-5 column chromatography, the enrichment gardenia extract.Yao Gan is by research [Yao Gan, He Zongyu, Fang Jinian. the research of total iridoid glycoside and jasminoidin in the purification with macroreticular resin cape jasmine. herbal medicine, 2006,37 (1): 57-61] think HPD450 macroporous adsorbent resin effectively enrichment and purifying Fructus Gardeniae total iridoid glycosides, jasminoidin.Lv Maoping [Lv Maoping, Qiao Qingbin, Pang Chunyan, Deng. macroporous resin is to the research of jasminoidin separating effect. herbal medicine, 2002,33:794-796] etc. by relatively D301R, D396, D296 and four kinds of model macroporous resins of AB-8 the adsorption effect of jasminoidin is found that the D301R resin can be used to separate jasminoidin, but the preparation technology of jasminoidin and the purity of jasminoidin are not done further report research.Appoint direct troops, people such as He Kaize compared the absorption property of 5 kinds of macroporous adsorbent resins such as H103, NKA-II, HPD100A, HPD400A and D141 to Gardenia Yellow in the gardenia extract and jasminoidin.Determined to carry out the separation and purification of jasminoidin with H103 and two kinds of non-polar macroporous resin of HPD100A, and determined processing parameter, the jasminoidin purity that obtains reaches 81.3%, the rate of recovery is that 88.5%[appoints and directs troops, He Kaize, Tan Jian, etc. two kinds of macroporous adsorbent resins are in conjunction with the separation and purification Geniposide. ion-exchange and absorption, 2006,22 (2): 105-111].This shows, all be to adopt the macroporous adsorption resin technology purifying to prepare jasminoidin at present in the research, but adopt macroporous adsorption resin technology to prepare jasminoidin separately, and the purity of jasminoidin is all lower, needs to do further research in conjunction with other process for refining.
Summary of the invention
At the above-mentioned deficiency of prior art, technical problem to be solved by this invention provides that a kind of preparation technology is simple, the method for preparing high-purity gardenoside from cape jasmine fruit of low cost and environmentally safe.
The preparation method of high-purity gardenoside provided by the invention comprises the steps:
(1) preparation gardenia extract: it is an amount of to get dry cape jasmine fruit, soaks the back water and decocts 2-3 time, adds water 5-15 at every turn and doubly measures, and each 1-1.5h filters merging filtrate; Filtrate is concentrated into every ml contains the 1g crude drug, add 95% ethanol to concentrated solution and contain alcohol amount and be 70%, centrifugal, collect supernatant liquor, decompression recycling ethanol is not to there being the alcohol flavor, and is concentrated into every 1ml and contains the 0.5g crude drug, and this concentrated solution is gardenia extract;
(2) purifying: through macroporous adsorbent resin, the macroporous resin column volume is 1BV with above-mentioned gardenia extract, uses the 1BV water elution earlier, discards elutriant; Use the ethanol elution of 0%-30% again, collect elutriant, drying under reduced pressure, obtaining purity is the jasminoidin crude extract of 60-80%;
(3) refining: above-mentioned jasminoidin crude extract is made with extra care by following n-butanol extraction technology or alumina column chromatography technology and is obtained high-purity gardenoside:
N-butanol extraction technology: it is an amount of to get the jasminoidin crude extract, the water that adding 10-20 doubly measures makes it dissolving, add propyl carbinol respectively, extracting twice, the 10-20 of the amount that each propyl carbinol consumption is the jasminoidin crude extract doubly collects butanol extraction liquid, reclaims propyl carbinol, drying obtains purity and is higher than 90% high-purity gardenoside;
Alumina column chromatography technology: getting an amount of particle diameter is 100-200 order chromatography neutral alumina, pack in the glass column, blade diameter length ratio 7: 1-5: 1, the applied sample amount of jasminoidin crude extract is 1/30 of an aluminum oxide consumption, it is dissolved in a spot of distilled water as sample solution, sample solution is slowly joined in the alumina chromatographic column, is alcohol flushing alumina column more than 95% with concentration behind the last sample, and the elutriant consumption is a 6-15 times of column volume; Collect ethanol eluate, decompression recycling ethanol, drying obtains purity and is higher than 90% high-purity gardenoside.
Preferably, in the preparation method's of the above-mentioned high-purity gardenoside of the present invention the step (2), macroporous resin adopts the D301R weakly basic styrene type anion exchange resin, and the macroporous resin column volume is 1BV, cape jasmine sample solution applied sample amount is 1/3BV, the water flushing dose is 1BV, and the alcohol flushing amount of 0%-30% is 2-4BV.
The present invention according to jasminoidin in the relative more weak characteristics of cyclenes ether glycoside composition Semi-polarity, when adopting macroporous resin purification jasminoidin extract, earlier remove some water-soluble impurities (pigment, sugar etc.) and the big cyclenes ether glycoside composition of polarity with a large amount of washings, use the ethanol selective elution jasminoidin of 0%-30% again, can with the impurity and the component separating of low-pole.The jasminoidin purity that adopts macroporous resin purification jasminoidin prepared will obtain highly purified jasminoidin between 60%-80%, need in conjunction with other separation purification method refining highly purified jasminoidin.
Jasminoidin leaching process jasminoidin extraction yield is 70%-80% among the present invention; The rate of transform of macroporous resin adsorption elution process jasminoidin is 80%-85%; The rate of transform of jasminoidin is 60-70% in the alumina column chromatography technology; The rate of transform of jasminoidin is 55%-75% in the n-butanol extraction technology.Adopt in the macroporous adsorption resin technology combined aluminum oxide column chromatography prepared high-purity gardenoside process, the rate of transform of jasminoidin is about 40-50%, adopt macroporous adsorption resin technology in conjunction with in the n-butanol extraction prepared high-purity gardenoside process, the rate of transform of jasminoidin is 35%-45%.Adopt high performance liquid chromatography (HPLC) method to measure the content of jasminoidin in this powder, purity is higher than 92% by dry product.And carry out UV, MS, IR analysis, and with the comparison of jasminoidin standard substance collection of illustrative plates, carry out structural analysis, prove jasminoidin.
Adopt the inventive method to prepare purity and be higher than 90% jasminoidin, preparation technology is simple, is fit to suitability for industrialized production.
Description of drawings
Fig. 1 is jasminoidin highly finished product and jasminoidin reference substance ultra-violet absorption spectrum stacking diagram among the present invention.
Fig. 2 is jasminoidin highly finished product infrared spectrogram among the present invention.
Fig. 3 is jasminoidin reference substance infrared spectrogram among the present invention.
Fig. 4 is jasminoidin reference substance one-level full scan mass spectrum among the present invention.
Fig. 5 is jasminoidin highly finished product one-level full scan mass spectrum among the present invention.
Fig. 6 is jasminoidin reference substance high-efficient liquid phase chromatogram among the present invention.
Fig. 7 is jasminoidin highly finished product high-efficient liquid phase chromatogram among the present invention.
Embodiment
Below in conjunction with the drawings and specific embodiments, further set forth the present invention.These embodiment are interpreted as only being used to the present invention is described and are not used in restriction protection scope of the present invention.After the content of having read the present invention's record, those skilled in the art can make various changes or modifications the present invention, and these equivalences change and modify and fall into claim of the present invention institute restricted portion equally.
1. preparation gardenia extract: get dry cape jasmine medicinal material 1Kg (content of jasminoidin is 4.23%), 0.5h is soaked in water, decoct 3 times, add 10 times of amounts of water at every turn, each 1.5h, filter, merging filtrate, filtrate is concentrated into 1: 1 (every ml contains the 1g crude drug), adding 95% ethanol to concentrated solution, to contain alcohol amount be 70%, 48h is placed in refrigeration, and is centrifugal, collects supernatant liquor, decompression filtrate recycling ethanol is to there not being the alcohol flavor, and being concentrated into the concentrated solution that contains the 0.5g crude drug in every 1ml extracting solution, extracting liquid volume is 2L, i.e. gardenia extract.
2. macroporous resin purification jasminoidin: good macroporous resin 4.4Kg is encased in the glass column that is lined with a little absorbent cotton to get pre-treatment, treat that resin precipitated is complete, make that the blade diameter length ratio of resin column is 1: 7.5, coated with absorbent cotton a little on resin column, the macroporous resin column volume is 6.0L.Get above-mentioned gardenia extract and add, with sample on the flow velocity of 6.0L/h in the glass column top.After last sample finishes, standing adsorption 2h, water flushing macroporous resin column to effluent liquid with 6L is colourless, be adsorbed in jasminoidin on the macroporous resin with 20% ethanol elution again, the eluting solvent consumption is 12L, collects 20% alcohol flushing liquid, decompression recycling ethanol, drying gets light yellow medicinal extract, is the jasminoidin crude extract.Jasminoidin crude extract quality is 36.5g, and the purity of jasminoidin is 71%, and the jasminoidin rate of transform is 61.3%.
3. jasminoidin process for refining
N-butanol extraction: it is an amount of to get above-mentioned jasminoidin crude extract, and the water that adds 730ml makes it dissolving, adds n-butanol extraction twice respectively, and each propyl carbinol consumption is 730ml, collects butanol extraction liquid, and drying gets white or yellow powder powder jasminoidin.The jasminoidin finished product is 18.8g.Jasminoidin highly finished product yield 18.8%.
Adopting the content of jasminoidin in the high effective liquid chromatography for measuring jasminoidin finished product, is 98.0% according to peak area normalization method meter jasminoidin purity; By dry product, the content of high effective liquid chromatography for measuring jasminoidin is 92.0%.The jasminoidin yield is 40.9%.The HPLC analysis condition is: Kromasil 100-5C
18The ODS chromatographic column (5 μ m, 4.6mm*250mm); Acetonitrile-0.05% phosphate aqueous solution (15: 85) is a moving phase; Flow velocity: 1ml/min; Column temperature: 30 ℃; Sample size: 10 μ l; The detection wavelength is 238nm; Number of theoretical plate is fixed tentatively be by the jasminoidin peak and is lower than 1500.Jasminoidin reference substance and jasminoidin highly finished product high-efficient liquid phase chromatogram are as shown in Figure 1, 2.To the jasminoidin highly finished product carry out UV, MS, IR analyzes (shown in Fig. 2,5,7), with jasminoidin standard substance collection of illustrative plates (shown in Fig. 3,4,6) comparison, carries out structural analysis, is defined as jasminoidin.
1. preparation gardenia extract: get dry cape jasmine medicinal material 1Kg (content of jasminoidin is 4.23%), 0.5h is soaked in water, decoct 3 times, add 10 times of amounts of water at every turn, each 1.5h, filter, merging filtrate, filtrate is concentrated into 1: 1 (every ml contains the 1g crude drug), adding 95% ethanol to concentrated solution, to contain alcohol amount be 70%, 48h is placed in refrigeration, and is centrifugal, collects supernatant liquor, decompression filtrate recycling ethanol is to there not being the alcohol flavor, and being concentrated into the concentrated solution that contains the 0.5g crude drug in every 1ml extracting solution, extracting liquid volume is 2L, i.e. gardenia extract.
2. macroporous resin purification jasminoidin: good macroporous resin 4.4Kg is encased in the glass column that is lined with a little absorbent cotton to get pre-treatment, treat that resin precipitated is complete, make that the blade diameter length ratio of resin column is 1: 7.5, coated with absorbent cotton a little on resin column, the macroporous resin column volume is 6.0L.Get above-mentioned gardenia extract and add, with sample on the flow velocity of 6.0L/h in the glass column top.After last sample finishes, standing adsorption 2h, water flushing macroporous resin column to effluent liquid with 6L is colourless, be adsorbed in jasminoidin on the macroporous resin with water elution again, the eluting solvent consumption is 18L, collects 20% alcohol flushing liquid, decompression recycling ethanol, drying gets light yellow medicinal extract, is the jasminoidin crude extract.Jasminoidin crude extract quality is 34.3g, and the purity of jasminoidin is 73.1%, and the jasminoidin rate of transform is 57.6%.
3. jasminoidin process for refining
Alumina column chromatography: get chromatography neutral alumina (100-200 order) 347g, pack in the glass column, blade diameter length ratio 5: 1, get above-mentioned jasminoidin crude extract, it is dissolved in a spot of distilled water as sample solution, sample solution is slowly joined in the alumina chromatographic column, and with 95% alcohol flushing alumina column, the elutriant consumption is 2.2L behind the last sample.Collect ethanol eluate, decompression recycling ethanol, drying gets light yellow or yellow jasminoidin powder.The jasminoidin finished product is 17.1g.
Adopting the content of jasminoidin in the high effective liquid chromatography for measuring jasminoidin finished product, is 98.0% according to peak area normalization method meter jasminoidin purity; By dry product, the purity of high effective liquid chromatography for measuring jasminoidin is 92.3%.The jasminoidin rate of transform is 37.3%.The HPLC analysis condition is: Kromasil 100-5C
18The ODS chromatographic column (5 μ m, 4.6mm*250mm); Acetonitrile-0.05% phosphate aqueous solution (15: 85) is a moving phase; Flow velocity: 1ml/min; Column temperature: 30 ℃; Sample size: 10 μ l; The detection wavelength is 238nm; Number of theoretical plate is fixed tentatively be by the jasminoidin peak and is lower than 1500.To the jasminoidin highly finished product carry out UV, MS, IR analyzes (shown in Fig. 2,5,7), with jasminoidin standard substance collection of illustrative plates (shown in Fig. 3,4,6) comparison, carries out structural analysis, is defined as jasminoidin.
Claims (5)
1. the preparation method of a high-purity gardenoside is characterized in that, this method comprises the steps:
(1) preparation gardenia extract: it is an amount of to get dry cape jasmine fruit, soaks the back decocting routinely and extracts, and decocting liquid filters, merging filtrate; Filtrate is concentrated, add the ethanol alcohol precipitation in the concentrated solution, leave standstill, collect supernatant liquor, decompression recycling ethanol concentrates to there not being the alcohol flavor, and this concentrated solution is gardenia extract;
(2) purifying: above-mentioned gardenia extract is crossed macroporous adsorptive resins, and first water wash-out discards water elution liquid; Use the ethanol elution of lower concentration again, collect ethanol eluate, drying under reduced pressure, obtaining purity is the jasminoidin crude extract of 60-80%;
(3) refining: above-mentioned jasminoidin crude extract is made with extra care by following n-butanol extraction technology or alumina column chromatography technology and is obtained high-purity gardenoside:
N-butanol extraction technology: it is an amount of to get the jasminoidin crude extract, add-water makes it dissolving, adds propyl carbinol respectively, extracting twice ,-collect butanol extraction liquid, reclaim propyl carbinol, drying obtains purity and is higher than 90% high-purity gardenoside;
Alumina column chromatography technology: get an amount of chromatography neutral alumina, pack in the glass column, the jasminoidin crude extract is dissolved in a spot of distilled water as sample solution, slowly join sample solution in the alumina chromatographic column, be alcohol flushing alumina column more than 95% with concentration behind the last sample, collect ethanol eluate, decompression recycling ethanol, drying obtains purity and is higher than 90% high-purity gardenoside.
2. by the preparation method of the described high-purity gardenoside of claim 1, it is characterized in that during extraction, in the step (1), water consumption was that 5-15 doubly measures when decocting extracted, decocting time is 1-1.5h, and decocting number of times is 2-3 time.The water extract is concentrated into the concentrated solution that every ml contains the 1-1.5g crude drug in the alcohol precipitation process, and the ethanol alcohol precipitation concentration is a 60-70% ethanol, leaves standstill 24-48 hour, collects supernatant liquor, and decompression recycling ethanol is concentrated into the concentrated solution that every 1ml contains the 0.5-1g crude drug at last to there not being the alcohol flavor.
3. by the preparation method of the described high-purity gardenoside of claim 1, it is characterized in that during macroporous resin purification, in the step (2), macroporous resin adopts the D301R weakly basic styrene type anion exchange resin.In the macroporous resin purification process, establishing the macroporous resin column volume is 1BV, and cape jasmine sample solution applied sample amount scope is 1/3-1/2BV, and the water flushing dose is 0.8-1BV, and the flushing dose of low-concentration ethanol is 2-4BV, and concentration is 0%-30%.
4. by the preparation method of the described high-purity gardenoside of claim 1, it is characterized in that, when refining, in the n-butanol extraction technology of step (3), the propyl carbinol consumption be the jasminoidin crude extract amount 10-20 doubly.
5. press the preparation method of the described high-purity gardenoside of claim 1, it is characterized in that, when refining, in the alumina column chromatography technology of step (3), aluminum oxide adopts 100-200 order chromatography neutral alumina, and alumina column blade diameter length ratio scope is 7: 1-5: 1, and the applied sample amount scope of jasminoidin crude extract is the 1/10-1/15 of aluminum oxide consumption, last sample overflush fluid alcohol concn is 90-95%, and the elutriant amount ranges is a 6-15 times of column volume.
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| CN103211829A (en) * | 2012-01-13 | 2013-07-24 | 樊向德 | Compounds having virus resistance and composition thereof |
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| CN104666511A (en) * | 2014-11-27 | 2015-06-03 | 安徽农业大学 | Technique for preparing gardenia iridoid glycoside compound employing leaves of gardenia plant |
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| CN103211829A (en) * | 2012-01-13 | 2013-07-24 | 樊向德 | Compounds having virus resistance and composition thereof |
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| CN103372078A (en) * | 2012-04-19 | 2013-10-30 | 中国中医科学院中药研究所 | Medicine for treating influenza and preparation method thereof |
| CN103087129B (en) * | 2013-03-12 | 2015-07-22 | 广西山云生化科技有限公司 | Method for extracting geniposide from gardenia yellow pigment waste liquor |
| CN103087129A (en) * | 2013-03-12 | 2013-05-08 | 广西山云生化科技有限公司 | Method for extracting geniposide from gardenia yellow pigment waste liquor |
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| CN104666511A (en) * | 2014-11-27 | 2015-06-03 | 安徽农业大学 | Technique for preparing gardenia iridoid glycoside compound employing leaves of gardenia plant |
| CN110862425A (en) * | 2019-11-08 | 2020-03-06 | 河南中医药大学 | Method for extracting geniposide compound from fructus gardeniae jasminoides and application thereof |
| CN111840390A (en) * | 2020-09-01 | 2020-10-30 | 北京中医药大学 | Pharmaceutical composition for improving cognitive dysfunction and preparation method thereof |
| CN113480581A (en) * | 2021-07-21 | 2021-10-08 | 湖南朗林生物资源股份有限公司 | Method for extracting iridoid glycoside from rehmannia |
| CN113480581B (en) * | 2021-07-21 | 2022-05-24 | 湖南朗林生物资源股份有限公司 | Method for extracting iridoid glycoside from rehmannia |
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Application publication date: 20110810 |