CN101525357A - Method for separating and preparing penta-galloyl glucose from Chinese medicament - Google Patents
Method for separating and preparing penta-galloyl glucose from Chinese medicament Download PDFInfo
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- CN101525357A CN101525357A CN200810008080A CN200810008080A CN101525357A CN 101525357 A CN101525357 A CN 101525357A CN 200810008080 A CN200810008080 A CN 200810008080A CN 200810008080 A CN200810008080 A CN 200810008080A CN 101525357 A CN101525357 A CN 101525357A
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- 238000000034 method Methods 0.000 title claims abstract description 24
- 239000003814 drug Substances 0.000 title claims abstract description 22
- QJYNZEYHSMRWBK-NIKIMHBISA-N 1,2,3,4,6-pentakis-O-galloyl-beta-D-glucose Chemical compound OC1=C(O)C(O)=CC(C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(O)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(O)C(O)=C(O)C=2)=C1 QJYNZEYHSMRWBK-NIKIMHBISA-N 0.000 title abstract 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 23
- 238000000605 extraction Methods 0.000 claims abstract description 18
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 239000000287 crude extract Substances 0.000 claims abstract description 15
- 238000000926 separation method Methods 0.000 claims abstract description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000000746 purification Methods 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 239000000178 monomer Substances 0.000 claims abstract description 6
- 239000000284 extract Substances 0.000 claims abstract description 5
- 239000000843 powder Substances 0.000 claims abstract description 5
- 229920000296 Glucogallin Polymers 0.000 claims description 51
- GDVRUDXLQBVIKP-HQHREHCSSA-N 1-O-galloyl-beta-D-glucose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(=O)C1=CC(O)=C(O)C(O)=C1 GDVRUDXLQBVIKP-HQHREHCSSA-N 0.000 claims description 16
- 230000002411 adverse Effects 0.000 claims description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 10
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 7
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 claims description 7
- 239000000194 fatty acid Substances 0.000 claims description 6
- 241000736199 Paeonia Species 0.000 claims description 4
- 235000006484 Paeonia officinalis Nutrition 0.000 claims description 4
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005192 partition Methods 0.000 claims description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 4
- 241001116389 Aloe Species 0.000 claims description 2
- 244000020518 Carthamus tinctorius Species 0.000 claims description 2
- 235000003255 Carthamus tinctorius Nutrition 0.000 claims description 2
- 241000050051 Chelone glabra Species 0.000 claims description 2
- 235000007516 Chrysanthemum Nutrition 0.000 claims description 2
- 244000189548 Chrysanthemum x morifolium Species 0.000 claims description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- 241000208688 Eucommia Species 0.000 claims description 2
- 241000221079 Euphorbia <genus> Species 0.000 claims description 2
- -1 Fatty acid ester Chemical class 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 240000005001 Paeonia suffruticosa Species 0.000 claims description 2
- 235000003889 Paeonia suffruticosa Nutrition 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- 240000004980 Rheum officinale Species 0.000 claims description 2
- 235000008081 Rheum officinale Nutrition 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 235000011399 aloe vera Nutrition 0.000 claims description 2
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 2
- 238000004090 dissolution Methods 0.000 claims description 2
- 238000010828 elution Methods 0.000 claims description 2
- 229930195729 fatty acid Natural products 0.000 claims description 2
- 150000002191 fatty alcohols Chemical class 0.000 claims description 2
- 239000002994 raw material Substances 0.000 claims description 2
- 210000000582 semen Anatomy 0.000 claims description 2
- 238000002791 soaking Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 1
- 238000007670 refining Methods 0.000 claims 1
- 230000000694 effects Effects 0.000 abstract description 4
- 238000011084 recovery Methods 0.000 abstract description 3
- 239000007864 aqueous solution Substances 0.000 abstract 2
- 238000002137 ultrasound extraction Methods 0.000 abstract 1
- 239000012071 phase Substances 0.000 description 11
- 238000009834 vaporization Methods 0.000 description 6
- 230000008016 vaporization Effects 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 3
- 244000236658 Paeonia lactiflora Species 0.000 description 2
- 235000008598 Paeonia lactiflora Nutrition 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 238000005070 sampling Methods 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- 208000008589 Obesity Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 229940126678 chinese medicines Drugs 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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- Medicines Containing Plant Substances (AREA)
Abstract
The invention discloses a method for separating and preparing penta-galloyl glucose from Chinese medicament. The method comprises the following steps: 1, Extraction, namely crushing the Chinese medicament, taking an aqueous solution of ethanol or an aqueous solution of acetone as a solvent to soak the Chinese medicament powder, carrying out ultrasonic extraction, carrying out concentration under reduced pressure on the obtained extract liquid to obtain brown thick paste, dissolving the thick paste in water, carrying out extraction for 3 to 5 times by ethyl acetate, and distilling the extraction liquid to dryness under reduced pressure so as to obtain a crude extract of the penta-galloyl glucose; and 2, Purification, namely dissolving the crude extract of the penta-galloyl glucose, respectively using two different solvent systems to separate the crude extract twice through a high-speed countercurrent chromatograph, and finally obtaining penta-galloyl glucose monomers with the purity as high as above 95 percent. The process is simple and feasible, and has high extraction efficiency, good separation effect, high recovery rate and high generalization and application value.
Description
Technical field
The present invention relates to from the method for Chinese medicine extraction separation five galloyl glucoses, particularly adopt high speed adverse current chromatogram to separate the method for preparation five galloyl glucoses.
Background technology
Five galloyl glucoses are a kind of biologically active componentss with multiple pharmacological effect.Have recently and studies show that it has tangible antitumous effect and reduces the effects such as obesity that diabetes are followed.These research prompting five galloyl glucoses may become a kind of natural drug with huge potentiality to be exploited.
Bibliographical information (Ren Yulin, et al.J Med Chem.2006,49 (9): 2829.), can prepare five galloyl glucoses by the method for chemosynthesis are arranged.But technology is numerous and diverse, cost is expensive its application is very limited.The inventor studies confirm that contains five galloyl glucoses in some Chinese medicines, thereby extraction from Chinese medicine, separation and purifying five galloyl glucoses are with a wide range of applications.But the chemical structure complexity of five galloyl glucoses, solvability is relatively poor, and separation and purification is difficult.Usually the method for extracting effective components adopts the solid phase packed column chromatography to separate more from Chinese medicine; yet can produce very strong adsorption with the solid dielectric surface owing in five galloyl glucose molecules, contain a plurality of phenolic hydroxyl groups; cause serious irreversible adsorption; not only cause the rate of recovery very low, and separating technology is loaded down with trivial details.Adopt the high speed adverse current chromatogram isolation technique can improve the rate of recovery of sample, have characteristics such as simple to operate, favorable reproducibility, separation efficiency height, fractional dose are bigger simultaneously, can solve the defective of traditional separation method effectively.
Summary of the invention
The purpose of this invention is to provide a kind of method of from Chinese medicine, separating preparation five galloyl glucoses.
To achieve these goals, by the following technical solutions:
The extraction of (1) five galloyl glucose
Chinese medicine is pulverized, and is solvent soaking herb powder and supersound extraction with ethanol-water solution or acetone-water solution, and the extracting solution that obtains carries out concentrating under reduced pressure and obtains brown thick paste; With this thick paste of water dissolution, use ethyl acetate extraction 3-5 time again after, with the extraction liquid evaporated under reduced pressure, obtain the crude extract of five galloyl glucoses.
The preliminary purification of (2) five galloyl glucoses
The crude extract of five galloyl glucoses is carried out initial gross separation with the high speed adverse current chromatogram partition method.Collection contains the component of five galloyl glucoses, and the evaporated under reduced pressure solvent obtains first minute thing of five galloyl glucoses.
Making with extra care of (3) five galloyl glucoses
The first minute thing of (2) resulting five galloyl glucoses carried out separation and purification again with the high speed adverse current chromatogram partition method, finally obtain highly purified five galloyl glucose monomers.
As the Chinese medicine that extracts raw material is the root of herbaceous peony, the radix paeoniae rubrathe, Turkey-galls, Tree Peony Bark, the root of large-flowered skullcap, aloe, Semen Cassiae, Humifuse Euphorbia Herb, Semen Litchi, chrysanthemum, safflower, the bark of eucommia and rheum officinale etc.
In used ethanol-water solution or the acetone-water solution, the volume percent of ethanol or acetone is 40-60%; And soak with the ratio of 5-10ml solvent in every gram White Peony Root.The temperature of supersound extraction is 40-60 ℃, and ultrasonic time is 1-2 hour.Solvent concentrates, the exsiccant temperature is all less than 60 ℃.
During with the high speed adverse current chromatogram separation and purification, the system that solvent system is made up of alkane-fatty acid ester-Fatty Alcohol(C12-C14 and C12-C18)-water, wherein alkane can be selected normal hexane or hexanaphthene etc. for use; Fatty acid ester can be selected ethyl acetate or methyl acetate etc. for use; Fatty Alcohol(C12-C14 and C12-C18) can be selected methyl alcohol, ethanol, propyl alcohol, Virahol or propyl carbinol etc. for use, and the proportioning of alkane-fatty acid ester-Fatty Alcohol(C12-C14 and C12-C18)-water is (0.5-2): (8-12): (1-3): 10; The phase that fixes mutually in the employing is made the anti-phase type of elution of moving phase down mutually.
Use two kinds of different solvent systems respectively,, finally obtain highly purified five galloyl glucose monomers through twice separation of high speed adverse current chromatogram to crude extract.
Compare with column chromatography, adopt that the inventive method technology is simple, sample free of losses, purpose product yield height, good separating effect, can from the root of herbaceous peony, separation and purification obtain purity at five galloyl glucose monomers more than 95%.
Embodiment
Embodiment 1 usefulness ethanol-water solution extracts crude extract
1. the root of herbaceous peony was pulverized 40 mesh sieves, took by weighing the 20g White Peony Root, and added 100ml ethanol-water solution (the alcoholic acid volume fraction is 50%) and soak and carry out supersound extraction.Extracting temperature is 60 ℃, and ultrasonic time is 1h, filters, and keeps filtrate.Under similarity condition, add ethanol-water solution once more, filter residue is extracted again, 3 times repeatedly, three filtrates are merged.Under 50 ℃, reduction vaporization concentrates, and removes organic solvent and obtains brown thick paste.
2. add suitable quantity of water thick paste is dissolved, with water saturated ethyl acetate extraction 3 times, combined ethyl acetate layer extraction liquid, under 50 ℃, reduction vaporization is concentrated into solvent evaporated, obtains five galloyl glucose crude extracts.
Embodiment 2 usefulness acetone-water solution extract crude extract
1. the radix paeoniae rubrathe was pulverized 40 mesh sieves, taken by weighing 20g radix paeoniae rubrathe powder, and added 100ml acetone-water solution (volume fraction of acetone is 60%) and soak and carry out supersound extraction.Extracting temperature is 60 ℃, and ultrasonic time is 1h, filters, and keeps filtrate.Under similarity condition, add acetone-water solution once more, filter residue is extracted again, 3 times repeatedly, three filtrates are merged.Under 50 ℃, reduction vaporization concentrates, and removes organic solvent and obtains brown thick paste.
2. add suitable quantity of water thick paste is dissolved, with water saturated ethyl acetate extraction 3 times, combined ethyl acetate layer extraction liquid, under 50 ℃, reduction vaporization is concentrated into solvent evaporated, obtains five galloyl glucose crude extracts.
The preliminary purification of embodiment 3 five galloyl glucose crude extracts
Measure normal hexane 87ml, ethyl acetate 870ml, methyl alcohol 174ml and water 870ml, place the 2000ml separating funnel, fully shake up, behind the standing demix, get the phase that fixes mutually, make moving phase down mutually.With the last chromatographic column of injecting high-speed counter-current chromatograph with the flow velocity of 25ml/min.Open counter current chromatograph to 800 commentaries on classics/min, go into moving phase with the flow pump of 2.0ml/min then, balance high speed adverse current chromatogram system.With phase solution dissolving 200mg five galloyl glucose crude extracts under the 20ml, treat the system balance after, by the sampling valve sample introduction, under 280nm, monitor elutant with the ultraviolet-visible detector.According to the collection of illustrative plates that detector is gathered, collect the component that contains five galloyl glucoses.Under 50 ℃, reduction vaporization is concentrated into solvent evaporated, obtains five galloyl glucoses and just divides thing, and wherein five galloyl glucose content are about 40%.
Making with extra care of embodiment 3 five galloyl glucose crude extracts
Measure normal hexane 90ml, ethyl acetate 900ml, methyl alcohol 90ml and water 900ml, place the 2000ml separating funnel, fully shake up, behind the standing demix, get the phase that fixes mutually, make moving phase down mutually.With the last chromatographic column of injecting high-speed counter-current chromatograph with the flow velocity of 25ml/min.Open counter current chromatograph to 800 commentaries on classics/min, go into moving phase with the flow pump of 2ml/min then, balance high speed adverse current chromatogram system.Just divide thing with phase solution dissolving 10mg five galloyl glucoses under the 20ml, treat the system balance after, by the sampling valve sample introduction, monitor elutant at 280nm with the ultraviolet-visible detector.According to the collection of illustrative plates that detector is gathered, collect the component that contains five galloyl glucose peaks.Under 50 ℃, reduction vaporization is concentrated into solvent evaporated, obtains brown five galloyl glucose solids, and through the HPLC check, purity is 95.8%.
Claims (8)
1. one kind is separated the method for preparing five galloyl glucoses from Chinese medicine, it is characterized in that step is as follows:
The extraction of (1) five galloyl glucose
Chinese medicine is pulverized, and is solvent soaking herb powder and supersound extraction with ethanol-water solution or acetone-water solution, and the extracting solution that obtains carries out concentrating under reduced pressure and obtains brown thick paste; With this thick paste of water dissolution, use ethyl acetate extraction 3-5 time again after, with the extraction liquid evaporated under reduced pressure, obtain the crude extract of five galloyl glucoses.
The preliminary purification of (2) five galloyl glucoses
The crude extract of five galloyl glucoses is carried out initial gross separation with the high speed adverse current chromatogram partition method.Collection contains the component of five galloyl glucoses, and the evaporated under reduced pressure solvent obtains first minute thing of five galloyl glucoses.
Making with extra care of (3) five galloyl glucoses
First minute thing of (2) gained five galloyl glucoses carried out separation and purification again with the high speed adverse current chromatogram partition method, finally obtain highly purified five galloyl glucose monomers.
2. method of separating preparation five galloyl glucoses from Chinese medicine according to claim 1 is characterized in that: as the Chinese medicine that extracts raw material is the root of herbaceous peony, the radix paeoniae rubrathe, Turkey-galls, Tree Peony Bark, the root of large-flowered skullcap, aloe, Semen Cassiae, Humifuse Euphorbia Herb, Semen Litchi, chrysanthemum, safflower, the bark of eucommia and rheum officinale etc.
3. method of from Chinese medicine, separating preparation five galloyl glucoses according to claim 1, it is characterized in that: in used ethanol-water solution or the acetone-water solution, the volume percent of ethanol or acetone is 40-60%; And soak with the ratio of 5-10ml in every gram herb powder.
4. method of from Chinese medicine, separating preparation five galloyl glucoses according to claim 1, it is characterized in that: the temperature of supersound extraction is 40-60 ℃, ultrasonic time is 1-2 hour.
5. method of separating preparation five galloyl glucoses from Chinese medicine according to claim 1, it is characterized in that: the temperature of all concentrating under reduced pressure or drying under reduced pressure is all less than 60 ℃ in described step.
6. method of separating preparation five galloyl glucoses from Chinese medicine according to claim 1 is characterized in that: adopt the phase that fixes mutually when separating with high speed adverse current chromatogram, make the anti-phase type of elution of moving phase down mutually.
7. method of from Chinese medicine, separating preparation five galloyl glucoses according to claim 1, it is characterized in that: carrying out isolating solvent system with high speed adverse current chromatogram is the system that alkane-fatty acid ester-Fatty Alcohol(C12-C14 and C12-C18)-water is formed, and wherein alkane can be selected normal hexane or hexanaphthene for use; Fatty acid ester can be selected ethyl acetate or methyl acetate for use; Fatty Alcohol(C12-C14 and C12-C18) can be selected methyl alcohol, ethanol, propyl alcohol, Virahol or propyl carbinol for use, and the proportioning of alkane-fatty acid ester-Fatty Alcohol(C12-C14 and C12-C18)-water is (0.5-2): (8-12): (1-3): 10.
8. method of from Chinese medicine, separating preparation five galloyl glucoses according to claim 1; it is characterized in that: select two kinds of different solvent systems respectively for use; through twice separation of high speed adverse current chromatogram (is preliminary purification for the first time; for the second time for refining), obtain highly purified five galloyl glucose monomers.
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| CN200810008080A CN101525357A (en) | 2008-03-07 | 2008-03-07 | Method for separating and preparing penta-galloyl glucose from Chinese medicament |
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Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102119953A (en) * | 2010-11-17 | 2011-07-13 | 首都医科大学 | Application of euphorbia humifusa wild extract |
| CN102127125A (en) * | 2011-01-05 | 2011-07-20 | 中国林业科学研究院林产化学工业研究所 | Multielement combined purification preparation process of refined tannic acid serie and combined preparation of products |
| CN102657666A (en) * | 2012-05-16 | 2012-09-12 | 中国药科大学 | Medical application of 1,2,3,4,6-O-pentagalloylglucose and composition thereof in preparation of demulcent medicaments |
| CN104394863A (en) * | 2012-06-21 | 2015-03-04 | 碧雅诗株式会社 | Agent for inducing myeloid stem cells and method for inducing myeloid stem cells |
| CN104998263A (en) * | 2015-09-02 | 2015-10-28 | 集美大学 | Method for quickly separating alpha-glucosidase inhibitor from camellia pollen |
| CN105859803A (en) * | 2016-05-09 | 2016-08-17 | 中国农业科学院特产研究所 | Galloyl glucose preparation method |
| CN107530368A (en) * | 2015-04-16 | 2018-01-02 | 高雄医学大学 | Anti-cancer composition and application thereof |
| CN110003290A (en) * | 2019-04-22 | 2019-07-12 | 浙江工业大学 | A kind of mechanochemistry extracting method preparing hydrolyzable tannins crude extract from Shell of Water Chestnut |
| CN110437289A (en) * | 2019-09-02 | 2019-11-12 | 广东省农业科学院茶叶研究所 | A kind of preparation method of four galloyl glucoses |
| CN112263521A (en) * | 2020-10-30 | 2021-01-26 | 广东丸美生物技术股份有限公司 | Peony extract and preparation method and application thereof |
| CN112770790A (en) * | 2018-08-03 | 2021-05-07 | 奈克塞罗医学有限公司 | Purified pentagalloylglucose and delivery device |
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2008
- 2008-03-07 CN CN200810008080A patent/CN101525357A/en active Pending
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102119953A (en) * | 2010-11-17 | 2011-07-13 | 首都医科大学 | Application of euphorbia humifusa wild extract |
| CN102127125B (en) * | 2011-01-05 | 2015-10-14 | 中国林业科学研究院林产化学工业研究所 | The modularization preparation of series of purification Weibull multiplexed combination purification technique and products thereof |
| CN102127125A (en) * | 2011-01-05 | 2011-07-20 | 中国林业科学研究院林产化学工业研究所 | Multielement combined purification preparation process of refined tannic acid serie and combined preparation of products |
| CN102657666A (en) * | 2012-05-16 | 2012-09-12 | 中国药科大学 | Medical application of 1,2,3,4,6-O-pentagalloylglucose and composition thereof in preparation of demulcent medicaments |
| CN102657666B (en) * | 2012-05-16 | 2013-06-12 | 中国药科大学 | Medical application of 1,2,3,4,6-O-pentagalloylglucose and composition thereof in preparation of demulcent medicaments |
| US9486465B2 (en) | 2012-06-21 | 2016-11-08 | Pias Corporation | Attractant for bone marrow stem cells and method for attracting bone marrow stem cells |
| CN104394863A (en) * | 2012-06-21 | 2015-03-04 | 碧雅诗株式会社 | Agent for inducing myeloid stem cells and method for inducing myeloid stem cells |
| CN107530368A (en) * | 2015-04-16 | 2018-01-02 | 高雄医学大学 | Anti-cancer composition and application thereof |
| CN104998263A (en) * | 2015-09-02 | 2015-10-28 | 集美大学 | Method for quickly separating alpha-glucosidase inhibitor from camellia pollen |
| CN104998263B (en) * | 2015-09-02 | 2017-11-03 | 集美大学 | A kind of method of the quick separating α glucosidase inhibitors from camellia pollen |
| CN105859803A (en) * | 2016-05-09 | 2016-08-17 | 中国农业科学院特产研究所 | Galloyl glucose preparation method |
| CN112770790A (en) * | 2018-08-03 | 2021-05-07 | 奈克塞罗医学有限公司 | Purified pentagalloylglucose and delivery device |
| US11331102B2 (en) | 2018-08-03 | 2022-05-17 | Nectero Medical, Inc. | Purified pentagalloyl glucose and devices for delivery |
| CN110003290A (en) * | 2019-04-22 | 2019-07-12 | 浙江工业大学 | A kind of mechanochemistry extracting method preparing hydrolyzable tannins crude extract from Shell of Water Chestnut |
| CN110003290B (en) * | 2019-04-22 | 2021-01-26 | 浙江工业大学 | Mechanochemical extraction method for preparing hydrolysable tannin crude extract from water chestnut shells |
| CN110437289A (en) * | 2019-09-02 | 2019-11-12 | 广东省农业科学院茶叶研究所 | A kind of preparation method of four galloyl glucoses |
| CN112263521A (en) * | 2020-10-30 | 2021-01-26 | 广东丸美生物技术股份有限公司 | Peony extract and preparation method and application thereof |
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