CN110818768B - New method for extracting euscaphium acid from plant body and new raw material - Google Patents
New method for extracting euscaphium acid from plant body and new raw material Download PDFInfo
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- 239000002253 acid Substances 0.000 title claims abstract description 34
- 238000000034 method Methods 0.000 title claims abstract description 25
- 239000002994 raw material Substances 0.000 title claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims abstract description 51
- 241000196324 Embryophyta Species 0.000 claims abstract description 21
- 239000011347 resin Substances 0.000 claims abstract description 18
- 229920005989 resin Polymers 0.000 claims abstract description 18
- 238000001179 sorption measurement Methods 0.000 claims abstract description 13
- 238000004440 column chromatography Methods 0.000 claims abstract description 9
- 238000010898 silica gel chromatography Methods 0.000 claims abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 4
- 239000000178 monomer Substances 0.000 claims abstract description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 26
- 239000000284 extract Substances 0.000 claims description 22
- 241001523357 Euscaphis japonica Species 0.000 claims description 12
- 238000001914 filtration Methods 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- 239000003480 eluent Substances 0.000 claims description 9
- 238000002156 mixing Methods 0.000 claims description 9
- 238000009835 boiling Methods 0.000 claims description 8
- 239000012535 impurity Substances 0.000 claims description 8
- 239000000843 powder Substances 0.000 claims description 8
- OXVUXGFZHDKYLS-QUFHAEKXSA-N euscaphic acid Chemical compound C1[C@@H](O)[C@@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@](O)(C)[C@H]5C4=CC[C@@H]3[C@]21C OXVUXGFZHDKYLS-QUFHAEKXSA-N 0.000 claims description 7
- 229930182603 Euscaphic acid Natural products 0.000 claims description 6
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 claims description 6
- 241001523354 Euscaphis Species 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 238000001035 drying Methods 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- 238000010828 elution Methods 0.000 claims description 2
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical group O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 claims description 2
- 239000002024 ethyl acetate extract Substances 0.000 claims description 2
- 230000001376 precipitating effect Effects 0.000 claims description 2
- 238000007873 sieving Methods 0.000 claims description 2
- 238000010298 pulverizing process Methods 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 241000441077 Euscaphis konishii Species 0.000 abstract description 12
- 239000000463 material Substances 0.000 abstract description 4
- 238000002360 preparation method Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 5
- 239000000741 silica gel Substances 0.000 description 5
- 229910002027 silica gel Inorganic materials 0.000 description 5
- 238000000926 separation method Methods 0.000 description 4
- 240000007651 Rubus glaucus Species 0.000 description 3
- 235000011034 Rubus glaucus Nutrition 0.000 description 3
- 235000009122 Rubus idaeus Nutrition 0.000 description 3
- 241000208173 Apiaceae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000011068 loading method Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- 244000061508 Eriobotrya japonica Species 0.000 description 1
- 235000009008 Eriobotrya japonica Nutrition 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 241000220222 Rosaceae Species 0.000 description 1
- 241001618264 Rubus coreanus Species 0.000 description 1
- 244000173853 Sanguisorba officinalis Species 0.000 description 1
- 235000008282 Sanguisorba officinalis Nutrition 0.000 description 1
- 229920005654 Sephadex Polymers 0.000 description 1
- 239000012507 Sephadex™ Substances 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 230000036436 anti-hiv Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000005227 gel permeation chromatography Methods 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 238000012856 packing Methods 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- -1 triterpene compound Chemical class 0.000 description 1
- OOTXFYSZXCPMPG-BMYLZFHVSA-N ursane Chemical compound C1CCC(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C)CC[C@@H](C)[C@H](C)[C@H]5[C@H]4CC[C@@H]3[C@]21C OOTXFYSZXCPMPG-BMYLZFHVSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/73—Rosaceae (Rose family), e.g. strawberry, chokeberry, blackberry, pear or firethorn
- A61K36/739—Sanguisorba (burnet)
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/30—Extraction of the material
- A61K2236/33—Extraction of the material involving extraction with hydrophilic solvents, e.g. lower alcohols, esters or ketones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2236/00—Isolation or extraction methods of medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicine
- A61K2236/50—Methods involving additional extraction steps
- A61K2236/51—Concentration or drying of the extract, e.g. Lyophilisation, freeze-drying or spray-drying
Abstract
The invention provides a novel method for extracting euscaphium acid from plant bodies and novel raw materials; the method takes plants containing euscaphium acid as raw materials, and comprises the steps of crushing, extracting by ethyl acetate solution, concentrating the extracting solution to extract, eluting by silica gel column chromatography, separating the eluting solution by PRP512A macroporous adsorption resin column chromatography, concentrating the eluting solution, and recrystallizing to obtain euscaphium acid monomer compound; the euscaphis konishii hayata has rich sources of plant materials and high content, and is an ideal new material.
Description
Technical Field
The invention relates to a novel method for extracting euscaphium acid from plant bodies and a novel raw material for extracting euscaphium acid.
Background
Euscaphis japonica acid, also known as rosacic acid, CAS number 53155-25-2, english name euscaphic acid, white powdery crystal or needle crystal, molecular formula C 30 H 48 O 5 Molecular weight 488; the compound is ursane type triterpene compound, and is dissolved in organic solvents such as dichloromethane, ethyl acetate, chloroform, etc. The literature reports that the euscaphis japonica acid has remarkable anti-HIV, anti-inflammatory and anti-tumor activities and has huge market development value.
The component is prepared from radix Euonymi Fortunei of the family of the Umbelliferae at the earliest stageEuscaphis japonicaIs separated from the pericarp of the seed. Literature studies show that the euscaphis acid exists in plants such as the Bulleidae, the Rosaceae, the Theaceae and the like, has been separated from plants such as the euscaphis, the Rubus coreanus, the Sanguisorba officinalis, the Eriobotrya japonica and the like, has complex process and five formsThe preparation of the euscaphis japonica acid is limited to a certain plant species; in a plurality of processes, the she medicine is put on the male button, namely the raspberryRubus chingiiThe obtained euscaphium acid in the dried roots and rhizomes of Hu is the highest, the yield is about 1 percent, but the euscaphium acid is obtained by extraction-repeated silica gel and gel column chromatography separation, the separation method is more complicated, the loss of components in the preparation process is large, the column chromatography packing sephadex used in the process is high in price, and the preparation process cost is high; the process can prepare euscaphis japonica acid in other plants, and the obtained euscaphis japonica acid has small amount and low purity. In addition, although the sources of the plant raw materials of raspberry used in the process are rich, the sources are limited to roots and rhizomes, the biomass in the plant body is low, and the development is low.
Euscaphis konishii hayataEuscaphis konishii Hayata is a plant of the genus Euscaphis of the family of the genus Umbelliferae, also known as Euscaphis japonica, which is a unique medical ornamental tree species in our country. In recent years, the planting area of peripheral provinces such as Fujian, jiangxi and the like is continuously enlarged, and only Fujian Sanming Qing Liu, taining, nan Ping Shaowu, jianyang, quanzhou Germany and the like are over 5000 mu, so that plant resources are rich. The task group is always devoted to the resource development and utilization of the euscaphis konishii, and a large amount of euscaphis konishii acid is separated from the plant in the early stage. Through further optimization of the preparation process, the subject group explores a preparation method which has high yield and original process rate, simpler operation and lower cost, gel chromatography is not needed, silica gel chromatography is separated for multiple times, and the process is applied to other plants for preparing euscaphic acid and is also applicable.
Disclosure of Invention
The invention aims to provide a novel method for extracting euscaphium acid from plant bodies, and the preparation process only needs ethyl acetate extraction-silica gel column chromatography elution-PRP-512A macroporous adsorption resin column chromatography separation to obtain euscaphium acid monomers with high purity. The preparation method is simple, easy to operate and suitable for large-scale production.
The technical method provided by the invention comprises the following steps:
the method for extracting the euscaphium acid from the plant body takes dry branches of the plant rich in the euscaphium acid as raw materials, and comprises the following specific steps of crushing, extracting by using an ethyl acetate solution, concentrating an extracting solution to extract, eluting by using a silica gel column chromatography, concentrating an eluent to extract, eluting by using a PRP-512A macroporous adsorption resin chromatography, and recrystallizing by using ethanol to obtain the euscaphium acid monomer compound:
taking euscaphis konishii branches, drying, crushing into coarse powder, and sieving with a 0.178 mm sieve for later use;
extracting with ethyl acetate solution: taking 1000 g of euscaphis konishii, adding 10000 mL of ethyl acetate solution, heating and boiling for 2 hours, and filtering to obtain an extracting solution; adding 10000 mL ethyl acetate solution into the filter residue, boiling for 2 hours again, and filtering to obtain an extract;
concentrating the extract to obtain extract: mixing the ethyl acetate extracts, concentrating under reduced pressure to obtain extract;
eluting by silica gel column chromatography: considering the separation effect, organic solvent toxicity and production cost, a methylene dichloride-ethanol system is preferred; eluting 3-5 column volumes with eluting solvent at a ratio of 50:1, and removing impurities; dichloromethane was then used: eluting with ethanol at a ratio of 20:1 for 4-6 column volumes, collecting eluate, and concentrating to obtain high concentration euscaphium acid extract.
PRP-512A macroporous adsorption resin column chromatography elution: mixing the high-concentration euscaphis acid extract with equal-mass PRP-512A macroporous adsorption resin; the eluting solvent system is ethanol-water; eluting 3-5 column volumes with eluting solvent ratio of 75:25, and removing impurities; eluting with eluting solvent at a ratio of 95:5 for 4-6 column volumes, and collecting eluate to obtain macroporous adsorbent resin 95% ethanol eluate.
Concentrating and recrystallizing macroporous adsorption resin 95% ethanol eluent: concentrating the macroporous adsorption resin 95% ethanol eluent under reduced pressure to 200-300mL, naturally cooling, standing, precipitating white solid, and suction filtering to obtain white powder, namely euscaphic acid.
The preparation yield of the euscaphis konishii branches by the process ranges from 0.98% to 1.15%, and compared with the process for obtaining euscaphis japonica acid from the dried roots and rhizomes of raspberry, the final yield of the euscaphis konishii branches is improved by 13%.
Meanwhile, because the euscaphis konishii has large-area artificial forests, euscaphis konishii branches are the preferred new material for extracting euscaphis konishii acid.
Detailed Description
The invention will be better understood from the following examples. However, it will be readily understood by those skilled in the art that the specific material ratios, process conditions and results thereof described in the examples are illustrative of the present invention and should not be construed as limiting the invention described in detail in the claims.
Example 1
Taking 1000 g parts of euscaphis konishii branches, adding 10000 parts of ethyl acetate solution mL parts, heating and boiling for 2 hours, and filtering to obtain an extracting solution; adding 10000 mL ethyl acetate solution into the filter residue, boiling for 2 hours again, and filtering to obtain an extract; mixing the two extractive solutions, concentrating under reduced pressure to obtain extract 35 g; mixing the extract with 35 g 60-100 mesh silica gel, loading 350 g 200-300 mesh silica gel on column by dry method, eluting with dichloromethane-ethanol (50:1) 4000 mL, removing impurities, eluting with dichloromethane-ethanol (20:1) 5000 mL, collecting eluate, and recovering solvent under reduced pressure to obtain extract 18.3 g. Dissolving the extract with ethyl acetate, mixing with 18.3g PRP-512A macroporous adsorbent resin, eluting with PRP-512A macroporous adsorbent resin column chromatography, eluting with 75% ethanol solution to remove impurities by 2000mL, eluting with 2500 mL of 95% ethanol solution, collecting eluate, recovering solvent under reduced pressure to 200 mL, naturally cooling, standing, separating out white solid, and suction filtering to obtain euscaphic acid white powder 1.15 g with yield of 1.15% and purity of 95.8%.
Example 2
Taking the euscaphis japonica peel powder 1000 g, adding an ethyl acetate solution 10000 mL, heating and boiling for 2 hours, and filtering to obtain an extracting solution; adding 10000 mL ethyl acetate solution into the filter residue, boiling for 2 hours again, and filtering to obtain an extract; mixing the two extractive solutions, concentrating under reduced pressure to obtain extract 39.3 g; mixing the extract with 39.3g 60-100 mesh silica gel, loading 393 g 200-300 mesh silica gel on column by dry method, eluting with dichloromethane-ethanol (50:1) 4500 mL, removing impurities, eluting with dichloromethane-ethanol (20:1) 6000 mL, collecting eluate, and recovering solvent under reduced pressure to obtain extract 17.6 g. Dissolving the extract with ethyl acetate, mixing with 17.6g PRP-512A macroporous adsorbent resin, eluting with PRP-512A macroporous adsorbent resin column chromatography, eluting with 75% ethanol solution to remove impurities by 2000mL, eluting with 2500 mL of 95% ethanol solution, collecting eluate, recovering solvent under reduced pressure to 200 mL, naturally cooling, standing, separating out white solid, and suction filtering to obtain 0.91g of euscaphic acid white powder with yield of 0.91% and purity of 92.5%.
Example 3
Drying radix Sangusorbae plants, and extracting euscaphis japonica acid by the process of example 1 or 2.
Example 4
Drying folium Eriobotryae, and extracting euscaphium acid by the process of example 1 or 2.
Example 5
The dry root of raspberry of China is taken, the process of the embodiment 1 or 2 is adopted to extract the euscaphis japonica acid, and compared with the traditional process for obtaining the euscaphis japonica acid, the final yield of the patent is improved by 13%.
Claims (1)
1. A method for extracting euscaphium acid from plant body is characterized by taking euscaphium branches as raw materials, crushing, extracting with ethyl acetate solution, concentrating the extracting solution to extract, eluting with silica gel column chromatography, separating the eluent with PRP512A macroporous adsorption resin column chromatography, concentrating the eluent, and recrystallizing to obtain euscaphium acid monomer compound, which comprises the following steps:
(1) Drying the branches of the euscaphis japonica plants, pulverizing into coarse powder, and sieving with a 0.178 mm sieve for later use;
(2) Extracting with ethyl acetate solution: taking 1000 g parts of plant powder (1), adding 10000 mL parts of ethyl acetate solution, heating and boiling for 2 hours, and filtering to obtain an extracting solution; adding 10000 mL ethyl acetate solution into the filter residue, boiling for 2 hours again, and filtering to obtain an extract;
(3) Concentrating the extract to obtain extract: combining the ethyl acetate extracts, concentrating under reduced pressure to dry to obtain extract;
(4) Eluting by silica gel column chromatography: selecting a dichloromethane-ethanol system; eluting 3-5 column volumes with eluting solvent at a ratio of 50:1, and removing impurities; dichloromethane was then used: eluting with ethanol at a ratio of 20:1 for 4-6 column volumes, collecting eluate, and concentrating to obtain euscaphium acid extract;
(5) PRP-512A macroporous adsorption resin column chromatography elution: mixing the euscaphis acid extract with equal-mass PRP-512A macroporous adsorption resin, and stirring; the eluting solvent system is ethanol-water; eluting 3-5 column volumes with eluting solvent ratio of 75:25, and removing impurities; eluting 4-6 column volumes by using an eluting solvent with the ratio of 95:5, and collecting the eluent to obtain macroporous adsorption resin 95% ethanol eluent;
(5) Concentrating and recrystallizing macroporous adsorption resin 95% ethanol eluent: concentrating the macroporous adsorption resin 95% ethanol eluent under reduced pressure to 200-300mL, naturally cooling, standing, precipitating white solid, and suction filtering to obtain white powder, namely euscaphic acid.
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| Application Number | Priority Date | Filing Date | Title |
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| CN201911062579.3A CN110818768B (en) | 2019-11-03 | 2019-11-03 | New method for extracting euscaphium acid from plant body and new raw material |
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| CN201911062579.3A CN110818768B (en) | 2019-11-03 | 2019-11-03 | New method for extracting euscaphium acid from plant body and new raw material |
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| CN110818768B true CN110818768B (en) | 2024-02-06 |
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| CN112778394A (en) * | 2021-01-06 | 2021-05-11 | 西南科技大学 | Preparation method of rosaceous acid extract in rosa roxburghii tratt pomace |
| CN112661768A (en) * | 2021-01-27 | 2021-04-16 | 福建农林大学 | New plant raw material for preparing sesamin and method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101590134A (en) * | 2009-06-30 | 2009-12-02 | 沈阳药科大学 | Has total triterpene of garden burnet root of anti-inflammatory and analgesic effect and preparation method thereof |
| CN106074560A (en) * | 2013-11-29 | 2016-11-09 | 江西中医药大学 | The application of Fructus Rubi extract |
| CN106905304A (en) * | 2017-03-08 | 2017-06-30 | 福建农林大学 | A kind of plant and its new method for extracting rich in isobiflorin |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101590134A (en) * | 2009-06-30 | 2009-12-02 | 沈阳药科大学 | Has total triterpene of garden burnet root of anti-inflammatory and analgesic effect and preparation method thereof |
| CN106074560A (en) * | 2013-11-29 | 2016-11-09 | 江西中医药大学 | The application of Fructus Rubi extract |
| CN106905304A (en) * | 2017-03-08 | 2017-06-30 | 福建农林大学 | A kind of plant and its new method for extracting rich in isobiflorin |
Non-Patent Citations (2)
| Title |
|---|
| Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica;Cheng, Jing-Jy等;Journal of Natural Products;第73卷(第10期);第1655-1658页 * |
| 野鸦椿属植物化学成分和药理活性研究进展;梁文贤等;中草药;第49卷(第5期);第1220-1226页 * |
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