CN115448968A - Supercritical CO 2 Method for extracting stigmasterol by combining method with chromatographic technology - Google Patents
Supercritical CO 2 Method for extracting stigmasterol by combining method with chromatographic technology Download PDFInfo
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- 238000000034 method Methods 0.000 title claims abstract description 39
- OILXMJHPFNGGTO-UHFFFAOYSA-N (22E)-(24xi)-24-methylcholesta-5,22-dien-3beta-ol Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)C=CC(C)C(C)C)C1(C)CC2 OILXMJHPFNGGTO-UHFFFAOYSA-N 0.000 title claims abstract description 33
- OQMZNAMGEHIHNN-UHFFFAOYSA-N 7-Dehydrostigmasterol Natural products C1C(O)CCC2(C)C(CCC3(C(C(C)C=CC(CC)C(C)C)CCC33)C)C3=CC=C21 OQMZNAMGEHIHNN-UHFFFAOYSA-N 0.000 title claims abstract description 33
- HZYXFRGVBOPPNZ-UHFFFAOYSA-N UNPD88870 Natural products C1C=C2CC(O)CCC2(C)C2C1C1CCC(C(C)=CCC(CC)C(C)C)C1(C)CC2 HZYXFRGVBOPPNZ-UHFFFAOYSA-N 0.000 title claims abstract description 33
- LGJMUZUPVCAVPU-UHFFFAOYSA-N beta-Sitostanol Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(C)CCC(CC)C(C)C)C1(C)CC2 LGJMUZUPVCAVPU-UHFFFAOYSA-N 0.000 title claims abstract description 33
- BFDNMXAIBMJLBB-UHFFFAOYSA-N stigmasterol Natural products CCC(C=CC(C)C1CCCC2C3CC=C4CC(O)CCC4(C)C3CCC12C)C(C)C BFDNMXAIBMJLBB-UHFFFAOYSA-N 0.000 title claims abstract description 33
- 229940032091 stigmasterol Drugs 0.000 title claims abstract description 33
- 235000016831 stigmasterol Nutrition 0.000 title claims abstract description 33
- HCXVJBMSMIARIN-PHZDYDNGSA-N stigmasterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)/C=C/[C@@H](CC)C(C)C)[C@@]1(C)CC2 HCXVJBMSMIARIN-PHZDYDNGSA-N 0.000 title claims abstract description 31
- 238000005516 engineering process Methods 0.000 title description 10
- 238000000926 separation method Methods 0.000 claims abstract description 48
- 238000000605 extraction Methods 0.000 claims abstract description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 33
- 241000446281 Eschenbachia blinii Species 0.000 claims abstract description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 24
- 239000002904 solvent Substances 0.000 claims abstract description 16
- 238000007605 air drying Methods 0.000 claims abstract description 13
- 238000004587 chromatography analysis Methods 0.000 claims abstract description 11
- 238000010298 pulverizing process Methods 0.000 claims abstract description 11
- 238000001914 filtration Methods 0.000 claims abstract description 4
- 238000011068 loading method Methods 0.000 claims abstract description 4
- 239000012528 membrane Substances 0.000 claims abstract description 4
- 238000002390 rotary evaporation Methods 0.000 claims abstract description 3
- 238000000746 purification Methods 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 9
- 241000594394 Hedyotis Species 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 241001071795 Gentiana Species 0.000 claims 1
- 238000000227 grinding Methods 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 3
- 206010011224 Cough Diseases 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 240000006394 Sorghum bicolor Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000012530 fluid Substances 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- -1 stigmasterol compound Chemical class 0.000 description 2
- 238000000194 supercritical-fluid extraction Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 206010006458 Bronchitis chronic Diseases 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000012671 Gastrointestinal haemorrhages Diseases 0.000 description 1
- 206010062717 Increased upper airway secretion Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010023126 Jaundice Diseases 0.000 description 1
- 206010027514 Metrorrhagia Diseases 0.000 description 1
- 206010053476 Traumatic haemorrhage Diseases 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229930013930 alkaloid Natural products 0.000 description 1
- 208000002399 aphthous stomatitis Diseases 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 208000007451 chronic bronchitis Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 208000001780 epistaxis Diseases 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 208000035861 hematochezia Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229930014626 natural product Natural products 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic 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
- 208000026435 phlegm Diseases 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J75/00—Processes for the preparation of steroids in general
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
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Abstract
The application discloses a method for extracting stigmasterol by combining a supercritical CO2 method with a chromatographic technique, which belongs to the technical field of chemical separation and extraction and comprises the following steps: s1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 The extraction device is used for extracting to obtain an extract of the overground part of the conyza blinii; s2, extracting stigmasterol: dissolving the extract in a certain amount of solvent, wherein the solvent comprises dichloromethane and methanol, and the volume ratio of the dichloromethane to the methanol is 1:1, filtering by a microporous filter membrane, loading a sample by a wet method, passing through an LH-20 gel column, eluting three column volumes by a solvent again, collecting to obtain four components, analyzing and combining the components by a TLC point plate, performing rotary evaporation to separate out the components, and repeatedly recrystallizing to obtain the stigmasterol. The extraction method provided by the application has the characteristics of simple process, controllability of the separation method, good reproducibility, low cost, simplicity in operation and the like.
Description
Technical Field
The invention relates to the technical field of separation and extraction, and particularly relates to a method for extracting stigmasterol by combining a supercritical CO2 method with a chromatographic technique.
Background
Conyza blinii (Conyza blinii) is a Chinese medicinal material in Taoism area of Chuanqin of China, has effects of clearing heat and detoxicating, relieving cough and asthma, and is mainly used for treating cough and other inflammation caused by chronic bronchitis. It is commonly used for treating cough due to lung heat, excessive phlegm, asthma, pharyngalgia, aphtha, jaundice due to damp-heat pathogen, epistaxis, hematochezia, metrorrhagia, traumatic hemorrhage, etc., and clinically applied to Jinlongdan grass extract tablet, etc. The chemical components of the conyza blinii reported in the literature mainly comprise terpenoids, saponins, phenolic substances, acidic substances, volatile oil, alkaloids and the like.
Stigmasterol is a typical representation of phytosterol, widely exists in deodorized distillates refined from various plants and vegetable oils, has various biological activities, is non-toxic, has the characteristics of emulsibility, stability, oxidation resistance and the like, and is widely applied to the fields of food, medicine and the like.
The Supercritical Fluid Extraction (SFE) technology is a new Extraction and separation technology developed in recent years. Due to CO 2 The supercritical carbon dioxide is low in supercritical temperature, colorless, nontoxic, tasteless, nonflammable, easy to prepare high-purity gas, low in price and good in solvent property, so that CO 2 Is the preferred supercritical fluid. The natural product extracted by the supercritical CO2 fluid has better extraction and separation effects, and is widely used at presentCan be used for extracting natural effective components such as vegetable oil and spice.
At present, no report that supercritical fluid extraction is applied to extraction of stigmasterol in conyza blinii exists, and the extraction method provided by the application has the characteristics of simple process, controllability of the separation method, good reproducibility, low cost, simplicity in operation and the like.
Disclosure of Invention
The invention aims to provide a method for extracting stigmasterol by combining a supercritical CO2 method with a chromatographic technology, so as to provide a strain which has multiple growth promoting properties and can promote the growth of sorghum, and thus, the quality and the yield of the sorghum are improved.
In order to achieve the purpose, the invention provides the following technical scheme:
a method for extracting stigmasterol by combining a supercritical CO2 method with a chromatographic technique comprises the following steps:
s1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device, wherein the extraction pressure is 32-45 MPa, the temperature is 40-50 ℃, the time is 3-5 h, CO 2 The flow is 3-9L/h, the first purification and separation pressure is 5-8 MPa, and the separation temperature is 34-38 ℃; the second purification and separation pressure is 12-17 MPa, the separation temperature is 48-52 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction;
s2, stigmasterol extraction: dissolving the extract in a certain amount of solvent, wherein the solvent comprises dichloromethane and methanol, and the volume ratio of dichloromethane to methanol is 1:1, filtering by a microporous filter membrane, loading a sample by a wet method, passing through an LH-20 gel column, eluting three column volumes by the solvent again, collecting to obtain four components, analyzing and merging the components by a TLC point plate, performing rotary evaporation to separate out the components, and repeatedly recrystallizing to obtain the stigmasterol.
The working principle and the beneficial effects of the invention are as follows: the invention firstly adopts the supercritical CO2 method and the chromatographic technique to extract the stigmasterol with good biological activity from the overground part of the conyza blinii, and the provided extraction method has the advantages of simple process, good controllability and reproducibility of the separation method, low cost and simple operation. The structure of the compound is identified by using a spectroscopic technology which mainly comprises nuclear magnetic resonance spectroscopy (1H-NMR, 13C-NMR), the compound is white needle-shaped crystals, and the compound is determined to be stigmasterol by the nuclear magnetic technology.
Further, S1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device, wherein the extraction pressure is 32MPa, the temperature is 40 ℃, the time is 3h, and CO is added 2 The flow is 3L/h, the first purification and separation pressure is 5MPa, and the separation temperature is 34 ℃; and the second purification and separation pressure is 12MPa, the separation temperature is 48 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction.
Further, S1, extracting the conyza blinii: collecting aerial parts of herba Hedyotis Auriculariae, air drying, pulverizing, and adding supercritical CO 2 An extraction device with the extraction pressure of 40MPa, the temperature of 45 ℃ and the time of 4h 2 The flow is 6L/h, the first purification and separation pressure is 6MPa, and the separation temperature is 36 ℃; and the second purification and separation pressure is 15MPa, the separation temperature is 50 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction.
Further, S1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device, the extraction pressure is 45MPa, the temperature is 50 ℃, the time is 5h 2 The flow is 9L/h, the first purification and separation pressure is 8MPa, and the separation temperature is 38 ℃; the second purification and separation pressure is 17MPa, the separation temperature is 52 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction.
Further, S1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device with the extraction pressure of 45MPa, the temperature of 50 ℃ and the time of 5h 2 The flow is 9L/h, the first purification and separation pressure is 8MPa, and the separation temperature is 38 ℃; the second purification and separation pressure is 17MPa, the separation temperature is 52 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction.
Furthermore, the water content of the overground part of the conyza blinii is 6-15% after air drying, and the granularity of the grinded powder is 30-80 meshes.
Further, in the process of repeatedly recrystallizing to obtain stigmasterol, the used solvents are methanol and ethyl acetate 1:1 and mixing to obtain the product.
Drawings
FIG. 1 is a structural diagram of a stigmasterol compound according to the present invention;
FIG. 2 is a 13C-NMR chart of a stigmasterol compound in the present invention.
Detailed Description
The following is further detailed by way of specific embodiments:
example (b): a method for extracting stigmasterol by combining a supercritical CO2 method with a chromatographic technique comprises the following steps:
s1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device with the extraction pressure of 32MPa, the temperature of 40 ℃ and the time of 3h 2 The flow is 3L/h, the first purification and separation pressure is 5MPa, and the separation temperature is 34 ℃; and extracting at the second purification and separation pressure of 12MPa and the separation temperature of 48 ℃ to obtain an extract of the overground part of the conyza blinii.
S2, stigmasterol extraction: dissolving the extract in a certain amount of solvent, wherein the solvent comprises dichloromethane and methanol, and the volume ratio of dichloromethane to methanol is 1:1, filtering by a microporous filter membrane, loading a sample by a wet method, passing through an LH-20 gel column, eluting three column volumes by the solvent again, collecting to obtain four components, analyzing and combining the components by a TLC (thin layer chromatography) point plate, evaporating and separating out the components in a rotary mode, recrystallizing repeatedly to obtain stigmasterol, and recrystallizing repeatedly to obtain the stigmasterol, wherein the used solvent is methanol and ethyl acetate 1:1 are mixed to obtain the product.
The invention firstly adopts the supercritical CO2 method and the chromatographic technology to extract the stigmasterol with good biological activity from the overground part of the conyza blinii, and the provided extraction method has the advantages of simple process, good controllability and reproducibility of the separation method, low cost and simple operation. The structure of the compound is identified by using a spectroscopic technology which mainly comprises nuclear magnetic resonance spectroscopy (1H-NMR, 13C-NMR), the compound is white needle-shaped crystals, and the compound is determined to be stigmasterol by the nuclear magnetic technology, and the structure is shown in a table 1 and a figure 2.
Table 1: nuclear magnetic data of the compound (100MHz, CDCl) 3 )
It will be apparent to those skilled in the art that various changes and modifications can be made therein without departing from the spirit and scope of the invention, which should not be construed as affecting the scope of the invention as embodied in the invention and the utility of the patent. The scope of the claims of the present application shall be determined by the contents of the claims, and the description of the embodiments and the like in the specification shall be used to explain the contents of the claims.
Claims (6)
1. A method for extracting stigmasterol by combining a supercritical CO2 method with a chromatographic technique is characterized by comprising the following steps,
s1, extracting the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device, the extraction pressure is 32-45 MPa, the temperature is 40-50 ℃, the time is 3-5h 2 The flow is 3-9L/h, the first purification and separation pressure is 5-8 MPa, and the separation temperature is 34-38 ℃; the second purification and separation pressure is 12-17 MPa, the separation temperature is 48-52 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction;
s2, stigmasterol extraction: dissolving the extract in a certain amount of solvent, wherein the solvent comprises dichloromethane and methanol, and the volume ratio of dichloromethane to methanol is 1:1, filtering by a microporous filter membrane, loading a sample by a wet method, passing through an LH-20 gel column, eluting three column volumes by the solvent again, collecting to obtain four components, analyzing and merging the components by a TLC point plate, performing rotary evaporation to separate out the components, and repeatedly recrystallizing to obtain the stigmasterol.
2. According toThe method for extracting stigmasterol by combining the supercritical CO2 method and the chromatographic technique as claimed in claim 1, wherein the S1 extraction and the golden gentian extraction are as follows: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device with the extraction pressure of 32MPa, the temperature of 40 ℃ and the time of 3h 2 The flow is 3L/h, the first purification and separation pressure is 5MPa, and the separation temperature is 34 ℃; and extracting at the second purification and separation pressure of 12MPa and the separation temperature of 48 ℃ to obtain an extract of the overground part of the conyza blinii.
3. The method for extracting stigmasterol by combining the supercritical CO2 method and the chromatographic technique according to claim 2, is characterized in that S1, the extraction of the conyza blinii: collecting aerial parts of herba Hedyotidis Diffusae, air drying, pulverizing, and adding supercritical CO 2 An extraction device with the extraction pressure of 40MPa, the temperature of 45 ℃ and the time of 4h 2 The flow is 6L/h, the first purification and separation pressure is 6MPa, and the separation temperature is 36 ℃; and the second purification and separation pressure is 15MPa, the separation temperature is 50 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction.
4. The method for extracting stigmasterol by combining the supercritical CO2 method and the chromatographic technique according to claim 3, is characterized in that S1, the extraction of the conyza blinii: collecting aerial parts of herba Hedyotis Auriculariae, air drying, pulverizing, and adding supercritical CO 2 An extraction device, the extraction pressure is 45MPa, the temperature is 50 ℃, the time is 5h 2 The flow is 9L/h, the first purification and separation pressure is 8MPa, and the separation temperature is 38 ℃; the second purification and separation pressure is 17MPa, the separation temperature is 52 ℃, and the extractum of the overground part of the conyza blinii is obtained by extraction.
5. The method for extracting stigmasterol by combining the supercritical CO2 method and the chromatographic technique according to any one of claims 1 to 4, wherein the water content of the aerial part of the conyza blinii is 6 to 15 percent after air drying, and the granularity of the ground conyza blinii is 30 to 80 meshes after the grinding.
6. The method for extracting stigmasterol by combining the supercritical CO2 method and the chromatographic technique according to claim 5, wherein in the process of repeatedly recrystallizing to obtain stigmasterol, the solvents used in the process of obtaining the stigmasterol are methanol and ethyl acetate 1:1 are mixed to obtain the product.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101822785A (en) * | 2009-08-14 | 2010-09-08 | 山东福田糖醇有限公司 | Method for extracting corn sterol |
| CN102391219A (en) * | 2011-10-17 | 2012-03-28 | 南京泽朗医药科技有限公司 | Method for preparing blinin from golden Chinese gentian |
| CN107669728A (en) * | 2017-09-15 | 2018-02-09 | 浙江康恩贝制药股份有限公司 | A kind of rape pollen total phytosterol for treating hyperplasia of prostate and preparation method thereof |
| CN113679748A (en) * | 2021-06-07 | 2021-11-23 | 重庆威迪特药业有限责任公司 | Preparation and detection method and application of saponin in conyza blinii |
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- 2022-09-26 CN CN202211180395.9A patent/CN115448968B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101822785A (en) * | 2009-08-14 | 2010-09-08 | 山东福田糖醇有限公司 | Method for extracting corn sterol |
| CN102391219A (en) * | 2011-10-17 | 2012-03-28 | 南京泽朗医药科技有限公司 | Method for preparing blinin from golden Chinese gentian |
| CN107669728A (en) * | 2017-09-15 | 2018-02-09 | 浙江康恩贝制药股份有限公司 | A kind of rape pollen total phytosterol for treating hyperplasia of prostate and preparation method thereof |
| CN113679748A (en) * | 2021-06-07 | 2021-11-23 | 重庆威迪特药业有限责任公司 | Preparation and detection method and application of saponin in conyza blinii |
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