CN102432534A - Method for extracting norisoboldine from combined spicebush roots - Google Patents
Method for extracting norisoboldine from combined spicebush roots Download PDFInfo
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- CN102432534A CN102432534A CN2011104100965A CN201110410096A CN102432534A CN 102432534 A CN102432534 A CN 102432534A CN 2011104100965 A CN2011104100965 A CN 2011104100965A CN 201110410096 A CN201110410096 A CN 201110410096A CN 102432534 A CN102432534 A CN 102432534A
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- norisoboldine
- extracting
- radix linderae
- ethanol
- elutriant
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- 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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- Medicines Containing Plant Substances (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention relates to a method for extracting norisoboldine from combined spicebush roots, comprising the following steps: supercritically extracting to obtain an extract; adding the extract into a macroporous adsorption resin column for adsorbing; eluting by using ethanol; recycling the ethanol at reduced pressure and concentrating; adding the ethanol on a silica gel chromatographic column; eluting dichloromethane-methanol mixed solvent; adding an acetone crystal; separating the crystal; and washing and drying to obtain the norisoboldine. The method has the advantages of simplicity in operation, low solvent consumption, low production cost, stable process, low energy consumption, low pollution and high product purity (99%) and can be suitable for laboratories and industrialized semi-preparation and preparative production.
Description
Technical field
The present invention relates to a kind of process for extracting of norisoboldine, particularly a kind of method of from radix linderae, extracting norisoboldine.
Background technology
Taiwan aggregata (Combined? Spicebush? Root), also known as its next, bitterling barb, dwarf camphor, etc. for dicotyledon herbal Lauraceae obtusiloba roots.Nature and flavor are hot, temperature.Its form is: evergreen shrubs or dungarunga, and up to 4～5 meters.Root is wooden, expands sturdyly, slightly becomes the beads shape.The bark greyish-green.Close during the sprig children by the rust pubescence, level and smooth nothing hair when old; The stem branch is tough and tensile, and is not easily broken.Be used for all pains of chest abdomen card, frequent micturition, the enuresis due to the QI stagnated by cold.Have promoting the circulation of QI to relieve pain, the effect of warming kidney for dispelling cold.
Wherein contain norisoboldine, structural formula is:
Research shows: norisoboldine not only has antioxidation in vitro effect (Acta Pharmaceutica Sinica 200641 (10): 956-962); Also can be used for treating autoimmune disorder; As: rheumatoid arthritis, multiple sclerosis, system lupus erythematosus, multiple sclerosis, psoriatic, ulcerative colitis, scleroderma, polymyositis, chronic active hepatitis, mixed connective tissue disease, primary biliary cirrhosis, autoimmune hemolytic anemia, chronic lymphocytic thyroiditis, myasthenia gravis, ankylosing spondylitis, allergy osteo-arthritis, allergic vasculitis, autoimmunity are bitten neutrocytopenia, the purple paralysis of the special property sent out thrombocytopenic etc., have significant application value clinically.Patent documentation 201110087992.2 is reported, adopt band refining counter current chromatography in pH district to crude product separation and purification norisoboldine, but its method energy consumption is big, pollution is not suitable for industrialized production greatly.In the prior art, still be not applicable to preparation technology's report of high purity norisoboldine industrialized production.
Summary of the invention
The object of the present invention is to provide a kind of process for extracting that is beneficial to big production operation, the high norisoboldine of product purity.
The objective of the invention is to realize like this:
Get radix linderae, pulverize, join CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2-5%, extracting pressure 30-40MPa, temperature 50-60 ℃, CO
2Flow 2-4ml/g crude drug min, extraction time 80-120min gets extract, joins on the macroporous adsorptive resins and adsorbs; The 50-70% ethanol elution is collected 3-8 and is doubly measured the column volume elutriant, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part, and decompression and solvent recovery also concentrates; Add the acetone crystallization, fractional crystallization washs, is drying to obtain.
Above-mentioned a kind of method of from radix linderae, extracting norisoboldine, said CO
2The volume percent that the supercritical extraction entrainment agent accounts for total extraction solvent is 4%.
Above-mentioned a kind of method of from radix linderae, extracting norisoboldine, said CO
2Supercritical extraction pressure 35MPa, 55 ℃ of temperature, CO
2Flow 3ml/g crude drug min.
Above-mentioned a kind of method of from radix linderae, extracting norisoboldine, said CO
2Supercritical extraction time 100min.
Above-mentioned a kind of method of from radix linderae, extracting norisoboldine, said macroporous adsorbent resin are selected from a kind of among D101 type, D102 type, AB-8 type, HPD400, the HPD826.
Above-mentioned a kind of method of from radix linderae, extracting norisoboldine, it is 60% that said macroporous adsorbent resin wash-out uses concentration of ethanol.
It is 5 times of amount column volumes that above-mentioned a kind of method of from radix linderae, extracting norisoboldine, said macroporous adsorbent resin wash-out are used the alcoholic acid collecting amount.
Preparation gained norisoboldine adopts following method to detect.
Embodiment 1HPLC method is measured norisoboldine purity
The chromatographic condition chromatographic column: octadecylsilane bonding glue silica gel is weighting agent; Moving phase: second eyeball-methyl alcohol (90: 10); Flow velocity: 1ml/min; Detect wavelength: 226nm; Column temperature: 30 ℃.
The measuring method precision takes by weighing norisoboldine 2mg, places the 50mL measuring bottle, adds people's methyl alcohol 20mL, and sonic oscillation makes dissolving, and methanol constant volume is drawn 10uL to scale, injects high performance liquid chromatograph, adopts normalization method working sample purity.
Adopt the present invention to prepare norisoboldine, compared with prior art, method of the present invention has simple to operate, and solvent consumption is few; Production cost is low, process stabilizing, and energy consumption is little; Pollute for a short time, products obtained therefrom purity high (99%) is applicable to laboratory and industriallization half preparation and the production of preparation property.
Specific embodiment
Below form through embodiment foregoing of the present invention is remake further detailed description; But should this be interpreted as that the scope of the above-mentioned theme of the present invention only limits to following instance, all technology that realizes based on foregoing of the present invention all belong to scope of the present invention.
Embodiment 1 gets radix linderae 10kg, pulverizes, and joins CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2%, extracting pressure 30MPa, 50 ℃ of temperature, CO
2Flow 2ml/g crude drug min, extraction time 80min gets extract, joins on the D101 type macroporous adsorptive resins and adsorbs; 50% ethanol elution is collected 3 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part; Decompression and solvent recovery also concentrates, and adds the acetone crystallization, fractional crystallization; Wash, be drying to obtain norisoboldine 1.62g, detect through HPLC, purity is 99.1%.
Embodiment 2 gets radix linderae 10kg, pulverizes, and joins CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 3%, extracting pressure 35MPa, 55 ℃ of temperature, CO
2Flow 3ml/g crude drug min, extraction time 100min gets extract, joins on the D102 type macroporous adsorptive resins and adsorbs; 60% ethanol elution is collected 5 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part; Decompression and solvent recovery also concentrates, and adds the acetone crystallization, fractional crystallization; Wash, be drying to obtain norisoboldine 1.52g, detect through HPLC, purity is 99.3%.
Embodiment 3 gets radix linderae 10kg, pulverizes, and joins CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 5%, extracting pressure 40MPa, 60 ℃ of temperature, CO
2Flow 4ml/g crude drug min, extraction time 120min gets extract, joins on the AB-8 type macroporous adsorptive resins and adsorbs; 70% ethanol elution is collected 8 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part; Decompression and solvent recovery also concentrates, and adds the acetone crystallization, fractional crystallization; Wash, be drying to obtain norisoboldine 1.57g, detect through HPLC, purity is 99.2%.
Embodiment 4 gets radix linderae 10kg, pulverizes, and joins CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 4%, extracting pressure 35MPa, 55 ℃ of temperature, CO
2Flow 3ml/g crude drug min, extraction time 100min gets extract, joins on the HPD400 type macroporous adsorptive resins and adsorbs; 60% ethanol elution is collected 5 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part; Decompression and solvent recovery also concentrates, and adds the acetone crystallization, fractional crystallization; Wash, be drying to obtain norisoboldine 1.68g, detect through HPLC, purity is 99.7%.
Embodiment 5 gets radix linderae 10kg, pulverizes, and joins CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 4%, extracting pressure 35MPa, 55 ℃ of temperature, CO
2Flow 3ml/g crude drug min, extraction time 100min gets extract, joins on the HPD826 type macroporous adsorptive resins and adsorbs; 60% ethanol elution is collected 5 times of amount column volume elutriants, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part; Decompression and solvent recovery also concentrates, and adds the acetone crystallization, fractional crystallization; Wash, be drying to obtain norisoboldine 1.6849g, detect through HPLC, purity is 99.4%.
Claims (7)
1. method of from radix linderae, extracting norisoboldine is characterized in that described method is made up of the following step: get radix linderae, pulverize, join CO
2In the supercritical extraction device, ETHYLE ACETATE is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2-5%, extracting pressure 30-40MPa, temperature 50-60 ℃, CO
2Flow 2-4ml/g crude drug min, extraction time 80-120min gets extract, joins on the macroporous adsorptive resins and adsorbs; The 50-70% ethanol elution is collected 3-8 and is doubly measured the column volume elutriant, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With ratio is 4: 1 methylene chloride-methanol mixed solvent wash-out, and elutriant is pressed the column volume portioning and collected, and merges the elutriant of 5-9 part, and decompression and solvent recovery also concentrates; Add the acetone crystallization, fractional crystallization washs, is drying to obtain.
2. according to the said a kind of method of from radix linderae, extracting norisoboldine of claim 1, it is characterized in that said CO
2The volume percent that the supercritical extraction entrainment agent accounts for total extraction solvent is 4%.
3. according to the said a kind of method of from radix linderae, extracting norisoboldine of claim 1, it is characterized in that said CO
2Supercritical extraction pressure 35MPa, 55 ℃ of temperature, CO
2Flow 3ml/g crude drug min.
4. according to the above a kind of method of from radix linderae, extracting norisoboldine of claim, it is characterized in that said CO
2Supercritical extraction time 100min.
5. according to the said a kind of method of from radix linderae, extracting norisoboldine of claim 1, it is characterized in that said macroporous adsorbent resin is selected from a kind of among D101 type, D102 type, AB-8 type, HPD400, the HPD826.
6. according to the above a kind of method of from radix linderae, extracting norisoboldine of claim, it is characterized in that it is 60% that said macroporous adsorbent resin wash-out uses concentration of ethanol.
7. according to the said a kind of method of from radix linderae, extracting norisoboldine of claim 1, it is characterized in that it is 5 times of amount column volumes that said macroporous adsorbent resin wash-out uses the alcoholic acid collecting amount.
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| CN2011104100965A CN102432534A (en) | 2011-12-11 | 2011-12-11 | Method for extracting norisoboldine from combined spicebush roots |
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| CN2011104100965A CN102432534A (en) | 2011-12-11 | 2011-12-11 | Method for extracting norisoboldine from combined spicebush roots |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299298A (en) * | 2018-02-07 | 2018-07-20 | 浙江省林业科学研究院 | A kind of method of norisoboldine high efficiency extraction |
| CN109180584A (en) * | 2018-07-25 | 2019-01-11 | 湖南农业大学 | A method of separating norisoboldine from the root of three-nerved spicebush |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101375850A (en) * | 2008-10-07 | 2009-03-04 | 中国药科大学 | Application of norisoboldine in preparing medicament for treating autoimmune disease |
| CN102040557A (en) * | 2010-09-27 | 2011-05-04 | 南京泽朗医药科技有限公司 | Extracting method of laurotetanine |
-
2011
- 2011-12-11 CN CN2011104100965A patent/CN102432534A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101375850A (en) * | 2008-10-07 | 2009-03-04 | 中国药科大学 | Application of norisoboldine in preparing medicament for treating autoimmune disease |
| CN102040557A (en) * | 2010-09-27 | 2011-05-04 | 南京泽朗医药科技有限公司 | Extracting method of laurotetanine |
Non-Patent Citations (1)
| Title |
|---|
| TAO FENG，等: "Antimicrobially Active Isoquinoline Alkaloids from Litsea cubeba", 《PLANTA. MED.》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108299298A (en) * | 2018-02-07 | 2018-07-20 | 浙江省林业科学研究院 | A kind of method of norisoboldine high efficiency extraction |
| CN108299298B (en) * | 2018-02-07 | 2021-06-01 | 浙江省林业科学研究院 | Efficient extraction method of norisoboldine |
| CN109180584A (en) * | 2018-07-25 | 2019-01-11 | 湖南农业大学 | A method of separating norisoboldine from the root of three-nerved spicebush |
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Application publication date: 20120502 |
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