CN102329322A - Method for extracting cis-3',4'-diisovalerylkhellactone from peucedanum japonicum thunb. - Google Patents
Method for extracting cis-3',4'-diisovalerylkhellactone from peucedanum japonicum thunb. Download PDFInfo
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- CN102329322A CN102329322A CN201110143946A CN201110143946A CN102329322A CN 102329322 A CN102329322 A CN 102329322A CN 201110143946 A CN201110143946 A CN 201110143946A CN 201110143946 A CN201110143946 A CN 201110143946A CN 102329322 A CN102329322 A CN 102329322A
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- Prior art keywords
- khellactone
- diisoamyl
- japonicum thunb
- acyl
- peucedanum japonicum
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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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Abstract
The invention relates to a method for extracting cis-3',4'-diisovalerylkhellactone from peucedanum japonicum thunb., which is easy and convenient to operate and has small pollution and low energy consumption. The method comprises the following process steps of: smashing peucedanum japonicum thunb. herb; adding into a CO2 supercritical extractor to obtain an extract by taking n-hexane as an entrainer; adsorbing with a macroporous absorption resin column; eluting with 70-90 percent ethanol; collecting an eluent which is 3-8 times the volume of the column; recovering ethanol under reduced pressure and concentrating; adding onto a silica gel chromatography column; eluting with a methanol-chloroform mixed solvent; collecting an eluent; concentrating; adding methanol for crystalizing; separating crystals; and washing and drying. Due to the adoption of the method for preparing cis-3',4'-diisovalerylkhellactone, the product purity is high and industrial amplification is easy to realize.
Description
Technical field
The present invention relates to a kind of suitable-3 ＇, the preparation method of 4 ＇-diisoamyl acyl khellactone, especially a kind of suitable-3 ＇, preparation method of 4 ＇-diisoamyl acyl khellactone of from plant, extracting.
Background technology
Suitable-3 ＇, 4 ＇-diisoamyl acyl khellactone (
Cis-3 ', 4 '-Diisovalerylkhellactone), molecular formula: C
24H
30O
7, molecular weight: 430.497, CAS accession number: 54676-87-8 mainly is present in the samphire Peucedanum japonicum Thunb.
Peucedanum japonicumThunb. in.Its molecular formula is following.
Modern study shows, suitable-3 ＇, and 4 ＇-diisoamyl acyl khellactone has very strong antiplatelet aggregative activity, and it is also as the raw material that synthesizes other reactive derivative simultaneously.
The samphire Peucedanum japonicum Thunb.
Peucedanum japonicumThunb. velamen uses as the Chinese medicine Peucedanum japonicum Thunb., ability clearing and antitussive, diuresis detoxifcation.
In the prior art, still be not applicable to suitable-3 ＇ of high purity, preparation technology's report of 4 ＇-diisoamyl acyl khellactone industrialized production.
Summary of the invention
Technical problem to be solved by this invention provides a kind of big production operation, suitable-3 ＇ that product purity is high, preparation method of 4 ＇-diisoamyl acyl khellactone of being beneficial to.
For solving the problems of the technologies described above, the present invention adopts following technical proposal.
Get the Peucedanum japonicum Thunb. herb, pulverize, join CO
2In the supercritical extraction device, normal hexane is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2-4%, extracting pressure 10-30MPa, temperature 30-50 ℃, CO
2Flow 1-3ml/g crude drug min, extraction time 120-180min gets extract, adsorbs through macroporous adsorptive resins; The 70-90% ethanol elution is collected the elutriant that 3-8 doubly measures column volume, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With methyl alcohol-chloroform mixed solvent wash-out, the ratio of methyl alcohol and chloroform is 1:6 in this mixed solvent, and elutriant is pressed the column volume portioning and collected, and merges 5-8 part elutriant; Concentrate, add methanol crystallization, fractional crystallization washs, is drying to obtain.
CO
2The volume percent that the supercritical extraction entrainment agent accounts for total extraction solvent is 3%.
CO
2Supercritical extraction pressure 20MPa, 40 ℃ of temperature, CO
2Flow 2ml/g crude drug min.
CO
2Supercritical extraction time 150min.
Macroporous adsorbent resin is selected from a kind of in D101 type, H-50 type, the CD-180 type macroporous adsorbent resin.
It is 80% that the macroporous adsorbent resin wash-out uses concentration of ethanol.
It is 5 times of amount column volumes that the macroporous adsorbent resin wash-out uses the alcoholic acid collecting amount.
Suitable-3 ＇ of preparation gained, 4 ＇-diisoamyl acyl khellactone can adopt following method to detect.
Test Example 1 HPLC method is measured suitable-3 ＇, 4 ＇-diisoamyl acyl khellactone purity.
Chromatographic condition
Chromatographic column: octadecylsilane bonding glue silica gel is weighting agent; Moving phase: methyl alcohol-acetonitrile (15: 85); Flow velocity: 1mL/min; Detect wavelength: 260nm; Column temperature: 30 ℃.
Measuring method
Precision takes by weighing suitable-3 ＇, 4 ＇-diisoamyl acyl khellactone 2mg place the 50mL measuring bottle, add people's methyl alcohol 20mL, and sonic oscillation makes dissolving, and methanol constant volume is drawn 10 μ L to scale, injects high performance liquid chromatograph, adopts normalization method working sample purity.
Adopt the present invention to prepare suitable-3 ＇, 4 ＇-diisoamyl acyl khellactone are beneficial to big production operation, and energy consumption is little, pollutes little.
Below in conjunction with the specific embodiment the present invention is further elaborated, but the scope of protection of present invention is not limited to following embodiment.
Embodiment
Embodiment 1
Get Peucedanum japonicum Thunb. herb 10Kg, pulverize, join CO
2In the supercritical extraction device, normal hexane is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2%, extracting pressure 10MPa, 30 ℃ of temperature, CO
2Flow 1ml/g crude drug min, extraction time 120min gets extract, adsorbs through D101 type macroporous adsorptive resins; 70% ethanol elution is collected 3 times of elutriants of measuring column volumes, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With methyl alcohol-chloroform mixed solvent wash-out, the ratio of methyl alcohol and chloroform is 1:6 in this mixed solvent, and elutriant is pressed the column volume portioning and collected, and merges 5-8 part elutriant; Concentrate, add methanol crystallization, fractional crystallization washs, is drying to obtain suitable-3 ＇; 4 ＇-diisoamyl acyl khellactone 5.2g detect through HPLC, and purity is 98.3%, UV, IR, MS,
2HNMR,
13The data and the prior art of its physical behavior of sign such as CNMR are consistent.
Embodiment 2
Get Peucedanum japonicum Thunb. herb 10Kg, pulverize, join CO
2In the supercritical extraction device, normal hexane is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 4%, extracting pressure 30MPa, 50 ℃ of temperature, CO
2Flow 3ml/g crude drug min, extraction time 180min gets extract, adsorbs through H-50 type macroporous adsorptive resins; 90% ethanol elution is collected 8 times of elutriants of measuring column volumes, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With methyl alcohol-chloroform mixed solvent wash-out, the ratio of methyl alcohol and chloroform is 1:6 in this mixed solvent, and elutriant is pressed the column volume portioning and collected, and merges 5-8 part elutriant; Concentrate, add methanol crystallization, fractional crystallization washs, is drying to obtain suitable-3 ＇; 4 ＇-diisoamyl acyl khellactone 7.3g detect through HPLC, and purity is 96.6%, UV, IR, MS,
2HNMR,
13The data and the prior art of its physical behavior of sign such as CNMR are consistent.
Embodiment 3
Get Peucedanum japonicum Thunb. herb 10Kg, pulverize, join CO
2In the supercritical extraction device, normal hexane is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 3%, extracting pressure 20MPa, 40 ℃ of temperature, CO
2Flow 2ml/g crude drug min, extraction time 150min gets extract, adsorbs through CD-180 type macroporous adsorptive resins; 80% ethanol elution is collected 5 times of elutriants of measuring column volumes, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With methyl alcohol-chloroform mixed solvent wash-out, the ratio of methyl alcohol and chloroform is 1:6 in this mixed solvent, and elutriant is pressed the column volume portioning and collected, and merges 5-8 part elutriant; Concentrate, add methanol crystallization, fractional crystallization washs, is drying to obtain suitable-3 ＇; 4 ＇-diisoamyl acyl khellactone 6.6g detect through HPLC, and purity is 99.2%, UV, IR, MS,
2HNMR,
13The data and the prior art of its physical behavior of sign such as CNMR are consistent.
Claims (7)
1. one kind is extracted suitable-3 ＇ from Peucedanum japonicum Thunb., and the method for 4 ＇-diisoamyl acyl khellactone is characterized in that described method is made up of the following step: get the Peucedanum japonicum Thunb. herb, pulverize, join CO
2In the supercritical extraction device, normal hexane is as entrainment agent, and the volume percent that entrainment agent accounts for total extraction solvent is 2-4%, extracting pressure 10-30MPa, temperature 30-50 ℃, CO
2Flow 1-3ml/g crude drug min, extraction time 120-180min gets extract, adsorbs through macroporous adsorptive resins; The 70-90% ethanol elution is collected the elutriant that 3-8 doubly measures column volume, and decompression recycling ethanol also concentrates, and is added on the silica gel column chromatography; With methyl alcohol-chloroform mixed solvent wash-out, the ratio of methyl alcohol and chloroform is 1:6 in this mixed solvent, and elutriant is pressed the column volume portioning and collected, and merges 5-8 part elutriant; Concentrate, add methanol crystallization, fractional crystallization washs, is drying to obtain.
2. according to said a kind of suitable-3 ＇ that from Peucedanum japonicum Thunb., extract of claim 1, the method for 4 ＇-diisoamyl acyl khellactone is characterized in that said CO
2The volume percent that the supercritical extraction entrainment agent accounts for total extraction solvent is 3%.
3. according to said a kind of suitable-3 ＇ that from Peucedanum japonicum Thunb., extract of claim 1, the method for 4 ＇-diisoamyl acyl khellactone is characterized in that said CO
2Supercritical extraction pressure 20MPa, 40 ℃ of temperature, CO
2Flow 2ml/g crude drug min.
4. according to said a kind of suitable-3 ＇ that from Peucedanum japonicum Thunb., extract of claim 1, the method for 4 ＇-diisoamyl acyl khellactone is characterized in that CO
2Supercritical extraction time 150min.
5. according to said a kind of suitable-3 ＇ that from Peucedanum japonicum Thunb., extract of claim 1, the method for 4 ＇-diisoamyl acyl khellactone is characterized in that said macroporous adsorbent resin is selected from a kind of in D101 type, H-50 type, the CD-180 type macroporous adsorbent resin.
6. according to said a kind of suitable-3 ＇ that from Peucedanum japonicum Thunb., extract of claim 1, the method for 4 ＇-diisoamyl acyl khellactone is characterized in that it is 80% that said macroporous adsorbent resin wash-out uses concentration of ethanol.
7. according to said a kind of suitable-3 ＇ that from Peucedanum japonicum Thunb., extract of claim 1, the method for 4 ＇-diisoamyl acyl khellactone 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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| Application Number | Priority Date | Filing Date | Title |
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| CN201110143946A CN102329322A (en) | 2011-05-31 | 2011-05-31 | Method for extracting cis-3',4'-diisovalerylkhellactone from peucedanum japonicum thunb. |
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| CN201110143946A CN102329322A (en) | 2011-05-31 | 2011-05-31 | Method for extracting cis-3',4'-diisovalerylkhellactone from peucedanum japonicum thunb. |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107073054A (en) * | 2014-08-01 | 2017-08-18 | 株式会社资生堂 | Longevity gene expression facilitator |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008015950A1 (en) * | 2006-08-02 | 2008-02-07 | Takara Bio Inc. | Acat inhibitor |
| CN101759705A (en) * | 2009-10-22 | 2010-06-30 | 南京泽朗医药科技有限公司 | Method for preparing praeruptorin A |
-
2011
- 2011-05-31 CN CN201110143946A patent/CN102329322A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008015950A1 (en) * | 2006-08-02 | 2008-02-07 | Takara Bio Inc. | Acat inhibitor |
| CN101759705A (en) * | 2009-10-22 | 2010-06-30 | 南京泽朗医药科技有限公司 | Method for preparing praeruptorin A |
Non-Patent Citations (2)
| Title |
|---|
| TING-TING JONG，等: "An antiplatelet aggregation principle and x-ray structural analysis of cis-khellactone diester from Peucedanum japonicum", 《JOURNAL OF NATURAL PRODUCTS》, vol. 55, no. 10, 31 October 1992 (1992-10-31) * |
| 张村，等: "白花前胡化学成分研究II", 《中国中药杂志》, vol. 31, no. 16, 31 August 2006 (2006-08-31) * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107073054A (en) * | 2014-08-01 | 2017-08-18 | 株式会社资生堂 | Longevity gene expression facilitator |
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Application publication date: 20120125 |