CN104058963A - Method for extracting 1'-acetoxychavicol acetate from alpinia chinensis - Google Patents
Method for extracting 1'-acetoxychavicol acetate from alpinia chinensis Download PDFInfo
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- CN104058963A CN104058963A CN201410297942.0A CN201410297942A CN104058963A CN 104058963 A CN104058963 A CN 104058963A CN 201410297942 A CN201410297942 A CN 201410297942A CN 104058963 A CN104058963 A CN 104058963A
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- huashan
- acetate
- concentrated
- chavicol
- ethanoyl
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C67/00—Preparation of carboxylic acid esters
- C07C67/48—Separation; Purification; Stabilisation; Use of additives
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to a method for extracting 1'-acetoxychavicol acetate from alpinia chinensis, which comprises the following steps: taking dry alpinia chinensis rhizome, pulverizing, heating under reflux to extract twice (1.5 hours each time), merging the reflux liquids, filtering, recovering the ethanol under reduced pressure, concentrating, carrying out counter-current extraction, and carrying out silica gel column chromatography. The method for preparing 1'-acetoxychavicol acetate is simple to operate, and the product purity is high.
Description
Technical field
The present invention relates to natural product field, especially from plant, extract compound technical.
Background technology
Huashan ginger
alpinia chinensis(Retz.) Rosc., is Zingiber Alpinia plants, upright draft, and blade lanceolar or ovum shape lanceolar, panicle is narrow, capsule red spherical, 5-July of florescence, really 6-December of phase.Mainly be distributed in the ground such as China and Laos, Vietnam.Root stock is used as medicine, and has the function of Wen Zhongnuan stomach, dispersing cold for relieving pain.
1 '-ethanoyl chavicol-acetate (1 '-acetoxychavicol acetate), CAS accession number: 108147-21-3, molecular formula C
13h
l40
4, structural formula is as follows:
Research shows, the multiple pharmacologically active such as that 1 '-ethanoyl chavicol-acetate has is antitumor, antiulcer agent.
In prior art, do not have about the relevant report that contains 1 '-ethanoyl chavicol-acetate in the ginger of the Huashan.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of method of extracting 1 '-ethanoyl chavicol-acetate from the ginger of the Huashan, makes that the method is easy and simple to handle, product purity is high.。
In order to solve the problems of the technologies described above, the present invention proposes following technical proposal:
A kind of method of extracting 1 '-ethanoyl chavicol-acetate from the ginger of the Huashan, is characterized in that described method comprises the following steps: get dry Huashan race stem, pulverize, extract and separate according to a conventional method, to obtain final product.
Preferably, described method comprises the following steps: get dry Huashan race stem, pulverize, add by every 1g meal the ethanol that the concentration of volume percent of 8-12mL is 80-90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated, ethyl acetate-the water mixed solvent that is 10:2 by ratio carries out the extraction of 6-9 stage countercurrent, the volume ratio of concentrated solution and the total consumption of mixed solvent is 1:8, combining extraction liquid, decompression and solvent recovery is also concentrated, be added on silica gel column chromatography, sherwood oil-the acetone that is 5:3 by volume ratio is eluent wash-out, collect elutriant taking column volume as unit by part, merge stream part of 4-6 part, reclaim solvent concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 1:1 by volume ratio carries out wash-out the 2nd time, collect elutriant taking column volume as unit by part, merge stream part of 7-9 part, decompression and solvent recovery, obtain.
Preferably, the condition of described heating and refluxing extraction is: add by every 1g meal the ethanol that the volume percent of 10mL is 85%.
Preferably, the progression of described counter-current extraction is 6 grades.
Adopt method of the present invention to prepare 1 '-ethanoyl chavicol-acetate, easy and simple to handle, product purity is high.
In order better to set forth technical scheme, below in conjunction with embodiment, the present invention is further illustrated, but protection domain of the presently claimed invention is not limited to the following example.
Embodiment
embodiment 1
Get dry Huashan race stem 100Kg, pulverize, add by every 1g meal the ethanol that the concentration of volume percent of 8mL is 80%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated, ethyl acetate-the water mixed solvent that is 10:2 by ratio carries out 6 stage countercurrent extractions, the volume ratio of concentrated solution and the total consumption of mixed solvent is 1:8, combining extraction liquid, decompression and solvent recovery is also concentrated, be added on silica gel column chromatography, sherwood oil-the acetone that is 5:3 by volume ratio is eluent wash-out, collect elutriant taking column volume as unit by part, merge stream part of 4-6 part, reclaim solvent concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 1:1 by volume ratio carries out wash-out the 2nd time, collect elutriant taking column volume as unit by part, merge stream part of 7-9 part, decompression and solvent recovery, obtain oily matter 22.3g.
Detect through HPLC, the purity of compound is 95.3%.
Its spectrum, mass spectrum, spectral data are as follows:
UV λ max ((EtOH) nm (ε): 220; IRv
maxcm
-1: 1753,1509,1374; EIS-MSm/z:257 (Na
+, C
13h
l40
4), EI-MSm/z:234 (M+, C
13h
140
4);
1h-NMR δ: 2.10 (3 H, s, acetyl-H), 2.29 (3H, s, acetyl-H), 5.23 (1H, ddd, H-3 ' b, J 3'b, 2'=10.2 Hz; J 3'b, 1'=1.5Hz; J 3'b, 3'a=1.5Hz), 5.30 (1H, ddd, H-3'a, J3'a, 2 '=16.8 Hz; J 3'a, 1'=1.5Hz; J 3'b, 3'a=1.5 Hz), 6.00 (1H, ddd, H-2', J2', 3'a=16.8Hz; J2'3'b=10.2Hz; J2', 1'=5.9 Hz), 6.25 (1H, brd, 1', 2'=5.9Hz), 7.27 (2H, d, fragrance-H, J=8.8 Hz), 7.42 (2H, d, fragrance-H, J=8.8Hz);
13cNMR δ: 21.0 (2s; on the carbon of 2x methyl, connect acetoxyl group group), 77.3 (s, C-l'); 117.0 (s; C-3'), 121.6 (s, C-2 and C-6); 128.3 (s; C-3 and C-5), 136.1 (s, C-2 '); 136.4 (s; C-l), 150.3 (s, C-4); 169.75 (2s; 2x acetoxyl group group), basically identical with document, therefore determine that this compound is 1 '-ethanoyl chavicol-acetate.
embodiment 2
Get dry Huashan race stem 100Kg, pulverize, add by every 1g meal the ethanol that the concentration of volume percent of 12mL is 90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated, ethyl acetate-the water mixed solvent that is 10:2 by ratio carries out 9 stage countercurrent extractions, the volume ratio of concentrated solution and the total consumption of mixed solvent is 1:8, combining extraction liquid, decompression and solvent recovery is also concentrated, be added on silica gel column chromatography, sherwood oil-the acetone that is 5:3 by volume ratio is eluent wash-out, collect elutriant taking column volume as unit by part, merge stream part of 4-6 part, reclaim solvent concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 1:1 by volume ratio carries out wash-out the 2nd time, collect elutriant taking column volume as unit by part, merge stream part of 7-9 part, decompression and solvent recovery, obtain oily matter 23.7g.
Detect through HPLC, the purity of compound is 94.8%.
Its spectrum, mass spectrum, spectral data are with embodiment 1.
embodiment 3
Get dry Huashan race stem 100Kg, pulverize, add by every 1g meal the ethanol that the concentration of volume percent of 10mL is 80%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated, ethyl acetate-the water mixed solvent that is 10:2 by ratio carries out 8 stage countercurrent extractions, the volume ratio of concentrated solution and the total consumption of mixed solvent is 1:8, combining extraction liquid, decompression and solvent recovery is also concentrated, be added on silica gel column chromatography, sherwood oil-the acetone that is 5:3 by volume ratio is eluent wash-out, collect elutriant taking column volume as unit by part, merge stream part of 4-6 part, reclaim solvent concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 1:1 by volume ratio carries out wash-out the 2nd time, collect elutriant taking column volume as unit by part, merge stream part of 7-9 part, decompression and solvent recovery, obtain oily matter 21.8g.
Detect through HPLC, the purity of compound is 95.6%.
Its spectrum, mass spectrum, spectral data are with embodiment 1.
Claims (4)
1. from the ginger of the Huashan, extract a method for 1 '-ethanoyl chavicol-acetate, it is characterized in that described method comprises the following steps: get dry Huashan race stem, pulverize, extract and separate according to a conventional method, to obtain final product.
2. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from the ginger of the Huashan according to claim 1, it is characterized in that described method comprises the following steps: get dry Huashan race stem, pulverize, add by every 1g meal the ethanol that the concentration of volume percent of 8-12mL is 80-90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated, ethyl acetate-the water mixed solvent that is 10:2 by ratio carries out the extraction of 6-9 stage countercurrent, the volume ratio of concentrated solution and the total consumption of mixed solvent is 1:8, combining extraction liquid, decompression and solvent recovery is also concentrated, be added on silica gel column chromatography, sherwood oil-the acetone that is 5:3 by volume ratio is eluent wash-out, collect elutriant taking column volume as unit by part, merge stream part of 4-6 part, reclaim solvent concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 1:1 by volume ratio carries out wash-out the 2nd time, collect elutriant taking column volume as unit by part, merge stream part of 7-9 part, decompression and solvent recovery, obtain.
3. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from the ginger of the Huashan according to claim 2, is characterized in that, the condition of described heating and refluxing extraction is: add by every 1g meal the ethanol that the volume percent of 10mL is 85%.
4. a kind of method of extracting 1 '-ethanoyl chavicol-acetate from the ginger of the Huashan according to claim 2, is characterized in that, the progression of described counter-current extraction is 6 grades.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1958057A (en) * | 2006-11-16 | 2007-05-09 | 南昌弘益科技有限公司 | Application of extractive of Daliangjiang, and application in medication |
| CN101020638A (en) * | 2007-03-18 | 2007-08-22 | 南昌弘益科技有限公司 | 1'-acetoxy chavicol acetic ester |
| CN101029005A (en) * | 2007-04-11 | 2007-09-05 | 南昌弘益科技有限公司 | Method for producing 1-acetoxy-piperonyl acetate |
| JP2012056886A (en) * | 2010-09-09 | 2012-03-22 | Akiko Yuasa | Anti-obesity agent |
-
2014
- 2014-06-30 CN CN201410297942.0A patent/CN104058963B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1958057A (en) * | 2006-11-16 | 2007-05-09 | 南昌弘益科技有限公司 | Application of extractive of Daliangjiang, and application in medication |
| CN101020638A (en) * | 2007-03-18 | 2007-08-22 | 南昌弘益科技有限公司 | 1'-acetoxy chavicol acetic ester |
| CN101029005A (en) * | 2007-04-11 | 2007-09-05 | 南昌弘益科技有限公司 | Method for producing 1-acetoxy-piperonyl acetate |
| JP2012056886A (en) * | 2010-09-09 | 2012-03-22 | Akiko Yuasa | Anti-obesity agent |
Non-Patent Citations (1)
| Title |
|---|
| 刘成梅 等: "超临界CO2 萃取法和乙醇回流提取法提取大高良姜中1"- 乙酰氧基胡椒酚乙酸酯的比较", 《第29卷》 * |
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