CN104045650A - Method for extracting homopterocarpin from galega officinalis - Google Patents
Method for extracting homopterocarpin from galega officinalis Download PDFInfo
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- CN104045650A CN104045650A CN201410297952.4A CN201410297952A CN104045650A CN 104045650 A CN104045650 A CN 104045650A CN 201410297952 A CN201410297952 A CN 201410297952A CN 104045650 A CN104045650 A CN 104045650A
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- ethanol
- extracting
- galega officinalis
- homoptercarpin
- homopterocarpin
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
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- Organic Chemistry (AREA)
- Medicines Containing Plant Substances (AREA)
Abstract
The invention relates to a method for extracting homopterocarpin from galega officinalis. The method comprises the steps of fetching dried whole galega officinalis, crushing, carrying out heated reflux extraction twice for 1.5 hours every time, combining reflux liquids, filtrating, carrying out ethanol recovery at reduced pressure, concentrating, adding to a macroporous adsorption resin column D101 for adsorption, eluting with ethanol, collecting an eluate, carrying out ethanol recovery at reduced pressure, concentrating, adding to a silica-gel chromatography column, eluting with an eluant with the methanol/dichloromethane volume ratio of 8: 3, recovering a solvent, concentrating, adding methanol to crystallize, separating crystals, washing and drying, thereby obtaining homopterocarpin. By adopting the method disclosed by the invention to prepare homopterocarpin, the operation is simple and convenient, 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
Galega officinalis L (Galega officinalis L.) is leguminous plants, perennial herb, high 40-100 centimetre.Stem is upright, and internode work is tortuous, cylindrical in a zigzag, and hollow, without hair or slightly by subsides volt hair.Stipule is wealthy drapes over one's shoulders needle-like shape, the sharp point of tip, and base portion flechette-type, vein is clear; Rachis tool is indulged rib; Leaflet is closely to life, raceme.Pod is narrow coniform linear, seed kidney shape.Can make cattle food; Spending and beautiful for viewing and admiring, dry rear hyoscine, is warm nature astringent matter, has the usefulness such as strong, sweating, lactagogue.
Its seed is used as Chinese medicine Galega officinalis L, the effect of tool Yin-nourishing and body fluid promoting.Control and quench one's thirst, many drinks, many foods, diuresis.
Homoptercarpin (Homopterocarpin), has another name called homopterocarpin, CAS accession number: 606-91-7, molecular formula C
17h
l60
4, structural formula is as follows:
Research shows, homoptercarpin has the very strong multiple pharmacologically active such as antitumor, antimycotic.
In prior art, homoptercarpin often extracts from red sandalwood, and raw material red sandalwood is very expensive, and this has just limited the industrialization development of homoptercarpin.
This just makes to find the Botanical origin that homoptercarpin is new, and tool is of great significance.
In prior art, do not have about containing the relevant report of homoptercarpin in Galega officinalis L.
Summary of the invention
Technical problem to be solved by this invention is to provide a kind of method of extracting homoptercarpin from Galega officinalis L, 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:
From Galega officinalis L, extract a method for homoptercarpin, it is characterized in that described method comprises the following steps: get dry Galega officinalis L herb, pulverize, extract according to a conventional method separation and get final product.
Preferably, described extracting method is: every 1g meal adds the ethanol that the concentration of volume percent of 8-12mL is 75-90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 60-70% with concentration of volume percent, collect the elutriant that 3-8 doubly measures column volume, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 5:1 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 4-8 part, reclaim solvent concentrated, add sherwood oil crystallization, fractional crystallization, washing, be drying to obtain.
Preferably, the condition of heating and refluxing extraction is: by every 1g meal, add the ethanol that the volume percent of 10mL is 80%.
Preferably, described macroporous resin wash-out is 65% by the concentration of ethanol.
Preferably, the collecting amount of described macroporous resin elutriant is 5 times of column volumes.
Adopt method of the present invention to prepare homoptercarpin, 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 Galega officinalis L herb 100Kg, pulverize, by every 1g meal, add the ethanol that the concentration of volume percent of 8mL is 75%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 60% with concentration of volume percent, collect the elutriant of 3 times of amount column volumes, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 5:1 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 4-8 part, reclaim solvent concentrated, add sherwood oil crystallization, fractional crystallization, washing, be drying to obtain 15.9g.
Through HPLC, detect, the purity of compound is 99.3%.
Physico-chemical property and the spectral data of this compound are as follows:
IR(KBr)cm
-1:2996,2947,2839,1621,1580,1494,1379,1465,1120,938,838,791。Bunch shape crystallization (sherwood oil) of white pin, mp78-80 ℃, Hcl-Mg reaction negative.IMSm/z(%):285(M
++1,17.5),284(M
+,100.0),283(M-1,45.0),254(M-CH3-CH3,13.4),161(19.8),148(30.7)。
1hNMR (300MHz, CDCL
3, mark in TMS) and δ ppm:3.49-3.57 (1H, m, C
6a-H), 3.63 (1H, d), 3.63 (1H, t, J=10.5Hz, C
6-aH), 4.25 (1H, dd, J=10.5,4.6Hz, C
6-eH), 5.51 (1H, d, J=6.5, C
11a-H), 6.43 ~ 6.47 (3H, m, C
4-H, C
8-H, C
10-H), 6.64 (1H, dd, J=8.8,2.1Hz, C
2-H), 7.13 (IH, d, J=8.7, C
7-H), 7.42 (1H, d, J=8.9Hz, C
1-H.
13cNMR (300MHz, CDCL
3, mark in TMS) and δ ppm:131.8(1-C), 112.3 (1a-C), 109.8 (2-C), 161.0 (3-C), 101.6 (4-C), 156.6 (4a-C), 66.6 (6-C), 39.5 (6a-C), 124.7 (7-C), 119.1 (7a-C), 106.3 (8-C), 161.2 (9-C), 96.9 (10-C), 160.7 (10a-C), 79.0 (11a-C), 55.5,55.4 (OMe).The data of the homoptercarpin of above-mentioned data and bibliographical information (Homopterocarpin) are basically identical, therefore identify that this compound is homoptercarpin.
embodiment 2
Get dry Galega officinalis L herb 100Kg, pulverize, by every 1g meal, add 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 into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 70% with concentration of volume percent, collect the elutriant of 3 times of amount column volumes, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 5:1 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 4-8 part, reclaim solvent concentrated, add sherwood oil crystallization, fractional crystallization, washing, be drying to obtain 16.8g.
Through HPLC, detect, the purity of compound is 98.1%.
Its spectrum, mass spectrum, spectral data are with embodiment 1.
embodiment 3
Get dry Galega officinalis L herb 100Kg, pulverize, by every 1g meal, add 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 into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 65% with concentration of volume percent, collect the elutriant of 3 times of amount column volumes, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 5:1 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 4-8 part, reclaim solvent concentrated, add sherwood oil crystallization, fractional crystallization, washing, be drying to obtain 16.3g.
Through HPLC, detect, the purity of compound is 99.5%.
Its spectrum, mass spectrum, spectral data are with embodiment 1.
Claims (5)
1. from Galega officinalis L, extract a method for homoptercarpin, it is characterized in that described method comprises the following steps: get dry Galega officinalis L herb, pulverize, extract according to a conventional method separation and get final product.
2. a kind of method of extracting homoptercarpin from Galega officinalis L according to claim 1, it is characterized in that described extracting method is: every 1g meal adds the ethanol that the concentration of volume percent of 8-12mL is 75-90%, heating and refluxing extraction 2 times, each 1.5 hours, merge phegma, filter, decompression recycling ethanol is also concentrated into thick paste, join on D101 type macroporous adsorptive resins and adsorb, the ethanol elution that is 60-70% with concentration of volume percent, collect the elutriant that 3-8 doubly measures column volume, decompression recycling ethanol is also concentrated, be added on silica gel column chromatography, the petroleum ether-ethyl acetate that is 5:1 by volume ratio is eluent wash-out, the column volume of take is collected elutriant by part as unit, the stream part that merges 4-8 part, reclaim solvent concentrated, add sherwood oil crystallization, fractional crystallization, washing, be drying to obtain.
3. a kind of method of extracting homoptercarpin from Galega officinalis L according to claim 2, is characterized in that, the condition of described heating and refluxing extraction is: by every 1g meal, add the ethanol that the volume percent of 10mL is 80%.
4. a kind of method of extracting Quercetin from Roundpimma Maidenhair according to claim 2, is characterized in that, described macroporous resin wash-out is 65% by the concentration of ethanol.
5. a kind of method of extracting homoptercarpin from Galega officinalis L according to claim 2, is characterized in that, the collecting amount of described macroporous resin elutriant is 5 times of column volumes.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110734449A (en) * | 2019-10-16 | 2020-01-31 | 武汉大学 | Pterocarpin compound in fenugreek, and preparation method and application thereof |
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Non-Patent Citations (4)
| Title |
|---|
| 杨成雄: "昌都锦鸡儿紫檀素类化学成分的研究", 《中国优秀硕士学位论文全文数据库 医药卫生科技辑》, no. 8, 15 August 2009 (2009-08-15), pages 057 - 13 * |
| 石荣火等: "刺果甘草二氯甲烷提取部位化学成分研究", 《中药材》, vol. 24, no. 1, 31 January 2001 (2001-01-31), pages 38 - 39 * |
| 路静: "柠条锦鸡儿化学成分研究", 《万方数据企业知识服务平台》, 6 December 2011 (2011-12-06), pages 1 - 64 * |
| 阚毓铭等: "刺果甘草化学成分的研究", 《中草药》, vol. 25, no. 1, 31 December 1994 (1994-12-31), pages 3 - 6 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110734449A (en) * | 2019-10-16 | 2020-01-31 | 武汉大学 | Pterocarpin compound in fenugreek, and preparation method and application thereof |
| CN110734449B (en) * | 2019-10-16 | 2020-11-03 | 武汉大学 | Pterocarpin compound in fenugreek, and preparation method and application thereof |
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Effective date of registration: 20171109 Address after: 350700 building, two Financial Bureau, Yongtai County, Fujian, Fuzhou Patentee after: Yongtai County State owned asset management company Address before: No. 2 Taishan Road, Jiangsu science and Technology Park, 215000 Canton City of Suzhou province high tech Zone 2-104 Patentee before: Suzhou Paiteng Biopharmaceutical Technology Co., Ltd. |