CN105315295A - Method for separating and purifying psoralen and isopsoralen from fructus psoraleae - Google Patents
Method for separating and purifying psoralen and isopsoralen from fructus psoraleae Download PDFInfo
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- CN105315295A CN105315295A CN201510179427.7A CN201510179427A CN105315295A CN 105315295 A CN105315295 A CN 105315295A CN 201510179427 A CN201510179427 A CN 201510179427A CN 105315295 A CN105315295 A CN 105315295A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- 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
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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
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Abstract
The invention belongs to the field of chemical engineering and pharmacy, and relates to a method for separating and purifying isopsoralen and psoralen from fructus psoraleae extracts. The method includes the steps of smashing fructus psoraleae medicine materials, adding absolute methanol, conducting heating, backward flowing and extracting, filtering, decompressing and concentrating an extracted solution to obtain extracts, dispersing the extracts in water, conducting extracting through petroleum ether, combining petroleum ether layers, conducting decompressing and distilling to obtain fructus psoraleae extracts, dissolving fructus psoraleae extracts in methanol, and conducting supercritical fluid chromatographic separation after filtering, wherein the chromatographic column is a diol chromatographic column, the flowing phase is supercritical fluid, and the modifier is methanol. The supercritical carbon dioxide is used in the purifying process, organic solvent harmful to the environment is not used, environmental friendliness is achieved in the producing process, and the obtained product is free of harmful substance residues.
Description
Technical field
The invention belongs to chemical industry and pharmacy field, specifically relate to a kind of method of separation and purification isopsoralen and psoralene from Fructus Psoraleae extract.
Background technology
Psoralea corylifolia is leguminous plants
psoraleacorylifolia(l.) dry mature fruit.Its main active ingredient is psoralen and isopsorapen furocoumarin(e) constituents, has the effects such as calmness, spasmolysis, hemostasis, is treatment vitiligo, alopecia areata, psoriasis and the dermopathic active drug of knurl sample.Clinical experimental study shows, the growth of psoralene to tumour has obvious restraining effect, the endocrine disturbance of the adjustable body of isopsoralen, alleviates climacteric syndrome.
At present, organic reagent is mainly adopted to extract to the separation and purification of coumarins composition in Psoralea corylifolia, macroporous resin purification method or high-speed countercurrent chromatography.Although macroporous resin purification method technical maturity, complex operation, in high-speed countercurrent chromatography, the selection of solvent system is more difficult, and lacks theoretical direction.In addition, two kinds of methods all need to consume a large amount of organic solvents, are difficult to realize recycling, and in product, organic reagent is residual serious.
Summary of the invention
The object of the invention is to overcome the deficiencies in the prior art, a kind of easy and simple to handle, fractional dose is large, comprehensive cost is low, the fast purifying of environmental protection prepares isopsoralen and psoralene method is provided, high purity isopsoralen and psoralene monomeric compound can be obtained by a step separation and purification from Fructus Psoraleae extract.
The solution of the present invention is as follows:
A method for separation and purification isopsoralen and psoralene from Psoralea corylifolia, step is:
Step 1: corylifolia L is pulverized, and adds anhydrous methanol heating and refluxing extraction, extracting liquid filtering, concentrating under reduced pressure are obtained medicinal extract, be scattered in by medicinal extract in water, use petroleum ether extraction.Merge petroleum ether layer, underpressure distillation obtains Psoralea corylifolia medicinal extract.
Step 2: by Psoralea corylifolia medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is glycol-based chromatographic column, and moving phase is supercutical fluid, and properties-correcting agent is methyl alcohol.Sepn process is detected by UV-detector, collects target components cut according to detection signal.
Foregoing method, preferred scheme is, in step 1, the ratio of anhydrous methanol heating and refluxing extraction methyl alcohol and medicinal material is 5:1 ~ 20:1, and optimum is 10:1; The number of times extracted is 3 times, and return time is 0.5-2 hour.
Foregoing method, preferred scheme is, is scattered in water in step 1 by medicinal extract, and the ratio of water and medicinal extract is 100:1 ~ 10:1, and optimum is 50:1.
Foregoing method, preferred scheme is, with petroleum ether extraction in step 1, the ratio of sherwood oil and aqueous phase is 0.5:1 ~ 10:1, and optimum is 1:1, and extraction times is 3 times.
Foregoing method, preferred scheme is, filtering filter membrane used in step 2 is 0.45 μm of filter membrane.
Foregoing method, preferred scheme is, in step 2, supercutical fluid is supercritical co, and the pressure of supercritical co is 9 ~ 14MPa, and optimum is 10MPa; The flow velocity of supercritical co be 1-8 times of column volume/minute, optimum be 3 times of column volumes/minute.
Foregoing method, preferred scheme is, in step 2, chromatogram column temperature is 35 ~ 50 DEG C, and optimum is 40 DEG C.
Foregoing method, preferred scheme is, in step 2, the ratio of properties-correcting agent methyl alcohol is 1% ~ 5%, and optimum is 2%.
The method of the present invention a kind of separation and purification isopsoralen and psoralene from Fructus Psoraleae extract, has following advantage:
(1) active constituent content high (as can be seen from Figure 1) in the Fructus Psoraleae extract obtained.
(2) do not need to carry out separating for several times purifying to sample as prior art, only need a separating step can obtain two kinds of high-purity compounds, just can obtain isopsoralen and psoralene through a step separation and purification.
(3) use supercritical co in purge process, do not use organic solvent environment being had to harm, production process environmental protection, products obtained therefrom unharmful substance remains.
(4) carbon dioxide recovery utilizes easily, and energy consumption is low, and production cost is low.
(5) method is simple to operate, is easy to Automated condtrol, and efficiency is high, and process cycle is short.
Accompanying drawing explanation
Fig. 1 is embodiment 1 supercritical fluid chromatography figure.
Embodiment
Describe technical scheme of the present invention in detail below in conjunction with embodiment and accompanying drawing, but protection domain is not by this restriction.In embodiment, equipment used or starting material all can obtain from market.Agents useful for same is analytical pure, and purchased from Tianjin reagent four factory, carbonic acid gas used is high-purity carbon dioxide.
Embodiment 1
Take Psoralea corylifolia 100 grams, pulverize with pulverizer, put into Glass Containers, add 1000ml anhydrous methanol heating and refluxing extraction 2 hours, extract 3 times, extracting liquid filtering, concentrating under reduced pressure are obtained medicinal extract, medicinal extract is scattered in 200ml water, with 200ml petroleum ether extraction 3 times.Merge petroleum ether extraction liquid, underpressure distillation is reclaimed sherwood oil and is obtained Psoralea corylifolia medicinal extract.
By Psoralea corylifolia medicinal extract dissolve with methanol, after filtration after (filter membrane used is 0.45 μm of filter membrane), carry out supercritical fluid chromatography separation, chromatographic column is glycol-based chromatographic column, and chromatogram column temperature is 40 DEG C.Moving phase is supercritical co, flow velocity be 3 times of column volumes/minute, pressure is 10MPa.Improving agent is methyl alcohol, and its ratio is 2%.Sepn process is detected by UV-detector, and determined wavelength is 254nm, collects target components cut, obtain isopsoralen and psoralene respectively according to detection signal.
Fig. 1 is embodiment 1 supercritical fluid chromatography figure.It can thus be appreciated that products therefrom purity is very high.
Embodiment 2
Take Psoralea corylifolia 100 grams, pulverize with pulverizer, put into Glass Containers, add 500ml anhydrous methanol heating and refluxing extraction 2 hours, extract 3 times, extracting liquid filtering, concentrating under reduced pressure are obtained medicinal extract, medicinal extract is scattered in 100ml water, with 100ml petroleum ether extraction 3 times.Merge petroleum ether extraction liquid, underpressure distillation is reclaimed sherwood oil and is obtained Psoralea corylifolia medicinal extract.
By Psoralea corylifolia medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is glycol-based chromatographic column, and chromatogram column temperature is 45 DEG C.Moving phase is supercritical co, flow velocity be 5 times of column volumes/minute, pressure is 12MPa.Improving agent is methyl alcohol, and its ratio is 5%.Sepn process is detected by UV-detector, and determined wavelength is 254nm, collects target components cut, obtain isopsoralen and psoralene respectively according to detection signal.
Embodiment 3
Take Psoralea corylifolia 100 grams, pulverize with pulverizer, put into Glass Containers, add 1500ml anhydrous methanol heating and refluxing extraction 1.5 hours, extract 3 times, extracting liquid filtering, concentrating under reduced pressure are obtained medicinal extract, medicinal extract is scattered in 300ml water, with 300ml petroleum ether extraction 3 times.Merge petroleum ether extraction liquid, underpressure distillation is reclaimed sherwood oil and is obtained Psoralea corylifolia medicinal extract.
By Psoralea corylifolia medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is glycol-based chromatographic column, and chromatogram column temperature is 40 DEG C.Moving phase is supercritical co, flow velocity be 4 times of column volumes/minute, pressure is 13MPa.Improving agent is methyl alcohol, and its ratio is 1%.Sepn process is detected by UV-detector, and determined wavelength is 254nm, collects target components cut, obtain isopsoralen and psoralene respectively according to detection signal.
Through HPLC area normalization method analytical test, the purity of each component that embodiment 1-3 obtains is very high, all more than 98%.
Through NMR, MS qualification, in Fig. 1, A is isopsoralen, and B is psoralene, and its chemical structure is as follows:
Claims (10)
1. the method for separation and purification isopsoralen and psoralene from Psoralea corylifolia, it is characterized in that, step is:
Step 1: corylifolia L is pulverized, and adds anhydrous methanol heating and refluxing extraction, extracting liquid filtering, concentrating under reduced pressure are obtained medicinal extract, be scattered in by medicinal extract in water, with petroleum ether extraction, merge petroleum ether layer, underpressure distillation obtains Psoralea corylifolia medicinal extract;
Step 2: by Psoralea corylifolia medicinal extract dissolve with methanol, after filtering, carry out supercritical fluid chromatography separation, chromatographic column is glycol-based chromatographic column, and moving phase is supercutical fluid, and properties-correcting agent is methyl alcohol, sepn process is detected by UV-detector, collects target components cut according to detection signal.
2. method according to claim 1, is characterized in that, in step 1, the ratio of anhydrous methanol heating and refluxing extraction methyl alcohol and medicinal material is 5:1 ~ 20:1, and optimum is 10:1.
3. method according to claim 1, is characterized in that, the number of times of extraction is 3 times, and return time is 0.5-2 hour.
4. method according to claim 1, is characterized in that, is scattered in water in step 1 by medicinal extract, and the ratio of water and medicinal extract is 100:1 ~ 10:1, and optimum is 50:1.
5. method according to claim 1, is characterized in that, with petroleum ether extraction in step 1, the ratio of sherwood oil and aqueous phase is 0.5:1 ~ 10:1, and optimum is 1:1, and extraction times is 3 times.
6. method according to claim 1, is characterized in that, filtering filter membrane used in step 2 is 0.45 μm of filter membrane.
7. method according to claim 1, is characterized in that, in step 2, supercutical fluid is supercritical co, and the pressure of supercritical co is 9 ~ 14MPa, and optimum is 10MPa.
8. method according to claim 7, is characterized in that, the flow velocity of supercritical co be 1-8 times of column volume/minute, optimum be 3 times of column volumes/minute.
9. method according to claim 1, is characterized in that, in step 2, chromatogram column temperature is 35 ~ 50 DEG C, and optimum is 40 DEG C.
10. method according to claim 1, is characterized in that, in step 2, the ratio of properties-correcting agent methyl alcohol is 1% ~ 5%, and optimum is 2%.
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| CN201510179427.7A CN105315295A (en) | 2015-04-16 | 2015-04-16 | Method for separating and purifying psoralen and isopsoralen from fructus psoraleae |
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1605327A (en) * | 1968-08-03 | 1974-08-02 | Psoralen and isopsoralen prepn. - from psoralea corylifolia by extn. and sepn. of psoralen leaving isopsoralen | |
| CN1446814A (en) * | 2003-03-07 | 2003-10-08 | 上海大学 | Method for preparing psoralen and isopsoralen |
| CN101229223A (en) * | 2008-02-03 | 2008-07-30 | 中国科学院化学研究所 | Applications of fructus psoraleae extractive on preparing antitumor medicines |
| CN101531665A (en) * | 2008-03-11 | 2009-09-16 | 上海中医药大学 | Purification method of psoralen and isopsoralen |
| US20110223267A1 (en) * | 2005-05-09 | 2011-09-15 | Unigen, Inc. | Compositions of bakuchiol and methods of making the same |
| CN102875562A (en) * | 2012-07-27 | 2013-01-16 | 天津中医药大学 | Method for preparing psoralen and isopsoralen or extract containing psoralen and isopsoralen |
| CN103626785A (en) * | 2013-11-05 | 2014-03-12 | 黄河科技学院 | Anticoagulant fructus psoraleae active ingredient and extraction and separation method and application thereof |
-
2015
- 2015-04-16 CN CN201510179427.7A patent/CN105315295A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1605327A (en) * | 1968-08-03 | 1974-08-02 | Psoralen and isopsoralen prepn. - from psoralea corylifolia by extn. and sepn. of psoralen leaving isopsoralen | |
| CN1446814A (en) * | 2003-03-07 | 2003-10-08 | 上海大学 | Method for preparing psoralen and isopsoralen |
| US20110223267A1 (en) * | 2005-05-09 | 2011-09-15 | Unigen, Inc. | Compositions of bakuchiol and methods of making the same |
| CN101229223A (en) * | 2008-02-03 | 2008-07-30 | 中国科学院化学研究所 | Applications of fructus psoraleae extractive on preparing antitumor medicines |
| CN101531665A (en) * | 2008-03-11 | 2009-09-16 | 上海中医药大学 | Purification method of psoralen and isopsoralen |
| CN102875562A (en) * | 2012-07-27 | 2013-01-16 | 天津中医药大学 | Method for preparing psoralen and isopsoralen or extract containing psoralen and isopsoralen |
| CN103626785A (en) * | 2013-11-05 | 2014-03-12 | 黄河科技学院 | Anticoagulant fructus psoraleae active ingredient and extraction and separation method and application thereof |
Non-Patent Citations (2)
| Title |
|---|
| 邱蓉丽，等: "补骨脂化学成分研究", 《中药材》 * |
| 陆峰，等: "超临界流体色谱法测定补骨脂中补骨脂素和异补骨脂素含量", 《药学学报》 * |
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Address after: 350200 Fujian, Fuzhou, North Atlantic Road, No. 268, Minsheng District, building 1-302, No. 6, Applicant after: Huo Xiuju Address before: 250000 Shandong Province, Ji'nan City District Shun Road No. 1 Applicant before: Huo Xiuju |
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Application publication date: 20160210 |