CN102206244A - Method for extracting betulinic acid from firmiana bark - Google Patents
Method for extracting betulinic acid from firmiana bark Download PDFInfo
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- CN102206244A CN102206244A CN 201110083158 CN201110083158A CN102206244A CN 102206244 A CN102206244 A CN 102206244A CN 201110083158 CN201110083158 CN 201110083158 CN 201110083158 A CN201110083158 A CN 201110083158A CN 102206244 A CN102206244 A CN 102206244A
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Abstract
The invention discloses a method for extracting betulinic acid from firmiana bark, which comprises the following steps of: collecting firmiana bark, adding water, boiling, filtering to remove water, adding a hydrophilic organic solvent to the boiled bark, soaking and extracting at room temperature, filtering, collecting the filtrate, concentrating at reduced pressure to volatilize the hydrophilic organic solvent and drying to obtain betulinic acid. The method for extracting betulinic acid from firmiana bark uses hot water extraction for pre-treatment and uses the hydrophilic organic solvent for extraction, thus directly extracting high-purity betulinic acid from firmiana bark, all betulinic acid in firmiana bark is basically extracted, and the method is simple and feasible and has high efficiency and low cost; and the purity of the extracted betulinic acid is more than 95% and the yield reaches 5.7%.
Description
Technical field
The invention belongs to the traditional Chinese medicine extraction technical field, be specifically related to from phoenix tree section bark, extract the method for betulinic acid.
Background technology
Betulinic acid is a kind of material with physiologically active, and it has functions such as anticancer, anti-infective, anti-inflammatory, AIDS resisting poison.Usually utilize solvent to extract out produces by the betulin oxidation or from phoenix tree section bark.But, usually since in the bark content of betulinic acid seldom (greatly about 5～8wt%), and bark extracts complicated component out, comprises a lot of polar materials, is difficult to obtain purified product by the way that solvent is extracted out.
Chinese patent 200710025418.8 discloses a kind of method for preparing high purity betulinic acid, adopt ethanol or ethyl acetate extraction 2～4 times earlier, use water crystallization at last, obtain purity and be the betulinic acid water white transparency crystallization more than 95%, but the productive rate of this method has only 1.8～2%.
U.S. Pat 6,175,035 B1 discloses a kind of way of extracting betulinic acid out with neutral hydrophobic solvent such as methylene dichloride, chloroform, ether, and this method organic solvent usage quantity is big, and the productive rate of the betulinic acid that obtains also has only about 2%.
German patent DE 19713768A1 discloses a kind of method of extracting betulinic acid out with ethyl acetate and other hydrophobic organic solvents, obtain the higher betulinic acid crystal of purity, but it also is to realize that productive rate has only 2-3% in the repeatable operation of multistage extraction and recrystallization.
Summary of the invention
Technical problem to be solved by this invention provides a kind of advantages of simplicity and high efficiency is extracted betulinic acid from phoenix tree section bark method.
For solving the problems of the technologies described above, the technical solution used in the present invention is as follows:
A kind of method of extracting betulinic acid from phoenix tree section bark is collected phoenix tree section bark and is added water boil, and filtration dewaters, bark after boiling adds under the hydrophilic organic solvent room temperature and soaks extracting, filtering and collecting filter liquid, concentrating under reduced pressure vapors away hydrophilic organic solvent, and drying makes betulinic acid again.
Wherein, described phoenix tree section comprises London plane (Platanus acerifolia), Platanus occidentalis (Platanus occidentalis), platanus (Platanus Orientalis).
Wherein, phoenix tree used in the present invention section bark need not crushing operation, the bark that the bark that general nature comes off or think peels off all can, preferred length 1～3cm, the sheet of thickness 0.5～6mm.
Wherein, add water boil and can divide and carry out for 1～4 time, each boiling time maintains 0.5～2 hour, and preferred 1 hour is 0.5～2mL/g bark with volume of water at every turn, preferred 1～1.2mL/g bark.
Wherein, described hydrophilic organic solvent is methyl alcohol, acetone, ethanol or butanols, particular methanol.
Wherein, add hydrophilic organic solvent and soak extracting and can divide and carry out for 1～4 time, soak extractive time dimension at every turn and be held in 10～30 hours, preferred 24 hours, it was 1～2.5mL/g bark that each hydrophilic organic solvent adds volume, preferred 1.5～2mL/g bark.
Wherein, the concentrating under reduced pressure temperature is 20～55 ℃, and preferred 30～40 ℃, pressure is 250～500Kpa, preferred 300～350Kpa.
Wherein, drying mode is at P
2O
5Have drying down, temperature is 0～50 ℃, and preferred 20～25 ℃, pressure is 2-10mmHg, preferred 3-6mmHg.
The present invention earlier with poach handle bark be for can effectively remove debark in water-soluble a large amount of polarity extract impurity such as compositions and corticole dust out so that it is wide to make follow-up organic solvent extract the solvent scope that becomes out, extract the efficient height out.Simultaneously, hot water boils this process makes the abundant swelling of bark, follow-up selection hydrophilic organic solvent, make solvent can effectively be penetrated into the bark depths, institute (passes through poach so that extraction efficient increases, extraction efficiency is compared with patent of invention in the past have been increased more than 2 times), [Japan's chemistry is big takes leave the hydrophobic organic solvent of mentioning in selection of these hydrophilic organic solvents simultaneously and other the relevant report (ethyl acetate etc.) of using, the chemistry dictionary editing council compiles, 8, P.336A, 1980, the upright altogether press of Japan publishes] or neutral organic solvent (chloroform, methylene dichloride, ether) [U.S. Pat 6175035B1] compares, and has price low, the advantage that toxicity is little.
Beneficial effect: the method for extracting betulinic acid from phoenix tree section bark of the present invention is extracted out with hot water and is done pre-treatment, extract out with hydrophilic organic solvent then, from the bark of phoenix tree, can directly obtain highly purified betulinic acid, purity is greater than 95%, productive rate reaches 5.7%, substantially can extracting go out betulinic acids all in the bark, method is simple, efficient is high, cost is low.
Description of drawings
Fig. 1 is the infrared spectrum of the betulinic acid product of the inventive method preparation.
Fig. 2 is the hydrogen nuclear magnetic resonance spectrogram of the betulinic acid product of the inventive method preparation.
Fig. 3 is the carbon-13 nmr spectra figure of the betulinic acid product of the inventive method preparation.
Fig. 4 is the mass spectrum of the betulinic acid product of the inventive method preparation.
Above-mentioned spectrogram is consistent with the standard spectrogram of the betulinic acid that Aldrich.Co drugmaker provides.
Embodiment
According to following embodiment, the present invention may be better understood.Yet, those skilled in the art will readily understand that the described concrete material proportion of embodiment, processing condition and result thereof only are used to illustrate the present invention, and should also can not limit the present invention described in detail in claims.
Embodiment 1:
Get Sterculiaceae class bark 500g, add the clear water of 1000mL, heated and boiled half an hour, suction filtration is removed filtrate and is added isopyknic water later on again, boils again 1 hour, removes filtrate once more.Subsequently, add 600mL methyl alcohol in the bark after boiling, soaked 24 hours 30 ℃ of concentrating under reduced pressure of the filtrate that suction filtration obtains under the room temperature, remove methanol solvate, obtain the betulinic acid crystal powder, after gas is done in the presence of Vanadium Pentoxide in FLAKES reduced pressure at room temperature 24 hours, obtain betulinic acid highly finished product 28.5 and restrain, productive rate 5.70%, purity 95.8%, 315.8 ℃ of fusing points, the infrared spectrum of betulinic acid product, hydrogen nuclear magnetic resonance spectrogram, carbon-13 nmr spectra figure, mass spectrum are seen Fig. 1～4.
Embodiment 2:
Get Sterculiaceae class bark 300g, add the clear water of 500mL, heated and boiled 40 minutes, suction filtration is removed the water that filtrate adds 350mL later on again, and secondary boiled 2 hours, removed filtrate once more.Subsequently, add 400mL acetone in the bark after boiling, soaked 26 hours under the room temperature, 40 ℃ of concentrating under reduced pressure of the filtrate that suction filtration obtains are removed acetone solvent, obtain the betulinic acid crystal powder, after gas is done in the presence of Vanadium Pentoxide in FLAKES reduced pressure at room temperature 20 hours.Obtain betulinic acid highly finished product 16.3 grams, productive rate 5.43%, purity 95.9%, 316.5 ℃ of fusing points.
Embodiment 3:
Get Sterculiaceae class bark 600g, add the clear water of 800mL, heated and boiled one hour, suction filtration is removed after the filtrate, directly adds 750mL ethanol in the bark after boiling, soaked 24 hours under the room temperature, suction filtration is washed bark with small amount of ethanol then, merges washing lotion, 50 ℃ of concentrating under reduced pressure of the amalgamation liquid that obtains, remove alcohol solvent, obtain the betulinic acid crystal powder, after gas is done in the presence of Vanadium Pentoxide in FLAKES reduced pressure at room temperature 30 hours.Obtain betulinic acid highly finished product 32.8 grams, productive rate 5.46%, purity 95.4%, 317 ℃ of fusing points.
Embodiment 4:
Get Sterculiaceae class bark 1000g, add the 1500mL clear water, heated and boiled 1.5 hours, suction filtration is removed the water that filtrate adds 800mL later on again, boils again 1 hour, removes filtrate once more.Subsequently, add the 1500mL butanols in the bark after boiling, soaked 30 hours under the room temperature, add the 800mL butanols behind the suction filtration again, soaked 10 hours, merge the filtrate that obtains behind the suction filtration, 30 ℃ of concentrating under reduced pressure, remove the butanols solvent, obtain the betulinic acid crystal powder, after gas is done in the presence of Vanadium Pentoxide in FLAKES reduced pressure at room temperature 24 hours.Obtain betulinic acid highly finished product 55.7 grams, productive rate 5.57%, purity 95.9%, 316.3 ℃ of fusing points.
Claims (6)
1. method of from phoenix tree section bark, extracting betulinic acid, it is characterized in that collecting phoenix tree section bark and add water boil, filtration dewaters, bark after boiling adds under the hydrophilic organic solvent room temperature and soaks extracting, filtering and collecting filter liquid, concentrating under reduced pressure vapors away hydrophilic organic solvent, and drying makes betulinic acid again.
2. the method for extracting betulinic acid from phoenix tree section bark according to claim 1 is characterized in that adding water boil and can divide and carry out for 1～4 time, and each boiling time maintains 0.5～2 hour, is 0.5～2mL/g bark with volume of water at every turn.
3. the method for extracting betulinic acid from phoenix tree section bark according to claim 1 is characterized in that described hydrophilic organic solvent is methyl alcohol, acetone, ethanol or butanols.
4. according to claim 1 or the 3 described methods of from phoenix tree section bark, extracting betulinic acid, it is characterized in that adding hydrophilic organic solvent soaks extracting and can divide and carry out for 1～4 time, the extractive time dimension of each immersion is held in 10～30 hours, and it is 1～2.5mL/g bark that each hydrophilic organic solvent adds volume.
5. the method for extracting betulinic acid from phoenix tree section bark according to claim 1 is characterized in that the concentrating under reduced pressure temperature is 20～55 ℃, and pressure is 250～500Kpa.
6. the method for extracting betulinic acid from phoenix tree section bark according to claim 1 is characterized in that drying mode is at P
2O
5Have drying down, temperature is 0～50 ℃, and pressure is 2～10mmHg.
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| Application Number | Priority Date | Filing Date | Title |
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| CN2011100831586A CN102206244B (en) | 2011-04-02 | 2011-04-02 | Method for extracting betulinic acid from firmiana bark |
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| CN2011100831586A CN102206244B (en) | 2011-04-02 | 2011-04-02 | Method for extracting betulinic acid from firmiana bark |
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| CN102206244B CN102206244B (en) | 2012-07-04 |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103768108A (en) * | 2012-10-25 | 2014-05-07 | 奇复康药物研发(苏州)有限公司 | Extraction method for Chinese parasol tree bark tannin |
| CN108558984A (en) * | 2018-01-22 | 2018-09-21 | 枣庄市杰诺生物酶有限公司 | A kind of preparation method of betulinic acid |
| CN111333693A (en) * | 2020-04-22 | 2020-06-26 | 南京林业大学 | Method for extracting betulinic acid |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6175035B1 (en) * | 1997-04-03 | 2001-01-16 | Birgit Draeger | Method of producing betulinic acid |
| US20070149490A1 (en) * | 2005-10-12 | 2007-06-28 | Puder Carsten H | process for the extraction of betulinic acid |
| CN101357934A (en) * | 2007-07-30 | 2009-02-04 | 杨春华 | Method for preparing high purity betulinic acid |
| CN101485703A (en) * | 2009-02-27 | 2009-07-22 | 李岩 | Method for extracting and separating anti-tumor effective component from Japanese birch bark |
-
2011
- 2011-04-02 CN CN2011100831586A patent/CN102206244B/en not_active Expired - Fee Related
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6175035B1 (en) * | 1997-04-03 | 2001-01-16 | Birgit Draeger | Method of producing betulinic acid |
| US20070149490A1 (en) * | 2005-10-12 | 2007-06-28 | Puder Carsten H | process for the extraction of betulinic acid |
| CN101357934A (en) * | 2007-07-30 | 2009-02-04 | 杨春华 | Method for preparing high purity betulinic acid |
| CN101485703A (en) * | 2009-02-27 | 2009-07-22 | 李岩 | Method for extracting and separating anti-tumor effective component from Japanese birch bark |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103768108A (en) * | 2012-10-25 | 2014-05-07 | 奇复康药物研发(苏州)有限公司 | Extraction method for Chinese parasol tree bark tannin |
| CN108558984A (en) * | 2018-01-22 | 2018-09-21 | 枣庄市杰诺生物酶有限公司 | A kind of preparation method of betulinic acid |
| CN111333693A (en) * | 2020-04-22 | 2020-06-26 | 南京林业大学 | Method for extracting betulinic acid |
| CN111333693B (en) * | 2020-04-22 | 2021-02-12 | 南京林业大学 | Method for extracting betulinic acid |
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| CN102206244B (en) | 2012-07-04 |
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