CN101648901A - Method for preparing indirubin - Google Patents
Method for preparing indirubin Download PDFInfo
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- CN101648901A CN101648901A CN200910027241A CN200910027241A CN101648901A CN 101648901 A CN101648901 A CN 101648901A CN 200910027241 A CN200910027241 A CN 200910027241A CN 200910027241 A CN200910027241 A CN 200910027241A CN 101648901 A CN101648901 A CN 101648901A
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- indirubin
- preparation
- methyl alcohol
- wash
- vinyl acetic
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Abstract
The invention relates to a method for preparing indirubin with simple and convenient operation, small pollution and little equipment investment. The method comprises the following technological steps:adding methanol with the quantity of 5-10 times of raw materials into the raw materials, extracting by ultrasonic for 1-3 times, extracting for 0.2-1 hour each time, merging extracting liquid, recovering the methanol by depressurization, concentrating, filtering liquor by a macroporous resin column, eluting with water firstly, removing impurities, then eluting with ethyl acetate, concentrating eluent, adopting chromatographic separation by an alumina column, eluting with chloroform-ethyl acetate, concentrating eluent, recrystallizing with methanol-acetone, washing, drying to obtain the indirubin. By adopting the invention to prepare the indirubin, the product purity is high and industrialization amplification is easy to realize.
Description
Technical field
The present invention relates to a kind of preparation method of Indirubin, especially a kind of method of from plant, extracting Indirubin.
Background technology
Indirubin (Indirubin), chemical name be 2,2 '-Lian Ya indoles-3,3 '-diketone, be that a chemical structure is different from the medicine that China of known antitumour drug finds, mainly be present in the Chinese medicinal materialss such as Leaf of Indigowoad, Root of Indigowoad, indigo naturalis.Its molecular formula is C
15H
10N
2O
2, formula weight is 262.26.Indirubin is weakly alkaline, and is water insoluble, is insoluble in cold ethanol, but is dissolved in vinyl acetic monomer etc. and has volatility.Indirubin has better curative effect to the treatment chronic myelocytic leukemia.
In the prior art, the extraction separation of Indirubin mainly contains chloroform extraction method, ethanol extraction method and ethyl acetate extraction method etc., but the content of the Indirubin that these extraction processes obtain is very low, and unfavorable big production operation.
Summary of the invention
Technical problem to be solved by this invention provides a kind of preparation method who is beneficial to big production operation, Indirubin that product purity is high.
For solving the problems of the technologies described above, the present invention adopts following technical proposal:
Raw material adds 5-10 and doubly measures the methyl alcohol supersound extraction 1-3 time, and each 0.2-1 hour, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, soup is crossed macroporous resin column, washes with water earlier to remove assortedly, uses the vinyl acetic monomer wash-out then, elutriant concentrates, the employing aluminum oxide column chromatography separates, and with chloroform-vinyl acetic monomer wash-out, elutriant concentrates, with methyl alcohol-acetone recrystallization, wash, be drying to obtain.
The raw material that extracts Indirubin is selected from Leaf of Indigowoad, Root of Indigowoad and indigo naturalis.
The methanol usage of supersound extraction is preferably 8 times of amounts, and the supersound extraction number of times is preferably 2 times, and extraction time is preferably each 0.5 hour, and the supersound extraction frequency is 50KHZ.
The macroporous resin model is a kind of among AB-8, H-103, the D-101.
Wash-out is 2-7 with the proportioning of chloroform-vinyl acetic monomer: 1.
Recrystallization is 1 with the proportioning of methyl alcohol-acetone: 1-3.
Adopt technique scheme to prepare Indirubin, easy and simple to handle, pollute less, equipment drops into for a short time, is beneficial to big production operation.
Below in conjunction with 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 Leaf of Indigowoad 10Kg, add 5 times of amount methyl alcohol supersound extraction 1 time, each 0.2 hour, ultrasonic frequency is 50KHZ, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, and soup is crossed AB-8 type macroporous resin column, wash with water earlier remove assorted, use the vinyl acetic monomer wash-out then, elutriant concentrates, and adopts aluminum oxide column chromatography to separate, with chloroform-vinyl acetic monomer (2: 1) wash-out, elutriant concentrates, and with methyl alcohol-acetone (1: 1) recrystallization, washs, is drying to obtain the 1.8g red powder, detect through HPLC, its purity is 95.3%.
Embodiment 2
Get Leaf of Indigowoad 10Kg, add 10 times of amount methyl alcohol supersound extraction 3 times, each 1 hour, ultrasonic frequency is 50KHZ, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, and soup is crossed H-103 type macroporous resin column, wash with water earlier remove assorted, use the vinyl acetic monomer wash-out then, elutriant concentrates, and adopts aluminum oxide column chromatography to separate, with chloroform-vinyl acetic monomer (7: 1) wash-out, elutriant concentrates, and with methyl alcohol-acetone (1: 3) recrystallization, washs, is drying to obtain the 2.6g red powder, detect through HPLC, its purity is 93.2%.
Embodiment 3
Get Leaf of Indigowoad 10Kg, add 8 times of amount methyl alcohol supersound extraction 2 times, each 0.5 hour, ultrasonic frequency is 50KHZ, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, and soup is crossed D-101 type macroporous resin column, wash with water earlier remove assorted, use the vinyl acetic monomer wash-out then, elutriant concentrates, and adopts aluminum oxide column chromatography to separate, with chloroform-vinyl acetic monomer (5: 1) wash-out, elutriant concentrates, and with methyl alcohol-acetone (1: 2) recrystallization, washs, is drying to obtain the 2.4g red powder, detect through HPLC, its purity is 98.1%.
Embodiment 4
Get Root of Indigowoad 10Kg, add 8 times of amount methyl alcohol supersound extraction 2 times, each 0.5 hour, ultrasonic frequency is 50KHZ, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, and soup is crossed D-101 type macroporous resin column, wash with water earlier remove assorted, use the vinyl acetic monomer wash-out then, elutriant concentrates, and adopts aluminum oxide column chromatography to separate, with chloroform-vinyl acetic monomer (5: 1) wash-out, elutriant concentrates, and with methyl alcohol-acetone (1: 2) recrystallization, washs, is drying to obtain the 1.7g red powder, detect through HPLC, its purity is 97.3%.
Embodiment 5
Get indigo naturalis 10Kg, add 8 times of amount methyl alcohol supersound extraction 2 times, each 0.5 hour, ultrasonic frequency is 50KHZ, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, and soup is crossed D-101 type macroporous resin column, wash with water earlier remove assorted, use the vinyl acetic monomer wash-out then, elutriant concentrates, and adopts aluminum oxide column chromatography to separate, with chloroform-vinyl acetic monomer (5: 1) wash-out, elutriant concentrates, and with methyl alcohol-acetone (1: 2) recrystallization, washs, is drying to obtain the 16.5g red powder, detect through HPLC, its purity is 98.4%.
Claims (9)
1, a kind of preparation method of Indirubin is characterized in that described method comprises the following steps: that raw material adds 5-10 and doubly measures the methyl alcohol supersound extraction 1-3 time, each 0.2-1 hour, united extraction liquid, reclaim under reduced pressure methyl alcohol also concentrates, and soup is crossed macroporous resin column, wash with water earlier remove assorted, use the vinyl acetic monomer wash-out then, elutriant concentrates, and adopts aluminum oxide column chromatography to separate, with chloroform-vinyl acetic monomer wash-out, elutriant concentrates, and with methyl alcohol-acetone recrystallization, washs, is drying to obtain.
2,, it is characterized in that described raw material is selected from Leaf of Indigowoad, Root of Indigowoad and indigo naturalis according to the preparation method of the described a kind of Indirubin of claim 1.
3,, it is characterized in that described methanol usage is 8 times of amounts according to the preparation method of the described a kind of Indirubin of claim 1.
4,, it is characterized in that described supersound extraction number of times is 2 times according to the preparation method of the described a kind of Indirubin of claim 1.
5,, it is characterized in that the described supersound extraction time is each 0.5 hour according to the preparation method of the described a kind of Indirubin of claim 1.
6,, it is characterized in that described supersound extraction frequency is 50KHZ according to the preparation method of the described a kind of Indirubin of claim 1.
7,, it is characterized in that described macroporous resin model is a kind of among AB-8, H-103, the D-101 according to the preparation method of the described a kind of Indirubin of claim 1.
8, according to the preparation method of the described a kind of Indirubin of claim 1, the proportioning that it is characterized in that described chloroform-vinyl acetic monomer is 2-7: 1.
9, according to the preparation method of the described a kind of Indirubin of claim 1, the proportioning that it is characterized in that described methyl alcohol-acetone is 1: 1-3.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910027241A CN101648901A (en) | 2009-05-26 | 2009-05-26 | Method for preparing indirubin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200910027241A CN101648901A (en) | 2009-05-26 | 2009-05-26 | Method for preparing indirubin |
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| Publication Number | Publication Date |
|---|---|
| CN101648901A true CN101648901A (en) | 2010-02-17 |
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| CN200910027241A Pending CN101648901A (en) | 2009-05-26 | 2009-05-26 | Method for preparing indirubin |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103509835A (en) * | 2013-09-29 | 2014-01-15 | 重庆市中药研究院 | Method for preparing indirubin with fresh folium isatidis as raw material |
| CN103735635A (en) * | 2014-01-13 | 2014-04-23 | 李绍华 | Medicinal composition for treating cancers and leukemia |
| CN103992260A (en) * | 2014-05-29 | 2014-08-20 | 哈尔滨医科大学 | Method for extracting indirubin from folium isatidis |
| CN104800271A (en) * | 2015-04-14 | 2015-07-29 | 南京多宝生物科技有限公司 | Preparation method of folium isatidis extract |
| CN104971081A (en) * | 2015-06-16 | 2015-10-14 | 陕西师范大学 | Method for ultrasonic-assisted extraction of indigo and indirubin from folium isatidis |
| CN110483365A (en) * | 2019-09-05 | 2019-11-22 | 章月贵 | A kind of preparation method for isolating indigo red from indigo naturalis |
| CN112824386A (en) * | 2019-11-20 | 2021-05-21 | 哈工大机器人南昌智能制造研究院 | Method for continuously preparing indigo naturalis, indigo and indirubin from fresh leaves of kale |
| CN112824385A (en) * | 2019-11-20 | 2021-05-21 | 哈工大机器人南昌智能制造研究院 | Method for preparing indirubin by taking fresh leaves of kale as raw materials |
-
2009
- 2009-05-26 CN CN200910027241A patent/CN101648901A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103509835A (en) * | 2013-09-29 | 2014-01-15 | 重庆市中药研究院 | Method for preparing indirubin with fresh folium isatidis as raw material |
| CN103509835B (en) * | 2013-09-29 | 2016-08-31 | 重庆市中药研究院 | A kind of method preparing indigo red for raw material with fresh and alive folium isatidis |
| CN103735635A (en) * | 2014-01-13 | 2014-04-23 | 李绍华 | Medicinal composition for treating cancers and leukemia |
| CN103992260A (en) * | 2014-05-29 | 2014-08-20 | 哈尔滨医科大学 | Method for extracting indirubin from folium isatidis |
| CN104800271A (en) * | 2015-04-14 | 2015-07-29 | 南京多宝生物科技有限公司 | Preparation method of folium isatidis extract |
| CN104971081A (en) * | 2015-06-16 | 2015-10-14 | 陕西师范大学 | Method for ultrasonic-assisted extraction of indigo and indirubin from folium isatidis |
| CN110483365A (en) * | 2019-09-05 | 2019-11-22 | 章月贵 | A kind of preparation method for isolating indigo red from indigo naturalis |
| CN112824386A (en) * | 2019-11-20 | 2021-05-21 | 哈工大机器人南昌智能制造研究院 | Method for continuously preparing indigo naturalis, indigo and indirubin from fresh leaves of kale |
| CN112824385A (en) * | 2019-11-20 | 2021-05-21 | 哈工大机器人南昌智能制造研究院 | Method for preparing indirubin by taking fresh leaves of kale as raw materials |
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Open date: 20100217 |