CN101768201A - Preparation method of oleanolic acid - Google Patents
Preparation method of oleanolic acid Download PDFInfo
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- CN101768201A CN101768201A CN201010111779A CN201010111779A CN101768201A CN 101768201 A CN101768201 A CN 101768201A CN 201010111779 A CN201010111779 A CN 201010111779A CN 201010111779 A CN201010111779 A CN 201010111779A CN 101768201 A CN101768201 A CN 101768201A
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- oleanolic acid
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Abstract
The invention relates to a preparation method of oleanolic acid. In the process, glossy privet fruit is taken as the raw material, a crude product is obtained through extraction for 2-3 times by oversaturated lime water with 2-3 hours for each time, liquid medicine combination, acidification by adding acid and filtration; backflow extraction is carried out on the crude product by 50-60% of methanol; and the product can be obtained through heated filtration, microfiltration and impurity removing of the filtrate, nanofiltration, concentration and drying. The process has the advantages of simple and convenient operation, little pollution and less equipment investment and is beneficial for large-scale operation.
Description
Technical field
The present invention relates to a kind of preparation method of Oleanolic Acid, especially a kind of method of from Glossy Privet Fruit, extracting Oleanolic Acid.
Background technology
Glossy Privet Fruit is the dry mature fruit of Oleaceae plant glossy privet Ligustrum Lucidumt, is conventional Chinese medicine, is the main ingredient of the multiple patent medicine and the side of one-tenth.Main component is an Oleanolic Acid.
Oleanolic Acid (Oleanolic acid, OA) have another name called celebrating four elements, be a kind of natural product chemistry composition, extensively be present in the plants such as Spreading Hedyotis Herb, hawthorn, cloves, date, Glossy Privet Fruit, Loquat Leaf, oak, Spica Prunellae with form free or that be combined into glycosides.Pentacyclic triterpenoid, chemistry (3 β)-3-Hydroxyolean-12-en-28-oic acid by name.Molecular formula: C
30H
48O
3, molecular weight: 456.707, white crystalline powder, odorless, tasteless, water insoluble, dissolve in methyl alcohol, ethanol, benzene, ether, acetone and chloroform.308～310 ℃ of fusing points, specific optical rotation [a]+79.5 ° (in the chloroform).Structural formula is as follows:
Oleanolic Acid protects the liver, protects except that having stomach, cardiac stimulant, anti-arrhythmia, hypoglycemic, reducing blood-fat, the antihypertensive biological activity, also have multiple pharmacological effect such as anti-inflammatory, antiviral, immunomodulatory, anticoagulant and anti-peroxidation, and toxic side effect is little, safe, has broad clinical application prospect.
In the prior art, the extraction separation of Oleanolic Acid mainly adopts solvent-extraction process etc., but this method need consume a large amount of solvents, and also can cause dissolvent residual when using some organic solvent, the selectivity of extracting is not high, the pharmaceutical dosage form that makes is more single, mostly is decoction or pill, powder etc., and dose is big and carry inconvenience.
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, Oleanolic Acid that product purity is high.
For solving the problems of the technologies described above, the present invention adopts following technical proposal:
Get Glossy Privet Fruit, the buck that adding 10-15 doubly measures (V/W) decocts 2-3 time, and each 2-3 hour, filter, merge soup, be acidified with acid, suction filtration obtains the triterpenic acid crude product, and crude product adds the methanol solution refluxing extraction, filtered while hot, filtrate are through the micro-filtration removal of impurities, and nanofiltration concentrates, and is drying to obtain.
Described buck is a supersaturation liming.
It is 2-3 that pH is regulated in described acidifying, uses hydrochloric acid, sulfuric acid or phosphoric acid.
Described methanol concentration is 50-60%, and consumption is that the 4-5 of crude product doubly measures (V/W), and extraction time is 1.5-2 hour.
Described micro-filtration adopts the ceramic membrane of aperture 50-500nm.
It is the nanofiltration membrane of 300-500 that described micro-filtration adopts molecular weight cut-off.
In sum, there is following advantage in the present invention: the oil soluble composition is more in the Glossy Privet Fruit, and organic solvent extraction can make the extracting solution foreign matter content very high, and the waste solvent then only dissolves small amounts of water soluble composition and organic acid with buck; Can make the PH of extracting solution be stabilized in the top condition of extraction with the supersaturation limewater extraction; Itself is insoluble in water Oleanolic Acid, can acid sink, and separates with water soluble component.
Adopt technique scheme to prepare Oleanolic Acid, 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 fresh Leaf of Glossy Privet 10kg (Oleanolic Acid content 1.2%), add 100L supersaturation liming, decocted 2 hours, in the insolubles that leaches, add 100L supersaturation liming in addition, decocted 2 hours, filter.Merge twice soup, add hydrochloric acid, regulate pH and be about 3, suction filtration, the triterpenic acid crude product 218g that obtains separating out.Add 900ml 50% methanol eddy and extracted 1.5 hours, filtered while hot, filtrate is the nanofiltration membrane of 300-500 by molecular weight cut-off by the ceramic membrane of aperture 50-500nm again, and drying under reduced pressure promptly gets Oleanolic Acid 93g, detects through HPLC, and purity is 98.5%.
Embodiment 2
Get fresh Leaf of Glossy Privet 10kg (Oleanolic Acid content 1.2%), add 110L supersaturation liming, decocted 2.5 hours, in the insolubles that leaches, add supersaturation liming in addition, with twice of conditional operation.Merge three times soup, add sulfuric acid, regulate pH and be about 3, suction filtration, the triterpenic acid crude product 223g that obtains separating out.Add 1000ml 55% methanol eddy and extracted 2 hours, filtered while hot, filtrate is the nanofiltration membrane of 300-500 by molecular weight cut-off by the ceramic membrane of aperture 50-500nm again, and drying under reduced pressure promptly gets Oleanolic Acid 107g, detects through HPLC, and purity is 98.2%.
Embodiment 3
Get fresh Leaf of Glossy Privet 10kg (Oleanolic Acid content 1.1%), add 110L supersaturation liming, decocted 3 hours, in the insolubles that leaches, add supersaturation liming in addition, with conditional operation 1 time.Merge twice soup, add phosphoric acid acid, regulate pH and be about 2, suction filtration, the triterpenic acid crude product 213g that obtains separating out.Add 900ml 60% methanol eddy and extracted 1.5 hours, filtered while hot, filtrate is the nanofiltration membrane of 300-500 by molecular weight cut-off by the ceramic membrane of aperture 50-500nm again, and drying under reduced pressure promptly gets Oleanolic Acid 96g, detects through HPLC, and purity is 98.5%.
Embodiment 4
Get fresh Leaf of Glossy Privet 10kg (Oleanolic Acid content 1.3%), add 120L supersaturation liming, decocted 3 hours, in the insolubles that leaches, add supersaturation liming in addition, with twice of conditional operation.Merge three times soup, add hydrochloric acid, regulate pH and be about 2, suction filtration, the triterpenic acid crude product 248g that obtains separating out.Add 900ml 60% methanol eddy and extracted 1.5 hours, filtered while hot, filtrate is the nanofiltration membrane of 300-500 by molecular weight cut-off by the ceramic membrane of aperture 50-500nm again, and drying under reduced pressure promptly gets Oleanolic Acid 104, detects through HPLC, and purity is 99.1%.
Claims (6)
1. the preparation method of an Oleanolic Acid is characterized in that comprising following steps:
Get Glossy Privet Fruit, the buck that adding 10-15 doubly measures (V/W) decocts 2-3 time, and each 2-3 hour, filter, merge soup, be acidified with acid, suction filtration obtains the triterpenic acid crude product, and crude product adds the methanol solution refluxing extraction, filtered while hot, filtrate are through the micro-filtration removal of impurities, and nanofiltration concentrates, and is drying to obtain.
2. preparation method as claimed in claim 1 is characterized in that described buck is a supersaturation liming.
3. preparation method as claimed in claim 1 is characterized in that it is 2-3 that pH is regulated in described acidifying, uses hydrochloric acid, sulfuric acid or phosphoric acid.
4. preparation method as claimed in claim 1 is characterized in that described methanol concentration is 50-60%, and consumption is that the 4-5 of crude product doubly measures (V/W), and extraction time is 1.5-2 hour.
5. preparation method as claimed in claim 1 is characterized in that described micro-filtration adopts the ceramic membrane of aperture 50-500nm.
6. preparation method as claimed in claim 1 is characterized in that it is the nanofiltration membrane of 300-500 that described micro-filtration adopts molecular weight cut-off.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201010111779A CN101768201A (en) | 2010-02-08 | 2010-02-08 | Preparation method of oleanolic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN201010111779A CN101768201A (en) | 2010-02-08 | 2010-02-08 | Preparation method of oleanolic acid |
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| CN101768201A true CN101768201A (en) | 2010-07-07 |
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| CN201010111779A Pending CN101768201A (en) | 2010-02-08 | 2010-02-08 | Preparation method of oleanolic acid |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464697A (en) * | 2010-11-11 | 2012-05-23 | 曾超 | Method for combined preparation of high purity ursolic acid and high purity oleanolic acid from Ligustrum lucidum |
| CN102532239A (en) * | 2010-12-24 | 2012-07-04 | 苏州宝泽堂医药科技有限公司 | Method for extracting demethylzeylasteral from thunder god vine |
| CN102659899A (en) * | 2012-04-24 | 2012-09-12 | 劲牌有限公司 | Method for extracting purified oleanolic acid from glossy privet fruits |
| CN107468761A (en) * | 2017-08-09 | 2017-12-15 | 山东省皮肤病性病防治研究所 | A kind of Preparation method and use of glossy privet fruit total triterpenic acid extract |
| CN110850022A (en) * | 2019-11-28 | 2020-02-28 | 贵州远程制药有限责任公司 | Method for detecting quality of Shuangdong capsule |
-
2010
- 2010-02-08 CN CN201010111779A patent/CN101768201A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102464697A (en) * | 2010-11-11 | 2012-05-23 | 曾超 | Method for combined preparation of high purity ursolic acid and high purity oleanolic acid from Ligustrum lucidum |
| CN102532239A (en) * | 2010-12-24 | 2012-07-04 | 苏州宝泽堂医药科技有限公司 | Method for extracting demethylzeylasteral from thunder god vine |
| CN102659899A (en) * | 2012-04-24 | 2012-09-12 | 劲牌有限公司 | Method for extracting purified oleanolic acid from glossy privet fruits |
| CN107468761A (en) * | 2017-08-09 | 2017-12-15 | 山东省皮肤病性病防治研究所 | A kind of Preparation method and use of glossy privet fruit total triterpenic acid extract |
| CN107468761B (en) * | 2017-08-09 | 2019-01-25 | 山东省皮肤病性病防治研究所 | A kind of Preparation method and use of glossy privet fruit total triterpenic acid extract |
| CN110850022A (en) * | 2019-11-28 | 2020-02-28 | 贵州远程制药有限责任公司 | Method for detecting quality of Shuangdong capsule |
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Addressee: Suzhou Baozetang Medical Technology Co.,Ltd. Document name: Notification of before Expiration of Request of Examination as to Substance |
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Addressee: Suzhou Baozetang Medical Technology Co.,Ltd. Document name: Notification that Application Deemed to be Withdrawn |
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Application publication date: 20100707 |