CN1358733A - Process for extracting ursolic acid from fructus ligustri lucidi leaf - Google Patents
Process for extracting ursolic acid from fructus ligustri lucidi leaf Download PDFInfo
- Publication number
- CN1358733A CN1358733A CN 01138325 CN01138325A CN1358733A CN 1358733 A CN1358733 A CN 1358733A CN 01138325 CN01138325 CN 01138325 CN 01138325 A CN01138325 A CN 01138325A CN 1358733 A CN1358733 A CN 1358733A
- Authority
- CN
- China
- Prior art keywords
- ethanol
- ursolic acid
- extract
- dry
- leaf
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229940096998 ursolic acid Drugs 0.000 title claims abstract description 25
- PLSAJKYPRJGMHO-UHFFFAOYSA-N ursolic acid Natural products CC1CCC2(CCC3(C)C(C=CC4C5(C)CCC(O)C(C)(C)C5CCC34C)C2C1C)C(=O)O PLSAJKYPRJGMHO-UHFFFAOYSA-N 0.000 title claims abstract description 25
- WCGUUGGRBIKTOS-GPOJBZKASA-N (3beta)-3-hydroxyurs-12-en-28-oic acid Chemical compound C1C[C@H](O)C(C)(C)[C@@H]2CC[C@@]3(C)[C@]4(C)CC[C@@]5(C(O)=O)CC[C@@H](C)[C@H](C)[C@H]5C4=CC[C@@H]3[C@]21C WCGUUGGRBIKTOS-GPOJBZKASA-N 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 50
- 239000000284 extract Substances 0.000 claims abstract description 15
- 239000000287 crude extract Substances 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000010992 reflux Methods 0.000 claims abstract description 8
- 241000830535 Ligustrum lucidum Species 0.000 claims description 12
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 7
- 238000001556 precipitation Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000741 silica gel Substances 0.000 claims description 5
- 229910002027 silica gel Inorganic materials 0.000 claims description 5
- 238000005406 washing Methods 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 238000002791 soaking Methods 0.000 claims description 3
- 125000002220 ursolic acid group Chemical group 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 241000735234 Ligustrum Species 0.000 abstract description 6
- 239000002699 waste material Substances 0.000 abstract description 6
- 239000003337 fertilizer Substances 0.000 abstract description 2
- 239000002994 raw material Substances 0.000 abstract description 2
- 239000002244 precipitate Substances 0.000 abstract 2
- 238000000605 extraction Methods 0.000 abstract 1
- 239000007788 liquid Substances 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 4
- 238000012856 packing Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- 241000196324 Embryophyta Species 0.000 description 2
- 230000006837 decompression Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 238000010183 spectrum analysis Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 235000012871 Arctostaphylos uva ursi Nutrition 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 244000003892 Vaccinium erythrocarpum Species 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- -1 triterpene compound Chemical class 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fertilizers (AREA)
Abstract
本发明涉及一种从女贞叶中提取熊果酸的方法,将粉碎过的女贞叶用乙醇回流提取,得到流浸膏状提取物,回收乙醇,上述提取物用水充分洗涤后干燥得到干浸膏,干浸膏用乙醇溶解后脱色,脱色液经回收乙醇后加水析出大量沉淀,调pH值至2－2.5,分离、收集沉淀物,并用水洗涤至中性,真空干燥,得到主要成份为熊果酸的粗提物。本发明采用上述方法,以廉价易得的女真叶为原料用乙醇回流提取。“三废”处理量小且容易,乙醇可回收再用,提取后所剩废渣可用作肥料。因而本发明对环境基本不产生污染,而且所获得的熊果酸成本较低。另外,本发明的方法简便、快捷。The invention relates to a method for extracting ursolic acid from Ligustrum leaves. The pulverized Ligustrum leaves are extracted with ethanol under reflux to obtain a liquid extract, and the ethanol is recovered. The above extracts are fully washed with water and then dried to obtain dried The extract, the dry extract is dissolved in ethanol and then decolorized. The decolorized solution is recovered from ethanol and then added with water to precipitate a large amount of precipitates. Adjust the pH value to 2-2.5, separate and collect the precipitates, wash with water until neutral, and dry in vacuum to obtain the main components Crude extract of ursolic acid. The present invention adopts the above-mentioned method, and takes the cheap and easy-to-obtain Jurchen leaves as raw materials and extracts them by refluxing ethanol. The "three wastes" are small and easy to treat, ethanol can be recycled and reused, and the residue left after extraction can be used as fertilizer. Therefore, the present invention basically does not pollute the environment, and the cost of the obtained ursolic acid is relatively low. In addition, the method of the present invention is simple and fast.
Description
One. technical field
The present invention relates to a kind of method of from Leaf of Glossy Privet, extracting ursolic acid.
Two. background technology
Glossy privet is an Oleaceae Ligustrum plant, and formal name used at school is Ligustrum Lucidum Ait, and it is the four seasons evergreen big shrubs or dungarunga, and the whole world is had an appointment 50 kinds, just there are 38 kinds in China, are distributed widely in East China, south China, southwest and Central China, plant resources is abundant, and distributed pole is wide.
Along with going deep into of pharmacological research, find that the Ligustrum plant has multiple physiologically active, but also also insufficient to the Chemical Composition research of Ligustrum plant.For a long time, the position that we are studied to the Ligustrum plant utilizes not thorough, is not used as medicine substantially, wastes very big.
Ursolic acid is a kind of triterpene compound, and molecular formula is C
30H
18O
3, chemical name is 3 beta-hydroxies-black bearberry alkane-12-alkene-28-carboxylic acid, is clear crystal, 289～292 ℃ of fusing points.Ursolic acid is distributed widely in the vegitabilia, has multiple biological activity, can be used as the effective constituent of multiple medicine.
Though ursolic acid can be synthetic by chemical process, these class methods not only " three wastes " treatment capacity are big and difficult, easily environment is produced and pollute, and the ursolic acid cost that is obtained is higher.
Three. summary of the invention
Problem to be solved by this invention provides a kind of method of extracting ursolic acid from Leaf of Glossy Privet, and " three wastes " treatment capacity is little and easy in this way, environment is not produced pollution substantially, and the ursolic acid cost that is obtained is lower.
Technical scheme provided by the invention is: a kind of method of extracting ursolic acid from the glossy privet plant, with the Leaf of Glossy Privet alcohol reflux of pulverizing, obtain the flowing soaking paste extract, reclaim ethanol, said extracted thing water thorough washing after drying obtains dry extract, dry extract dissolve with ethanol rear decoloring, destainer adds elutriation and goes out a large amount of precipitations after reclaiming ethanol, adjust pH is to 2-2.5, separation, collecting precipitation thing, and being washed with water to neutrality, vacuum-drying obtains the crude extract that major ingredient is a ursolic acid.
Add silica gel after above-mentioned crude extract is dissolved in hot ethanol, mix the back thoroughly and volatilize ethanol under infrared lamp, the dry method upper prop obtains product and is ursolic acid.The dry method upper prop belongs to a kind of that post analyses layer by layer, in chromatography column, and the silica gel of packing into, decompression is taken out tight, the crude extract of above-mentioned ursolic acid is dissolved in an amount of anhydrous acetic acid, mixes with a small amount of silica gel, infrared lamp is oven dry down, the chromatography column top of carefully packing into, with hexanaphthene and eluent ethyl acetate, after wash-out is finished, the crude extract of ursolic acid, collect the required branch of washing, the anhydrous acetic acid recrystallization promptly gets product.
The per kilogram Leaf of Glossy Privet can be used 5000-6000ml alcohol reflux 2-3 time in said process.Product is through Spectrum Analysis, the conformance to standard of its result and ursolic acid.
The present invention adopts aforesaid method, is the raw material alcohol reflux with Nuzhen, an ancient nationality in China, ancestors of the Manchus, who founded the Jin Dynasty's leaf cheap and easy to get." three wastes " treatment capacity is little and easy, and the recyclable usefulness again of ethanol is extracted the last waste residue in back and be can be used as fertilizer.Thereby the present invention do not produce pollution substantially to environment, and the ursolic acid cost that is obtained is lower.In addition, method of the present invention is easy, quick.
Four, embodiment
With the Leaf of Glossy Privet pulverized with 5-6 alcohol reflux 2-3 time of (W/V) doubly, obtain the flowing soaking paste extract, reclaim ethanol, obtain dry extract in 80 ℃ of dryings behind the said extracted thing water thorough washing, dry extract with dissolve with ethanol after, use activated carbon decolorizing, destainer adds elutriation and goes out a large amount of precipitations after reclaiming ethanol, and adjust pH is to 2-2.5, separation, collecting precipitation thing, and being washed with water to neutrality, vacuum-drying obtains the crude extract that major ingredient is a ursolic acid.
Add silica gel after above-mentioned crude extract is dissolved in hot ethanol, mix the back thoroughly and under infrared lamp, volatilize ethanol, the dry method upper prop, promptly in 110cm * 5.5cm chromatography column, the 200 order silica gel G of evenly packing into (Haiyang Chemical Plant, Qingdao produces, and thin-layer chromatography is used), decompression is taken out tight, sample 3 grams are dissolved in an amount of anhydrous acetic acid, mix with a small amount of silica gel G, infrared lamp is oven dry down, the chromatography column top of carefully packing into, hexanaphthene: ethyl acetate=2: 1 is wash-out at the uniform velocity, after wash-out is finished, wash branch every the 1cm collection, thin-layer chromatography is identified, collect the required branch of washing, the anhydrous acetic acid recrystallization promptly gets the product ursolic acid.Product is through Spectrum Analysis, the conformance to standard of its result and ursolic acid.
Claims (2)
1. method of from the glossy privet plant, extracting ursolic acid, it is characterized in that: the Leaf of Glossy Privet alcohol reflux that will pulverize, obtain the flowing soaking paste extract, reclaim ethanol, said extracted thing water thorough washing after drying obtains dry extract, dry extract dissolve with ethanol rear decoloring, destainer add elutriation and go out a large amount of precipitations after reclaiming ethanol, adjust pH is to 2-2.5, separate, the collecting precipitation thing, and being washed with water to neutrality, vacuum-drying obtains the crude extract that major ingredient is a ursolic acid, add silica gel after above-mentioned crude extract is dissolved in hot ethanol, mix the back thoroughly and volatilize ethanol under infrared lamp, the dry method upper prop obtains product and is ursolic acid.
2. method according to claim 1 is characterized in that: per kilogram Leaf of Glossy Privet 5000-6000ml alcohol reflux.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01138325 CN1126757C (en) | 2001-12-20 | 2001-12-20 | Process for extracting ursolic acid from fructus ligustri lucidi leaf |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 01138325 CN1126757C (en) | 2001-12-20 | 2001-12-20 | Process for extracting ursolic acid from fructus ligustri lucidi leaf |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1358733A true CN1358733A (en) | 2002-07-17 |
| CN1126757C CN1126757C (en) | 2003-11-05 |
Family
ID=4674531
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN 01138325 Expired - Fee Related CN1126757C (en) | 2001-12-20 | 2001-12-20 | Process for extracting ursolic acid from fructus ligustri lucidi leaf |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1126757C (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1324044C (en) * | 2003-11-28 | 2007-07-04 | 中国科学院武汉植物研究所 | Ursolic acid extracting method from privet leaf |
| CN1326867C (en) * | 2005-06-03 | 2007-07-18 | 南京大学 | Process for united separation and purification of ursolic acid and oligomeric proanthocyanidin and application thereof |
| CN100360551C (en) * | 2003-12-19 | 2008-01-09 | 杨庆尧 | Preparation of ursolic acid by acid-base method |
| CN101220076B (en) * | 2008-01-10 | 2011-05-11 | 刘富来 | Method for extracting and separating prunol from Mesona Procumbens Hemsl |
| US8748658B2 (en) | 2010-03-22 | 2014-06-10 | Council Of Scientific And Industrial Research | Fast isolation method for the natural scaffold ursolic acid from Diospyros melanoxylon |
-
2001
- 2001-12-20 CN CN 01138325 patent/CN1126757C/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1324044C (en) * | 2003-11-28 | 2007-07-04 | 中国科学院武汉植物研究所 | Ursolic acid extracting method from privet leaf |
| CN100360551C (en) * | 2003-12-19 | 2008-01-09 | 杨庆尧 | Preparation of ursolic acid by acid-base method |
| CN1326867C (en) * | 2005-06-03 | 2007-07-18 | 南京大学 | Process for united separation and purification of ursolic acid and oligomeric proanthocyanidin and application thereof |
| CN101220076B (en) * | 2008-01-10 | 2011-05-11 | 刘富来 | Method for extracting and separating prunol from Mesona Procumbens Hemsl |
| US8748658B2 (en) | 2010-03-22 | 2014-06-10 | Council Of Scientific And Industrial Research | Fast isolation method for the natural scaffold ursolic acid from Diospyros melanoxylon |
Also Published As
| Publication number | Publication date |
|---|---|
| CN1126757C (en) | 2003-11-05 |
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|---|---|---|---|
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C06 | Publication | ||
| PB01 | Publication | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| C17 | Cessation of patent right | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20031105 Termination date: 20100120 |