CN101948501A - Preparation method of hydroxyl asiaticoside - Google Patents
Preparation method of hydroxyl asiaticoside Download PDFInfo
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- CN101948501A CN101948501A CN 201010269888 CN201010269888A CN101948501A CN 101948501 A CN101948501 A CN 101948501A CN 201010269888 CN201010269888 CN 201010269888 CN 201010269888 A CN201010269888 A CN 201010269888A CN 101948501 A CN101948501 A CN 101948501A
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Abstract
The invention discloses a preparation method of hydroxyl asiaticoside. Centella serves as raw material and is heated, reflowed and extracted by ethanol; the obtained extract enters a macroporous resin column for chromatography after filtered by a ceramic membrane; the resin column is washed by water and is extracted until effluent is clear; the column is successively washed by 30-40% of ethanol and 70-80% of ethanol, and 70-80% of ethanol eluate is collected and concentrated into extract; the extract is performed with alcohol precipitation by 90-100% of ethanol and filtered; the content of ethanol in the filtrate is regulated to 70-80%; then a decoloring resin column is decolored to collect effluent; the effluent is concentrated so that ethanol content in the effluent is 10-15%, and devitrification and filteration are carried out; mother liquor enters the macroporous resin column for chromatography; the resin column is washed by water until the effluent is clear; then, the column is washed by 10-20% of ethanol and 35-45% of ethanol successively; and 35-45% of ethanol eluate is collected, concentrated and dried to obtain the hydroxyl asiaticoside. Compared with the prior art, the method of the invention has simple operation, low production cost and high product purity.
Description
Technical field
The present invention relates to a kind of preparation method of Madecassoside, belong to the extractive technique field of active pharmaceutical ingredients.
Background technology
Herba Centellae is herb or the whole herb with root of dicotyledons samphire Herba Centellae, has clearing heat and promoting diuresis, the effect of subduing swelling and detoxicating; Be used for the treatment of jaundice due to damp-heat, dysentery rubella, larynx are swollen, pyogenic infections and wound etc.Total Of Triterpenes is the activeconstituents of Herba Centellae, and Madecassoside is one of main component of Total Of Triterpenes.Having and discover that Madecassoside has thymoleptic usefulness preferably, is more rising natural antidepressive.
At present disclosed from Herba Centellae extraction separation to go out the method for Madecassoside few, specifically have:
1, publication number is to disclose the method that can make Madecassoside in the patent of invention of CN1377649, specifically be after earlier Total Of Triterpenes being dissolved in methyl alcohol, carry out silica gel normal-phase chromatography chromatography, mixed solution with chloroform and methyl alcohol is an eluting solvent, collect wherein chloroform: the elutriant of methyl alcohol=2: 1 proportional part, the reclaim under reduced pressure elutriant obtains white crystal shape simplification compound Madecassoside.The purity of the Madecassoside that this method makes is not ideal enough, and contains chloroform in the eluting solvent, not enough environmental protection, harm operator's health.
2, publication number is the patent of invention of CN101210039, a kind of method for separating and preparing of Madecassoside chemical reference substance is disclosed, it is that Madecassoside extract with weight content 30～97% is a raw material, with the preparative high performance liquid chromatography is separation means, with methanol-water solution is eluent system, obtains purity 98% above Madecassoside chemical reference substance.Though this method can obtain highly purified Madecassoside Dan Pin, it is that Asiaticoside extract with weight content 30～97% is that raw material separates purification, must extract earlier the Asiaticoside extract of certain content from Herba Centellae; In addition, this method equipment used preparative high performance liquid chromatography price is higher, causes production cost of products higher.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of preparation method of with low cost, the simple to operate and Madecassoside that products obtained therefrom purity is high.
For solving the problems of the technologies described above, the present invention by the following technical solutions:
A kind of preparation method of Madecassoside, its step is as follows:
1) get Herba Centellae, pulverize, with 50～80% alcoholic acid heating and refluxing extraction 1～3 time, each 30～90min, united extraction liquid;
2) extracting solution is through the laggard macroporous resin column chromatography of ceramic membrane filter, and the washed resin post is limpid to effluent liquid, washes post with 30～40% ethanol and 70～80% ethanol successively again, collects 70～80% ethanol eluates, is concentrated into medicinal extract;
3) medicinal extract is with 90～100% ethanol alcohol precipitations, suction filtration, and filtrate adds water, and to make ethanol content wherein be 70～80%, advances the decolouring of decolorizing resin post then, collects effluent liquid;
4) to be concentrated into ethanol content be 10～15% to effluent liquid, put the cold analysis crystalline substance, suction filtration, mother liquor advances macroporous resin column chromatography, and the washed resin post is limpid to effluent liquid, washes post with 10～20% ethanol and 35～45% ethanol successively again, collect 35～45% ethanol eluates, concentrate, drying promptly gets Madecassoside.
Among the above-mentioned preparation method:
In the step 1), 50～80% consumption of ethanol are 6～12 times of raw material weight.
Step 2) in, described ceramic membrane is that the aperture is the alumina ceramic membrane of 0.25～1 μ m.30～40% consumption of ethanol are 1.5～2.5 times of resin column bed volume, and 70～80% consumption of ethanol are 2～3 times of resin column bed volume.
In the step 3), 90～100% consumption of ethanol are 8～12 times of medicinal extract weight.Described decolorizing resin post can be macroporous type decolorizing resin post, neutral alumina resin column or activated carbon column.
In the step 4), 10～20% consumption of ethanol are 1.5～3 times of resin column bed volume, and 35～45% consumption of ethanol are 2～3 times of resin column bed volume.
Step 2) and 4) in, the model of described macroporous resin can be D101, D130 or AB-8.
Concentrating described in the aforesaid method all can be adopted with drying and be had identical operations in the preparation Madecassoside method now.
Compared with prior art, the invention has the advantages that:
1, extracting solution has reduced the working load of macroporous resin earlier with using macroporous resin column chromatography after the ceramic membrane removal of impurities again, has also promptly reduced water, consumption of ethanol that follow-up wash-out is used, has reduced production cost;
2, all adopt during twice column chromatography from low to high Different concentrations of alcohol to carry out wash-out, can promptly remove more water-fast alcohol dissolubility impurity in elution step with the ethanol of lower concentration, thereby improve the purity of product, also avoided the expensive expense that only causes on the other hand with the ethanol elution of same concentration;
3, adopt common macroporous resin to realize the separation of Madecassoside, compare with adopting preparative high performance liquid chromatography, its cost significantly reduces, thereby has further reduced production cost of products;
4, entire method is simple to operation, and prepared Madecassoside purity height, can reach (HPLC mensuration) more than 95%.
Embodiment
Below among each embodiment, concentration of ethanol is volumetric concentration.
Embodiment 1
1) gets Herba Centellae, pulverize, place extractor, add 65% alcohol reflux of 10 times of raw material weights, temperature is controlled at 90 ℃, and refluxing extraction 90min leaches soup for the first time, 65% ethanol that adds 10 times of raw material weights again, refluxing extraction 30min, united extraction liquid;
2) extracting solution is the alumina-ceramic membrane filtration of 0.25 μ m with the aperture, advance the D101 macroporous resin column chromatography then, the washed resin post is limpid to effluent liquid, wash post with 30% ethanol of 2 times of resin column bed volumes and 70% ethanol of 2.5 times of resin column bed volumes successively again, collect 70% ethanol eluate, be evaporated to medicinal extract;
3) medicinal extract is used for the 95% ethanol alcohol precipitation of 10 times of its weight, suction filtration, and filtrate adds water makes wherein second
Alcohol content is 70%, advances activated carbon column decoloring then, collects effluent liquid;
4) to be evaporated to ethanol content be 10% to effluent liquid, place 20h for 4 ℃, separate out suction filtration behind a large amount of crystal, mother liquor advances the AB-8 macroporous resin column chromatography, and the washed resin post is limpid to effluent liquid, washes post with 15% ethanol of 2 times of resin column bed volumes and 40% ethanol of 2.5 times of resin column bed volumes successively again, collect 40% ethanol eluate, concentrating under reduced pressure, drying promptly gets Madecassoside.
After measured, the purity of gained Madecassoside is 98.2%.
Embodiment 2
1) get Herba Centellae, pulverize, place extractor, add 80% alcohol reflux 90min of 12 times of raw material weights, temperature is controlled at 95 ℃, collects extracting solution;
2) extracting solution is the alumina-ceramic membrane filtration of 0.5 μ m with the aperture, advance the AB-8 macroporous resin column chromatography then, the washed resin post is limpid to effluent liquid, wash post with 40% ethanol of 1.5 times of resin column bed volumes and 75% ethanol of 3 times of resin column bed volumes successively again, collect 75% ethanol eluate, be evaporated to medicinal extract;
3) medicinal extract is used for the 100% ethanol alcohol precipitation of 8 times of its weight, suction filtration, and filtrate adds water, and to make ethanol content wherein be 75%, advances the decolouring of neutral alumina resin column then, collects effluent liquid;
4) to be evaporated to ethanol content be 15% to effluent liquid, place 24h for 6 ℃, separate out suction filtration behind a large amount of crystal, mother liquor advances the AB-8 macroporous resin column chromatography, and the washed resin post is limpid to effluent liquid, washes post with 10% ethanol of 3 times of resin column bed volumes and 40% ethanol of 3 times of resin column bed volumes successively again, collect 40% ethanol eluate, concentrating under reduced pressure, drying promptly gets Madecassoside.
After measured, the purity of gained Madecassoside is 96.7%.
Embodiment 3
1) gets Herba Centellae, pulverize, place extractor, 70% alcohol reflux that adds 10 times of raw material weights, temperature is controlled at 100 ℃, and refluxing extraction 60min leaches soup for the first time, 70% ethanol that adds 8 times of raw material weights again, refluxing extraction 30min leaches soup, adds 70% ethanol of 6 times of raw material weights for the third time, refluxing extraction 30min, united extraction liquid;
2) extracting solution is the alumina-ceramic membrane filtration of 1 μ m with the aperture, advance the D130 macroporous resin column chromatography then, the washed resin post is limpid to effluent liquid, wash post with 30% ethanol of 2.5 times of resin column bed volumes and 70% ethanol of 2 times of resin column bed volumes successively again, collect 70% ethanol eluate, be evaporated to medicinal extract;
3) medicinal extract is used for the 90% ethanol alcohol precipitation of 12 times of its weight, suction filtration, and filtrate adds water, and to make ethanol content wherein be 80%, advances the decolouring of macropore decolorizing resin post then, collects effluent liquid;
4) to be evaporated to ethanol content be 12% to effluent liquid, place 15h for 3 ℃, separate out suction filtration behind a large amount of crystal, mother liquor advances the D101 macroporous resin column chromatography, and the washed resin post is limpid to effluent liquid, washes post with 20% ethanol of 1.5 times of resin column bed volumes and 35% ethanol of 2 times of resin column bed volumes successively again, collect 35% ethanol eluate, concentrating under reduced pressure, drying promptly gets Madecassoside.
After measured, the purity of gained Madecassoside is 96.5%.
Embodiment 4
1) gets Herba Centellae, pulverize, place extractor, add 50% alcohol reflux of 12 times of raw material weights, temperature is controlled at 95 ℃, and refluxing extraction 60min leaches soup for the first time, 50% ethanol that adds 10 times of raw material weights again, refluxing extraction 60min, united extraction liquid;
2) extracting solution is the alumina-ceramic membrane filtration of 0.8 μ m with the aperture, advance the D101 macroporous resin column chromatography then, the washed resin post is limpid to effluent liquid, wash post with 35% ethanol of 2 times of resin column bed volumes and 80% ethanol of 3 times of resin column bed volumes successively again, collect 80% ethanol eluate, be evaporated to medicinal extract;
3) medicinal extract is used for the 95% ethanol alcohol precipitation of 9 times of its weight, suction filtration, and filtrate adds water, and to make ethanol content wherein be 70%, advances activated carbon column decoloring then, collects effluent liquid;
4) to be evaporated to ethanol content be 10% to effluent liquid, normal temperature is placed 65h down, separate out suction filtration behind a large amount of crystal, mother liquor advances the D101 macroporous resin column chromatography, and the washed resin post is limpid to effluent liquid, washes post with 20% ethanol of 2.5 times of resin column bed volumes and 45% ethanol of 3 times of resin column bed volumes successively again, collect 45% ethanol eluate, concentrating under reduced pressure, drying promptly gets Madecassoside.
After measured, the purity of gained Madecassoside is 98.7%.
Claims (8)
1. the preparation method of a Madecassoside is characterized in that step is as follows:
1) gets Herba Centellae, pulverize, extract 1～3 time each 30～90min, united extraction liquid with 50～80% alcohol heating reflux;
2) extracting solution is through the laggard macroporous resin column chromatography of ceramic membrane filter, and the washed resin post is limpid to effluent liquid, washes post with 30～40% ethanol and 70～80% ethanol successively again, collects 70～80% ethanol eluates, is concentrated into medicinal extract;
3) medicinal extract is with 90～100% ethanol alcohol precipitations, suction filtration, and filtrate adds water, and to make ethanol content wherein be 70～80%, advances the decolouring of decolorizing resin post then, collects effluent liquid;
4) to be concentrated into ethanol content be 10～15% to effluent liquid, put the cold analysis crystalline substance, suction filtration, mother liquor advances macroporous resin column chromatography, and the washed resin post is limpid to effluent liquid, washes post with 10～20% ethanol and 35～45% ethanol successively again, collect 35～45% ethanol eluates, concentrate, drying promptly gets Madecassoside.
2. the preparation method of Madecassoside according to claim 1, it is characterized in that: in the step 1), 50～80% consumption of ethanol are 6～12 times of raw material weight.
3. the preparation method of Madecassoside according to claim 1 is characterized in that: step 2) in, described ceramic membrane is that the aperture is the alumina ceramic membrane of 0.25～1 μ m.
4. the preparation method of Madecassoside according to claim 1 is characterized in that: step 2) in, 30～40% consumption of ethanol are 1.5～2.5 times of resin column bed volume, 70～80% consumption of ethanol are 2～3 times of resin column bed volume.
5. the preparation method of Madecassoside according to claim 1, it is characterized in that: in the step 3), 90～100% consumption of ethanol are 8～12 times of medicinal extract weight.
6. the preparation method of Madecassoside according to claim 1, it is characterized in that: in the step 3), described decolorizing resin post is macroporous type decolorizing resin post, neutral alumina resin column or activated carbon column.
7. the preparation method of Madecassoside according to claim 1, it is characterized in that: in the step 4), 10～20% consumption of ethanol are 1.5～3 times of resin column bed volume, and 35～45% consumption of ethanol are 2～3 times of resin column bed volume.
8. the preparation method of Madecassoside according to claim 1 is characterized in that: step 2) and 4) in, the model of macroporous resin is D101, D130 or AB-8.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102617696A (en) * | 2012-03-16 | 2012-08-01 | 广州汉方现代中药研究开发有限公司 | Preparation method of asiaticoside |
| CN106336448A (en) * | 2016-08-25 | 2017-01-18 | 桂林益天成生物科技有限公司 | Method for extracting madecassic acid from herba centellae |
| CN106380504A (en) * | 2016-08-25 | 2017-02-08 | 桂林益天成生物科技有限公司 | Method for extraction of madecassoside from Centella asiatica |
| CN106977579A (en) * | 2017-04-28 | 2017-07-25 | 南宁馨艺荣生物科技有限公司 | A kind of technique that madecassoside is extracted from centella |
| CN110179841A (en) * | 2019-07-02 | 2019-08-30 | 江西青春康源制药有限公司 | A kind of industrial extraction method of high level of water soluble asiaticoside |
| CN111285916A (en) * | 2020-02-14 | 2020-06-16 | 浏阳朗林生物科技有限公司 | Preparation method of centella asiatica extract with high content of total asiaticosides |
| US11464247B2 (en) | 2006-09-07 | 2022-10-11 | Guilin Gfs Monk Fruit Corp. | Sweetening compositions and processes for preparing them |
| US11576412B2 (en) | 2016-10-24 | 2023-02-14 | Guilin Gfs Monk Fruit Corporation | Extracts from fruits of the Cucurbitaceae family, and methods of preparing thereof |
| CN115894597A (en) * | 2022-11-03 | 2023-04-04 | 广州好肌肤科技有限公司 | Extraction process and application of madecassoside with multiple repair effects |
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| CN101210039A (en) * | 2006-12-27 | 2008-07-02 | 中国科学院大连化学物理研究所 | Method for separating and preparing madecassoside chemical reference substance |
| CN101396384A (en) * | 2007-09-28 | 2009-04-01 | 天津天士力现代中药资源有限公司 | Asiatic centella extract and preparation methode thereof |
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| CN101210039A (en) * | 2006-12-27 | 2008-07-02 | 中国科学院大连化学物理研究所 | Method for separating and preparing madecassoside chemical reference substance |
| CN101396384A (en) * | 2007-09-28 | 2009-04-01 | 天津天士力现代中药资源有限公司 | Asiatic centella extract and preparation methode thereof |
Non-Patent Citations (2)
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| 《Journal of Chromatography A》 20080416 Guangtao Jia, et al. Enrichment and purification of madecassoside and asiaticoside from Centella asiatica extracts with macroporous resins 第136-141页 1-8 第1193卷, 第1-2期 * |
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Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US11464247B2 (en) | 2006-09-07 | 2022-10-11 | Guilin Gfs Monk Fruit Corp. | Sweetening compositions and processes for preparing them |
| CN102617696B (en) * | 2012-03-16 | 2014-10-22 | 广州白云山汉方现代药业有限公司 | Preparation method of asiaticoside |
| CN102617696A (en) * | 2012-03-16 | 2012-08-01 | 广州汉方现代中药研究开发有限公司 | Preparation method of asiaticoside |
| CN106336448A (en) * | 2016-08-25 | 2017-01-18 | 桂林益天成生物科技有限公司 | Method for extracting madecassic acid from herba centellae |
| CN106380504A (en) * | 2016-08-25 | 2017-02-08 | 桂林益天成生物科技有限公司 | Method for extraction of madecassoside from Centella asiatica |
| CN106380504B (en) * | 2016-08-25 | 2018-01-26 | 桂林益天成生物科技有限公司 | The method that madecassoside is extracted from centella |
| US11576412B2 (en) | 2016-10-24 | 2023-02-14 | Guilin Gfs Monk Fruit Corporation | Extracts from fruits of the Cucurbitaceae family, and methods of preparing thereof |
| CN106977579B (en) * | 2017-04-28 | 2019-05-07 | 南宁馨艺荣生物科技有限公司 | A kind of technique for extracting madecassoside from centella |
| CN106977579A (en) * | 2017-04-28 | 2017-07-25 | 南宁馨艺荣生物科技有限公司 | A kind of technique that madecassoside is extracted from centella |
| CN110179841A (en) * | 2019-07-02 | 2019-08-30 | 江西青春康源制药有限公司 | A kind of industrial extraction method of high level of water soluble asiaticoside |
| CN111285916A (en) * | 2020-02-14 | 2020-06-16 | 浏阳朗林生物科技有限公司 | Preparation method of centella asiatica extract with high content of total asiaticosides |
| CN111285916B (en) * | 2020-02-14 | 2021-07-02 | 浏阳朗林生物科技有限公司 | Preparation method of centella asiatica extract with high content of total asiaticosides |
| CN115894597A (en) * | 2022-11-03 | 2023-04-04 | 广州好肌肤科技有限公司 | Extraction process and application of madecassoside with multiple repair effects |
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| CN101948501B (en) | 2012-12-26 |
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Address after: No. 19 Renmin South Road, Lingui District, Guilin City, Guangxi Zhuang Autonomous Region, 541100 Patentee after: GUILIN LAYN NATURAL INGREDIENTS Corp. Address before: 541100 Rhine biology Co., Ltd., Yangtang Industrial Park, Lingui Town, Lingui County, Guilin City, Guangxi Zhuang Autonomous Region Patentee before: GUILIN LAYN NATURAL INGREDIENTS Corp. |