CN101991624B - Method for preparing total asiatic acid, asiatic acid and madecassic acid from asiatic pennywort herb and use of prepared product - Google Patents
Method for preparing total asiatic acid, asiatic acid and madecassic acid from asiatic pennywort herb and use of prepared product Download PDFInfo
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- CN101991624B CN101991624B CN 200910194671 CN200910194671A CN101991624B CN 101991624 B CN101991624 B CN 101991624B CN 200910194671 CN200910194671 CN 200910194671 CN 200910194671 A CN200910194671 A CN 200910194671A CN 101991624 B CN101991624 B CN 101991624B
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Abstract
The invention relates to a method for preparing total asiatic acid, asiatic acid and madecassic acid from asiatic pennywort herb and use of a prepared product. The method comprises the following steps of: preparing asiaticoside from coarse powder of the asiatic pennywort herb; treating the asiaticoside by using alkali liquor, acidifying, extracting by using n-butyl alcohol, and recrystallizing by using alcohol to prepare the total asiatic acid; and performing chromatography on the total asiatic acid to obtain the asiatic acid and the madecassic acid. Meanwhile, the total asiatic acid, the asiatic acid and the madecassic acid can be used for reducing postmeal glucose and preventing and treating diabetes. The method has the characteristics that the process is simple, the cost is low, and the method is suitable for promotion and large-scale production.
Description
Technical field
The invention belongs to Chinese drug preparation and purposes technical field, be specifically related to a kind of method of Herba Centellae total acid, asiatic acid, Madecassic acid and purposes of gained prepared product of from Herba Centellae, preparing.
Background technology
Herba Centellae is the conventional Chinese medicine that Chinese Pharmacopoeia records, and is the herb of samphire Herba Centellae (Centella asiaticaLinn.), and Shennong's Herbal begins to be stated from, classify middle product as, bitter, hot, cold, return the liver,spleen,kidney warp, has clearing away heat-damp and promoting diuresis, the effect of removing toxic substances and promoting subsidence of swelling.Be used for jaundice due to damp-heat, heatstroke diarrhoea, sand Stranguria stranguria with blood, carbuncle sore tumefacting virus, traumatic injury.Research in recent years report Herba Centellae has the promotion wound healing, softening cicatrix, and psoriasis, antidepressant, resisting hyperplasia of mammary glands, anti-hepatic fibrosis, anticancer, the treatment edema such as protects the liver at the effect.
The effective ingredient of Herba Centellae is asiatic centella total saponins, asiatic acid, Madecassic acid etc., at present, the preparation method of asiatic acid and Madecassic acid mainly is directly to extract from the grass of accumulated snow grassland, because asiatic acid and Madecassic acid content in the Herba Centellae are very low, therefore needing to separate purge process through loaded down with trivial details extraction, chromatography etc. could obtain, comparatively waste time and energy, and consume a large amount of solvents.Report was once arranged, prepared asiatic acid with asiaticoside, so that the asiatic acid output increased, but the method can not prepare asiaticoside simultaneously take asiaticoside as raw material.
Summary of the invention
One of technical problem to be solved by this invention is to provide a kind of method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid take the Herba Centellae coarse powder as raw material, the method not only will prepare a small amount of asiatic acid and the Madecassic acid that wherein exists from Herba Centellae total glycosides, and will be converted into corresponding asiatic acid and Madecassic acid to the asiaticoside in the Herba Centellae total glycosides and asiaticoside.
Two of technical problem to be solved by this invention is to provide the purposes of utilizing the prepared product that said method obtains.
The asiaticoside that the present invention relates to (1), asiaticoside (2), asiatic acid (3), the chemical structural formula of Madecassic acid (4) is as follows:
The method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid from Herba Centellae as first aspect present invention specifically comprises the steps:
The extraction of a, asiatic centella total saponins: with extracting solvent extraction, gained extracts solution through the concentrating under reduced pressure first time with the Herba Centellae coarse powder, and add precipitant and precipitate, subsequent filtration, filtrate is through being evaporated to for the second time the dried asiatic centella total saponins that obtains;
The preparation of b, Herba Centellae total acid: asiatic centella total saponins poured into stir hydrolysis in the basic hydrolysis liquid and obtain hydrolyzed solution, hydrolyzed solution adds subsequently ethyl acetate and distributes, the water layer that obtains after the distribution neutralizes with the acid of rare ore deposit, aqueous solution after the neutralization concentrates and forms concentrated solution, concentrated solution n-butanol extraction, the backwash of gained extract infrequent menstruation water gaging, be evaporated to dried, obtain the asiatic centella total acid crude, described asiatic centella total acid crude obtains the Herba Centellae total acid through decolorizing with activated carbon with pure recrystallization;
The preparation of c, asiatic acid and Madecassic acid: the Herba Centellae total acid is carried out column chromatography, successively obtain asiatic acid and Madecassic acid.
Wherein the extraction solvent described in a step can be water or lower alcohol, selects water or lower alcohol as extracting solvent the effective ingredient in the Herba Centellae is extracted as far as possible, reaches the purpose that takes full advantage of raw material.Used extracting mode can be the common extractive technique in this area, and for example, the technical staff can mix afterwards the form of reflux, extract, and extracts extracting solvent with the Herba Centellae coarse powder, as for common 2～3 times of extraction time, and common 1.5～2h of extraction time.When the extraction solvent in a step is lower alcohol, extract solvent be weight percentage concentration 30%～70% ethanol or weight percent concentration 30%～70% methanol.
In addition, because the dissolubility of effective ingredient in lower alcohol is large, so use lower alcohol as precipitant in a step, can make effective ingredient and water-solubility impurity such as the effective separations such as polysaccharide and inorganic salt.Described lower alcohol is methanol or ethanol, is preferably ethanol.
The present invention carries out being evaporated to concentrated solution proportion to gained extraction solution the first time in a step be 1.1～1.3.
The present invention's employed basic hydrolysis liquid in the b step is inorganic alkali solution, and described inorganic alkali solution is that mass percent concentration is 0.5%～2.0% potassium hydroxide or sodium hydrate aqueous solution.
The present invention is in the b step, and the temperature of hydrolysis is generally 55 ℃～65 ℃, and hydrolysis time is 2～3 hours, and the consumption of basic hydrolysis liquid is generally 4～8 times of asiatic centella total saponins weight, and the present invention adopts such hydrolysising condition to guarantee that hydrolysis fully.
The present invention's employed rare ore deposit acid in the b step can be dilute hydrochloric acid or the dilute sulfuric acid of commonly using.
As a kind of optimum condition, the weight of the column chromatography used chromatographic silica gel of the present invention in the c step can be 20～30 times of Herba Centellae total acid weight, and used eluant can be the mixed liquor of chloroform and methanol, and the volume ratio of chloroform and methanol is 5: 1.
In sum, a kind of method of from Herba Centellae, extracting Herba Centellae total acid, asiatic acid, Madecassic acid of the present invention, it is to utilize asiatic centella total saponins to obtain total triterpene acid after the alkali liquor hydrolysis, gets main two triterpenic acid one asiatic acids, Madecassic acid through silica gel column chromatography again.The inventive method technique is simple, only need finish conventional the extraction, extraction, and the routine operations such as column chromatography, the save trouble and labor, agents useful for same also only is a little lower alcohols, and is with low cost, is beneficial to popularization.
In addition, the present invention finds that also effective ingredient Herba Centellae total acid, asiatic acid, Madecassic acid in the Herba Centellae has the effect that reduces post-prandial glycemia and prevent and treat diabetes after deliberation, and its principle is that the activity by Inhibiting α-glucosidase produces effect.
The specific embodiment
Embodiment 1
Below the present invention is described further:
The extraction of asiatic centella total saponins:
Herb coarse powder 1Kg adds 10 liter water reflux, extract, three times, each 1.5 hours, filters merging filtrate, be evaporated to proportion 1.1, add 95% long-pending alcohol precipitation of triploid, placement is spent the night, and filters, filtrate decompression is concentrated into dried, gets 51g, is asiatic centella total saponins, yield 5.1%.
Same with 1 kilogram of herb coarse powder, add 10 liters, 60% reflow of alcohol and extract three times, each 1.5 hours, as follows upper operation got total saponins 56g, yield 5.6%.
The preparation of Herba Centellae total acid:
With above-mentioned asiatic centella total saponins 51g, add 200ml 1% potassium hydroxide solution, at 60 ℃ of heating in water bath and stirred 2 hours, let cool rear basic hydrolysis liquid and distribute 2 times with ethyl acetate, each ethyl acetate 80ml.
The aqueous alkali layer is evaporated to 100ml after transferring pH=7 with dilute hydrochloric acid, with n-butanol extraction three times (each 25ml), merge n-butanol layer, use again a small amount of water backwash once after, with the n-butanol layer evaporated under reduced pressure, get thick Herba Centellae total acid, after a small amount of methanol heating for dissolving, decolorizing with activated carbon, filter, reclaim methanol to small size, place, crystallize filters, and crystallization is washed with a small amount of acetone, get Herba Centellae total acid 13g, yield 1.3%.
The preparation of asiatic acid and Madecassic acid:
Above-mentioned Herba Centellae total acid 10g is dissolved in methanol, mix 20g chromatographic silica gel (200～300 order), dried being placed on the chromatographic column that 500g silica gel is housed, with the mixed solvent eluting of chloroform and methanol, its volume ratio is 5: 1, collects 80ml for every part, thin layer chromatography (TLC) is followed the tracks of the inspection side, merge same stream part, successively get asiatic acid 1.2g, Madecassic acid 3.7g.
The asiatic acid of getting and Madecassic acid through fusing point, thin layer chromatography (TLC) Rf value, and HPLC retention time and reference substance is consistent, and they
13The further affirmation with the consistent of document of CNMR data.
The inhibitory action of alpha-glucosidase activity is measured:
(1) reagent
The acarbose reference substance available from the Shanghai history is auspicious can biological company limited, alpha-glucosidase (α-glucosidase, TypeI; From bakers Yeast), 4-nitrophenol-α-D-pyranglucoside (4-Nitrophenyl-α-D-glucopyranoside, PNPG) is all available from Sigma company; Medical material is available from large pharmacy, Huifeng, Shanghai; All the other reagent are analytical pure.
(2) instrument
HWS26 type electric-heated thermostatic water bath, PHS-25 acidometer, DL-5 low speed large capacity centrifuge, the multiplex vacuum pump SHB-IIIA of circulating water type, Rotary Evaporators RE52-98, Shanghai rib light S54PC ultraviolet-uisible spectrophotometer.
(3) alpha-glucosidase suppresses determination of activity
Take 4-nitrophenol-α-D-pyranglucoside (PNPG) as substrate, be to add testing sample 100 μ l (sample dissolves with 50%DMSO by specified amount), the reduced glutathione 50 μ l of 1mg/ml and the alpha-glucosidase 100 μ l of 5.7U/ml in the phosphate buffer of 2ml0.1mol/L pH=6.8 to reaction system, shake up rear 37 ℃ of temperature and bathed 10 minutes; Then add 37 ℃ of temperature and bathe the substrate PNPG200 μ l of good 20mmol/L, behind 37 ℃ of water-bath 20min, add 0.1mol/L Na
2CO
3Solution 10mi cessation reaction is measured absorbance at wavelength 400nm place.Positive control is the acarbose of 5mg/ml.It is as follows that alpha-glucosidase suppresses active computing formula:
In the following formula: A
BlankFor not adding the reacted absorption value of sample, A
SampleBe the absorption value behind the adding example reaction, A
BackgroundFor only adding the absorption value of sample.
Table 1 has reflected that Herba Centellae total acid, asiatic acid, Madecassic acid are to the inhibition percentage of alpha-glucosidase activity:
Table 1
| Group | Concentration μ g/ml in the reaction system | Suppression ratio (%) |
| Acarbose | 120 | 55.0 |
| The Herba Centellae total acid | 16 8 | 96.1 37.8 |
| Asiatic acid | 8 2 | 83.9 86.3 |
| Madecassic acid | 8 2 | 85.6 73.8 |
| Asiatic centella total saponins | 100 | - |
| Asiaticoside | 100 | - |
| Asiaticoside | 100 | - |
Herba Centellae is conventional Chinese medicine, it is rich in the asiaticoside constituents, be hydrolyzed to get the Herba Centellae total acid from asiatic centella total saponins, get asiatic acid, two compositions of Madecassic acid from the Herba Centellae total acid, the present invention finds that first Herba Centellae total acid, asiatic acid, Madecassic acid have very strong inhibitory action to alpha-glucosidase activity again.Because accumulated snow medical herbs source is abundant, and is inexpensive, extraction and conversion, separating technology are simple, and not only therefore safety but also economic be convenient to promote large-scale production, can be developed into and prevent and treat diabetes, cancer therapy drug.
Should be appreciated that those skilled in the art can make various changes or modifications the present invention after having read instruction foregoing of the present invention, these equivalent form of values fall within the application's appended claims limited range equally.
Claims (9)
1. a method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid from Herba Centellae is characterized in that, comprises the steps:
The extraction of a, asiatic centella total saponins: with extracting solvent extraction, gained extracts solution through the concentrating under reduced pressure first time with the Herba Centellae coarse powder, and add precipitant and precipitate, subsequent filtration, filtrate is through being evaporated to for the second time the dried asiatic centella total saponins that obtains;
The preparation of b, Herba Centellae total acid: asiatic centella total saponins poured into stir hydrolysis in the basic hydrolysis liquid and obtain hydrolyzed solution, hydrolyzed solution adds subsequently ethyl acetate and distributes, the water layer that obtains after the distribution neutralizes with the acid of rare ore deposit, aqueous solution after the neutralization concentrates and forms concentrated solution, concentrated solution n-butanol extraction, the backwash of gained extract infrequent menstruation water gaging, be evaporated to dried, obtain the asiatic centella total acid crude, described asiatic centella total acid crude obtains the Herba Centellae total acid through decolorizing with activated carbon with pure recrystallization;
The preparation of c, asiatic acid and Madecassic acid: the Herba Centellae total acid is carried out column chromatography for separation, successively obtain asiatic acid and Madecassic acid;
Described extraction solvent is water or lower alcohol,
Described precipitant is lower alcohol.
2. a kind of method that from Herba Centellae, prepares Herba Centellae total acid, asiatic acid, Madecassic acid according to claim 1, it is characterized in that described lower alcohol as extracting solvent is mass percent concentration 30%～70% ethanol or mass percent concentration 30%～70% methanol.
3. a kind of method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid from Herba Centellae according to claim 1 is characterized in that, described lower alcohol as precipitant is methanol or ethanol.
4. a kind of method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid from Herba Centellae according to claim 1 is characterized in that in a step gained extraction solution being carried out being evaporated to concentrated solution proportion the first time is 1.1～1.3.
5. a kind of method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid from Herba Centellae according to claim 1 is characterized in that b step neutral and alkali hydrolyzed solution is inorganic alkali solution.
6. a kind of method for preparing Herba Centellae total acid, asiatic acid, Madecassic acid from Herba Centellae according to claim 5 is characterized in that described inorganic alkali solution is that mass percent concentration is 0.5%～2.0% potassium hydroxide or sodium hydrate aqueous solution.
7. a kind of method that from Herba Centellae, prepares Herba Centellae total acid, asiatic acid, Madecassic acid according to claim 1, it is characterized in that hydrolysis temperature is 55 ℃～65 ℃ in the b step, hydrolysis time is 2～3 hours, and the consumption of basic hydrolysis liquid is 4～8 times of asiatic centella total saponins weight.
8. a kind of method that from Herba Centellae, prepares Herba Centellae total acid, asiatic acid, Madecassic acid according to claim 1, the weight that it is characterized in that the used chromatographic silica gel of column chromatography in the c step is 20～30 times of Herba Centellae total acid weight, used eluant is the mixed liquor of chloroform and methanol, and chloroform and methanol volume ratio are 5:1.
9. the purposes of a Herba Centellae total acid, asiatic acid, Madecassic acid is characterized in that for the preparation of reducing post-prandial glycemia and preventing and treating the medicine of diabetes; Wherein the Herba Centellae total acid is made by method claimed in claim 1.
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| CN 200910194671 CN101991624B (en) | 2009-08-27 | 2009-08-27 | Method for preparing total asiatic acid, asiatic acid and madecassic acid from asiatic pennywort herb and use of prepared product |
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| CN 200910194671 CN101991624B (en) | 2009-08-27 | 2009-08-27 | Method for preparing total asiatic acid, asiatic acid and madecassic acid from asiatic pennywort herb and use of prepared product |
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Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102579589B (en) * | 2012-04-05 | 2013-09-11 | 赵全成 | Application of Chinese medicinal composition in preparing hypoglycemic drugs or health-promoting products |
| CN104892719B (en) * | 2014-12-04 | 2016-09-21 | 陕西君碧莎制药有限公司 | A kind of preparation method of asiaticoside |
| CN104926914B (en) * | 2015-05-18 | 2019-02-26 | 中国人民解放军海军医学研究所 | Asiatic acid derivative and preparation method thereof and its preparing the application in hypoglycemic medicine |
| CN106176848A (en) * | 2016-08-25 | 2016-12-07 | 桂林益天成生物科技有限公司 | The method extracting asiatic centella total saponins from Herba Centellae |
| CN106349323B (en) * | 2016-08-25 | 2018-04-10 | 桂林益天成生物科技有限公司 | The method that hydrolysis asiatic centella total saponins prepare asiaticoside member |
| CN106214710A (en) * | 2016-08-25 | 2016-12-14 | 桂林益天成生物科技有限公司 | The method extracting triterpene acid from Herba Centellae |
| CN107739399B (en) * | 2017-11-29 | 2020-05-05 | 陶坤秀 | Method for extracting madecassic acid |
| CN109320580A (en) * | 2018-10-30 | 2019-02-12 | 天峨县科学技术情报研究所 | A method of extracting asiatic acid from centella |
| CN111518859B (en) * | 2019-02-01 | 2023-11-24 | 鲁南制药集团股份有限公司 | Preparation method of asiaticoside |
| CN109879926B (en) * | 2019-02-27 | 2021-07-23 | 江西省药品检验检测研究院 | Triterpene glycoside compounds in Glechomae herba and extraction and separation method thereof |
| 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 |
| CN111297877A (en) * | 2019-12-31 | 2020-06-19 | 中国药科大学 | Pharmaceutical use of asiaticoside or its analogue |
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