CN1765917A - Gen-seng saponin Rb2 preparation process - Google Patents
Gen-seng saponin Rb2 preparation process Download PDFInfo
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- CN1765917A CN1765917A CN 200510016844 CN200510016844A CN1765917A CN 1765917 A CN1765917 A CN 1765917A CN 200510016844 CN200510016844 CN 200510016844 CN 200510016844 A CN200510016844 A CN 200510016844A CN 1765917 A CN1765917 A CN 1765917A
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Abstract
The invention discloses a preparation technique for panaxoside Rb2, which comprises: breaking fresh panax ginseng, extracting with alcohol at room temperature; decompressing to recycle solvent and condense into water solution; adding caustic soda, caustic potash or ammonium hydroxide into the condensed liquid, hydrolyzing; putting on macroporous resin column; cleaning with water, eluting with alcohol, and obtaining total saponin; recycling alcohol, extracting with n-butylalcohol to obtain panaxadiol saponin; with ODS method, eluting the product with alcohol and water in gradient; recycling solvent, freeze drying to obtain the coarse Rb2; recrystallizing with alcohol and n-butylalcohol to prepare the product. This method can extract and enrich the RB2 in maximum limit.
Description
Technical field
The present invention relates to ginsenoside preparation technology, disclose and a kind ofly prepare ginsenoside Rb with the enrichment of malonyl ginsenoside
2Technology belongs to Chinese materia medica extracts active ingredients separation technology field.
Background technology
The malonyl ginsenoside (Malonyl-ginsenosides) that the present invention relates to is called the malonyl ginsenoside again, comprises M-Rb
1, M-Rb
2, M-Rc and M-Rd.The Kitagawa of Osaka, Japan university equals nineteen eighty-three and separate malonyl ginsenoside-Rb first from genseng
1,-Rb
2,-Rc and-Rd, from then on opened research to this compounds; Wang Jiyan (1993) also separates from the fresh ginseng of Jilin and obtains wherein three kinds of malonyl ginsenosides (Malonyl ginsenosedes)-Rb
1,-Rb
2And-Rd; Zhou Yu etc. (1998) separate first from the chemical constitution study process of Radix Panacis Quinquefolii and have identified a kind of malonyl ginsenoside, i.e. malonyl ginsenoside-Rb
1The malonyl ginsenoside all is the crystallization of colourless powder shape, is the sour water soluble saponin, and polarity is strong.Fusing point (mp) is generally between 150～161 ℃, and soluble in water, methyl alcohol is insoluble in ethanol, propyl carbinol, is insoluble to chloroform, ether.Acyl bond is extremely unstable in its molecule, is easy to hydrolysis.Meet acid, alkali or hydrolysis reaction all can take place under hot water, hot methanol condition and slough propanedioic acid, become corresponding ginsenoside.Liebermann-Burchard reaction, the reaction of butter of antimony chloroform saturated solution are all positive reaction.
The malonyl ginsenoside is in present commercialization preparation, and during with the n-butanol extraction total saponins, this part saponin(e is easily miscible in water layer, is taken as water-soluble impurity such as sugar, inorganic salt and removes.The water-solubility saponin of unconverted is directly gone up macroporous resin column, also can cause a part of water-solubility saponin to run off with water.The content of the malonyl ginsenoside at each position of genseng after testing is with malonyl ginsenoside Rb in its fresh ginseng fibrous root
2With ginsenoside Rb
2The content sum the highest, the former is 1.792%, the latter is 1.172%, and both sums obviously reduce in sun-cured suncured ginseng and the red ginseng, particularly malonyl ginsenoside Rb
2Content difference apart from great disparity, although the content of this saponins in aquatic foods ginsengs is bigger,, in the extraction process of total saponins, usually go out of use together with water-soluble impurity because its polarity is big.One side malonyl ginsenoside Rb in ginseng product
2A work in-process loss part is that the conversion of processing back generates other saponin(es on the other hand, rather than ginsenoside Rb
2
Summary of the invention
The present invention discloses and a kind ofly prepares ginsenoside Rb with the enrichment of malonyl ginsenoside
2Technology can be obtained ginsenoside Rb to greatest extent
2, solved the big shortcoming of existing preparation technology's product loss.
The ginsenoside Rb that the present invention relates to
2Have its structure down:
Molecular formula: C
53H
90O
22
Molecular weight: 1078
Technical solution of the present invention may further comprise the steps:
Fresh ginseng or Radix Panacis Quinquefolii (being comprised: fibrous root, supporting root, rhizome, main root etc.) be raw material, chopping, ethanol with 60～98% (dosage is 1/10～1/20 in the ratio of ethanol consumption) at room temperature cold soaking extracts 2～6 times, each 8-16 hour, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds alkali in every kg feed material is 30 1 70 grams to add sodium hydroxide or potassium hydroxide or ammonium hydroxide in concentrated solution, concentration is 3%-5%, PH=9～10), (＜40 ℃) are at ambient temperature treated to go up macroporous resin column D after the whole hydrolysis of sample
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the panoxadiol saponins with n-butanol extraction.
Adopt ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 150-300 gram panoxadiol saponins, elutriant ethanol: water, gradient elution, every 1000mL are a stream part, constantly detect with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product then through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2
Among the present invention used ODS pressurized column chromatography method fineness ratio greater than 1: 9 for well, preparation purity is more than 90%, yield is 20%, invert point should be less than 40 ℃, alkali lye is at 3%-5%, PH=9～10.
Adopt preparation property high performance liquid chromatography, produce type high performance liquid chromatograph fully, chromatographic condition: ODS post with waters company, with 30% acetonitrile and 70% water is moving phase, the ultraviolet detection wavelength is 203nm, and flow velocity 145mL/min. prepares purity more than 98%, and yield is more than 90%.
Product of the present invention can be made any formulation on the pharmacology such as tablet, capsule, pulvis or injection, is used for the treatment of diabetes, hyperlipidemia, and cardiac muscle or cerebral ischemia, cancer, tumour, body's immunity is impaired, impotence due to deficiency of the kidney, and disease such as Digestive tract.
Positively effect of the present invention is: adopt new technology the malonyl ginsenoside has been carried out full conversion, both M-Rb
1, M-Rb
2, M-Rc, M-Rd change into Rb
1, Rb
2, Rc, Rd, simulate high-efficient liquid phase chromatogram technology then, employing can be carried out the column chromatography pressurization way of suitability for industrialized production, separates, preparation ginseng saponins Rb
2, in order to make full use of resource, extract to greatest extent, enrichment ginsenoside Rb
2, reach simple, quick, low-cost enrichment Rb
2Purpose, guarantee for the preparation of suitability for industrialized production, new drug provides technology.
Description of drawings
Fig. 1 is a process flow sheet of the present invention.
Embodiment
By following examples the present invention is described for example further, and do not limit the present invention in any way, under the prerequisite that does not deviate from technical solution of the present invention, any change or change that those of ordinary skills that the present invention did are realized easily all will fall within the claim scope of the present invention.
Embodiment 1
1kg fresh ginseng (comprising: fibrous root, supporting root, rhizome, main root) is cleaned, shreds, with 68% the ethanol of 15kg, at room temperature cold soaking extracts 3 times, each 8-16 hour, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds sodium hydroxide in every kg feed material is 30 grams to add sodium hydroxide in concentrated solution, concentration is 3%, PH=9), (＜40 ℃) are at ambient temperature treated to go up macroporous resin column D after the whole hydrolysis of sample
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the panoxadiol saponins with n-butanol extraction.The imitation high-efficient liquid phase chromatogram technology adopts ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 150 gram panoxadiol saponins, elutriant ethanol: water, gradient elution, every 1000mL is a stream part, constantly detects with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product then through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2Be 31 grams.
Embodiment 2
Get panoxadiol saponins 200 grams of embodiment 1 preparation, adopt ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, last sample, elutriant ethanol: water, the every 1000mL of gradient elution are a stream part, constantly detect with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product then through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2Be 42 grams.
Embodiment 3
Fibrous root, supporting root main root with fresh ginseng are raw material, chopping, and the ethanol with 98% at room temperature cold soaking extracts 6 times, each 16 hours, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds sodium hydroxide in every kg feed material is 70 grams to add sodium hydroxide in concentrated solution, concentration is 5%, PH=10), and (＜40 ℃) at ambient temperature, make the whole hydrolysis of sample behind the 5-6h, go up macroporous resin column D again
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the panoxadiol saponins with n-butanol extraction.The imitation high-efficient liquid phase chromatogram technology adopts ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 300 gram panoxadiol saponins, elutriant ethanol: water, gradient elution, every 1000mL is a stream part, constantly detects with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product again through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2Be 65 grams.
Embodiment 4
With bright Radix Panacis Quinquefolii rhizome is raw material, chopping, and the ethanol with 80% at room temperature cold soaking extracts 5 times, each 12 hours, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds potassium hydroxide in every kg feed material is 50 grams to add potassium hydroxide in concentrated solution, concentration is 4%, PH=9.5), and (＜40 ℃) at ambient temperature, make the whole hydrolysis of sample behind the 5-6h, go up macroporous resin column D again
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the Radix Panacis Quinquefolii glycol saponins with n-butanol extraction.The imitation high-efficient liquid phase chromatogram technology adopts ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 150 gram Radix Panacis Quinquefolii glycol saponins, elutriant ethanol: water, gradient elution, every 1000mL is a stream part, constantly detects with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product again through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2Be 29 grams.
Embodiment 5
With bright Radix Panacis Quinquefolii is raw material, chopping, and the ethanol with 70% at room temperature cold soaking extracts 4 times, each 10 hours, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds ammonium hydroxide in every kg feed material is 30 grams to add ammonium hydroxide in concentrated solution, concentration is 3%, PH=9), and (＜40 ℃) at ambient temperature, make the whole hydrolysis of sample behind the 5-6h, go up macroporous resin column D again
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the Radix Panacis Quinquefolii glycol saponins with n-butanol extraction.The imitation high-efficient liquid phase chromatogram technology adopts ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 200 gram Radix Panacis Quinquefolii glycol saponins, elutriant ethanol: water, gradient elution, every 1000mL is a stream part, constantly detects with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product again through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2Be 35 grams.
Embodiment 6
With bright Radix Panacis Quinquefolii fibrous root, supporting root, main root is raw material, chopping, and the ethanol with 60% at room temperature cold soaking extracts 3 times, each 8 hours, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds sodium hydroxide in every kg feed material is 70 grams to add sodium hydroxide in concentrated solution, concentration is 5%, PH=10), and (＜40 ℃) at ambient temperature, make the whole hydrolysis of sample behind the 5-6h, go up macroporous resin column D again
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the Radix Panacis Quinquefolii glycol saponins with n-butanol extraction.The imitation high-efficient liquid phase chromatogram technology adopts ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 300 gram Radix Panacis Quinquefolii glycol saponins, elutriant ethanol: water, gradient elution, every 1000mL is a stream part, constantly detects with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product, recrystallization in ethanol and propyl carbinol solvent obtains pure product monomer ginsenoside Rb again
2Be 58 grams.
Embodiment 7
With fresh ginseng (fibrous root, supporting root, rhizome, main root etc.) is raw material, chopping, ethanol with 80% at room temperature cold soaking extracts 5 times, each 8-16 hour, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds alkali in every kg feed material is the 30-70 gram to add sodium hydroxide or potassium hydroxide or ammonium hydroxide in concentrated solution, concentration is 3%-5%, PH=9～10), (＜40 ℃) at ambient temperature, make the whole hydrolysis of sample behind the 5-6h, go up macroporous resin column D again
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the panoxadiol saponins with n-butanol extraction.Adopt preparation property high performance liquid chromatography, produce type high performance liquid chromatograph fully with waters company, chromatographic condition: the ODS post is a moving phase with 30% acetonitrile and 70% water, and the ultraviolet detection wavelength is 203nm, flow velocity 145mL/min. monomer ginsenoside Rb
2Yield is more than 90% of genseng glycol saponins.
Embodiment 8
With the Radix Panacis Quinquefolii rhizome is raw material, chopping, and the ethanol with 80% at room temperature cold soaking extracts 5 times, each 8-16 hour, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution, (amount that adds alkali in every kg feed material is the 30-70 gram to add sodium hydroxide or potassium hydroxide or ammonium hydroxide in concentrated solution, concentration is 3%-5%, PH=9～10), (＜40 ℃) at ambient temperature, make the whole hydrolysis of sample behind the 5-6h, go up macroporous resin column D again
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the Radix Panacis Quinquefolii glycol saponins with n-butanol extraction.Adopt preparation property high performance liquid chromatography, produce type high performance liquid chromatograph fully with waters company, chromatographic condition: the ODS post is a moving phase with 30% acetonitrile and 70% water, and the ultraviolet detection wavelength is 203nm, flow velocity 145mL/min. monomer ginsenoside Rb
2Yield is more than 90% of genseng glycol saponins.
The crystallization of gained has following physicochemical property through spectroscopic analysis in the foregoing description:
Crystallization is white powder (n-BuOH-AcOEt), mp.200-203 ℃, after launching on the TLC plate, uses 10%H
2SO
4The reagent spray heating presents red-purple; The Liebermann-Burchard reaction is positive; The Molish reaction is positive, and prompts for triterpene saponin componds.
Partial hydrolysis detects disaccharide, and that continues carries out all-hydrolytic, detects glucose and pectinose.Because of pyranoside than the difficult hydrolysis of furanoside, pectinose is a pyranose form in prompting C-20 position banded two kinds of sugar.It is consistent with reference substance panoxadiol Rf value that aglycon Rf value is known in the TLC inspection.
Crystallization and reference substance ginsenoside-Rb
2With three kinds of different solvents [A:CHCl of plate
3-MeOH-H
2O (65: 35: 10) lower floor; B:CHCl
3-MeOH-H
2O (6: 4: 1); C:CHCl
3-MeOH-AcOEt-H
2O (2: 2: 4: 1)] be total to thin layer, the Rf value of the two, color are all consistent, and do not descend with the reference substance mixed melting point.
By m/z 1077[M-H in the LCQ-MS spectrum]
+, its molecular weight is 1078 as can be known, with ginsenoside-Rb
2Conform to.945[M-H-132]
-For losing a part pectinose and a H
+Fragment peak.The prompting pectinose is terminal sugar.915[M-H-162]
-For losing a part glucose and a H
+Fragment peak.Point out a glucose molecule to be terminal sugar.621[M-H-132-162-162]
-For losing two molecule glucoses, a part pectinose and a H
+Fragment peak.Its aglycon molecular weight is 460, and is the diol type aglycon.Glycosides deduction aglycon shows and contains 3 glucose molecules and a part pectinose (1078-460-3 * 162-132) (attribution data sees Table) in the molecule.
Table crystalline LCQ-MS attribution data
| m/z | The fragment ownership |
| 1077 945 915 783 621 459 | [M-H] - [M-H-132] - [M-H-162] - [M-H-162-132] - [M-H-132-162-162] - [M-H-132-162-162-162] - |
Above data show that crystallization is ginsenoside-Rb
2
Claims (3)
1, a kind of ginsenoside Rb
2Preparation technology may further comprise the steps:
The panoxadiol saponins extracts
With fresh ginseng or Radix Panacis Quinquefolii is raw material, and chopping is with 60～98% ethanol of 10～20 times of amounts, at room temperature cold soaking extracts 2～6 times, and each 8-16 hour, leaching process will fully stir, with extracting solution decompression and solvent recovery under 40 ℃ of conditions, the simmer down to aqueous solution adds sodium hydroxide or potassium hydroxide or ammonium hydroxide in concentrated solution, the amount that adds alkali in every kg feed material is the 30-70 gram, concentration is 3%-5%, PH=9～10 at ambient temperature, treat to go up macroporous resin column D after the whole hydrolysis of sample
101, wash five column volumes earlier with water, use 70% ethanol elution again, obtain total saponins, behind the recovery ethanol, obtain the panoxadiol saponins with n-butanol extraction;
Ginsenoside Rb
2Preparation
Adopt ODS pressurized column chromatography method, 8 kilograms of dress posts of ODS post material, get sample on the 150-300 gram panoxadiol saponins, elutriant ethanol: water, gradient elution, every 1000mL are a stream part, constantly detect with thin layer plate, will contain ginsenoside Rb
2Elutriant reclaim solvent after freeze-drying obtain ginsenoside Rb
2Crude product then through ethanol and propyl carbinol recrystallization, obtains pure product monomer ginsenoside Rb
2
2, preparation technology according to claim 1 is characterized in that: ginsenoside Rb
2The ODS pressurized column chromatography method fineness ratio of preparation usefulness greater than 1: 9, invert point should be less than 40 ℃, alkali lye is at 3%-5%, PH=9～10.
3, preparation technology according to claim 1 is characterized in that: ginsenoside Rb
2Preparation adopt preparation property high performance liquid chromatography, chromatographic condition: the ODS post is a moving phase with 30% acetonitrile and 70% water, the ultraviolet detection wavelength is 203nm, flow velocity 145mL/min.
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101156882B (en) * | 2007-10-23 | 2010-06-16 | 浙江大学 | Preparation method of pseudo-ginseng protopanoxadiol saponin |
| CN102068477A (en) * | 2010-12-31 | 2011-05-25 | 浙江省中医院 | Effective parts of ginseng and preparation method and application thereof |
| CN102600189A (en) * | 2011-01-24 | 2012-07-25 | 吉林农业大学 | Application of ginseng secondary saponin and aliphatic ester derivative thereof in preventing and treating diabetes mellitus |
| CN102920721A (en) * | 2012-11-21 | 2013-02-13 | 吉林大学 | Application of composition containing ginsenoside-Rb3and ginsenoside-Rb2 to treatment of heart and cerebral vascular diseases |
| CN105628845A (en) * | 2016-02-01 | 2016-06-01 | 北京理工大学 | Content measuring method of malonyl-ginsenoside |
| CN112843109A (en) * | 2019-11-12 | 2021-05-28 | 晨光生物科技集团股份有限公司 | Method for removing nicotine and triazole pesticide residues in total saponins of stems and leaves of saponin plant |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1513869A (en) * | 2003-03-13 | 2004-07-21 | 李向高 | Malonyl ginseng saponin structure modification, enriched ginseng saponin Rb1 technology |
-
2005
- 2005-06-03 CN CNB2005100168446A patent/CN100453550C/en not_active Expired - Fee Related
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101156882B (en) * | 2007-10-23 | 2010-06-16 | 浙江大学 | Preparation method of pseudo-ginseng protopanoxadiol saponin |
| CN102068477A (en) * | 2010-12-31 | 2011-05-25 | 浙江省中医院 | Effective parts of ginseng and preparation method and application thereof |
| CN102068477B (en) * | 2010-12-31 | 2012-07-25 | 浙江省中医院 | Effective parts of ginseng and preparation method and application thereof |
| CN102600189A (en) * | 2011-01-24 | 2012-07-25 | 吉林农业大学 | Application of ginseng secondary saponin and aliphatic ester derivative thereof in preventing and treating diabetes mellitus |
| CN102920721A (en) * | 2012-11-21 | 2013-02-13 | 吉林大学 | Application of composition containing ginsenoside-Rb3and ginsenoside-Rb2 to treatment of heart and cerebral vascular diseases |
| CN105628845A (en) * | 2016-02-01 | 2016-06-01 | 北京理工大学 | Content measuring method of malonyl-ginsenoside |
| CN112843109A (en) * | 2019-11-12 | 2021-05-28 | 晨光生物科技集团股份有限公司 | Method for removing nicotine and triazole pesticide residues in total saponins of stems and leaves of saponin plant |
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| CN100453550C (en) | 2009-01-21 |
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