CN103319562A - Method for preparation of ginsenoside Rg3 directly from ginseng power - Google Patents
Method for preparation of ginsenoside Rg3 directly from ginseng power Download PDFInfo
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- CN103319562A CN103319562A CN2013102072423A CN201310207242A CN103319562A CN 103319562 A CN103319562 A CN 103319562A CN 2013102072423 A CN2013102072423 A CN 2013102072423A CN 201310207242 A CN201310207242 A CN 201310207242A CN 103319562 A CN103319562 A CN 103319562A
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Abstract
The invention relates to a method for preparation of ginsenoside Rg3 from ginseng power which is directly extracted by a lactic acid aqueous solution. The ginseng power is extracted by the lactic acid aqueous solution having mild acidity so that a ginsenoside extraction ratio is improved and extracted ginsenoside can be transformed into ginsenoside Rg3 having anticancer and immunity improvement effects directly through structural modification under acidic conditions. The method combines ginsenoside extraction and ginsenoside structural modification so that in ginsenoside extraction, ginsenoside Rg3 preparation is directly finished; processes are simplified; and a cost is reduced. The method is suitable for industrial production.
Description
Technical field
The present invention relates to a kind ofly directly extract the method for preparing ginsenoside Rg3 by the ginseng powder, particularly is the method for extraction agent with the lactic acid aqueous solution.
Background technology
Ginsenoside Rg3 be protopanoxadiol saponins Rb1, Rb2, Rb3, Rc, Rd by the secondary ginsenoside that C-20 position selective hydrolysis obtains, effects such as having antifatigue, improve immunizing power, improve memory, be anticancer.As ginsenoside Rg3 liver cancer, lung cancer, colorectal carcinoma, carcinoma of the pancreas, mammary cancer, ovarian cancer, carcinoma of the pancreas etc. had obvious restraining effect, simultaneously when chemotherapy drugs in combination uses such as other cancer therapy drug such as ginsenoside Rg3 and taxol or CTX, can also effectively improve the treatment for cancer effect, and by strengthening immunity, significantly improve people's life quality.
Ginsenoside Rg3 is separated from red ginseng at the beginning of the eighties in last century by Japanese scientist at first and obtains, be genseng to be processed in the red ginseng process produce, so be called the peculiar saponin(e of red ginseng again, its content only is 20(R)-Rg3 0.014%, 20(S)-Rg3 0.015%, therefore far can not satisfy the demands, be necessary to utilize that higher protopanoxadiol saponins Rb1, Rb2, Rb3, Rc, the Rd of content prepares ginsenoside Rg3 in the genseng.
Ginsenoside Rg3 can prepare by acid catalysis, enzyme catalysis or semisynthesis usually.(Chinese patent such as Yang Ling, application number 01133409.6) adding under protective material such as xitix, sodium bisulfite, gallic acid and the protection of inert gas, make catalyzer with acid reagents such as hydrochloric acid, sulfuric acid, Glacial acetic acid, 10 ~ 50 ℃ of catalytic hydrolysis glycol saponins, 2 h ~ 5 days, obtain the ginsenoside Rg3 of content 〉=90% through separation; Bae E.A.(Biol. Pharm. Bull. 2002,25 (1): 58-63) wait the 2 hours ginsenoside Rb1s of HCl catalytic hydrolysis that use 0.1N, obtained the mixture of 0.6 g 20 (S)-Rg3 and 20 (R)-Rg3 by 2 g raw materials; Liu Zhihui etc. (the Chinese Hospitals pharmaceutical journal, 2009,29(11): 881-884) prepared ginsenoside Rg3 with 30% acetolysis Radix Notoginseng total arasaponins, yield is 30%; Cheng Leqin (Phytochemistry, 2008,69:218-224) grade utilizes genseng soil microorganisms Microbacterium sp. GS514 that the ginsenoside Rb1 is changed into 20 (S)-Rg3; (Carbohydrate Res. 304:179-182) such as Victor Ph is starting raw material with the betulafolien etriol, synthesized 20 (S)-Rg3 by semi-synthesis method; Li Yaping (Chinese patent, application number 98103433) etc. utilizes Panaxadiol saponin unit as raw material, obtains 20 (S)-ginsenoside Rg3s through semi-synthesis method.The semisynthesis step of ginsenoside Rg3 is long, and yield is low, so process acid-catalyzed hydrolysis and enzymatic hydrolysis preparation is again extracted and separating monomer ginsenoside, protopanoxadiol saponins or Radix Notoginseng total arasaponins in its preparation mostly earlier.
Summary of the invention
Lactic acid is acid comparatively gentle organic acid, claim alpha-hydroxypropionic acid again, acid bigger than acetic acid, the H+ ability of dissociating is higher than acetic acid, the acid catalysis ability is stronger, acidity is littler than hydrochloric acid and sulfuric acid again on the other hand, is conducive to control reaction process, makes the hydrolysis of ginsenoside major part rest on the ginsenoside Rg3 stage.
The invention provides a kind of aqueous acid is extraction agent, directly extracted the method for preparing ginsenoside Rg3 by the ginseng powder, it is acid extractant that characteristics are to have selected for use lactic acid aqueous solution, extract by normal pressure, from the ginseng powder, directly prepare ginsenoside Rg3, not only increased substantially the extraction efficiency of ginsenoside, simplified in the past the traditional preparation process technology of the Rg3 of extraction, hydrolysis again earlier simultaneously, can effectively reduce cost.
The preparation method of ginsenoside Rg3 of the present invention comprises following content:
The ginseng powder is the genseng main root powder of araliaceae ginseng plant Panax Ginseng C. A. Meyer;
The extracting mode of ginsenoside is that heating in water bath extracts;
Aqueous acid is lactic acid aqueous solution, and its pH value scope is between 1 ~ 6.0;
The consumption of acid extractant is at every gram ginseng powder 5 ~ 50mL/g;
Extracting temperature is between 50 ℃～100 ℃;
Extraction time is between 0.5～8 h;
Leaching process need not to add antioxidant and protection of inert gas.
The present invention relates to directly finish the preparation of ginsenoside Rg3 in the ginsenoside leaching process, simple to operate, yield is higher, uses present method to extract the preparation ginsenoside Rg3, only extracts by 1 time, the Radix Ginseng total saponins extraction yield just reaches 4.54%, and the yield of ginsenoside Rg3 reaches 1.16%.
Ginsenoside extraction yield in the step=Radix Ginseng total saponins extracted amount/ginseng powder's quality * 100%; Quality/the ginseng powder's of the yield=ginsenoside Rg3 of ginsenoside Rg3 quality * 100%, wherein, the quality of ginsenoside Rg3 is the quality sum of S-Rg3 and R-Rg3.
In the step, be reference substance with ginsenoside Re, detecting wavelength is 542 nm, adopts Vanillin-Glacial acetic acid-perchloric acid development process, with the content of determined by ultraviolet spectrophotometry Radix Ginseng total saponins; By high performance liquid chromatography (utilizing external standard method) ginsenoside Rg3 is carried out qualitative and quantitative analysis.In the efficient liquid phase chromatographic analysis, chromatographic column JH08504-2546WT(150 * 4.60 mm, 5 μ m); Flow velocity: 1.0 mL/min; Detect wavelength: 203 nm; Column temperature: room temperature; Sample size: 20 μ L; Moving phase, A: acetonitrile, B: pure water (ultrasonic degassing processing).Gradient elution program: 0.00～10.00 min, A:22%; 10.00～20.00 min, A:22%; 20.00～25.00 min, A:27%; 25.00～45.00 min, A:31%; 45.00～60.00 min, A:38%; 60.00～65.00 min, A:52%; 65～75 min, A:52%; 75.00～75.10 min, A:55%; 75.00～75.10 min, A:55%; 75.10～95.00 min, A:90%; 95.00～95.10 min, A:90%; 95.10～104.00 min, A:22%.
Description of drawings
The HPLC analysis chart of ginseng powder's water extract is seen Fig. 1, and ginseng powder's lactic acid aqueous solution extractive HPLC analysis chart is seen Fig. 2.
Acquisition of technology progress of the present invention:
The present invention directly prepares the high added value ginsenoside Rg3 in the leaching process of ginsenoside, the preparation of the extraction of past ginsenoside and ginsenoside Rg3 separately changed in the leaching process finish synchronously, simplify the operating process of preparation ginsenoside Rg3, reduced cost;
The present invention is by acid extraction, disposable ginsenoside extraction rate reached to 4.54%, significantly improved the extraction efficiency of ginsenoside.
Embodiment
Embodiment 1:
The water that adds 12.5 times of amounts among the ginseng powder, 4 h are extracted in heating in 90 ℃ of water-baths.Extracting solution is cooled to room temperature, after saturated Na2CO3 solution is neutralized to pH value 6-7, uses ether defatting, equal-volume water-saturated n-butanol extraction 3 times, and to utilize Rotary Evaporators to be concentrated under 50 ℃ of temperature dried being lower than.Residue is through ultraviolet spectrophotometry and high-efficient liquid phase chromatogram technique analysis, and the Radix Ginseng total saponins extraction yield is 2.8%, and the yield of ginsenoside Rg3 is 0.09%.
Embodiment 2:
The pH value that adds 12.5 times of amounts among the ginseng powder is 2.2 lactic acid aqueous solution, and 4 h are extracted in heating in 90 ℃ of water-baths.Extracting solution is cooled to room temperature, after saturated Na2CO3 solution is neutralized to pH value 6-7, uses ether defatting, equal-volume water-saturated n-butanol extraction 3 times, and to utilize Rotary Evaporators to be concentrated under 50 ℃ of temperature dried being lower than.Residue is through ultraviolet spectrophotometry and high-efficient liquid phase chromatogram technique analysis, and the ginsenoside extraction yield is 3.1%, be 1.11 times that direct water is carried, and the yield of ginsenoside Rg3 is 0.99%, is 11.0 times that direct water is carried.Why the yield of Radix Ginseng total saponins extraction yield and ginsenoside Rg3 significantly improves; be because lactic acid aqueous solution is made extraction agent; can make that the hydrolysis of malonyl ginsenoside becomes corresponding ginsenoside in the genseng; can increase for the amount of the ginsenoside that extracts; by being extracted the regioselectivity hydrolysis of ginsenoside under acidic conditions, effectively improved the output of ginsenoside Rg3 simultaneously.
Embodiment 3:
The pH value that adds 12.5 times of amounts among the ginseng powder is 3.0 lactic acid aqueous solution, and 4 h are extracted in heating in 90 ℃ of water-baths.Extracting solution is cooled to room temperature, after saturated Na2CO3 solution is neutralized to pH value 6-7, uses ether defatting, equal-volume water-saturated n-butanol extraction 3 times, and to utilize Rotary Evaporators to be concentrated under 50 ℃ of temperature dried being lower than.Residue is through ultraviolet spectrophotometry and high-efficient liquid phase chromatogram technique analysis, and the ginsenoside extraction yield is 3.0%, be 1.07 times that direct water is carried, and the yield of ginsenoside Rg3 is 0.17%, is 1.89 times that direct water is carried.
Embodiment 4:
The pH value that adds 17.5 times of amounts among the ginseng powder is 2.4 lactic acid aqueous solution, and 4 h are extracted in heating in 100 ℃ of water-baths.Extracting solution is cooled to room temperature, after saturated Na2CO3 solution is neutralized to pH value 6-7, uses ether defatting, equal-volume water-saturated n-butanol extraction 3 times, and to utilize Rotary Evaporators to be concentrated under 50 ℃ of temperature dried being lower than.Residue is through ultraviolet spectrophotometry and high-efficient liquid phase chromatogram technique analysis, and the ginsenoside extraction yield is 4.1%, be 1.46 times that direct water is carried, and the yield of ginsenoside Rg3 is 1.01%, is 11.2 times that direct water is carried.
Embodiment 5:
The pH value that adds 17.5 times of amounts among the ginseng powder is 2.4 lactic acid aqueous solution, and 4 h are extracted in heating in 85 ℃ of water-baths.Extracting solution is cooled to room temperature, after saturated Na2CO3 solution is neutralized to pH value 6-7, uses ether defatting, equal-volume water-saturated n-butanol extraction 3 times, and to utilize Rotary Evaporators to be concentrated under 50 ℃ of temperature dried being lower than.Residue is through ultraviolet spectrophotometry and high-efficient liquid phase chromatogram technique analysis, and the ginsenoside extraction yield is 4.3%, be direct water carry 1.54, and the yield of ginsenoside Rg3 is 0.51%, is 5.7 times that direct water is carried.
Claims (5)
1. one kind is directly extracted the method for preparing ginsenoside Rg3 by the ginseng powder, it is characterized in that: be that extraction agent extracts in ginseng powder's the process with the aqueous acid, protopanoxadiol saponins in the ginsenoside that extracts is directly changed into ginsenoside Rg3 by structural modification, make in the leaching process of ginsenoside, finish the preparation of ginsenoside Rg3 simultaneously, the structural modification of the extraction of ginsenoside and ginsenoside separately being changed the past into both carries out synchronously, effectively simplify the operation steps of preparation ginsenoside Rg3, raise the efficiency, reduce cost.
2. require 1 described ginseng powder to refer to the powder of the genseng main root of araliaceae ginseng plant Panax Ginseng C. A. Meyer according to letter of authorization.
3. requiring 1 described extracting mode according to letter of authorization is that heating in water bath extracts.
4. requiring 1 described aqueous acid according to letter of authorization is lactic acid aqueous solution, and its pH value scope is between 1 ~ 6.0, and its consumption is every gram ginseng powder 5 ~ 50mL/g.
5. require in the 3 described extracting modes according to letter of authorization, bath temperature is that extraction time is between 0.5～6 h between 50 ℃～100 ℃.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107188918A (en) * | 2017-06-05 | 2017-09-22 | 吉林大学 | A kind of pseudo-ginsenoside Rg3, Rh2, PPD preparation method |
| CN110917228A (en) * | 2019-11-26 | 2020-03-27 | 长春师范大学 | Method for simultaneously preparing total saponins, total flavonoids and oil unsaponifiable matter of ginseng stem leaves |
| CN110922442A (en) * | 2019-12-23 | 2020-03-27 | 吉林化工学院 | Green preparation method of ginseng extract rich in rare ginsenosides Rg3 and Rg5 |
| CN111087439A (en) * | 2020-01-04 | 2020-05-01 | 丁传波 | Preparation method of rare ginsenoside Rg3 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1508147A (en) * | 2002-12-13 | 2004-06-30 | 中国科学院大连化学物理研究所 | Method for preparing low-polarity ginseng saponin and its aglycone by catalytic pyrolysis |
| CN103059089A (en) * | 2013-01-25 | 2013-04-24 | 吉林化工学院 | Method for preparing secondary ginsenoside Rg3 via hydrolyzing primary panaxadiol saponins under catalysis of fresh grape juice |
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- 2013-05-30 CN CN2013102072423A patent/CN103319562A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1508147A (en) * | 2002-12-13 | 2004-06-30 | 中国科学院大连化学物理研究所 | Method for preparing low-polarity ginseng saponin and its aglycone by catalytic pyrolysis |
| CN103059089A (en) * | 2013-01-25 | 2013-04-24 | 吉林化工学院 | Method for preparing secondary ginsenoside Rg3 via hydrolyzing primary panaxadiol saponins under catalysis of fresh grape juice |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107188918A (en) * | 2017-06-05 | 2017-09-22 | 吉林大学 | A kind of pseudo-ginsenoside Rg3, Rh2, PPD preparation method |
| CN110917228A (en) * | 2019-11-26 | 2020-03-27 | 长春师范大学 | Method for simultaneously preparing total saponins, total flavonoids and oil unsaponifiable matter of ginseng stem leaves |
| CN110917228B (en) * | 2019-11-26 | 2022-01-18 | 长春师范大学 | Method for simultaneously preparing total saponins, total flavonoids and oil unsaponifiable matter of ginseng stem leaves |
| CN110922442A (en) * | 2019-12-23 | 2020-03-27 | 吉林化工学院 | Green preparation method of ginseng extract rich in rare ginsenosides Rg3 and Rg5 |
| CN111087439A (en) * | 2020-01-04 | 2020-05-01 | 丁传波 | Preparation method of rare ginsenoside Rg3 |
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Application publication date: 20130925 |