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Method for preparing C25-hydroxyl aglucon and rare saponin of radix ginseng through metal ion catalysis

A technology of metal ions and hydroxyaglycones, applied in organic chemistry, steroids, etc., to achieve the effects of simple operation, high yield and low cost

Active Publication Date: 2017-12-22
鱼红闪
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0013] The above invention patents do not involve metal ions catalyzing the addition of water molecules to the unsaturated bond of the 24th-25th carbon of ginsenosides to prepare a series of highly active 25-hydroxy ginsenosides and rare ginseng saponins: including ginseng diols 20( S )-25-OH-Panaxadiol aglycon and 20( R )-25-OH-Panaxadiol aglycone, 20( S )-25-OH-Rh2 and 20( R )-25-OH-Rh2, 20( S )-25-OH-Rg3 and 20( R )-25-OH-Rg3; Panaxatriol 20( S )-25-OH-Panaxatriol aglycon and 20( R )-25-OH-Panaxatriol glycoside, 20( S )-25-OH-Rh1 and 20( R )-25-OH-Rh1, 20( S )-25-OH-Rg2 and 20( R )-25-OH-Rg2

Method used

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  • Method for preparing C25-hydroxyl aglucon and rare saponin of radix ginseng through metal ion catalysis
  • Method for preparing C25-hydroxyl aglucon and rare saponin of radix ginseng through metal ion catalysis
  • Method for preparing C25-hydroxyl aglucon and rare saponin of radix ginseng through metal ion catalysis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1: Metal ion catalysis prepares 20(S)-25-OH-Rh2 and 20(R)-25-OH-Rh2 from panaxadiol saponin F2 or Gyp17 or C-O or C-Mx1 or C-Mc1

[0029] Take 200 g RuCl 3 Dissolve in 1000 ml of ethanol water with a concentration of 36% by mass, then add 10 grams of panaxadiol saponin F2 and stir to dissolve, then stir and react at 40-60°C for 40 hours. After the reaction, 500 ml of water-saturated n-butanol was extracted 3 to 4 times, the n-butanol layer was combined, washed 2 to 4 times with a small amount of water, concentrated under reduced pressure, and dried to obtain about 7.6 grams of 20(S)-25-OH -Rh2 and 20(R)-25-OH-Rh2 isomer mixture. The content of 20(S)-25-OH-Rh2 and 20(R)-25-OH-Rh2 is more than 80% as detected by evaporative light dispersion high performance liquid chromatography (HPLC-ELSD).

[0030] Use 10 grams of Gyp17 or C-O or C-Mx1 or Mc1 to replace F2 respectively, and under the same reaction conditions, about 6 grams of 20(S)-25-OH-Rh2 and 20(R)- 25-OH-...

Embodiment 2

[0034] Embodiment 2: Metal ion catalysis prepares 20( S )-25-OH-Panaxadiol aglycon and 20( R )-25-OH-Panaxadiol Aglycone

[0035] Take 270 grams of FeCl 3 ·6H 2 O (equivalent to 100 mmol), completely dissolved in 1000 ml of methanol water with a concentration of 40% by mass, added 12 grams of ginsenoside C-K, stirred and dissolved, and reacted with stirring for 38 hours at a temperature of 40-60°C. After the reaction is over, the reaction solution is absorbed by a macroporous adsorption resin with a volume of 250 ml (20 times the volume of the sample) to absorb saponin, and washed with 2000 ml (8 times the volume of the macroporous adsorption resin) to remove impurities such as salt ions and sugars. The saponin was then eluted with 60%-95% ethanol, and the ethanol eluate was collected, concentrated under reduced pressure, and dried to obtain 8.2 g of the product. Detected by HPLC-ELSD, 20( S )-25-OH-Panaxadiol aglycon and 20( R )-25-OH-Panaxadiol aglycon content is more ...

Embodiment 3

[0039] Example 3: metal ion catalyzed preparation of rare ginsenoside 20( S )-25-OH-Rg3 and 20( R )-25-OH-Rg3

[0040] Take 27 grams of FeCl 3 Dissolve in 100 ml of 20% ethanol water, add 1 g of protopanaxadiol (PPD) saponins (including ginsenosides Rb1, Rb2, Rc, Rd) and stir to dissolve, then stir and react at 30-50°C for 40 hours. After the reaction is over, the reaction liquid is absorbed by a 50 ml volume of macroporous adsorption resin to absorb saponin, washed with 400 ml of water to remove salt ions and sugar and other impurities; then use 50%~80% ethanol to elute the saponin and collect the ethanol eluate , obtain the product of about 0.52 gram after drying; Through HPLC-ELSD detection, 20 ( S )-25-OH-Rg3 and 20( R )-25-OH-Rg3 content of more than 75%.

[0041] Saponin Rb1 or Rb2 or Rb3 or Rc or Rd monomer, replace PPD saponin, obtain 20 ( S )-25-OH-Rg3 and 20( R )-25-OH-Rg3 mixture.

[0042] Will 20( S )-25-OH-Rg3 and 20( R )-25-OH-Rg3 isomer mixture, can ob...

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Abstract

The invention discloses a method for preparing C25-hydroxyl aglucon and rare saponin of radix ginseng through metal ion catalysis. The method is simple in operation, low in cost and high in yield and purity and is applicable to large-batch production. According to the method, the C25-hydroxyl aglucon and rare saponin of the radix ginseng are prepared through catalytically hydrolyzing 20-O-glycosyl or saccharide chain of C20 of ginsenoside in a mixed solution of an organic solvent and water and catalytically adding water molecules to an unsaturated bond between C24 and C25 of the ginsenoside. The products can be applied to pharmaceutical development, radix ginseng products, healthy products and cosmetics.

Description

technical field [0001] The invention relates to a preparation method of ginseng rare saponins and aglycones, in particular to a method for preparing ginseng 25 carbon-hydroxyl aglycones and rare saponins by metal ion catalysis with simple operation, low cost, high yield and purity, and suitable for mass production Methods. Background technique [0002] More than 80-90% of the saponins in ginseng are Rb1, Rb2, Rb3, Rc, Rd, Re and Rg1 proginsenosides. After oral administration, these saponins are transformed into rare saponins under the action of intestinal enzymes and microorganisms, absorbed and effective. However, its conversion rate is very limited. Although the rare saponins contained in ginseng have high physiological activity and high human absorption rate, their content is very low. In the process of traditional red ginseng processing, saponins Rb1, Rb2, Rb3, Rc, Rd, Re and Rg1, which are high in ginseng, can be converted into S -Rg3 、R - Rg3, Rg5 and Rk1 saponins,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00
Inventor 鱼红闪刘春莹金凤燮
Owner 鱼红闪
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