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Method for efficiently and rapidly preparing and separating three kinds of ginsenoside isomers Rg6, Z type and E type F4

A technology of ginsenosides and isomers, applied in chemical instruments and methods, glycoside steroids, steroids, etc., can solve the problems of difficulty in obtaining standard products, limited activity, low yield, etc., and is convenient for pharmacodynamics research. , The effect of high utilization rate of raw materials and high separation efficiency

Active Publication Date: 2017-09-08
深圳振强生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Studies have shown that Rg6, Z-type and E-type F4 have different pharmacological effects, but due to the difficulty in obtaining standard products, they cannot be prepared in large quantities, which limits researchers to further study their activities.
Although CN102911238 A mentioned above discloses a method for preparing Rg6, F4, the method yield is low (less than 20%); Obtain three isomers (more than 100 mg each) to separate Rg6, Z-type and E-type F4
[0014] In short, it is difficult to obtain a large number of ginsenoside Rg6, Z-type and E-type F4 standard products

Method used

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  • Method for efficiently and rapidly preparing and separating three kinds of ginsenoside isomers Rg6, Z type and E type F4
  • Method for efficiently and rapidly preparing and separating three kinds of ginsenoside isomers Rg6, Z type and E type F4
  • Method for efficiently and rapidly preparing and separating three kinds of ginsenoside isomers Rg6, Z type and E type F4

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Example 1 Preparation of Ginsenoside Isomer Rg6, Z Type and E Type F4 Mixture and Separation of Mixture

[0033] How to prepare the mixture:

[0034] Take 500mg ginsenoside Rg2 (self-made, purity greater than 95%), dissolve with 200mL methanol aqueous solution (methanol concentration is 50% by volume) containing formic acid, the volume of formic acid added is 0.05% of the volume of methanol water. After dissolving, 50 mg of lead dioxide particles were added to the reaction system, and the reaction was refluxed at 85° C. for 2.5 hours. After the reaction, it is naturally cooled to room temperature, filtered to remove lead dioxide particles, the filtrate is concentrated into an aqueous solution substantially free of methanol, and freeze-dried to obtain a freeze-dried powder.

[0035] High-speed countercurrent separation method for mixtures:

[0036] Prepare ethyl acetate-ethanol-water-acetic acid (volume ratio 4:1:5:0.08) solvent system 12 hours before separation. The s...

Embodiment 2

[0043] Example 2 Preparation of ginsenoside isomer Rg6, Z-type and E-type F4 mixture and separation of the mixture

[0044] How to prepare the mixture:

[0045]Get 500mg ginsenoside Rg2 (self-made, purity greater than 95%), dissolve with 200mL ethanol aqueous solution (volume percent concentration of ethanol is 50%) containing acetic acid, and the volume of acetic acid added is 0.05% of the volume of ethanol water. After dissolving, 50 mg of lead dioxide particles were added to the reaction system, and the reaction was refluxed at 85° C. for 2.5 hours. After the reaction, cool naturally to room temperature, filter to remove lead dioxide particles, concentrate the filtrate into an aqueous solution substantially free of ethanol, and freeze-dry to obtain freeze-dried powder.

[0046] High-speed countercurrent separation method for mixtures:

[0047] Prepare ethyl acetate-ethanol-water-acetic acid (volume ratio 4:1:5:0.08) solvent system 12 hours before separation. The specific ...

Embodiment 3

[0051] Example 3 Preparation of ginsenoside isomer Rg6, Z-type and E-type F4 mixture and separation of the mixture

[0052] How to prepare the mixture:

[0053] Take 500mg of ginsenoside Rg2 (self-made, purity greater than 95%), dissolve with 200mL of methanol aqueous solution (40% by volume of methanol) containing formic acid, the volume of formic acid added is 0.06% of the volume of methanol water. After dissolving, 50 mg of lead dioxide particles were added to the reaction system, and the reaction was refluxed at 80° C. for 3 hours. After the reaction, it is naturally cooled to room temperature, filtered to remove lead dioxide particles, the filtrate is concentrated into an aqueous solution substantially free of methanol, and freeze-dried to obtain a freeze-dried powder.

[0054] High-speed countercurrent separation method for mixtures:

[0055] Prepare ethyl acetate-ethanol-water-acetic acid (volume ratio 4:1:5:0.08) solvent system 12 hours before separation. The specifi...

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Abstract

The invention discloses a method for efficiently and rapidly preparing and separating three kinds of ginsenoside isomers Rg6, Z type and E type F4. The preparation method of a saponin mixture is as follows: ginsenoside Rg2 is used as a raw material, an acid-containing alcohol-water solution is used as a reaction system, a thermal dehydration reaction is carried out, and lead dioxide is used as a catalyst. A separation method of the saponin mixture is as follows: high-speed countercurrent chromatography is used for separation, and ethyl acetate-ethanol-water-acetic acid (volume ratio is 4:1:5:0.08) is used as a solvent system. The method for preparing a mixture of ginsenoside isomers Rg6, Z type and E type F4 has high yield, 90% or above of ginsenoside Rg2 is converted into Rg6, (Z)-F4 and (E)-F4, and utilization rate of raw materials is high; The method for separating the mixture of ginsenoside isomers Rg6, Z type and E type F4 by high speed countercurrent has high separation efficiency and good separation degree, three kinds of isomers can be effectively separated, and once separation is carried out in order to obtain three kinds of isomers, wherein each mass of the isomers is 100mg or above.

Description

technical field [0001] The invention belongs to the field of medicine preparation and relates to the separation and preparation of natural product isomers, in particular to an efficient and rapid method for preparing and separating three ginsenoside isomers Rg6, Z-type and E-type F4. Background technique [0002] The C20 position of dammarane-type ginsenosides mostly has a hydroxyl group, which is widely found in plants of the genus Panax genus, and its content is relatively high. After heat treatment, the C20 hydroxyl group of dammarane type saponins and their aglycones is prone to dehydration reaction, forming double bonds, and generating a series of C20 dehydroxylated dammarane type rare ginsenosides and their aglycones. [0003] CN102911238 A discloses the following reaction formula: [0004] [0005] But in fact, the dehydration products also include rare ginsenosides with D structure, whose chemical formula is as follows: [0006] [0007] Rare ginsenosides B, ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00
CPCC07J17/005
Inventor 陈云张思泽王斌
Owner 深圳振强生物技术有限公司
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