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Novel antitumor compound ginsenoside Rg3 derivant and preparation thereof

A technology of ginsenosides and derivatives, applied in antitumor drugs, steroids, organic chemistry, etc., can solve the problems of inability to achieve high-efficiency tumor inhibition and low bioavailability, and achieve strong anticancer activity and bioavailability. High, simple and easy to implement effect

Inactive Publication Date: 2012-06-27
CHANGCHUN FENGDIYUAN TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, limited by its insolubility in water, its bioavailability is extremely low, and it cannot achieve efficient anti-tumor effect.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: prepare A3 with potassium permanganate oxidation method

[0015] Take 100kg of ginseng, decoct in water, and use macroporous resin D 101 Adsorption, elution with 80% ethanol, decolorization of anion and cation resins, to obtain 3000 g of total ginsenosides. Dissolve this material in 5000-6000ml of ethanol, add an aqueous solution containing 1000-1200g of sodium hydroxide under stirring, heat to 40°C, precipitate diol group saponins, and filter to obtain 1810g. Put this material into a stainless steel reactor, add 18000g of glycerin, heat, add 2300-2500g of sodium hydroxide, heat to 160-200°C, keep for 20-40 minutes, and the hydrolysis is complete. The reaction solution was dropped into water, and precipitates were precipitated, filtered and dried to obtain 590 g of hydrolyzate. Dissolve this product in acetone, add an appropriate amount of aqueous solution containing potassium permanganate, oxidize at 50°C-60°C, filter to remove the generated manganese...

Embodiment 2

[0016] Embodiment 2: prepare A3 with sodium dichromate oxidation method

[0017] According to the preparation method of Implementation 1, 600 g of diol group saponin hydrolyzate was obtained, which was dissolved in acetone, and an aqueous solution containing 160-200 g of sodium dichromate was added, oxidized at 50°C-80°C to obtain the intermediate of ginsenoside derivatives, filtered , The residue was discarded, the filtrate recovered acetone, and dried to obtain 390g. This thing is carried out column chromatography, operation is the same as embodiment 1, obtains ginsenoside Rg 3 151.50g of the derivative intermediate is reacted with 40% sodium hydroxide solution to obtain A3 with a yield of 156 。 28g.

Embodiment 3

[0018] Embodiment 3: prepare A3 with potassium permanganate oxidation method

[0019] Get 100kg of ginseng, extract it by decoction, and use macroporous resin D 101 Adsorption, elution with 80% ethanol, decolorization of anion and cation resins, to obtain 3000 g of total ginsenosides. Dissolve this product in 5000-6000ml of ethanol, add an aqueous solution containing 1000-1200g of potassium hydroxide under stirring, heat to 40°C, precipitate diol group saponins, and filter to obtain 1750g. Put this material into a stainless steel reactor, add 18,000g of glycerin, heat, add 2,000-2,300g of potassium hydroxide, heat to 180-200°C, keep for 20-40 minutes, and carry out hydrolysis. The reaction solution was added dropwise into water, and a precipitate was precipitated, filtered and dried to obtain 570 g of a hydrolyzate. Dissolve this product in acetone, add an appropriate amount of aqueous solution containing potassium permanganate, oxidize at 50°C-60°C, filter to remove the g...

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Abstract

The invention relates to a novel antitumor compound ginsenoside Rg3 derivant and preparation thereof and is characterized in that ginseng is extracted with a water decoction method, and then ginsenoside is separated out with macroporous resin D101. After the ginsenoside is provided with alcohol to be completely dissolved, alkali is added to separate Panaxadiol Saponins, then the Panaxadiol Saponins is hydrolyzed, and obtained hydrolysate is oxidized by oxidants (potassium permanganate and sodium dichromate) to oxidize C24 into carboxyl. Column chromatography and thin-layer chromatography tracking detection is carried out on the carboxyl, and a ginsenoside Rg3 derivant intermediate is obtained through separation, the intermediate is reacted with 40% of alkaline solution (including sodium hydroxide or potassium hydroxide) to generate salt, and then A3 is obtained. According to the invention, the structure of the ginsenoside Rg3 is chemically modified, the key technology water-solubility is broken through to achieve the effects of good water solubility, high bioavailability and strong anticancer activity. The derivant disclosed by the invention has a simple and feasible process, controllable quality and good repeatability, and is suitable for mass production.

Description

technical field [0001] The invention relates to a novel antitumor compound ginsenoside Rg 3 Derivatives and their preparation. Background technique [0002] Pharmacological studies confirm that: ginsenoside Rg 3 It has the functions of promoting tumor cell apoptosis; inhibiting tumor cell proliferation; inhibiting tumor cell invasion and metastasis; inhibiting tumor angiogenesis; affecting the expression of tumor signal transduction-related genes, enhancing the immunity of patients with tumor radiotherapy and chemotherapy; reversing the role of tumor multidrug resistance , with low toxicity, broad-spectrum anti-tumor characteristics. However, limited by its insolubility in water, its bioavailability is extremely low, and it cannot achieve efficient anti-tumor effect. In order to achieve high efficiency, low toxicity, and broad spectrum, it is necessary to break through the water solubility of its key technology. Contents of the invention [0003] The object of the pres...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J17/00A61P35/00
Inventor 宋长春张春选刘兴汉杨丽俊
Owner CHANGCHUN FENGDIYUAN TECH DEV