Process for producing a pair of novel ginsengenin and its compound body, and preparations thereof

A technology of total ginseng saponins and mixtures, applied in the field of medicine, can solve problems such as undiscovered preparation methods and the like

Inactive Publication Date: 2008-08-20
CHIA TAI TIANQING PHARMA GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] 25Rmdt and 25Smdt and their mixture (racemate) are derivatives of PPD, so far no ...

Method used

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  • Process for producing a pair of novel ginsengenin and its compound body, and preparations thereof
  • Process for producing a pair of novel ginsengenin and its compound body, and preparations thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Embodiment 1: sodium hydroxide hydrolysis method prepares 25Rmdt and 25Smdt and their mixture (racemate)

[0027] Take by weighing 10 g of total saponins of ginseng fruit, dissolve in 1000 ml of sodium hydroxide with a concentration of 2.5 mol / L, and a concentration of 80% in methanol aqueous solution for 24 h, and then use 2.5 mol / L hydrochloric acid to neutralize the reaction solution, recover methanol under reduced pressure, and use The reaction solution was extracted with chloroform, and the chloroform phase was washed with water, dried over anhydrous sodium sulfate, and evaporated to dryness to collect the residue, separated by silica gel column chromatography, and gradient eluted with petroleum ether: ethyl acetate (10:1-1:1) to obtain 86 Fractions, fractions 52-55 were recrystallized from ethyl acetate to obtain 25Rmdt; fractions 56-58 were combined after TLC inspection, and after removing the solvent, ethyl acetate recrystallized to obtain a mixture of 25Rmdt and...

Embodiment 2

[0028] Embodiment 2: hydrochloric acid hydrolysis method prepares 25Rmdt and 25Smdt and their mixture (racemate)

[0029] Weigh 10 g of total saponins from American ginseng leaves, dissolve in 1000 ml of 80% methanol aqueous solution with hydrochloric acid concentration of 2.5 mol / L and sonicate. Ultrasonic conditions: frequency: 50kHz; power: 3KW; time: 30 minutes; hydrolyze at a temperature of 40°C for 12 hours, neutralize the reaction solution with 2.5mol / L sodium hydroxide, recover methanol under reduced pressure, extract the reaction solution with chloroform, and chloroform phase Washed with water, dried over anhydrous sodium sulfate, evaporated to dryness to collect the residue, separated by silica gel column chromatography, chloroform: ethyl acetate (15:1-1:1) gradient elution to obtain 58 fractions, fractions 30-35 were 25Rmdt was obtained after ethyl acetate recrystallization; Fractions 36-38 were combined after TLC inspection, and after removing the solvent, ethyl ac...

Embodiment 3

[0030] Embodiment 3: Acid hydrolysis method prepares 25Rmdt and 25Smdt and their mixture (racemate)

[0031]Weigh 10g of Panax notoginseng total saponins, dissolve it in a mixed solution of 1000ml concentrated hydrochloric acid and 1000ml methanol and sonicate, ultrasonic conditions: frequency: 50kHz; power: 3KW; time: 10 minutes; Sodium oxide neutralized the reaction solution, recovered methanol under reduced pressure, extracted the reaction solution with ether, washed the extract with water, dried over anhydrous sodium sulfate, and evaporated to dryness to collect the residue, separated by silica gel column chromatography, chloroform:methanol (30:1- 5:1) gradient elution yielded 58 fractions, fractions 30-35 were recrystallized from ethyl acetate to obtain 25Rmdt; fractions 36-38 were combined after TLC inspection, and 25Rmdt was obtained after solvent removal and ethyl acetate recrystallization and 25Smdt mixture (racemate); Fractions 38-41 were combined after TLC inspectio...

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Abstract

The invention pertains to the field of medical technology, which relates to a pair of new ginsengenins, the preparation method of the mixture thereof (raceme) and a novel anti-tumor preparation which contains the compounds as active ingredients. The names of the pair of compounds are 20(R)-25-methoxyl-dammarane-3 Beta, 12 Beta, 20-triol(known as 25Rmdt for short) and 20(S)-25-methoxy-dammarane-3 Beta, 12 Beta, 20-triol(known as 25Smdt for short). The compounds of the invention can be prepared by adopting acid hydrolysis method, alkaline hydrolysis method and synthesis method, and the preparation method is simple and feasible. The 25Rmdt, the 25Smdt, the mixture (raceme) and a pharmaceutically acceptable carrier can be made into the clinical feasible various formulations, studies prove that: the compounds and the preparations have significant anti-tumor effects, and can be made into any medicinal and health care formulation for the treatment of different cancers and be mainly applied in the prevention and the treatment of malignant tumors with the broad application prospect.

Description

Technical field: [0001] The invention belongs to the technical field of medicine, and relates to a preparation method and preparation of a pair of new ginsenosides and their mixture. The pair of compounds are named 20(R)-25-methoxy-dammarane-3β,12β,20-triol and 20(S)-25-methoxy-dammarane-3β,12β,20- Triol [20(R)-25-methoxyl-dammarane-3β, 12β, 20-triol (25Rmdt for short) and 20(S)-25-me-thoxyl-dammarane-3β, 12β, 20-triol (25Smdt for short) ]. 25Rmdt and 25Smdt and their mixtures (racemate) have significant anti-tumor effects, and can be made into any medicinal and health product dosage forms for different cancer treatments. They are mainly used in the prevention and treatment of malignant tumors and have broad application prospects. Background technique: [0002] Studies by many scholars have shown that ginsenosides have obvious anti-tumor and immunoregulatory effects, improve microcirculation, and improve the quality of life and other biological activities. However, becau...

Claims

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Application Information

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IPC IPC(8): C07J9/00A61K31/575A61P35/00
Inventor 孙宝山赵余庆赵骏铭韩凌
Owner CHIA TAI TIANQING PHARMA GRP CO LTD
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