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New hopane-type triterpene and preparation method and application thereof

A technology of homo-alkane type and triterpenoid compounds, which can be applied to medical preparations containing active ingredients, pharmaceutical formulas, steroids, etc., and can solve the problems that have not been seen before.

Inactive Publication Date: 2010-11-10
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, it has been reported abroad that some compounds with quinone reductase induction have been found from natural products, such as dithiolthiones (oltipraz, ultipraz), sulphoraphane, a sulfur-containing compound found in cruciferous plants; Compounds such as: withanolides; flavonoids such as 7,4'-dihydroxy-3',5'-dimethoxyisoflavones, etc.; but so far, there is no relevant report on the Hobane-type triterpenes

Method used

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  • New hopane-type triterpene and preparation method and application thereof
  • New hopane-type triterpene and preparation method and application thereof
  • New hopane-type triterpene and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0017] (1) 15 kg of dry twigs of Cymbidium cerevisiae were extracted three times through reflux of 95% ethanol, each for 2 hours, and the extraction solution was recovered under reduced pressure to obtain the crude ethanol extract;

[0018] (2) The ethanol extract was suspended in 8L of distilled water, and extracted three times with equal volumes of petroleum ether, dichloromethane, ethyl acetate and n-butanol;

[0019] (3) The dichloromethane extract obtained in step (2) was separated by silica gel column chromatography, eluting with petroleum ether: ethyl acetate 8:1, 5:1, 3:1, 2:1,

[0020] (4) Petroleum ether obtained in the above step (3): 5: 1 fraction of ethyl acetate is separated by semi-preparative HPLC chromatography, eluted with acetonitrile / water gradient, acetonitrile / water 50: 50~100: 0, elution time After 50 minutes and a flow rate of 8 mL / min, compound 1 was obtained at a retention time of 25 minutes, and compound 2 was obtained at a retention time of 44 minut...

Embodiment 2

[0031] (1) Dried the above-ground part (10kg) of Cymbidium chinensis is reflux extracted with 75% ethanol as a solvent, and the extract is recovered under reduced pressure to obtain the ethanol crude extract;

[0032] (2) The ethanol extract was suspended in 5L of distilled water, and extracted twice with equal volumes of petroleum ether, dichloromethane, ethyl acetate and n-butanol;

[0033] (3) The dichloromethane extract obtained in step (2) was separated by silica gel column chromatography, eluting with petroleum ether: acetone 8:1, 6:1, 4:1, 3:1,

[0034] (4) The obtained petroleum ether: acetone 4: 1 fraction in the above-mentioned step (3) is separated by semi-preparative HPLC chromatography, eluted with methanol / water gradient, methanol / water 75: 25~100: 0, elution time 60 Minutes, flow rate 8mL / min, compound 1 was obtained at a retention time of 33 minutes, and compound 2 was obtained at a retention time of 54 minutes.

[0035] The petroleum ether: acetone 9: 1 fract...

Embodiment 3

[0037] Quinone reductase-inducing activity test of the compounds 1, 2 and 3 of embodiment 3

[0038] Experimental Materials:

[0039] (1) Main reagents and main equipment: calf serum (purchased from Hyclone); fetal bovine serum (TBD company); tetramethylazozolium salt (MTT) American Sigma (St.Louis, MO); glucose-6- Phosphate dehydrogenase (Shanghai Sangong); 96-well cell culture plate (Costar); cell line: mouse liver cancer cell line Hepa 1c1c7 Experimental method:

[0040] (1) Cell culture:

[0041] Seed 10 per hole 4cells were grown for 24 hours in a culture solution containing 10% (v / v) fetal bovine serum, 0.01% penicillin G, 0.15% sodium bicarbonate, and 0.01% streptomycin sulfate, and the environmental conditions were 37°C and 5% CO 2 of humid air.

[0042] (2) Preparation of drugs

[0043] The compound to be tested was dissolved in DMSO to make a mother solution with a concentration of 50mmol / L, and stored at -20°C.

[0044] (3) Crystal violet method to determine ...

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Abstract

The invention belongs to the technical filed of medicines, and relates to the preparation of three new hopane-type triterpenes and applications thereof. The new hopane-type triterpene saponins have the following structure shown in the specification. The new hopane-type triterpene compounds have quinone reductase induced activity, and can be used for development and application of anti-tumor drugsand tumor chemoprevention drugs.

Description

technical field [0001] The invention belongs to the technical field of medicine, and relates to the separation, preparation and application of hooperane-type triterpenes, in particular to three new hoperane-type triterpenes, a preparation method and their application in antitumor drugs. Background technique [0002] The occurrence and development of cancer are closely related to metabolic enzymes. Metabolic enzymes are divided into phase I metabolic enzymes and phase II metabolic enzymes. Phase II metabolic enzymes include reduced glutathione S-transferase, glucuronosyltransferase, Quinone reductase NAD(P)H: quinone reductase(QR), etc. Phase I metabolic enzymes can activate the precursors of carcinogens, and without the action of phase II metabolic enzymes, they can easily interact with macromolecules such as DNA, thereby initiating the generation of cancer; and when phase II metabolic enzymes are activated, they can catalyze The products activated by phase I metabolic enzy...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/56A61P35/00
Inventor 李宁马忠俊李铣肖皖
Owner SHENYANG PHARMA UNIVERSITY
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