New hopane-type triterpene and preparation method and application thereof

A technology of Hobane type and petroleum ether, which is applied in the field of medicine and can solve problems such as unseen

Inactive Publication Date: 2013-02-13
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, foreign countries have reported that some compounds with quinone reductase induction have been found from natural products, such as dithiolthiones (oltipraz, ultipraz), sulphoraphane; steroids found in cruciferous plants. Compounds such as: withanolides; flavonoids such as 7,4'-dihydroxy-3',5'-dimethoxyisoflavone, 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 spp. were extracted three times by reflux of 95% ethanol, each time for 2 hours, and the extract was recovered under reduced pressure to obtain 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:ethyl acetate 5:1 fraction obtained in the above step (3) was separated by semi-preparative HPLC chromatography, and eluted with acetonitrile / water gradient, acetonitrile / water 50:50~100:0, elution time 50 minutes, the flow rate is 8 mL / min, and the compound is obtained at a retention time of 25 minutes 1 , compound 2 was obtained with a retention time of 44 minutes.

[0021] The petrol...

Embodiment 2

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

[0032] (2) Suspend the ethanol extract in 5L of distilled water, and extract 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, and eluted with petroleum ether: acetone 8:1, 6:1, 4:1, 3:1,

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

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

Embodiment 3

[0037] Example 3 Test of quinone reductase-inducing activity of compounds 1, 2 and 3

[0038] Experimental Materials:

[0039] (1) Main reagents and main equipment: calf serum (purchased from Hyclone); fetal bovine serum (TBD);

[0040] Tetramethylazolium 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 Strain Hepa 1c1c7

[0041] experimental method:

[0042] (1) Cell culture:

[0043] Seed 10 per hole 4 Cells were grown for 24 hours in a culture medium containing 10% (v / v) fetal bovine serum, 0.01% penicillin G, 0.15% sodium bicarbonate, 0.01% streptomycin sulfate, the environmental conditions were 37 ℃, containing 5% CO 2 of humid air.

[0044] (2) Preparation of drugs

[0045] 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.

[0046] (3) Crystal violet meth...

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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 drugs and 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) and so on. 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 production of cancer; and after activated phase II metabolic enzymes, they can catalyze The products activated by phase I metaboli...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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