Novel triterpenoid compound, preparation method and medical application thereof

A compound and composition technology, applied in the field of new compounds, can solve the problems of killing tumors, low immune function, toxic and side effects, etc., and achieves the effects of mild process conditions, killing tumor cells, and simple preparation method.

Active Publication Date: 2015-11-11
福建仙芝楼生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemotherapy is the main means of treating tumors today. It has obvious curative effect in tumor treatment, but its specificity to tumor cells is still not ideal. While killing tumors, it also affects normal cells such as liver cells, gastrointestinal tract and bone marrow cells. Larger toxic and side effects (such as low immune function, bone marrow suppression and acute renal failure, etc.); in addition, many tumors are not sensitive to chemotherapy clinically, or show group resistance after the initial sensitivity, which becomes chemotherapy to treat A major obstacle to tumors

Method used

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  • Novel triterpenoid compound, preparation method and medical application thereof
  • Novel triterpenoid compound, preparation method and medical application thereof
  • Novel triterpenoid compound, preparation method and medical application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] Example 1 Formula (Ⅰ) Compound preparation

[0037] Material source Ganoderma ( Ganodermalucidum (Leys.exFr.) Karst) was purchased from Fujian Xianzhilou Biotechnology Co., Ltd., China. The specimen of the Ganoderma lucidum is deposited in the School of Pharmacy of Fujian Medical University.

[0038] Extraction and separation The dried and crushed Ganoderma lucidum was refluxed and extracted with absolute ethanol for 3 times, 2 hours each time, the extract was filtered with No. 2 filter paper, and the ethanol was removed with a rotary evaporator to obtain an alcohol extract. After adding appropriate amount of water to the alcohol extraction extract, it was extracted with petroleum ether and ethyl acetate successively, and the obtained ethyl acetate extract was extracted with saturated sodium bicarbonate aqueous solution. The ethyl acetate phase was taken out under reduced pressure and evaporated to dryness to obtain a crude product. Column chromatography was performed o...

Embodiment 2

[0039] Example 2 Formula (Ⅰ) Chemical structure determination of compounds

[0040] Structure determination Use Shimadzu-3100 spectrophotometer to measure the ultraviolet spectrum, in CDCl 3 In the solution, the NMR spectrum was recorded with a BRUKER nuclear magnetic resonance spectrometer, and the mass spectrum was measured with an Agilent 6210 time-of-flight mass spectrometer.

[0041] Formula (Ⅰ) The physical and chemical properties of the compound The compound of formula (I) of the present invention is white crystal, UV (EtOH) λmax254nm; Liebermann-Burchard reaction is positive; 1 H-NMR (CDCl 3 , 500MHz): δ 1.74 (1H, m, H-1), δ 2.95 (1H, m, H-1'), δ 2.47 (1H, m, H-2), δ 2.58 (1H, m, H-2'), δ 2.24 (1H, m, H-5), δ 2.36 (1H, m, H-6), δ 2.52 (1H, m, H-6'), δ 2. 63(1H,m,H-12),δ2.71(1H,m,H-12'),δ1.62(1H,m,H-15),δ2.13(1H,m,H-15' ), δ 1.20 (1H, m, H-16), δ 2.10 (1H, m, H-16'), δ 1.65 (1H, m, H-17), δ 0.81 (3H, s, H-18), δ 1.26 (3H, s, H-19), δ 1.40 (1H, m, H-20), δ 0.89 (3H, d, ...

Embodiment 3

[0044] Example 3 Formula (Ⅰ) Biological experiment and analysis of compound anticancer effect

[0045] 1. Materials and methods

[0046] Cell lines and reagents Human esophageal cancer cell line OE-19 and human myeloid leukemia cell line HL60. These cells were cultured in RPMI1640 medium containing 10% calf serum, and placed in CO at 37°C and 5% saturated humidity. 2 Cultivate in an incubator. The above-mentioned triterpenoid formula (Ⅰ) Compound-chemical name 24(S)-24,25-dihydroxylanost-8-en-3,7,11-trione, from Obtained from the preparation of Example 1.

[0047] Cell proliferation analysis Take the OE-19 and HL60 cells in logarithmic growth phase and inoculate them in a 96-well culture plate at a certain density according to the cell line, 190 μl per well. Add medicine immediately after inoculating the cells. The experimental group was added with different concentrations of drugs 10μl / well, the cell control group was supplemented with serum-free culture medium containing ...

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PUM

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Abstract

The invention discloses a novel triterpenoid compound, a preparation method and a medical application thereof. The novel triterpenoid compound is represented as the formula (I) as follows. The preparation method includes the following steps: extracting ganoderma lucidum in alcohol or an alcohol solution for one or more than two times, filtering the extracts and collecting filtrates, performing pressure-reducing concentration and drying to obtain an alcohol extract; adding water to the alcohol extract, extracting and defatting the alcohol extract with petroleum ether, and extracting the extract with ethyl acetate to obtain an ethyl acetate extract liquid; extracting the ethyl acetate extract liquid in an alkaline water solution being 8-12 in pH; evaporate-drying an ethyl acetate phase to obtain a crude product, and performing chromatograph separation and purification to the crude product to obtain the pure compound (I). The compound can be used for treating tumor.

Description

technical field [0001] The invention relates to a new compound with antitumor effect isolated from the traditional Chinese medicine Ganoderma lucidum. [0002] The present invention also relates to the preparation method of the compound. [0003] The invention also relates to the application of the compound in the preparation of antitumor drugs. Background technique [0004] Malignant tumor, often called cancer, is a common and frequently-occurring disease that seriously threatens human health. Currently, the three main methods for treating malignant tumors include chemotherapy, surgery, and radiation therapy. Chemotherapy is the main means of treating tumors today. It has obvious curative effect in tumor treatment, but its specificity to tumor cells is still not ideal. While killing tumors, it also affects normal cells such as liver cells, gastrointestinal tract and bone marrow cells. Larger toxic and side effects (such as low immune function, bone marrow suppression and...

Claims

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Application Information

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IPC IPC(8): C07J9/00A61K31/575A61P35/00A61P35/02
CPCC07J9/00
Inventor 许建华李鹏张志强柯方沈翠娥熊小文
Owner 福建仙芝楼生物科技有限公司
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