Sesquiterpene compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs and immunosuppressive drugs

A sesquiterpene and immunosuppressive technology, which is applied in the field of natural medicinal chemistry, can solve the problems that anti-inflammatory and immunosuppressive active ingredients have not yet been discovered.

Active Publication Date: 2020-06-19
KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few literatures reporting the chemical constituents of Xinjiang pseudogentian. Only xanthones and iridoids have been isolated from them, but no active ingredients with anti-inflammatory and immunosuppressive effects have been found.

Method used

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  • Sesquiterpene compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs and immunosuppressive drugs
  • Sesquiterpene compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs and immunosuppressive drugs
  • Sesquiterpene compound, preparation method thereof and application thereof in preparation of anti-inflammatory drugs and immunosuppressive drugs

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0027] The present invention provides the preparation method of the sesquiterpene compound described in the above scheme, comprising the following steps:

[0028] (1) Extract Xinjiang False Gentiana with an organic solvent to obtain an extract;

[0029] (2) carry out decompression distillation to described extraction liquid, concentrate and obtain medicinal extract;

[0030] (3) after dissolving the extract, perform column chromatography separation and high performance liquid chromatography separation in sequence to obtain the sesquiterpene compound;

[0031] The column chromatography separation includes silica gel column chromatography, MCI column chromatography or reversed-phase C18 column chromatography, Sephadex column chromatography carried out in sequence; phase chromatography.

[0032] The invention uses an organic solvent to extract Xinjiang false gentian to obtain an extract. Before the extraction, the present invention preferably pulverizes the Xinjiang pseudogent...

Embodiment 1

[0043] The extraction and separation of the sesquiterpenoids with structures shown in formula 1 to formula 12, the steps are as follows:

[0044] (1) The whole stem of Xinjiang false gentian collected from Urumqi, Xinjiang, was dried in the shade and crushed to 30 mesh to obtain a 6.0kg sample, soaked and extracted with 40L petroleum ether at room temperature for 5 times, each time for 48h, filtered and combined the extracts, and decompressed After distilling off the solvent, 190 g of total extract was obtained;

[0045] (2) The extract was dissolved in 1.2L of chloroform, mixed with 210g of silica gel (200-300 mesh), placed to dry and ground and sieved, packed with 1.6kg of silica gel (200-300 mesh) for column chromatography, followed by Petroleum ether: chloroform (1:0, 1:1, 0:1, v / v) and chloroform: acetone (9:1, 4:1, 1:1, 0:1) for gradient elution, and the resulting stream Fractions were concentrated under reduced pressure and detected by thin-layer chromatography. After ...

Embodiment 2

[0078] Compounds 1-12 of Example 1 were tested for in vitro immunosuppressive activity:

[0079] CD3, CD28 monoclonal antibody, and IFN-γ detection kits were purchased from BD Bioscience, CCK-8 kits were purchased from Meilun Company, RPMI-1640 medium and fetal bovine serum were purchased from Biological Industries.

[0080] Preparation of samples to be tested: the 12 compounds of Example 1 were respectively dissolved in DMSO to prepare a 20 mM stock solution.

[0081] Specific method: Spleen cells were aseptically isolated from 6-8-week-old female C57BL / 6 mice, and T cells were isolated by nylon hair column method, and then inoculated with T cells (4×10 5 / well) in a 96-well plate (coated with 5 μg / ml CD3 monoclonal antibody), and each group was added with prepared 40, 20, 10, 5, 2.5, 1.25 μM compound and 2 μg / ml CD28 monoclonal antibody, placed in 37℃ / 5%CO 2 cultured in an incubator. After 48 hours, the cell supernatant was collected, and enzyme-linked immunosorbent assay...

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Abstract

The invention provides a sesterterpene compound, a preparation method thereof and an application thereof in preparation of anti-inflammatory drugs and immunosuppressive drugs, and relates to the technical field of natural pharmaceutical chemistry. The sesterterpene compound provided by the invention has any one of structures shown in formulas 1 to 12. The sesterterpene compound provided by the invention is a sesterterpene compound with a very rare skeleton, has anti-inflammatory and immunosuppressive effects, and can be applied to preparation of anti-inflammatory drugs and immunosuppressive drugs. Results of embodiments show that the sesterterpene compounds provided by the invention have obvious inhibition effects on CD3 and CD28 monoclonal antibodies for stimulating mouse T cell proliferation and generating cytokine IFN-gamma. The invention further provides a pharmaceutical composition. The pharmaceutical composition comprises pharmaceutically acceptable pharmaceutical excipients andone or more of the sesterterpene compounds in the scheme.

Description

technical field [0001] The invention relates to the technical field of natural medicinal chemistry, in particular to a sesquiterpene compound, a preparation method thereof and an application in preparation of anti-inflammatory drugs and immunosuppressive drugs. Background technique [0002] The treatment of autoimmune diseases and the rejection of organ transplantation are the current clinical problems. Autoimmune diseases are a group of diseases caused by the body's immune system to produce local or systemic abnormal immune responses to self-antigens, resulting in self-tissue damage, including rheumatoid arthritis, systemic lupus erythematosus, inflammatory bowel disease, multiple sclerosis disease etc. More than 80 kinds of autoimmune diseases have been reported so far, with various clinical manifestations and increasing incidence, which have seriously affected human health. Organ transplantation is the most effective way to save the lives of patients with organ failure....

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/513C07C49/633C07C49/743C07C49/727C07C45/79C07C45/82C07C45/78C07D301/32C07D303/48A61P29/00A61P37/02A61K31/122A61K31/336
CPCA61P29/00A61P37/02C07C49/513C07C49/633C07C49/727C07C49/743C07D301/32C07D303/48C07C2601/08C07C2601/10C07C2602/24C07C2603/40
Inventor 黎胜红郭凯刘艳春刘燕
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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