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Pyrrole sesquiterpene compound, preparation method and uses thereof

A technology for sesquiterpenes and compounds, which is applied in the field of pyrrole sesquiterpenes and their preparation, can solve the problems of low yield of chemical structures of heteroterpenes and the like, and achieve the effect of novel structure

Active Publication Date: 2019-10-22
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

Currently, the number of reported heteroterpenoid chemical structures is far below the potential production in nature

Method used

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  • Pyrrole sesquiterpene compound, preparation method and uses thereof
  • Pyrrole sesquiterpene compound, preparation method and uses thereof
  • Pyrrole sesquiterpene compound, preparation method and uses thereof

Examples

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preparation example Construction

[0059] In a second aspect, this embodiment provides a method for preparing the above-mentioned pyrrole sesquiterpenoids, which includes the following steps:

[0060] Step S1: fermenting and culturing Streptomyces sp.KIB 015 to obtain a culture solution;

[0061] Wherein, the Streptomyces sp.KIB 015 strain is a strain disclosed in literature (ie S.sp.KIB 015), which is: Isolation and Biosynthesis of Labdanmycins: Four New Labdane Diterpenes from Endophytic Streptomyces, Organic Chemistry Frontiers, 2018, 5 ,1272–1279.

[0062] Further, the conditions for fermenting and culturing the strains are: temperature 27-33°C, culture time 8-12 days; or temperature 29-31°C, culture time 9-11 days.

[0063] Further, the liquid medium for fermenting and cultivating the strains includes, in parts by weight: 15-25 parts of glucose, 3-8 parts of beef extract, 3-8 parts of peptone, 3-8 parts of yeast extract powder, sodium chloride 3-8 parts, calcium carbonate 1-5 parts.

[0064] Alternative...

Embodiment 1

[0080] Preparation and structure identification of compound 1-6:

[0081] 1. Preparation process:

[0082] 1. Fermentation conditions

[0083] Preparation of seed culture solution: Dissolve 6.0 g of beef extract and 10.0 g of tryptone in deionized water, add deionized water to make the volume 2000 mL, and adjust the pH to 7.0. The obtained seed culture solution was evenly distributed into 40 250 mL baffled Ermlenmeyer bottles, and sterilized at 121°C for 30 minutes for future use. Streptomyces sp.KIB 015 strains were inoculated into the above-mentioned medium, and cultured on a shaker at 30° C. and 200 rpm for 48 hours to obtain a seed culture solution.

[0084] Configuration of fermentation culture medium: Dissolve 800g of glucose, 200g of beef extract, 200g of peptone, 120g of yeast extract powder, 200g of sodium chloride, and 120g of calcium carbonate in 40L of deionized water, stir to fully dissolve, and adjust the pH to 7.0. The obtained 40L fermentation culture liquid...

experiment example

[0102] The immunosuppressive effects of the six pyrrole sesquiterpenoids provided in the examples of the present invention will be evaluated in combination with cell experiments below.

[0103] 1. Experimental process:

[0104] 1. The inhibitory effect of compounds 1-6 on the proliferation of Anti-human-CD3 / CD28-induced activation and phytohemagglutinin-induced activation of human T cells.

[0105] The inhibitory effects of compounds 1-6 on the proliferation of Anti-human-CD3 / CD28-induced activation and phytohemagglutinin-induced activation of human T cells were determined by flow cytometry analysis, and 5-carboxyfluorescein diacetatesuccinimide ester (CFSE) was selected as Marker, the situation that the T cells that are not induced and activated and the corresponding compound are treated as a negative control (0%), the situation that the T cells that are induced and activated are not treated by the corresponding compound is used as a positive control (100%), and the results a...

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Abstract

The invention provides a pyrrole sesquiterpene compound, a preparation method and uses thereof, and belongs to the field of medicine. According to the present invention, the pyrrole sesquiterpene compound has novel structure, has immunosuppressive action, can be used for preparing immunosuppressive agents, has broad application prospects, and has a structural general formula defined in the specification.

Description

technical field [0001] The invention relates to the field of medicine, in particular to a pyrrole sesquiterpene compound and its preparation method and application. Background technique [0002] The activation, proliferation, and differentiation of T lymphocytes are crucial to the host's immune response, and their functions need to be strictly controlled to ensure that the corresponding immune response is under appropriate control. Disordered T lymphocyte proliferation can lead to many autoimmune diseases, such as rheumatoid arthritis, systemic lupus erythematosus, inflammatory bowel disease, psoriasis, etc. Immunosuppressants such as rapamycin, cyclosporine, tacrolimus, and mycophenolate mofetil are widely used to treat such diseases. However, pathogens and drug susceptibility vary significantly from patient to patient. In the course of treatment, if the effect of monotherapy is not obvious, combination therapy, sequential therapy, etc. should be used. Therefore, we urge...

Claims

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Application Information

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IPC IPC(8): C07D405/06C07D207/333C12P17/10C12P17/16A61P37/06A61K31/40A61K31/4025C12R1/465
CPCC07D405/06C07D207/333C12P17/10C12P17/16A61P37/06
Inventor 黄胜雄刘阳王莉周知李洁罗剑英
Owner KUNMING INST OF BOTANY - CHINESE ACAD OF SCI
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