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Heterterpene compounds derived from marine fungi and their application in the preparation of anti-inflammatory drugs

A technology of marine fungi and compounds, which is applied in the field of pharmaceutical compounds, can solve problems such as adverse reactions and achieve good results in application prospects

Active Publication Date: 2022-06-17
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are two main types of anti-inflammatory drugs commonly used clinically: non-steroidal anti-inflammatory drugs and steroidal anti-inflammatory drugs. Long-term large-scale use will produce a series of adverse reactions and tolerance

Method used

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  • Heterterpene compounds derived from marine fungi and their application in the preparation of anti-inflammatory drugs
  • Heterterpene compounds derived from marine fungi and their application in the preparation of anti-inflammatory drugs
  • Heterterpene compounds derived from marine fungi and their application in the preparation of anti-inflammatory drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Example 1 Acquisition of marine fungus Aspergillus terreus GZU-31-1

[0039] The inventor's team isolated a marine fungus Aspergillus terreus GZU-31-1 from the trunk of the tumefaciens along the coast of Xuwen, Zhanjiang City, Guangdong Province. The fungus was identified by DNA amplification and sequencing of the fungal ITS region. The specific steps were referred to in the literature (Nature protocols, 2010, 5, 480-490; Journal of Natural Products, 2006, 69, 11, 1622-1625): using DNeasy Plant Mini Kit kit, according to the steps of the instructions, extract DNA, use ITS as the primer for PCR amplification, and the amplified product is sequenced. The sequence obtained by sequencing was searched for similarity through the BLAST database. After comparison, the sequence similarity with the Aspergillus terreus fungus sequence was 100%, and the fungus was determined to be the marine fungus Aspergillus terreus GZU-31-1. The strain was deposited in the Guangdong Provincial M...

Embodiment 2

[0040] Isolation of Example 2 Compounds

[0041] The novel heteroterpenoid derivatives are isolated from the fermentation broth of the marine fungus Aspergillus terreus GZU-31-1. The specific method is as follows:

[0042] (1) Seed liquid culture of the fungus Aspergillus terreus GZU-31-1: pick the strain and insert it into the slant, and after culturing it at 30°C for 3 days, insert it into the potato glucose water medium, and culture it at 30°C for 3 days to obtain the seed solution; among them, the slant culture The composition of the base by weight is: glucose 0.3%, yeast extract 0.1%, peptone 0.5%, agar 2.5%, sodium chloride 3%, water 98%; the composition of potato glucose water medium by weight is: In terms of mass ratio, potato 20%, glucose 0.3%, sodium chloride 3%, and water to make up to 100%.

[0043] (2) Fermentation culture of the fungus Aspergillus terreus GZU-31-1: transfer the strain in the seed liquid into the fermentation medium, and let it stand at 28°C for ...

Embodiment 3

[0046] Structural analysis of the compound of Example 3

[0047] The structural analysis of the new compounds 1 to 5 was carried out, and the following experimental data were obtained:

[0048] New compound 1: C 28 H 31 O 10 , HRESI-MS: 527.1915 [M-H] - (calculated 527.1911).

[0049] New compound 2: C 26 H 31 O 9 , HRESI-MS: 487.1959 [M-H] - (calculated 487.1962).

[0050] New compound 3: C 29 H 35 O 11 , HRESI-MS: 559.2183 [M-H] - (calculated 559.2173).

[0051] New compound 4: C 30 H 37 O 11 , HRESI-MS: 573.2361 [M-H] - (calculated 573.2330).

[0052] New compound 5: C 29 H 35 O 11 , HRESI-MS: 559.2181 [M-H] - (calculated 559.2173).

[0053] The NMR data of compounds 1 to 5 are shown in Table 1.

[0054] Table 1 NMR data of compounds 1 to 5 (CDCl 3 , 400MHz / 101MHz,ppm)

[0055]

[0056]

[0057]

[0058]

[0059] The structural formulas of compounds 1 to 5 are as follows:

[0060]

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Abstract

The invention discloses a heteroterpene compound derived from a marine fungus and its application in the preparation of anti-inflammatory drugs. The present invention separates the heteroterpenoids from the fermentation product of a marine fungus, Aspergillus terreus GZU-31-1, and its structural formulas are shown in formulas 1-5. These new compounds can significantly inhibit the production of inflammatory factor NO induced by LPS, and the ICs of compounds 1-5 50 They are: 6.74±0.77μmol / L, 22.18±0.94μmol / L, 25.87±3.1μmol / L, 26.47±0.98μmol / L, 29.59±3.9μmol / L, which have clinical application potential for treating and anti-inflammation and can be used for development A new type of anti-inflammatory drug with good application prospect.

Description

technical field [0001] The invention belongs to the technical field of medicinal compounds, in particular to a marine fungus-derived heteroterpene compound and its application in the preparation of anti-inflammatory drugs. Background technique [0002] Inflammation is the body's defense response to stimuli. However, this defense response must be rapid and controlled to prevent further inflammatory disturbances that can cause severe tissue damage. Inflammation has been reported to be directly linked to obesity, diabetes, blood clots, and even cancer. At present, there are two main types of anti-inflammatory drugs commonly used in clinical practice: non-steroidal anti-inflammatory drugs and steroidal anti-inflammatory drugs. In order to solve the drug tolerance and adverse reactions, the search for new anti-inflammatory drugs has become a hot spot in the field of anti-inflammatory drug research. [0003] In a unique environment, marine fungi have unique metabolic pathways a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/06C07D311/78A61P29/00C12N1/14C12P17/18C12P17/06C12R1/66
CPCC07D493/06C07D311/78A61P29/00C12N1/14C12P17/181C12P17/06
Inventor 崔辉唐渝茜陈晓聪周雨薇赵钟祥
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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