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A kind of 1,4-naphthoquinone compound derived from mangrove endophytic fungi, its preparation method and its application in the preparation of anti-inflammatory drugs

A technology of endophytic fungi and compounds in mangrove trees, applied in biochemical equipment and methods, microorganism-based methods, microorganisms, etc., and can solve problems such as adverse reactions

Active Publication Date: 2021-09-21
GUANGDONG MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these two types of anti-inflammatory drugs have certain clinical anti-inflammatory effects, long-term large-scale use will produce a series of adverse reactions and tolerance, such as gastric mucosal damage, liver damage, kidney damage, etc.

Method used

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  • A kind of 1,4-naphthoquinone compound derived from mangrove endophytic fungi, its preparation method and its application in the preparation of anti-inflammatory drugs
  • A kind of 1,4-naphthoquinone compound derived from mangrove endophytic fungi, its preparation method and its application in the preparation of anti-inflammatory drugs
  • A kind of 1,4-naphthoquinone compound derived from mangrove endophytic fungi, its preparation method and its application in the preparation of anti-inflammatory drugs

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] The preparation method of two 1,4-naphthoquinone compounds derived from mangrove endophytic fungi, the 1,4-naphthoquinone compounds are from the fermentation broth of mangrove endophytic Talaromyces sp.SK-S009 isolated from. The mangrove endophytic fungus Talaromyces sp.SK-S009 was isolated from the fruit of mangrove plant Kandelia obovata in Shankou, Guangxi.

[0031] The mangrove fungus Talaromyces sp. SK-S009 was deposited in the Guangdong Provincial Microbial Culture Collection Center (GDMCC) on May 9, 2018, with a preservation number of GDMCC No: 60369 and a classification name of Talaromyces sp. The address of the preservation unit is 5th Floor, Building 59, Compound, No. 100 Xianlie Middle Road, Guangzhou City.

[0032] The specific preparation method of the 1,4-naphthoquinone compound is as follows:

[0033] S1. Seed solution culture of the mangrove endophytic fungus Talaromyces sp.SK-S009: insert the mangrove endophytic fungus Talaromycessp.SK-S009 into the s...

Embodiment 2

[0036] Embodiment 2 (compound structural characterization)

[0037] Structural analysis of compounds Ⅰ (new) and Ⅱ was carried out, and the following experimental data were obtained:

[0038] Molecular formula C 15 h 16 o 5 , HRESI-MS: 275.09223 [M-H] - (calculated value 275.09195);

[0039] See Table 1 for the NMR data of this compound.

[0040] NMR data (500 / 125MHz, CDCl 3 )

[0041]

[0042] According to the above data results, it is confirmed that the structural formulas of compounds I and II are as follows:

[0043]

Embodiment 3

[0045] Anti-inflammatory cell screening model for compounds

[0046] 1. Cell culture and treatment

[0047] RAW 264.7 cells were cultured in vitro, using DMEM high-glucose medium containing 10% FBS, at 37°C and 5% carbon dioxide concentration for routine maintenance and passage.

[0048] 2. Compound intervention

[0049]Adjust RAW 264.7 cell density to 1×10 5 cells / well and in the logarithmic growth phase, adding LPS (final concentration 1 μg / mL) to induce macrophages to be in an inflammatory state, using DMSO to prepare the compound to be tested or indomethacin into different drug concentrations, each concentration was set at 3 A parallel well was set up, and positive control wells (only LPS added), negative control wells (cells and medium), and blank control wells (medium) were set. After culturing for 24 hours, take 50 μL of the cell supernatant and add it to a new 96-well plate, add 50 μL of reagents I and II of the NO detection kit, and use the Griess method to measure...

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Abstract

The invention discloses a 1,4-naphthoquinone compound derived from a mangrove endophytic fungus. The structural formulas of the 1,4-naphthoquinone compound are shown in formulas I and II. This kind of compound has a certain inhibitory effect on LPS-induced NO production in RAW 264.7 mouse macrophages, IC 50 Values ​​were 3.9 µ M and 1.7 µ M. Further research found that compound Ⅱ can inhibit the mRNA expression of inflammation-related inducible synthases such as iNOS, COX-2, TNF-α, IL-6 and IL-1β induced by LPS, and can also inhibit the iNOS and COX-2 induced by LPS protein expression. It shows that compounds I and II have the effect of inhibiting the inflammatory response of macrophages, have good anti-inflammatory activity in vitro, and can be used to prepare anti-inflammatory drugs. Therefore, the 1,4-naphthoquinone compound provided by the present invention has clinical application potential of anti-inflammation.

Description

technical field [0001] The invention belongs to the technical field of pharmaceutical compounds, and more specifically relates to a 1,4-naphthoquinone compound derived from mangrove endophytic fungi, a preparation method thereof, and an application in the preparation of anti-inflammatory drugs. Background technique [0002] Inflammation is a defensive response of body tissues to damaging stimuli such as noxious stimuli, germs or physical damage. The pathological changes of inflammation are mainly composed of three parts: degeneration, exudation and hyperplasia of local tissues. The clinical symptoms are redness, swelling, heat, pain and local dysfunction. Inflammation is also an important factor in the aging process of the human body, and is closely related to many chronic diseases such as arthritis, osteoporosis, asthma, Alzheimer's disease, cardiovascular disease, dementia, cancer, obesity and type Ⅱ diabetes[1-3] . Clinically, anti-inflammatory drugs are the second larg...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C50/32A61P29/00C12P7/66C12R1/645
CPCA61P29/00C07C50/32C12P7/66C07C2602/10
Inventor 刘红菊闫冲李静
Owner GUANGDONG MEDICAL UNIV
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