Pair of quinazolinone alkaloid enantiomers, and preparation method and application thereof

A quinazolinone and the technology of the quinazolinone, which are applied in the field of quinazolinone alkaloid enantiomers and their preparation, can solve problems such as toxic and side effects, and achieve the effect of good anti-inflammatory drug potential

Active Publication Date: 2019-12-20
SUN YAT SEN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The use of these drugs can produce some toxic side effects and adverse reactions, such as gastrointestinal adverse reactions of non-steroidal anti-inflammatory drugs, cardiovascular toxicity of COX-2 inhibitors

Method used

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  • Pair of quinazolinone alkaloid enantiomers, and preparation method and application thereof
  • Pair of quinazolinone alkaloid enantiomers, and preparation method and application thereof
  • Pair of quinazolinone alkaloid enantiomers, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 Isolation of ascidian symbiotic fungus Penicillium canescens SYSU-MS4829

[0038] 1. Strain isolation:

[0039] Sample: Styela plicata from Tai'ao Bay, Shenzhen.

[0040] Isolation method: Disinfect the surface of fresh Ascidian ascidian, dry it for a while, grind it, inoculate it into PDA medium, Martin medium or Chase medium under aseptic conditions, and culture it below 28°C for 5-7 days to obtain a single strain of Penicillium canescens SYSU-MS4829; the obtained bacterial strain Penicillium canescens SYSU-MS4829 was preserved at 4° C. on a common PDA medium slant.

Embodiment 2

[0041] Example 2 Identification of ascidian symbiotic fungus Penicillium canescens SYSU-MS4829

[0042] 1. Morphological and physiological and biochemical identification:

[0043] The biological characteristics of the strain, when cultured at a constant temperature of 28°C on PDA medium, the surface of the colony is white hairy hyphae, the back is dark red, and green spores are formed.

[0044] 2. Molecular identification:

[0045] The purely cultured DNA of Penicillium canescens SYSU-MS4829 was extracted by the CTAB method, and the ITS-rRNA gene fragment was amplified by a PCR amplification instrument using a pair of primers ITS1F and ITS4 in the ITS spacer region. The reaction system was 50uL. The conditions were: pre-denaturation at 94°C for 5 min, denaturation at 94°C for 40 s, annealing at 52°C for 40 s, extension at 72°C for 1 min, repeating denaturation, annealing and extension for 30 cycles, and finally extension at 72°C for 10 min.

[0046] It was determined by Sephad...

Embodiment 3

[0048] Example 3 The separation and identification of quinazolinone alkaloid enantiomer (±)-penicamide A

[0049] 1. The separation of quinazolinone alkaloid enantiomer (±)-penicamide A, the specific process is as follows:

[0050] S1. The enlarged culture of the symbiotic fungus Penicillium canescens SYSU-MS4829, and obtain the thalline of the symbiotic fungus ascidian;

[0051] The specific expansion process is as follows:

[0052] S11. Preparation of seed medium: 200g of potatoes, 20g of glucose, 1L of tap water, prepared as a medium according to a conventional method, evenly distributed in five 500mL Erlenmeyer flasks, and extinguished at 121°C for 30 minutes;

[0053] S12. Cultivation of seeds: Inoculate the strain of the marine fungus Penicillium canescens SYSU-MS4829 into the seed medium, place it on a shaker at a speed of 180 rpm at a temperature of 28°C, and cultivate it for 120 hours to obtain a seed culture solution;

[0054] S13. Preparation of fermentation mediu...

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Abstract

The invention discloses a pair of quinazolinone alkaloid enantiomers, and a preparation method and application thereof. Penicillium canescens SYSU-MS4829 is preserved in the Guangdong Microbial Culture Collection Center on July 11, 2018 with the preservation number of GDMCC 60402, and the Penicillium canescens SYSU-MS4829 can ferment to produce compounds with the structures shown in a formula (I)and a formula (II) (please see the specification for the formula (I) and the formula (II)). The Penicillium canescens SYSU-MS4829 is isolated from sea squirts in Daao Bay, Shenzhen, and can metabolizeto produce the compound quinazolinone alkaloid enantiomers (+/-)-penicamide A with the anti-inflammatory activity, optical voidness compounds (+)-penicamide A and (-)-penicamide A obtained after division of the Penicillium canescens SYSU-MS4829 have the same good anti-inflammatory effect and both can effectively inhibit production of NO by an LPS-induced inflammatory cell RAW264.7, and IC50 is 35.1 [mu]M, 47.5 [mu]M and 27.2 [mu]M respectively; meanwhile, all compounds have no cellular poison to the cell RAW264.7; therefore, a racemic compound (+/-)-penicamide A and the optical voidness compounds (+)-penicamide A and (-)-penicamide A have good potential as anti-inflammatory drugs and can be used for preparing anti-inflammatory drugs.

Description

technical field [0001] The invention relates to the technical field of microbial fermentation and pharmaceutical compounds, and more specifically, to a pair of quinazolinone alkaloid enantiomers and a preparation method and application thereof. Background technique [0002] Inflammation is the physiological and pathological response of the body to stimuli, manifested as redness, swelling, heat, pain and dysfunction. In general, inflammation, as a beneficial defense response, plays an important role in the body's resistance to external stimuli, but excessive and sustained inflammatory responses can cause tissue damage and functional impairment. The occurrence and development of many common diseases (such as tumors, asthma, hypertension, Alzheimer's disease, atherosclerosis, etc.) are closely related to inflammatory responses. Bacterial infectious inflammation induced by endotoxin component lipopolysaccharide (LPS) in the cell wall of Gram-negative bacteria is the most common...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07B57/00A61P29/00A61K31/519C12P17/18C12N1/14C12R1/80
CPCA61P29/00C07B57/00C07B2200/13C07D471/04C12P17/182C12N1/145C12R2001/80
Inventor 陈森华刘岚陈彬姜明华沈鸿杰
Owner SUN YAT SEN UNIV
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