New butanolide derivatives from the marine derived fungus Aspergillus terreus GZU-31-1 by chemical epigenetic manipulation

Chemical epigenetic manipulation of Aspergillus terreus GZU-31-1 led to the discovery of five butanolide derivatives (1-5), including two new ones (1 and 2), and four known diphenyl ether derivatives (6−9). Compound 1 featured a Z-configuration double bond in the isoprenyl group was a potential anti...

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Bibliographic Details
Published in:Natural product research 2024-04, Vol.38 (8), p.1334-1340
Main Authors: Zhou, Yuwei, Chen, Xiaocong, Tang, Yuqian, Liu, Yena, Zhao, Zhongxiang, Cui, Hui
Format: Article
Language:English
Subjects:
anti-inflammatory activity
Anti-inflammatory agents
Aspergillus terreus
Aspergillus terreus GZU-31-1
butanolide derivatives
Cell culture
chemical epigenetic manipulation
Diphenyl ether
Epigenetics
Indomethacin
Inflammation
Lipopolysaccharides
Liquid culture
Microglial cells
Natural products
Nitric oxide
Sodium citrate
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Summary:Chemical epigenetic manipulation of Aspergillus terreus GZU-31-1 led to the discovery of five butanolide derivatives (1-5), including two new ones (1 and 2), and four known diphenyl ether derivatives (6−9). Compound 1 featured a Z-configuration double bond in the isoprenyl group was a potential anti-inflammatory bioactive group. Compound 2 was a new natural product. Moreover, compound 3 with a deacetylated group at C-4 was rarely reported as a butanolide analogue, which was isolated from the liquid culture treated with polyketide pathway inhibitor sodium citrate dihydrate. All of the isolates (1−9) were tested for their anti-inflammatory effects on the production of nitric oxide in lipopolysaccharide-induced microglial cells (RAW 264.7 cells). Compounds 1, 7, 8 and 9 exhibited more potent anti-inflammatory activity with IC 50 values of 16.31, 20.16, 9.53 and 21.64 μM than the positive control (indomethacin, IC 50 , 24.0 μM).
ISSN:1478-6419
1478-6427
DOI:10.1080/14786419.2022.2140338