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

Abstract

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 IC₅₀ values of 16.31, 20.16, 9.53 and 21.64 μM than the positive control (indomethacin, IC₅₀, 24.0 μM).

Keywords:

• Aspergillus terreus GZU-31-1
• butanolide derivatives
• chemical epigenetic manipulation
• anti-inflammatory activity

Disclosure statement

No potential conflict of interest was reported by the authors.

Additional information

Funding

We thank the open foundation of Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education (RDZH2020005) and the foundation of State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources (Guangxi Normal University) (CMEMR2021-B09), the foundation for young innovative talents in higher education of Guangdong Province (2019KQNCX025), and system resource of Tianhe-2 of national supercomputer centre in Guangzhou for generous support.