Cyclohexenone Derivative and Drimane Sesquiterpenes from the Seagrass-Derived Fungus Aspergillus insuetus

Chem Biodivers. 2023 Jul;20(7):e202300424. doi: 10.1002/cbdv.202300424. Epub 2023 Jun 21.

Abstract

One new cyclohexenone derivative (1), and two undescribed drimane sesquiterpenes (2 and 3), together with another seven known drimane sesquiterpenes were isolated from a seagrass-derived fungus Aspergillus insuetus SYSU6925. Structures of these metabolites were elucidated by comprehensive spectroscopic analysis, including NMR analysis, mass spectrometry, and ECD calculations. Compounds 1-3, 5 and 7 displayed weak to moderate antifungal activities towards four phytopathogenic fungi, with Minimum inhibition concentration (MIC) values range from 50 to 200 μg/mL. Compound 1, a rare cyclohexenone derivative with n-propyl group exhibited more potent inhibitory activities (MIC, 50 μg/mL) against F. oxysporum than positive control (Triadimefon). Compounds 2 and 3 also exhibit potent anti-inflammatory activities by inhibiting the production of nitric oxide (NO) in RAW264.7 cells with IC50 values of 21.5±1.1 and 32.6±1.16 μM, respectively.

Keywords: Aspergillus insuetus; antifungal activity; cyclohexenone derivative; drimane sesquiterpene; seagrass-derived fungi.

MeSH terms

  • Cyclohexanones / chemistry
  • Fungi
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Sesquiterpenes* / chemistry

Substances

  • drimane
  • Sesquiterpenes
  • Cyclohexanones

Supplementary concepts

  • Aspergillus insuetus